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afaxine - Wikipedia, the free encyclopedia

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Venlafaxine

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1 : 1 mixture (racemate)

Systematic (IUPAC) name

(RS)-1-[2-dimethylamino-1- (4-methoxyphenyl)-

ethyl]cyclohexanol

Identifiers

CAS number 93413-69-5

ATC code N06AX16

PubChem CID 5656

DrugBank APRD00125

ChemSpider 5454

UNII GRZ5RCB1QG

Chemical data

Formula C17H27NO2

Mol.mass 277.402 g/mol

SMILES eMolecules & PubChem

InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12

17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1

3H3

Key: PNVNVHUZROJLTJ-UHFFFAOYSA-N

Pharmacokinetic data

From Wikipedia, the free encyclopedia

Venlafaxine (also called Effexor or Efexor) is

an antidepressant of the serotonin-

norepinephrine reuptake inhibitor (SNRI)

class.[2][ 3][4] First introduced by Wyeth in

1993, now marketed by Pfizer, it is licensed

for the treatment of major depressive disorder

(MDD), as a treatment for generalizedanxiety

disorder, and comorbidindications in certain

anxiety disorders with depression. In 2007,

venlafaxine was the sixth most commonly

prescribed antidepressant on the U.S. retail

market, with 17.2 million prescriptions.[5] In

children and adolescents, venlafaxine, like

other antidepressants, has a potential to

increase suicidal thoughts, attempts and

events of self-harm.[citation needed]

Contents[hide]

1 Indications

1.1 Approved

1.1.1 Depression

1.2 Off-label/investigational uses

2 Contraindications

2.1 Glaucoma

2.2 Pregnantwomen

2.3 Heartdisease and hypertension

3 Adverse effects

3.1 Suicide3.2 Commonside effects

3.3 Lesscommon to rare side effects

3.4 Dose dependency of adverse events

3.5 Memory loss

3.6 Discontinuation syndrome

3.7 Serotonin syndrome

3.8 Combined serotonintoxicity andSSRI

discontinuation syndrome (SSRI

withdrawal)

InChI

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Bioavailability 10-45%[1]

Protein

binding

27%

Metabolism Hepatic

Half-life 4.9 2.4 h (parent compound);[1] 10.3 4

h (active metabolite)[1]

Excretion Renal

Therapeutic considerations

Pregnancy

cat.

C

Legal status POM(UK)-only(US)

Routes Oral

(whatis this?) (verify)

4 Available forms

4.1Venlafaxine extended release (XR)

4.2Generic

5 Overdose

5.1Management of overdose

6 Mechanism ofaction

6.1Pharmacokinetics

7 Drug interactions

8 Physical/chemical properties

9 See also

10 References

11 Externallinks

11.1 Patient experiences

Venlafaxine is used primarily for the treatment of major depression in adults.[6]

Multiple double blind studies show venlafaxine's effectiveness in treating depression. Venlafaxine h

similar efficacy to the tricyclic antidepressantsamitriptyline (Elavil) and imipramine, and is better

tolerated than amitriptyline. Its efficacy is similar to or better than sertraline (Zoloft) and fluoxetine

(Prozac), depending on the criteria and rating scales used. Higher doses of venlafaxine are more

effective, and more patients achieved remission or were "very much improved". The efficacy was

similar if the number of patients who achieved "response" or were "improved" was considered. A

meta-analysis comparing venlafaxine and combined groups of SSRI or tricyclic antidepressants

showed venlafaxine's superiority.[7 ] Judged by the same criteria, venlafaxine was similar in efficacy

the atypical antidepressant bupropion (Wellbutrin); however, the remission rate was significantly

lower for venlafaxine.[8]

In a double-blind study, patients who did not respond to an SSRI wereswitched to venlafaxine or citalopram. Similar improvement was observed in both groups. [9]

Many doctors are starting to prescribe venlafaxine "off label" for the treatment of diabetic neuropat

(in a similar manner to duloxetine) and migraine prophylaxis (in some people, however, venlafaxine

can exacerbate or cause migraines). Studies have shown venlafaxine's effectiveness for these

conditions.[10 ][11] It has also been found to reduce the severity of 'hot flashes' in menopausal

women.[12][13]

Substantial weight loss in patients with major depression, generalized anxiety disorder, and social

phobia has been noted, but the manufacturer does not recommend use as an anorectic either alonor in combination with phentermine or other amphetamine-like drugs. [6 ] Venlafaxine hydrochloride

in the phenethylamine class of modern chemicals, which includes amphetamine,

methylenedioxymethamphetamine (MDMA), and methamphetamine. This chemical structure likely

lends to its activating properties; however, some patients find venlafaxine highly sedating, despite i

more common stimulatory effects.

Venlafaxine is not approved for the treatment of depressive phases of bipolar disorder; this has so

potential danger as venlafaxine can induce mania, mixed states, rapid cycling and/or psychosis in

some bipolar patients, particularly if they are not also being treated with a mood stabilizer.[6 ]

Due to its action on both the serotoninergic and adrenergic systems, venlafaxine is also used as a

[edit]Indications

[eApproved

[eDepression

[eOff-label/investigational uses
http://en.wikipedia.org/wiki/Bioavailabilityhttp://en.wikipedia.org/wiki/Plasma_protein_bindinghttp://en.wikipedia.org/wiki/Plasma_protein_bindinghttp://en.wikipedia.org/wiki/Drug_metabolismhttp://en.wikipedia.org/wiki/Drug_metabolismhttp://en.wikipedia.org/wiki/Hepatichttp://en.wikipedia.org/wiki/Biological_half-lifehttp://en.wikipedia.org/wiki/Excretionhttp://en.wikipedia.org/wiki/Excretionhttp://en.wikipedia.org/wiki/Pregnancy_categoryhttp://en.wikipedia.org/wiki/Pregnancy_categoryhttp://en.wikipedia.org/wiki/Pregnancy_categoryhttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/United_Kingdomhttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/Route_of_administrationhttp://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/w/index.php?&diff=cur&oldid=401735053http://en.wikipedia.org/wiki/Major_depressive_disorderhttp://en.wikipedia.org/wiki/Major_depressive_disorderhttp://en.wikipedia.org/wiki/Major_depressive_disorderhttp://en.wikipedia.org/wiki/Major_depressive_disorderhttp://en.wikipedia.org/wiki/Major_depressive_disorderhttp://en.wikipedia.org/wiki/Tricyclic_antidepressantshttp://en.wikipedia.org/wiki/Tricyclic_antidepressantshttp://en.wikipedia.org/wiki/Amitriptylinehttp://en.wikipedia.org/wiki/Amitriptylinehttp://en.wikipedia.org/wiki/Amitriptylinehttp://en.wikipedia.org/wiki/Imipraminehttp://en.wikipedia.org/wiki/Imipraminehttp://en.wikipedia.org/wiki/Sertralinehttp://en.wikipedia.org/wiki/Sertralinehttp://en.wikipedia.org/wiki/Fluoxetinehttp://en.wikipedia.org/wiki/Fluoxetinehttp://en.wikipedia.org/wiki/Remission_(medicine)http://en.wikipedia.org/wiki/Remission_(medicine)http://en.wikipedia.org/wiki/Remission_(medicine)http://en.wikipedia.org/wiki/Meta-analysishttp://en.wikipedia.org/wiki/Meta-analysishttp://en.wikipedia.org/wiki/Meta-analysishttp://en.wikipedia.org/wiki/SSRIhttp://en.wikipedia.org/wiki/Bupropionhttp://en.wikipedia.org/wiki/Bupropionhttp://en.wikipedia.org/wiki/Bupropionhttp://en.wikipedia.org/wiki/Citalopramhttp://en.wikipedia.org/wiki/Citalopramhttp://en.wikipedia.org/wiki/Diabetic_neuropathyhttp://en.wikipedia.org/wiki/Diabetic_neuropathyhttp://en.wikipedia.org/wiki/Diabetic_neuropathyhttp://en.wikipedia.org/wiki/Duloxetinehttp://en.wikipedia.org/wiki/Migrainehttp://en.wikipedia.org/wiki/Menopausehttp://en.wikipedia.org/wiki/Menopausehttp://en.wikipedia.org/wiki/Anorectichttp://en.wikipedia.org/wiki/Bipolar_disorderhttp://en.wikipedia.org/wiki/Bipolar_disorderhttp://en.wikipedia.org/wiki/Bipolar_disorderhttp://en.wikipedia.org/wiki/Maniahttp://en.wikipedia.org/wiki/Mixed_state_(psychology)http://en.wikipedia.org/wiki/Mixed_state_(psychology)http://en.wikipedia.org/wiki/Mixed_state_(psychology)http://en.wikipedia.org/wiki/Psychosishttp://en.wikipedia.org/wiki/Psychosishttp://en.wikipedia.org/wiki/Psychosishttp://en.wikipedia.org/wiki/Mood_stabilizerhttp://en.wikipedia.org/wiki/Mood_stabilizerhttp://en.wikipedia.org/wiki/Mood_stabilizerhttp://en.wikipedia.org/wiki/Mood_stabilizerhttp://en.wikipedia.org/wiki/Mood_stabilizerhttp://en.wikipedia.org/wiki/Mood_stabilizerhttp://en.wikipedia.org/wiki/Adrenergichttp://en.wikipedia.org/wiki/Adrenergichttp://en.wikipedia.org/wiki/Adrenergichttp://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=1http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=3http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=4http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=4http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=3http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=2http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=1http://en.wikipedia.org/wiki/Adrenergichttp://en.wikipedia.org/wiki/Mood_stabilizerhttp://en.wikipedia.org/wiki/Psychosishttp://en.wikipedia.org/wiki/Mixed_state_(psychology)http://en.wikipedia.org/wiki/Maniahttp://en.wikipedia.org/wiki/Bipolar_disorderhttp://en.wikipedia.org/wiki/Anorectichttp://en.wikipedia.org/wiki/Menopausehttp://en.wikipedia.org/wiki/Migrainehttp://en.wikipedia.org/wiki/Duloxetinehttp://en.wikipedia.org/wiki/Diabetic_neuropathyhttp://en.wikipedia.org/wiki/Citalopramhttp://en.wikipedia.org/wiki/Bupropionhttp://en.wikipedia.org/wiki/SSRIhttp://en.wikipedia.org/wiki/Meta-analysishttp://en.wikipedia.org/wiki/Remission_(medicine)http://en.wikipedia.org/wiki/Fluoxetinehttp://en.wikipedia.org/wiki/Sertralinehttp://en.wikipedia.org/wiki/Imipraminehttp://en.wikipedia.org/wiki/Amitriptylinehttp://en.wikipedia.org/wiki/Tricyclic_antidepressantshttp://en.wikipedia.org/wiki/Major_depressive_disorderhttp://en.wikipedia.org/w/index.php?&diff=cur&oldid=401735053http://en.wikipedia.org/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validationhttp://en.wikipedia.org/wiki/Route_of_administrationhttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/United_Kingdomhttp://en.wikipedia.org/wiki/Prescription_drughttp://en.wikipedia.org/wiki/Regulation_of_therapeutic_goodshttp://en.wikipedia.org/wiki/Pregnancy_categoryhttp://en.wikipedia.org/wiki/Pregnancy_categoryhttp://en.wikipedia.org/wiki/Excretionhttp://en.wikipedia.org/wiki/Biological_half-lifehttp://en.wikipedia.org/wiki/Hepatichttp://en.wikipedia.org/wiki/Drug_metabolismhttp://en.wikipedia.org/wiki/Plasma_protein_bindinghttp://en.wikipedia.org/wiki/Plasma_protein_bindinghttp://en.wikipedia.org/wiki/Bioavailability


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treatment to reduce episodes of cataplexy, a form of muscle weakness, in patients with the sleep

disordernarcolepsy.[14]

Venlafaxine was found in one study to be equal to anafranil (Clomipramine) in the treatment of OC

with fewer side effects.[15]

Due to its tendency to increase blood pressure and its modulative effects on the autonomic nervou

system, venlafaxine is often used to treat orthostatic intolerance and postural orthostatic tachycard

syndrome.[16]

Venlafaxine is contraindicated in children and adolescents because it can increase suicidal thought

attempts, and self-harm (see Venlafaxine#Suicide). Furthermore, studies of venlafaxine in these ag

groups have not established its efficacy or safety. [17] Venlafaxine is not recommended in patients

hypersensitive to it, nor should it be taken by anyone who is allergic to the inactive ingredients, wh

include gelatin, cellulose, ethylcellulose, iron oxide, titanium dioxide and hypromellose. It should

never be used with a monoamine oxidase inhibitor (MAOI), as it can cause potentially deadly

serotonin syndrome. At least 14 days must pass between the use of venlafaxine and MAO inhibito

Caution should also be used in those with a seizure disorder.

Venlafaxine can increase eye pressure, so those with glaucoma may require more frequent eye

checks.[6]

There are few, well-controlled studies of venlafaxine in pregnant women. A study released in May

2010 by the Canadian Medical Association Journal suggests use of venlafaxine doubles the risk of

miscarriage.[18] Consequently, venlafaxine should only be used during pregnancy if clearly

needed.[6 ] Prospective studies have not shown any statistically significant congenital

malformations.[19] There have, however, been some reports of self-limiting effects on newborn

infants.[20] As with other serotonin reuptake inhibitors, these effects are generally short-lived, lastinonly 3 to 5 days, [21] and rarely resulting in severe complications. [22] Use of Venlafaxine in

pregnancy should be considered on a case-by-case basis. Venlafaxine use during pregnancy

increases the risk of spontaneous abortion.[23][ 24]

The FDA asked the manufacturers of all SNRIs to include the risk of persistent pulmonary

hypertension (PPHN) in prescribing data as of July 19, 2006. Medications containing venlafaxine

caused a mean heart rate increase of 4 bpm in clinical trials, along with a sustained increase in

blood pressure in some.

The US Food and Drug Administration body (FDA) requires all antidepressants, including venlafax

to carry a black box warning with a generic warning about a possible suicide risk. In addition, the

most recent research[citation needed] indicated that patients taking venlafaxine are at increased risk

suicide.

A study conducted in Finland followed more than 15,000 patients for 3.4 years. Venlafaxine increa

suicide risk 1.6-fold (statistically significant), as compared to no treatment. At the same time,

[eContraindications

[eGlaucoma

[ePregnant women

[eHeart disease and hypertension

[eAdverse effects

[eSuicide
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fluoxetine (Prozac) halved the suicide risk.[25]

In another study, the data on more than 200,000 cases were obtained from the UK general practic

research database. The patients taking venlafaxine had significantly higher risk of completed suicid

than the ones on fluoxetine (Prozac) (2.8 times) or citalopram (Celexa) (2.4 times). Even after taki

into consideration the fact that venlafaxine was generally prescribed for more severe depression,

venlafaxine was associated with 1.6-1.7 times more suicides than fluoxetine or citalopram. This

difference was no longer statistically significant due to the rarity of completed suicides. However, fo

the attempted suicides (more frequent event) the 1.2-1.3 times higher risk for venlafaxine still stay

statistically significant after the adjustment. [26]

An analysis of clinical trials by the FDA statisticians showed the incidence of suicidal behaviour

among the adults on venlafaxine to be not significantly different from fluoxetine or placebo.[27] A

possible explanation for this discrepancy is that suicidal patients are generally excluded from clinic

trials, and so clinical trials do not represent the real population of patients. [citation needed]

Venlafaxine is contraindicated in children, adolescents and young adults. According to the FDA

analysis of clinical trials[27] venlafaxine caused a statistically significant 5-fold increase in suicidal

ideation and behavior in persons younger than 25. In another analysis, venlafaxine was no better

than placebo among children (711 years old), but improved depression in adolescents (1217 yea

old). However, in both groups, hostility and suicidal behavior increased in comparison to those

receiving a placebo.[28] In a study involving antidepressants that had failed to produce results in

depressed teenagers, teens whose SSRI treatment had failed who were randomly switched to eith

another SSRI or to venlafaxine showed an increased rate of suicide on venlafaxine. Among

teenagers who were suicidal at the beginning of the study, the rate of suicidal attempts and self-ha

was significantly higher, by about 60%, after the switch to venlafaxine than after the switch to an

SSRI.[29]

NOTE: The percentage of occurrences for each side effect listed comes from clinical trial data

provided by Wyeth Pharmaceuticals Inc. The percentages indicate the percentage of people that

experienced the side effect in clinical trials.

[6]

Headache (34%)

Nausea (21-35%)

Insomnia (15-23%)

Sexual dysfunction (14-34%)

Dry mouth (12-16%)

Dizziness (11-20%)

Sweating (10-14%)

Decreased appetite (8-20%)

Abnormalejaculation (8-16%)

Hypertension (4-5%)Vivid/abnormal dreams (3-7%)

Decreased libido (3-9%)

Increased yawning (3-5%)

Constipation

Fatigue

Vertigo

Anxiety

[eCommon side effects

[eLess common to rare side effects
http://en.wikipedia.org/wiki/Fluoxetinehttp://en.wikipedia.org/wiki/Fluoxetinehttp://en.wikipedia.org/wiki/Citalopramhttp://en.wikipedia.org/wiki/Placebohttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/SSRIhttp://en.wikipedia.org/wiki/Headachehttp://en.wikipedia.org/wiki/Headachehttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Insomniahttp://en.wikipedia.org/wiki/Insomniahttp://en.wikipedia.org/wiki/Sexual_dysfunctionhttp://en.wikipedia.org/wiki/Sexual_dysfunctionhttp://en.wikipedia.org/wiki/Sexual_dysfunctionhttp://en.wikipedia.org/wiki/Dry_mouthhttp://en.wikipedia.org/wiki/Dry_mouthhttp://en.wikipedia.org/wiki/Dizzinesshttp://en.wikipedia.org/wiki/Dizzinesshttp://en.wikipedia.org/wiki/Sweatinghttp://en.wikipedia.org/wiki/Sweatinghttp://en.wikipedia.org/wiki/Appetitehttp://en.wikipedia.org/wiki/Appetitehttp://en.wikipedia.org/wiki/Anorgasmiahttp://en.wikipedia.org/wiki/Anorgasmiahttp://en.wikipedia.org/wiki/Anorgasmiahttp://en.wikipedia.org/wiki/Anorgasmiahttp://en.wikipedia.org/wiki/Anorgasmiahttp://en.wikipedia.org/wiki/Hypertensionhttp://en.wikipedia.org/wiki/Hypertensionhttp://en.wikipedia.org/wiki/Hypertensionhttp://en.wikipedia.org/wiki/Dreamhttp://en.wikipedia.org/wiki/Dreamhttp://en.wikipedia.org/wiki/Libido#Libido_impairmenthttp://en.wikipedia.org/wiki/Libido#Libido_impairmenthttp://en.wikipedia.org/wiki/Libido#Libido_impairmenthttp://en.wikipedia.org/wiki/Libido#Libido_impairmenthttp://en.wikipedia.org/wiki/Libido#Libido_impairmenthttp://en.wikipedia.org/wiki/Yawninghttp://en.wikipedia.org/wiki/Yawninghttp://en.wikipedia.org/wiki/Constipationhttp://en.wikipedia.org/wiki/Constipationhttp://en.wikipedia.org/wiki/Constipationhttp://en.wikipedia.org/wiki/Fatigue_(physical)http://en.wikipedia.org/wiki/Fatigue_(physical)http://en.wikipedia.org/wiki/Vertigo_(medical)http://en.wikipedia.org/wiki/Anxietyhttp://en.wikipedia.org/wiki/Anxietyhttp://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=11http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=12http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=12http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=11http://en.wikipedia.org/wiki/Anxietyhttp://en.wikipedia.org/wiki/Vertigo_(medical)http://en.wikipedia.org/wiki/Fatigue_(physical)http://en.wikipedia.org/wiki/Constipationhttp://en.wikipedia.org/wiki/Yawninghttp://en.wikipedia.org/wiki/Libido#Libido_impairmenthttp://en.wikipedia.org/wiki/Dreamhttp://en.wikipedia.org/wiki/Hypertensionhttp://en.wikipedia.org/wiki/Anorgasmiahttp://en.wikipedia.org/wiki/Appetitehttp://en.wikipedia.org/wiki/Sweatinghttp://en.wikipedia.org/wiki/Dizzinesshttp://en.wikipedia.org/wiki/Dry_mouthhttp://en.wikipedia.org/wiki/Sexual_dysfunctionhttp://en.wikipedia.org/wiki/Insomniahttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Headachehttp://en.wikipedia.org/wiki/SSRIhttp://en.wikipedia.org/wiki/Wikipedia:Citation_neededhttp://en.wikipedia.org/wiki/Placebohttp://en.wikipedia.org/wiki/Citalopramhttp://en.wikipedia.org/wiki/Fluoxetinehttp://en.wikipedia.org/wiki/Fluoxetine


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Note 'Rare' adverse effects occur in fewer than 1 in 1000 patients.

Cardiac arrhythmia

Increased serum cholesterol

Gas or stomach pain

Abnormal vision

Nervousness, agitation or increased anxiety

Panic attacks

Hives

Depressed feelings

Suicidal thoughts

Confusion

Neuroleptic malignant syndrome

Tremor

Drowsiness

Allergic skin reactions

External bleeding

Serious bone marrow damage (thrombocytopenia, agranulocytosis)

Hepatitis

Pancreatitis

Seizure

Tardive dyskinesia

Dysphagia (difficulty swallowing)

Psychosis

Hair loss

Hostility

Activation of mania/hypomania

Weight loss (of concern when treating patients suffering from anorexia nervosa)

Weight gain (effect not clear, but of concern when treating people who may have body

dysmorphic disorder).Homicidal thoughts

Aggression

Depersonalization

Visual hallucinations

Swollen and/or bleeding gums

Frequent urination

A comparison of adverse event rates in a fixed-dose study comparing venlafaxine 75, 225, and

375 mg/day with placebo revealed a dose dependency for some of the more common adverse eveassociated with venlafaxine use. The rule for including events was to enumerate those that occurre

at an incidence of 5% or more for at least one of the venlafaxine groups and for which the inciden

was at least twice the placebo incidence for at least one venlafaxine group. Tests for potential dos

relationships for these events (Cochran-Armitage test, with a criterion of exact 2-sided p-value


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In a study of 70 patients that compared the tolerability of venlafaxine at standard doses, ranging fr

75 to 300 mg, against relatively high doses (rarely prescribed), ranging from 375 to 600 mg per day

for treating DSM-IV major depressive disorder, "failing memory" was reported in 44% of cases. Th

severity of venlafaxine-induced memory loss was also noted to increase with dose and length of

treatment.[30]

Main article:SSRI discontinuation syndrome

In vitro studies revealed venlafaxine has virtually no affinity for opiate, benzodiazepine, or N-methyD-aspartic acid (NMDA) receptors. It has no significant CNS stimulant activity in rodents. In primat

drug discrimination studies, venlafaxine showed no significant stimulant or depressant abuse

liability.[6 ]

Many patients stopping venlafaxine use experience SSRI discontinuation syndrome, i.e. withdrawa

symptoms. This is especially noted if a patient misses a dose, but can also occur when reduction o

dosage is gradual. The high risk of discontinuation syndrome symptoms may reflect venlafaxine's

short half-life.[31 ] Missing even a single dose can induce discontinuation effects in some patients. [

Discontinuation is similar in nature to those of SSRIs such as paroxetine (Paxil or Seroxat). Sudde

discontinuation of venlafaxine particularly seemed to cause discontinuation symptoms during the fir

3 days in a study of 18 patients.[33]

As reported in 2001 by Haddad in the journal Drug Safety,"another strategy to consider is switching to fluoxetine, which may suppress the discontinuation

symptoms, but which has little tendency to cause such symptoms itself," and then discontinuing

that.[31] Some psychiatrists actually prescribe the singular SSRIs to alleviate the symptoms of

venlafaxine withdrawal.

Although many other drugs can cause withdrawal symptoms which are not associated with addictio

or dependence, for example, anticonvulsants, beta-blockers, nitrates, diuretics, centrally acting

antihypertensives, sympathomimetics, heparin, tamoxifen, dopaminergic agents, antipsychotics, an

lithium,[31] addiction or dependence is a more common effect described for drugs that (are though

to, or may) improve mental well-being.[34]

The development of a potentially life-threatening serotonin syndrome (also more recently classified

"serotonin toxicity")[35 ] may occur with venlafaxine treatment, particularly with concomitant use of

serotonergic drugs (including but not limited to SSRI and SNRI)s, many hallucinogens such as

tryptamines and phenethylamines (LSD/LSA, DMT, MDMA, MDPV, mescaline for example),

dextromethorphan (DXM)/dextrorphan (DXO), tramadol, tapentadol, meperidine/pethidine and

triptans) and with drugs that impair metabolism of serotonin (including MAOIs). Serotonin syndrom

symptoms may include mental status changes (e.g., agitation, hallucinations, coma), autonomic

instability (e.g., tachycardia, labile blood pressure, hyperthermia), neuromuscular aberrations (e.g.,

hyperreflexia, incoordination) and/or gastrointestinal symptoms (e.g., nausea, vomiting, diarrhea).

Venlafaxine-induced serotonin syndrome has also been reported when venlafaxine has been takenisolation in overdose. [36] An abortive serotonin syndrome state, in which some but not all of the

symptoms of the full serotonin syndrome are present, has been reported with venlafaxine at mid-

range dosages (150 mg per day)[37] A case of a patient with serotonin syndrome induced by low-

dose venlafaxine (37.5 mg per day) has also been reported. [38]

Venlafaxine may be particularly hazardous to those individuals who are susceptible to both

venlafaxine-induced serotonin toxicity (also known as serotonin syndrome) and SSRI discontinuatio

[eDiscontinuation syndrome

[eSerotonin syndrome

[eCombined serotonin toxicity and SSRI discontinuation syndrome(SSRI withdrawal)
http://en.wikipedia.org/wiki/SSRI_discontinuation_syndromehttp://en.wikipedia.org/wiki/NMDAhttp://en.wikipedia.org/wiki/SSRI_discontinuation_syndromehttp://en.wikipedia.org/wiki/Paroxetinehttp://en.wikipedia.org/wiki/Paxilhttp://en.wikipedia.org/wiki/Seroxathttp://en.wikipedia.org/wiki/Anticonvulsantshttp://en.wikipedia.org/wiki/Beta-blockershttp://en.wikipedia.org/wiki/Diuretichttp://en.wikipedia.org/wiki/Sympathomimetichttp://en.wikipedia.org/wiki/Heparinhttp://en.wikipedia.org/wiki/Tamoxifenhttp://en.wikipedia.org/wiki/Antipsychoticshttp://en.wikipedia.org/wiki/Lithium_pharmacologyhttp://en.wikipedia.org/wiki/Serotonin_syndromehttp://en.wikipedia.org/wiki/Serotonin_syndromehttp://en.wikipedia.org/wiki/SSRIhttp://en.wikipedia.org/wiki/SSRIhttp://en.wikipedia.org/wiki/Serotonin-norepinephrine_reuptake_inhibitorhttp://en.wikipedia.org/wiki/Tryptaminehttp://en.wikipedia.org/wiki/Tryptaminehttp://en.wikipedia.org/wiki/Phenethylaminehttp://en.wikipedia.org/wiki/Phenethylaminehttp://en.wikipedia.org/wiki/Phenethylaminehttp://en.wikipedia.org/wiki/Phenethylaminehttp://en.wikipedia.org/wiki/LSDhttp://en.wikipedia.org/wiki/LSAhttp://en.wikipedia.org/wiki/DMThttp://en.wikipedia.org/wiki/MDMAhttp://en.wikipedia.org/wiki/MDPVhttp://en.wikipedia.org/wiki/MDPVhttp://en.wikipedia.org/wiki/Mescalinehttp://en.wikipedia.org/wiki/Dextromethorphanhttp://en.wikipedia.org/wiki/Dextromethorphanhttp://en.wikipedia.org/wiki/Dextromethorphanhttp://en.wikipedia.org/wiki/Dextromethorphanhttp://en.wikipedia.org/wiki/Dextromethorphanhttp://en.wikipedia.org/wiki/Dextrorphanhttp://en.wikipedia.org/wiki/Tramadolhttp://en.wikipedia.org/wiki/Tramadolhttp://en.wikipedia.org/wiki/Tramadolhttp://en.wikipedia.org/wiki/Tapentadolhttp://en.wikipedia.org/wiki/Tapentadolhttp://en.wikipedia.org/wiki/Tapentadolhttp://en.wikipedia.org/wiki/Meperidinehttp://en.wikipedia.org/wiki/Meperidinehttp://en.wikipedia.org/wiki/Triptanhttp://en.wikipedia.org/wiki/MAOIhttp://en.wikipedia.org/wiki/SSRI_discontinuation_syndromehttp://en.wikipedia.org/wiki/SSRI_discontinuation_syndromehttp://en.wikipedia.org/wiki/SSRI_discontinuation_syndromehttp://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=15http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=16http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=17http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=17http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=16http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=15http://en.wikipedia.org/wiki/SSRI_discontinuation_syndromehttp://en.wikipedia.org/wiki/MAOIhttp://en.wikipedia.org/wiki/Triptanhttp://en.wikipedia.org/wiki/Meperidinehttp://en.wikipedia.org/wiki/Tapentadolhttp://en.wikipedia.org/wiki/Tramadolhttp://en.wikipedia.org/wiki/Dextrorphanhttp://en.wikipedia.org/wiki/Dextromethorphanhttp://en.wikipedia.org/wiki/Mescalinehttp://en.wikipedia.org/wiki/MDPVhttp://en.wikipedia.org/wiki/MDMAhttp://en.wikipedia.org/wiki/DMThttp://en.wikipedia.org/wiki/LSAhttp://en.wikipedia.org/wiki/LSDhttp://en.wikipedia.org/wiki/Phenethylaminehttp://en.wikipedia.org/wiki/Tryptaminehttp://en.wikipedia.org/wiki/Serotonin-norepinephrine_reuptake_inhibitorhttp://en.wikipedia.org/wiki/SSRIhttp://en.wikipedia.org/wiki/Serotonin_syndromehttp://en.wikipedia.org/wiki/Lithium_pharmacologyhttp://en.wikipedia.org/wiki/Antipsychoticshttp://en.wikipedia.org/wiki/Tamoxifenhttp://en.wikipedia.org/wiki/Heparinhttp://en.wikipedia.org/wiki/Sympathomimetichttp://en.wikipedia.org/wiki/Diuretichttp://en.wikipedia.org/wiki/Beta-blockershttp://en.wikipedia.org/wiki/Anticonvulsantshttp://en.wikipedia.org/wiki/Seroxathttp://en.wikipedia.org/wiki/Paxilhttp://en.wikipedia.org/wiki/Paroxetinehttp://en.wikipedia.org/wiki/SSRI_discontinuation_syndromehttp://en.wikipedia.org/wiki/NMDAhttp://en.wikipedia.org/wiki/SSRI_discontinuation_syndrome


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syndrome. In such cases, individuals who have developed the potentially fatal serotonin toxicity

and/or may be at risk of doing so, may find cessation or dose reduction unachievable, placing them

continuing risk. As it is not possible to determine which patients are likely to develop the most seve

symptoms of the discontinuation syndrome before cessation or dose reduction is attempted, this du

risk requires that all patients are closely monitored during any increase in dosage (when the patien

is most at risk of developing serotonin toxicity) [39 ] and that such increases are carried out in the

smallest incremental steps possible. Additionally, patients who recommence venlafaxine or revert t

higher dosage following a failed attempt to discontinue the drug or reduce dosage are another gro

with an increased risk of developing serotonin toxicity.

[34]

Effexor is distributed in pentagon-shaped, peach-colored tablets of

25 mg, 37.5 mg, 50 mg, 75 mg, and 100 mg. There is also an

extended-release version distributed in capsules of 37.5 mg

(gray/peach), 75 mg (peach), and 150 mg (brownish red).

Venlafaxine extended release is chemically the same as normal

venlafaxine. The extended release version (sometimes referred to as

controlled release and made on spheronization equipment from Caleva

Process Solutions) controls the release of the drug into the

gastrointestinal tract over a longer period than normal venlafaxine. This

results in a lower peak plasma concentration. Studies have shown that

the extended release formula has a lower incidence of patients

suffering from nausea as a side effect, resulting in a lower number of

patients stopping their treatment due to nausea.[40] In Australia, New

Zealand and Switzerland, Wyeth sells their venlafaxine XR tablets

under the name "Efexor-XR" (note the spelling with one 'f', rather than

"Effexor-XR"). In Brazil, Medley sells a venlafaxine XR capsule under

the brand name Alenthus XR. In September 2008, OsmoticaPharmaceuticals began marketing venlafaxine extended release tablets

in the United States to compete with Wyeth's capsule-form, Effexor-

XR. Sales of branded Efexor XR have remained strong, at

US$2.7bn.[41] Teva may begin to offer generic Effexor XR in the US

on July 1, 2010, per a settlement agreement with Wyeth, but will have

to pay Wyeth a portion of the sale price, driving up the cost.[42] Impax may begin to offer generic

Effexor XR in the US on July 1, 2011, per a settlement agreement with Wyeth, but, like Teva, will

have to pay Wyeth a portion of the sale price. [43 ]

Generic venlafaxine is available in the UnitedStates as of August 2006 and in Canada as of

December 2006 due to patent expiry. Generic forms of the extended-release version have been

available in Canada as of January 2007 and currently include Co Venlafaxine XR (Cobalt

Pharmaceuticals Inc.), Gen-Venlafaxine XR (Genpharm), Riva-Venlafaxine XR (Laboratoire Riva

Inc.), Novo Venlafaxine XR (Novopharm Limited), PMS-Venlafaxine XR (Pharmascience Inc.), Rati

Venlafaxine XR (ratiopharm), Viepax (in Israel) and Sandoz Venlafaxine XR (Sandoz Canada Inc.)

Generic versions of both drug forms are available now in India. Generic versions are also available

the UK such as Vaxalin manufactured by RatioPharm GmbH. [44 ] On May 7, 2010 the Canadian

pharmaceutical company IntelliPharmaCeutics Inc. announced that the FDA had accepted its filing

a generic version of Venlafaxine XR utilizing its own proprietary technologies. [45 ]

[eAvailable forms

Effexor XR 75 mg and

150 mg capsules

Generic 75mg (top) and

150mg (bottom) venlafaxin

capsules by Krka

[edit]Venlafaxine extended release (XR)

[eGeneric
http://en.wikipedia.org/wiki/SSRI_discontinuation_syndromehttp://en.wikipedia.org/wiki/Gastrointestinal_tracthttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Wyethhttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=18http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=19http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=20http://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=19http://en.wikipedia.org/wiki/File:Venlafaxin_Krka.jpghttp://en.wikipedia.org/wiki/File:EffexorXR_75and150mg.pnghttp://en.wikipedia.org/w/index.php?title=Venlafaxine&action=edit&section=18http://en.wikipedia.org/wiki/United_Stateshttp://en.wikipedia.org/wiki/Wyethhttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Nauseahttp://en.wikipedia.org/wiki/Gastrointestinal_tracthttp://en.wikipedia.org/wiki/SSRI_discontinuation_syndrome


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Most patients overdosing with venlafaxine develop only mild symptoms. However, severe toxicity is

reported, with the most common symptoms being CNS depression, serotonin toxicity, seizure, or

cardiac conduction abnormalities.[46] Venlafaxine's toxicity appears to be higher than other SSRIs,

with a fatal toxic dose closer to that of the tricyclic antidepressants than the SSRIs. Doses of 900 m

or more are likely to cause moderate toxicity. [47] Deaths have been reported following very large

doses.[48][49] Plasma venlafaxine concentrations in overdose survivors have ranged from 624 mg

while postmortem blood levels in fatalities are often in the 1090 mg/l range. [50]

On May 31, 2006, The Medicinesand Healthcare Products Regulatory Agency (MHRA) UK has

concluded its review into all the latest safety evidence relating to venlafaxine, and particularly looke

at the risks associated with overdose. The advice is: the need for specialist supervision in those

severely depressed or hospitalized patients who need doses 300 mg or more; cardiac

contraindications are more targeted towards high risk groups; patients with uncontrolled hypertensi

should not take venlafaxine, and blood pressure monitoring is recommended for all patients; and

updated advice on possible drug interactions. [51]

On 17 October 2006, Wyeth and the FDA notified healthcare professionals of revisions to the

Overdosage/Human Experience section of the prescribing information for Effexor (venlafaxine),

indicated for treatment of major depressive disorder. In postmarketing experience, there have been

reports of overdose with venlafaxine, occurring predominantly in combination with alcohol and/or

other drugs. Published retrospective studies report that venlafaxine overdosage may be associated

with an increased risk of fatal outcome compared to that observed with SSRI antidepressant

products, but lower than that for tricyclic antidepressants. Healthcare professionals are advised to

prescribe Effexor and Effexor XR in the smallest quantity of capsules consistent with good patient

management to reduce the risk of overdose. [52]

A report in the British Medical Journal in 2002 by Dr. Nicholas Buckley and colleagues at the

Department of Clinical Pharmacology and Toxicology, Canberra Hospital, Australia studying fatal

toxicity index (deaths per million prescriptions), found that venlafaxine's fatal toxicity is higher than

that of other serotoninergic antidepressants, but it is similar to that of some of the less toxic tricycliantidepressants. Overall, they found serious toxicity could occur following venlafaxine overdose wit

reports of deaths, arrythmias, and seizures. They did, however, state that this type of data is open

criticism, pointing out that mortality data may be influenced by previous literature and that "less tox

drugs may be preferentially prescribed to patients at higher risk of poisoning and suicide, but they

also less likely to be listed as the sole cause of death from overdose. It also assumes that drugs a

taken in overdose with similar frequency and in similar amounts. They suggested "clinicians need t

consider whether factors in their patients reduce or compensate for this risk before prescribing

venlafaxine."[53]

The 27 February 2007 Vancouver Sun reported the BC Drug and Poison Information Centre has

alerted doctors that the drug poses a significant risk of death from overdose, saying that venlafaxin

"appears more toxic than it was originally hoped". [54] A doctor from the Department of Pharmacy

Services College of Pharmacy, Medical University of South Carolina, Charleston, South Carolina,

reported on the death of a 39-year-old patient with a 30 g overdose. [48] To put this into perspecti

a patient would have to take over 66 of the infrequently prescribed 450 mg high dosage pills, or 4

of the commonly prescribed 75 mg pills.

There is no specific antidote for venlafaxine, and management is generally supportive, providing

treatment for the immediate symptoms. Administration of activatedcharcoal can prevent absorption

the drug. Monitoring of cardiac rhythm and vital signs is indicated. Seizures are managed with

[eOverdose

[eManagement of overdose
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benzodiazepines or other anticonvulsants. Forced diuresis, hemodialysis, exchange transfusion, or

hemoperfusion are unlikely to be of benefit in hastening the removal of venlafaxine, due to the dru

high volume ofdistribution.[55]

Venlafaxine is a bicyclic antidepressant, and is usually categorized as a serotonin-norepinephrine

reuptake inhibitor (SNRI), but it has been referred to as a serotonin-norepinephrine-dopamine

reuptake inhibitor (SNDRI).[56][57] It works by blocking the transporter "reuptake" proteins for key

neurotransmitters affecting mood, thereby leaving more active neurotransmitters in the synapse. T

neurotransmitters affected are serotonin and norepinephrine. Additionally, in high doses it weakly

inhibits the reuptake of dopamine,[58 ] with recent evidence showing that the norepinephrine

transporter also transports some dopamine as well, implying that SNRIs may also increase dopam

transmission. This is because SNRIs work by inhibiting reuptake, i.e. preventing the serotonin and

norepinephrine transporters from taking their respective neurotransmitters back to their storage

vesicles for later use. If the norepinephrine transporter normally recycles some dopamine too, then

SNRIs will also enhance dopaminergic transmission. However, while concurrent increase in dopam

(particularly in the prefrontal cortex) is likely to occur,[59 ] the antidepressant effects of any drug ar

believed to result largely from the modulation of serotonin and norepinephrine; dopamine is though

play a comparatively small role in depression.[60]

Venlafaxine is well absorbed, with at least 92% of an oral dose being absorbed into systemic

circulation. It is extensively metabolized in the liver via the CYP2D6isoenzyme to desvenlafaxine

desmethylvenlafaxine), which is just as potent a serotonin-norepinephrine reuptake inhibitor as the

parent compound, meaning that the differences in metabolism between extensive and poor

metabolizers are not clinically important in terms of efficacy. Side effects, however, are reported to

more severe in CYP2D6 poor metabolizers.[61] Steady-state concentrations of venlafaxine and its

metabolite are attained in the blood within 3 days. Therapeutic effects are usually achieved within

to 4 weeks. No accumulation of venlafaxine has been observed during chronic administration in

healthy subjects. The primary route of excretion of venlafaxine and its metabolites is via the

kidneys.[6] The half-life of venlafaxine is relatively short, and, therefore, patients are directed to

adhere to a strict medication routine, avoiding missing a dose. Even a single missed dose can res

in the withdrawal symptoms.[32]

Carriers of the (T;T) allele of rs2032583 [62] SNP in the ABCB1 gene are seven times less likely to

respond to venlafaxine treatment. This genetic variant is present in about two-thirds of people of

European descent and 80% to 90% of East Asians.

Venlafaxine should be taken with caution when using St John's wort.

[63 ]

Venlafaxine may lower thseizure threshold, and coadministration with other drugs that lower the seizure threshold such as

bupropion and tramadol should be done with caution and at low doses.[64 ]

There have been false positive phencyclidine (PCP) results caused by venlafaxine, with certain on

site routine urine-based drug tests.[65][66]

Although the synergistic effects may not be as bad as with other antidepressants, it is still not

recommended to take venlafaxine with alcohol.[67]

[eMechanism of action

[ePharmacokinetics

[eDrug interactions

[ePhysical/chemical properties
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The chemical structure of venlafaxine is designated (R/S)-1- [2-(dimethylamino)-1- (4

methoxyphenyl)ethyl] cyclohexanol hydrochloride or ()-1-[a [a- (dimethylamino)methyl] p-

methoxybenzyl] cyclohexanol hydrochloride, and it has the empirical formula of C17H27NO2. It is a

white to off-white crystalline solid. Venlafaxine is structurally and pharmacologically related to the

atypical opioid analgesictramadol, and more distantly the newly-released opioid tapentadol, but no

to any of the conventional antidepressant drugs, including tricyclic antidepressants, SSRIs, MAOIs

RIMAs.[47]

Desvenlafaxine

Tramadol

Notes

1. ^ abcLaurence L Brunton, ed (2006).

Goodman & Gilman's The Pharmacological

Basis of Therapeutics(11th ed.). New York:

McGraw-Hill Medical Publishing Division.

ISBN0-07-142280-3.2. ^ Muth EA, Haskins JT, Moyer JA, Husbands

GE, Nielsen ST, Sigg EB (December 1986).

"Antidepressant biochemical profile of the novel

bicyclic compound Wy-45,030, an ethyl

cyclohexanol derivative" . Biochemical

Pharmacology35 (24): 44937.

doi:10.1016/0006-2952(86)90769-0 .

PMID3790168 .

3. ^ Yardley JP, Husbands GE, Stack G, et al.

(October 1990). "2-Phenyl-2-(1-

hydroxycycloalkyl)ethylamine derivatives:

synthesis and antidepressant activity". Journal

of Medicinal Chemistry33 (10): 2899905.

doi:10.1021/jm00172a035 .

PMID1976813 .

4. ^ Bymaster FP, Dreshfield-Ahmad LJ,

Threlkeld PG, et al. (December 2001).

"Comparative affinity of duloxetine and

venlafaxine for serotonin and norepinephrine

transporters in vitro and in vivo, human

serotonin receptor subtypes, and other

neuronal receptors".

Neuropsychopharmacology : Official Publicationof the American College of

Neuropsychopharmacology25 (6): 87180.

doi:10.1016/S0893-133X(01)00298-6 .

PMID11750180 .

5. ^ The number of prescriptions was calculated

as the total of prescriptions for the

corresponding generic and brand-name drugs

using data from the charts for generic and

brand-name drugs. "Top 200 generic drugs by

unitsin 2007." . Drug Topics, Feb 18, 2008.

Retrieved 2008-10-23. "Top 200 brand drugs

PMID17420682 .

29. ^ Brent DA, Emslie GJ, Clarke GN, et al. (A

2009). "Predictors of spontaneous and

systematically assessed suicidal adverse

events in the treatment of SSRI-resistantdepression in adolescents (TORDIA) study"

Am J Psychiatry166 (4): 41826.

doi:10.1176/appi.ajp.2008.08070976 .

PMID19223438 .

30. ^ Harrison CL, Ferrier N, Young AH (June

2004). "Tolerability of high-dose venlafaxine

depressed patients". J. Psychopharmacol.

(Oxford)18 (2): 2004.

doi:10.1177/0269881104042621 .

PMID15260908 .

31. ^ abcHaddad PM (2001). "Antidepressant

discontinuation syndromes". Drug Saf24 (3

18397. doi:10.2165/00002018-200124030

00003 . PMID11347722 .

32. ^ abParker G, Blennerhassett J (1998).

"Withdrawal reactions associated with

venlafaxine". Aust N Z J Psychiatry32 (2): 2

4. doi:10.3109/00048679809062742 .

PMID9588310 .

33. ^ Fava M, Mulroy R, Alpert J, Nierenberg A,

Rosenbaum J (1997). "Emergence of advers

events following discontinuation of treatmen

with extended-release venlafaxine". Am JPsychiatry154 (12): 17602. PMID9396960

34. ^ abDouble D (1997). "Prescribing

antidepressants in general practice. People

may become psychologically dependent on

antidepressants" . BMJ314 (7083): 829.

PMID9081020 .

35. ^ Dunkley EJ, Isbister GK, Sibbritt D, Dawso

AH, Whyte IM (September 2003). "The Hunt

Serotonin Toxicity Criteria: simple and accur

diagnostic decision rules for serotonin

[eSee also

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