Wikipedia

Venlafaxine

Venlafaxine,sold under the brand nameEffexoramong others, is anantidepressantmedication of theserotonin–norepinephrine reuptake inhibitor(SNRI) class.[6][9]It is used to treatmajor depressive disorder,generalized anxiety disorder,panic disorder,andsocial anxiety disorder.[9]Studies have shown that venlafaxine improvespost-traumatic stress disorder(PTSD).[10]It may also be used forchronic neuropathic pain.[11]It is takenorally(swallowed by mouth).[9]It is also available as the salt venlafaxine besylate (venlafaxinebenzenesulfonatemonohydrate) in an extended-release formulation (Venbysi XR).[7]

Venlafaxine
Clinical data
Pronunciation/ˌvɛnləˈfæksiːn/
VEN-lə-FAK-seen
Trade namesEffexor, Efexor, Venbysi XR, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa694020
License data
Pregnancy
category
Routes of
administration		Oral
Drug classSerotonin–norepinephrine reuptake inhibitor
ATC code
Legal status
Legal status
Pharmacokineticdata
Bioavailability42±15%[2]
Protein binding27±2% (parent compound), 30±12% (active metabolite,desvenlafaxine)[6]
MetabolismExtensively metabolised by theliver,[2][6]primarily viaCYP2D6[8]
MetabolitesO-desmethylvenlafaxine (ODV), seedesvenlafaxine
Eliminationhalf-life5±2 h (parent compound for immediate release preparations), 15±6 h (parent compound for extended release preparations), 11±2 h (active metabolite)[2][6]
ExcretionKidney(87%; 5% as unchanged drug; 29% asdesvenlafaxineand 53% as other metabolites)[2][6]
Identifiers
  • (RS)-1-[2-dimethylamino-1-(4-methoxyphenyl)-ethyl]cyclohexanol
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.122.418Edit this at Wikidata
Chemical and physical data
FormulaC17H27NO2
Molar mass277.408g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • OC2(C(c1ccc(OC)cc1)CN(C)C)CCCCC2
  • 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,4-6,11-13H2,1-3H3checkY
  • Key:PNVNVHUZROJLTJ-UHFFFAOYSA-NcheckY
(verify)

Common side effects include loss of appetite, constipation,dry mouth,dizziness, sweating, insomnia, drowsiness and sexual problems.[9]Severe side effects include an increased risk ofsuicide,mania,andserotonin syndrome.[9]Antidepressant withdrawal syndromemay occur if stopped.[9]There are concerns that use during the later part ofpregnancycan harm the baby.[9]How it works is not entirely clear, but it seems to be related to the potentiation of the activity of some neurotransmitters in the brain.[9]

Venlafaxine was approved for medical use in the United States in 1993.[9]It is available as ageneric medication.[9]In 2022, it was the 44th most commonly prescribed medication in the United States, with more than 13million prescriptions.[12][13]

Medical uses

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Venlafaxine is used primarily for the treatment ofdepression,general anxiety disorder,social phobia,panic disorder,andvasomotor symptoms.[14]

Venlafaxine has been usedoff labelfor the treatment ofdiabetic neuropathy[15]andmigraineprevention.[16]It may work on pain via effects on the opioid receptor.[17]It has also been found to reduce the severity of 'hot flashes' inmenopausalwomen and men on hormonal therapy for the treatment of prostate cancer.[18][19]

Due to its action on both theserotoninergicandadrenergicsystems, venlafaxine is also used as a treatment to reduce episodes ofcataplexy,a form of muscle weakness, in patients with thesleep disordernarcolepsy.[20]Some open-label and three double-blind studies have suggested the efficacy of venlafaxine in the treatment ofattention deficit-hyperactivity disorder(ADHD).[21]Clinical trials have found possible efficacy in those withpost-traumatic stress disorder(PTSD).[22]Case reports, open trials and blinded comparisons with established medications have suggested the efficacy of venlafaxine in the treatment ofobsessive–compulsive disorder.[23]

Depression

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A comparative meta-analysis of 21 major antidepressants found that venlafaxine,agomelatine,amitriptyline,escitalopram,mirtazapine,paroxetine,andvortioxetinewere more effective than other antidepressants, although the quality of many comparisons was assessed as low or very low.[24][25]

Venlafaxine was similar in efficacy to the atypical antidepressantbupropion;however, the remission rate was lower for venlafaxine.[26]In a double-blind study, patients who did not respond to an SSRI were switched to either venlafaxine or another SSRI (citalopram); similar improvement was observed in both groups.[27]

Studies have not established its efficacy for use by children.[28]In children and adolescents with depression, venlafaxine increases the risk of suicidal thoughts or attempts.[29][30][31][32][33][34]

Higher doses (e.g. 225 mg and 375 mg per day) of venlafaxine are more effective than lower doses (e.g. 75 mg per day), but also cause more side effects.[35]

Studies have shown that the extended release is superior to the immediate release form of venlafaxine.[36]

A meta-analysis has shown that efficacy of venlafaxine is not correlated with baseline severity of depression.[36]In other words, regardless of how severe a person's depression is initially, the efficacy of venlafaxine remains consistent and is not influenced by the severity of depression at the start of treatment.

Contraindications

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Venlafaxine is not recommended in patientshypersensitiveto it, nor should it be taken by anyone who is allergic to the inactive ingredients, which includegelatin,cellulose,ethylcellulose,iron oxide,titanium dioxideandhypromellose.It should not be used in conjunction with amonoamine oxidase inhibitor(MAOI), as it can cause potentially fatal serotonin syndrome.[2][6][37]Venlafaxine might interact withtramadolor other opioids, as well astrazodone,so caution is needed while mixing multipleserotonergicagents together.[38]

Adverse effects

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See also:List of adverse effects of venlafaxine

Venlafaxine can increase eye pressure, so those withglaucomamay require more frequent eye checks.[6]

A 2017 meta-analysis estimated venlafaxine discontinuation rate due to adverse effects to be 9.4%.[36]

Suicide

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The USFood and Drug Administration(FDA) requires all antidepressants, including venlafaxine, to carry ablack box warningwith a generic warning about a possible suicide risk.[citation needed]

A 2014 meta analysis of 21 clinical trials of venlafaxine for the treatment of depression in adults found that compared to placebo, venlafaxine reduced the risk of suicidal thoughts and behavior.[39]

A study conducted in Finland followed more than 15,000 patients for 3.4 years. Venlafaxine increased suicide risk by 60% (statistically significant), as compared to no treatment. At the same time,fluoxetine(Prozac) halved the suicide risk.[40]

In a study sponsored byWyeth,which produces and markets venlafaxine, the data on more than 200,000 cases were obtained from the UK general practice research database. At baseline, patients prescribed venlafaxine had a greater number of risk factors for suicide (such as prior suicide attempts) than patients treated with other anti-depressants. The patients taking venlafaxine had significantly higher risk of suicide than the ones onfluoxetineorcitalopram(Celexa). After adjusting for known risk factors, venlafaxine was associated with an increased risk of suicide relative to fluoxetine anddothiepinthat was not statistically significant. A statistically significant greater risk for attempted suicide remained after adjustment, but the authors concluded that it could be due to residual confounding.[41]

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 orplacebo.[42]

Venlafaxine is contraindicated in children, adolescents and young adults. In children and adolescents with depression, venlafaxine increases the risk of suicidal thoughts or attempts.[29][30][31][32][33][34]

Serotonin syndrome

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The development of a potentially life-threateningserotonin syndrome(also classified as "serotonin toxicity" )[43]may occur with venlafaxine treatment, particularly with concomitant use of serotonergic drugs, including but not limited toSSRIsandSNRIs,many hallucinogens such astryptaminesandphenethylamines(e.g.,LSD/LSA,DMT,MDMA,mescaline),dextromethorphan(DXM),tramadol,tapentadol,pethidine(meperidine) andtriptansand with drugs that impair metabolism of serotonin (includingMAOIs).[citation needed]Serotonin syndrome 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), or gastrointestinal symptoms (e.g. nausea, vomiting, diarrhea). Venlafaxine-induced serotonin syndrome has also been reported when venlafaxine has been taken in isolation in overdose.[44]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).[45]A case of a patient with serotonin syndrome induced by low-dose venlafaxine (37.5 mg per day) has also been reported.[46]

Pregnancy

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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 ofmiscarriage.[47][48]Consequently, venlafaxine should only be used during pregnancy if clearly needed.[6]A large case-control study done as part of the National Birth Defects Prevention Study and published in 2012 found a significant association of venlafaxine use during pregnancy and several birth defects including anencephaly, cleft palate, septal heart defects and coarctation of the aorta.[49]Prospective studies have not shown any statistically significantcongenital malformations.[50]There have, however, been some reports of self-limiting effects on newborn infants.[51]As with otherserotonin reuptake inhibitors(SRIs), these effects are generally short-lived, lasting only 3 to 5 days,[52]and rarely resulting in severe complications.[53]

Bipolar disorder

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According to theISBDTask Force report on antidepressant use in bipolar disorder,[54]during the course of treatment for depression with those suffering from bipolar I and II, venlafaxine "appears to carry a particularly high risk of inducing pathologically elevated states of mood and behavior." Because venlafaxine appears to be more likely thanSSRIsandbupropionto induce mania and mixed episodes in these patients, provider discretion is advised through "carefully evaluating individual clinical cases and circumstances."

Liver injury

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A rare but serious side effect of venlafaxine is liver injury. It appears to affect both male and female patients with a median age of 44. Cessation of venlafaxine is one of the appropriate measures of management. While the mechanism of venlafaxine-related liver injury remains unclear, findings suggest that it may be related to a CYP2D6 polymorphism.[55]

Overdose

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Most patients overdosing with venlafaxine develop only mild symptoms. Plasma venlafaxine concentrations in overdose survivors have ranged from 6 to 24 mg/L, while postmortem blood levels in fatalities are often in the 10–90 mg/L range.[56]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.[57]It is usually reserved as a second-line treatment for depression due to a combination of its superior efficacy to the first-line treatments like fluoxetine, paroxetine and citalopram and greater frequency of side effects like nausea, headache, insomnia, drowsiness, dry mouth, constipation, sexual dysfunction, sweating and nervousness.[24][58]

There is no specificantidotefor venlafaxine, and management is generally supportive, providing treatment for the immediate symptoms. Administration ofactivated charcoalcan prevent absorption of the drug. Monitoring of cardiac rhythm and vital signs is indicated. Seizures are managed withbenzodiazepinesor other anticonvulsants.Forced diuresis,hemodialysis,exchange transfusion,orhemoperfusionare unlikely to be of benefit in hastening the removal of venlafaxine, due to the drug's highvolume of distribution.[59]

Withdrawal syndrome

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Main article:Antidepressant withdrawal syndrome

People stopping venlafaxine commonly experienceSSRI withdrawal symptomssuch asdysphoria,headaches,nausea,irritability,emotional lability,sensation of electric shocks (commonly called "brain zaps"[60][61]), andsleep disturbance.[62]Venlafaxine has a higher rate of moderate to severe withdrawal symptoms relative to other antidepressants (similar to the SSRIparoxetine).[63]

The higher risk and increased severity of withdrawal symptoms relative to other antidepressants may be related to the shorthalf-lifeof venlafaxine and its active metabolite.[64]After stopping venlafaxine, the levels of both serotonin andnorepinephrinedecrease, leading to the hypothesis that the withdrawal symptoms could result from an overly rapid reduction of neurotransmitter levels.[65]

Other

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In rare cases, drug-inducedakathisiacan occur after use in some people.[66]

Venlafaxine should be used with caution inhypertensivepatients. Venlafaxine must be discontinued if significanthypertensionpersists.[67][68][69]It can also have undesirable cardiovascular effects.[70]

Pharmacology

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Transporter Ki[nM][71] IC50[nM][72]
SERT 82 27
NET 2480 535
DAT 7647 ND
Receptor Ki[nM][71][73] Species
5-HT2A 2230 Human
5-HT2C 2004 Human
5-HT6 2792 Human
α1A >1000 Human

Pharmacodynamics

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Venlafaxine is usually categorized as aserotonin-norepinephrine reuptake inhibitor(SNRI), but it has also been referred to as aserotonin-norepinephrine-dopamine reuptake inhibitor(SNDRI).[74][75]It is described as 'synthetic phenethylamine bicyclic derivative with antidepressant activity'.[76][77]It works by blocking thetransporter "reuptake" proteinsfor keyneurotransmittersaffecting mood, thereby leaving more active neurotransmitters in thesynapse.The neurotransmitters affected areserotoninandnorepinephrine.Additionally, in high doses it weakly inhibits the reuptake ofdopamine.[78]The frontal cortex largely lacks dopamine transporters; therefore venlafaxine can increase dopamine neurotransmission in this part of the brain.[79][80]

Venlafaxine selectively inhibits the serotonin transporter at lower doses, but at a dose of 225 mg per day it additionally blocks the norepinephrine transporter (NET), as measured by the intravenous tyramine pressor test.[81]

Venlafaxine indirectly affectsopioid receptorsas well as the α2-adrenergic receptor, and was shown to increase pain threshold in mice. These benefits with respect to pain were reversed withnaloxone,an opioid antagonist, thus supporting an opioid mechanism.[82][83]

Pharmacokinetics

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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 theCYP2D6isoenzymetodesvenlafaxine(O-desmethylvenlafaxine, now marketed as a separate medication named Pristiq[84]), which is just as potent an SNRI as the parent compound, meaning that the differences in metabolism between extensive andpoor metabolisersare not clinically important in terms of efficacy. Side effects, however, are reported to be more severe inCYP2D6poor metabolisers.[85][86]Steady-state concentrations of venlafaxine and itsmetaboliteare attained in thebloodwithin 3 days. Therapeutic effects are usually achieved within 3 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 thekidneys.[6]Thehalf-lifeof venlafaxine is relatively short, so patients are directed to adhere to a strict medication routine, avoiding missing a dose. Even a single missed dose can result in withdrawal symptoms.[87]

Venlafaxine is a substrate ofP-glycoprotein(P-gp), which pumps it out of the brain. The gene encoding P-gp, ABCB1, has theSNPrs2032583, withallelesC and T. The majority of people (about 70% of Europeans and 90% of East Asians) have the TT variant.[88][unreliable source?]A 2007 study[89]found that carriers of at least one C allele (variant CC or CT) are 7.72 times more likely than non-carriers to achieveremissionafter 4 weeks of treatment withamitriptyline,citalopram,paroxetineor venlafaxine (all P-gp substrates). The study included patients withmood disordersother thanmajor depression,such asbipolar II;the ratio is 9.4 if these other disorders are excluded. At the 6-week mark, 75% of C-carriers had remitted, compared to only 38% of non-carriers.[citation needed]

Chemistry

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TheIUPAC nameof venlafaxine is 1-[2-(dimethylamino)-1-(4 methoxyphenyl)ethyl]cyclohexanol, though it is sometimes referred to as (±)-1-[a-[a-(dimethylamino)methyl]-p-methoxybenzyl]cyclohexanol. It consists of twoenantiomerspresent in equal quantities (termed aracemic mixture), both of which have theempirical formulaof C17H27NO2.It is usually sold as a mixture of the respectivehydrochloridesalts,(R/S)-1-[2-(dimethylamino)-1-(4 methoxyphenyl)ethyl]cyclohexanol hydrochloride, C17H28ClNO2,which is a white to off-white crystalline solid. Venlafaxine is structurally and pharmacologically related to the atypical opioidanalgesictramadol,and more distantly to the newly released opioidtapentadol,but not to any of the conventional antidepressant drugs, includingtricyclic antidepressants,SSRIs,MAOIs, orRIMAs.[90]

Venlafaxine extended release is chemically the same as normal venlafaxine. The extended release (controlled release) version distributes the release of the drug into thegastrointestinal tractover 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 ofnauseaas a side effect, resulting in better compliance.[91]

Interactions

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Venlafaxine should be taken with caution when usingSt John's wort.[92]Venlafaxine may lower the seizure threshold, and coadministration with other drugs that lower the seizure threshold such asbupropionandtramadolshould be done with caution and at low doses.[93]

Society and culture

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Recreational use

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Venlafaxine can be abused as a recreational drug, with damages that can manifest within a month.[94]Hard data regarding the prevalence of abuse are not easy to find. Abusers reported usage of extremely high doses, 5 to 10 times the acceptable clinical doses. The adverse side effects were strong cases of the listed side effects. As a standard measure, treatment is to be supervised by a doctor with relevant education, such as a neurologist or psychiatrist.

Brand names

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Effexor XR 75 mg and 150 mg capsules
Generic 75mg (top) and 150mg (bottom) venlafaxine capsules by Krka

Venlafaxine was originally marketed as Effexor in most of the world; generic venlafaxine has been available since around 2008 and extended release venlafaxine has been available since around 2010.[95]

As of January 2020, venlafaxine is marketed under many brand names worldwide, many with alternative extended release forms (not shown): Adefaxin, Alenthus, Altven, Alventa, Amfax, Anapresin, Ansifix, Arafaxina, Argofan, Arrow Venlafaxine, Axone, Axyven, Benolaxe, Blossom, Calmdown, Dalium, Defaxine, Depefex, Depretaxer, Deprevix, Deprexor, Deprixol, Depurol, Desinax, Dislaven, Dobupal, Duofaxin, Easyfor, Ectien, Eduxon, Efastad, Efaxin, Efaxine, Efectin, Efegen, Efevelon, Efevelone, Efexiva, Efexor, Effegad, Effexine, Effexor, Elafax, Elaxine, Elify, Enpress, Enlafax, Envelaf, Falven, Faxigen, Faxine, Faxiprol, Faxiven, Faxolet, Flavix, Flaxen, Fobiless, Ganavax, Idixor, Idoxen, Intefred, Illovex, Lafactin, Lafaxin, Lanvexin, Laroxin, Levest, Limbic, Linexel, Maxibral, Mazda, Melocin, Memomax, Mezine, Neoxacina, Neoxacina, Nervix, Norafexine, Norezor, Norpilen, Noviser, Nulev, Odiven, Olwexya, Oriven, Paxifar, Politid, Pracet, Prefaxine, Psiseven, Quilarex, Rafax, Senexon, Sentidol, Sentosa, Serosmine, Seroxine, Sesaren, Subelan, Sulinex, Sunveniz, Sunvex, Symfaxin, Tedema, Tifaxin, Tonpular, Trevilor, Tudor, Vafexin, Valosine, Vandral, Velaf, Velafax, Velahibin, Velaxin, Velaxor, Velept, Velpine, Venax, Venaxin, Venaxx, Vencarm, Vencontrol, Vendep, Venegis, Venex, Venexor, Venfalex, Venfax, Ven-Fax, Venfaxine, Venforin, Venforspine, Veniba, Veniz, Venjoy, Venla, Venlabax, Venlablue, Venlabrain, Venladep, Venladex, Venladoz, Venlaf, Venlafab, Venlafaxin, Venlafaxina, Venlafaxine, Venlagamma, Venlalic, Venlamax, Venlamylan, Venlaneo, Venlapine, Venla-Q, Venlasand, Venlatrin, Venlavitae, Venlax, Venlaxin, Venlaxine, Venlaxor, Venlazid, Venlectine, Venlifax, Venlift, Venlix, Venlobax, Venlofex, Venlor, Venorion, Venozap, Vensate, Ventab, Venxin, Venxor, Vextor, Venzip, Vexamode, Vfax, Viepax, ViePax, Voxafen, Zacalen, Zanfexa, Zaredrop, Zarelis, Zarelix, and Zenexor.[1]

In some countries, Effexor is marketed byViatrisafter Upjohn was spun off from Pfizer.[96][97]

Veterinary uses

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Veterinary overdose indogsis very well treated byCyproheptadineHCl.[98]: 1371 

Venlafaxine is highly toxic toBacillariophytaandChlorophytaphytoplankton.[99]Cats are drawn to the smell of venlafaxine and tend to ingest the pills, which is highly toxic to them.[100]

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