Identification
- Summary
Desvenlafaxine is an antidepressant agent and SNRI used for the treatment of major depressive disorders in adults.
- Brand Names
- Pristiq
- Generic Name
- Desvenlafaxine
- DrugBank Accession Number
- DB06700
- Background
Desvenlafaxine (O-desmethylvenlafaxine) is the 0-demetyhlated active metabolite of venlafaxine. Like its parent drug, desvenlafaxine is also an antidepressant belonging to the class of serotonin-norepinephrine reuptake inhibitor (SNRI) class.9,9 It was approved by the FDA in 2008 for the treatment of adults with major depressive disorder (MDD).11,10
MDD is a highly prevalent psychiatric disorder, with a lifetime prevalence estimate of 16% in the US alone and 12.8% in Europe. Although the exact mechanism of pathophysiology is still unknown, imbalances or deficiencies of monoamines have been heavily implicated, thus the rationale behind the use of SNRI to treat MDD.10 Desvenlafaxine has a very similar pharmacological, efficacy, and safety profile as venlafaxine. The major difference is the potential for drug interaction since venlafaxine is mainly metabolized by CYP2D6 while desvenlafaxine is conjugated by UGT; therefore, desvenlafaxine is less likely to cause drug-drug interaction when taken with medications affecting the CYP2D6 pathway.9
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Desvenlafaxine (DB06700)
- Weight
- Average: 263.3752
Monoisotopic: 263.188529049 - Chemical Formula
- C16H25NO2
- Synonyms
- Desvenlafaxina
- Desvenlafaxine
- O-desmethylvenlafaxine
- ODV
- External IDs
- DVS 233
Pharmacology
- Indication
Desvenlafaxine is indicated for the treatment of major depressive disorder in adults.12 It has also been used off-label to treat hot flashes in menopausal women.7
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- Contraindications & Blackbox Warnings
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Desvenlafaxine is a selective serotonin and norepinephrine reuptake inhibitor.3,4,12 It lacks significant activity on muscarinic-cholinergic, H1-histaminergic, or α1-adrenergic receptors in vitro, or inhibitory activity against monoamine oxidase.12 Desvenlafaxine does not appear to exert activity against calcium, chloride, potassium and sodium ion channels and also lacks monoamine oxidase (MAO) inhibitory activity.4 It was also shown to lack significant activity against the cardiac potassium channel, hERG, in vitro.6
Electrocardiograms were obtained from 1,492 desvenlafaxine treated patients with major depressive disorder and 984 placebo-treated patients in clinical studies lasting up to 8 weeks. No clinically relevant differences were observed between desvenlafaxine treated and placebo-treated patients for QT, QTc, PR, and QRS intervals. In a thorough QTc study with prospectively determined criteria, desvenlafaxine did not cause QT prolongation. No difference was observed between placebo and desvenlafaxine treatments for the QRS interval.12
- Mechanism of action
The exact mechanism of the antidepressant action of desvenlafaxine is unknown but is thought to be related to the potentiation of serotonin and norepinephrine in the central nervous system, through inhibition of their reuptake.12 Particularly, desvenlafaxine has been found to inhibit the serotonin, norepinephrine, and dopamine transporters with varying degrees of affinity. Desvenlafaxine inhibits serotonin transporters with 10 times the affinity of norepinephrine transporters, and dopamine transporters with the lowest affinity.4
Target Actions Organism ASodium-dependent noradrenaline transporter inhibitorHumans ASodium-dependent serotonin transporter inhibitorHumans USodium-dependent dopamine transporter inhibitorHumans - Absorption
The absolute oral bioavailability of desvenlafaxine after oral administration is about 80%.12 The time to reach maximal concentration (Tmax) is estimated to be 7.5 hours after oral administration. The AUC in a 24 h dosing interval at steady state with a 100 mg dose was also calculated to be 6747 ng*h/mL, and the Cmax 376 ng/mL.8 Ingestion of a high-fat meal (800 to 1000 calories) increased desvenlafaxine Cmax about 16% and had no effect on AUC.12
- Volume of distribution
The steady-state volume of distribution of desvenlafaxine is 3.4 L/kg.12
- Protein binding
The plasma protein binding of desvenlafaxine is 30% and is independent of drug concentration.12
- Metabolism
Desvenlafaxine is primarily metabolized by conjugation (mediated by UGT isoforms) and, to a minor extent, through oxidative metabolism.12 O-glucuronide conjugation is likely be catalyzed by UGT1A1, UGT1A3, UGT2B4, UGT2B15, and UGT2B17.8 CYP3A4 and potentially CYP2C19 mediates the oxidative metabolism (N-demethylation) of desvenlafaxine to N,O-didesmethyl venlafaxine.12,8 The CYP2D6 metabolic pathway is not involved. The pharmacokinetics of desvenlafaxine was similar in subjects with CYP2D6 poor and extensive metabolizer phenotype.12
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- Route of elimination
Desvenlafaxine is mainly excreted in the urine.4 Approximately 45% of desvenlafaxine is excreted unchanged in urine at 72 hours after oral administration. Approximately 19% of the administered dose is excreted as the glucuronide metabolite and <5% as the oxidative metabolite (N,O-didesmethyl venlafaxine) in urine.12
- Half-life
The mean terminal half-life is 11.1 hours and may be prolonged in patients with renal and/or moderate to severe hepatic impairment.4
- Clearance
Following the administration of 100 mg of desvenlafaxine in healthy subjects from 18 to 45 years of age, the renal clearance was calculated to be 222 ± 82 mL/min.13
- Adverse Effects
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Published epidemiological studies of pregnant women exposed to the parent compound venlafaxine have not reported a clear association with major birth defects or miscarriage. Methodological limitations of these observational studies include possible exposure and outcome misclassification, lack of adequate controls, adjustment for confounders, and confirmatory studies; therefore, these studies cannot establish or exclude any drug-associated risk during pregnancy.12
Retrospective cohort studies based on claims data have shown an association between venlafaxine use and preeclampsia, compared to depressed women who did not take an antidepressant during pregnancy. One study that assessed venlafaxine exposure in the second trimester or first half of the third trimester and preeclampsia showed an increased risk compared to unexposed depressed women (adjusted (adj) RR 1.57, 95% CI 1.29 to 1.91). Preeclampsia was observed at venlafaxine doses equal to or greater than 75 mg/day and a duration of treatment >30 days. Another study that assessed venlafaxine exposure in gestational weeks 10 to 20 and preeclampsia showed an increased risk at doses equal to or greater than 150 mg/day. Available data are limited by possible outcome misclassification and possible confounding due to depression severity and other confounders.12
Retrospective cohort studies based on claims data have suggested an association between venlafaxine use near the time of delivery or through delivery and postpartum hemorrhage. One study showed an increased risk for postpartum hemorrhage when venlafaxine exposure occurred through delivery, compared to unexposed depressed women (adj RR 2.24, 95% CI 1.69 to 2.97). There was no increased risk in women who were exposed to venlafaxine earlier in pregnancy. Limitations of this study include possible confounding due to depression severity and other confounders. Another study showed an increased risk for postpartum hemorrhage when SNRI exposure occurred for at least 15 days in the last month of pregnancy or through delivery, compared to unexposed women (adj RR 1.64 to 1.76). The results of this study may be confounded by the effects of depression. Neonates exposed to SNRIs or SSRIs, late in the third trimester have developed complications requiring prolonged hospitalization, respiratory support, and tube feeding. Such complications can arise immediately upon delivery. Reported clinical findings have included respiratory distress, cyanosis, apnea, seizures, temperature instability, feeding difficulty, vomiting, hypoglycemia, hypotonia, hypertonia, hyperreflexia, tremor, jitteriness, irritability, and constant crying. These features are consistent with either a direct toxic effect of SSRIs and SNRIs or, possibly, a drug discontinuation syndrome. It should be noted that, in some cases, the clinical picture is consistent with serotonin syndrome.12
Antidepressants, such as desvenlafaxine, increase the risk of suicidal thoughts and behaviors in pediatric patient.12
Of the 4,158 patients in pre-marketing clinical studies with desvenlafaxine, 6% were 65 years of age or older. No overall differences in safety or efficacy were observed between these patients and younger patients; however, in the short-term placebo-controlled studies, there was a higher incidence of systolic orthostatic hypotension in patients ≥65 years of age compared to patients <65 years of age treated with desvenlafaxine. For elderly patients, possible reduced renal clearance of desvenlafaxine should be considered when determining dose. SSRIs and SNRIs, including desvenlafaxine, have been associated with cases of clinically significant hyponatremia in elderly patients, who may be at greater risk for this adverse event.12
There is limited clinical trial experience with desvenlafaxine succinate overdosage in humans. However, desvenlafaxine is the major active metabolite of venlafaxine. Overdose experience reported with venlafaxine (the parent drug of desvenlafaxine) is presented below; the identical information can be found in the Overdosage section of the venlafaxine package insert. In post-marketing experience, overdose with venlafaxine (the parent drug of desvenlafaxine) has occurred predominantly in combination with alcohol and/or other drugs. The most commonly reported events in overdosage include tachycardia, changes in level of consciousness (ranging from somnolence to coma), mydriasis, seizures, and vomiting. Electrocardiogram changes (e.g., prolongation of QT interval, bundle branch block, QRS prolongation), sinus and ventricular tachycardia, bradycardia, hypotension, rhabdomyolysis, vertigo, liver necrosis, serotonin syndrome, and death have been reported. Published retrospective studies report that venlafaxine overdosage may be associated with an increased risk of fatal outcomes compared to that observed with SSRI antidepressant products, but lower than that for tricyclic antidepressants. Epidemiological studies have shown that venlafaxine-treated patients have a higher pre-existing burden of suicide risk factors than SSRI-treated patients. The extent to which the finding of an increased risk of fatal outcomes can be attributed to the toxicity of venlafaxine in overdosage, as opposed to some characteristic(s) of venlafaxine-treated patients, is not clear.12
No specific antidotes for desvenlafaxine are known. In managing over dosage, consider the possibility of multiple drug involvement. In case of overdose, call Poison Control Center at 1-800-222-1222 for latest recommendations.12
Desvenlafaxine succinate administered by oral gavage to mice and rats for 2 years did not increase the incidence of tumors in either study. Mice received desvenlafaxine succinate at dosages up to 500/300 mg/kg/day (dosage lowered after 45 weeks of dosing). The AUC exposure at 300 mg/kg/day dose is estimated at 10 times the AUC exposure at an adult human dose of 100 mg per day. Rats received desvenlafaxine succinate at dosages up to 300 mg/kg/day (males) or 500 mg/kg/day (females). The AUC exposure at the highest dose is estimated at 11 (males) or 26 (females) times the AUC exposure at an adult human dose of 100 mg per day.12
Desvenlafaxine was not mutagenic in the in vitro bacterial mutation assay (Ames test) and was not clastogenic in an in vitro chromosome aberration assay in cultured CHO cells, an in vivo mouse micronucleus assay, or an in vivo chromosome aberration assay in rats. Additionally, desvenlafaxine was not genotoxic in the in vitro CHO mammalian cell forward mutation assay and was negative in the in vitro BALB/c-3T3 mouse embryo cell transformation assay.12
When desvenlafaxine succinate was administered orally to male and female rats, fertility was reduced at the high dose of 300 mg/kg/day, which is 10 (males) and 19 (females) times the AUC exposure at an adult human dose of 100 mg per day. There was no effect on fertility at 100 mg/kg/day, which is 3 (males) or 5 (females) times the AUC exposure at an adult human dose of 100 mg per day. These studies did not address reversibility of the effect on fertility. The relevance of these findings to humans is not known.12
- Pathways
Pathway Category Venlafaxine Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Desvenlafaxine. Abacavir Abacavir may decrease the excretion rate of Desvenlafaxine which could result in a higher serum level. Abametapir The serum concentration of Desvenlafaxine can be increased when it is combined with Abametapir. Abatacept The metabolism of Desvenlafaxine can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Desvenlafaxine is combined with Abciximab. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Desvenlafaxine. Abiraterone The metabolism of Desvenlafaxine can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Desvenlafaxine. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Desvenlafaxine. Acarbose The risk or severity of hypoglycemia can be increased when Desvenlafaxine is combined with Acarbose. 
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- Avoid alcohol.
- Avoid St. John's Wort.
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Desvenlafaxine fumarate ATX24E9M6L 93414-04-1 SQTJDJZCPOSWSC-WLHGVMLRSA-N Desvenlafaxine fumarate monohydrate R5JHD7L72A 313471-75-9 YETWCSLOYUZBLK-JITBQSAISA-N Desvenlafaxine hydrochloride 3TP4E4F972 300827-87-6 IMWPSXHIEURNKZ-UHFFFAOYSA-N Desvenlafaxine succinate ZB22ENF0XR 386750-22-7 PWPDEXVGKDEKTE-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Khedezla / Zyven-OD
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Desvenlafaxine Tablet, extended release 100 mg/1 Oral Sun Pharma Global FZE 2014-01-30 2017-02-04 US 
Desvenlafaxine Tablet, extended release 50 mg/1 Oral Sun Pharma Global FZE 2014-01-30 2017-02-04 US Desvenlafaxine Tablet, extended release 100 mg/1 Oral Alembic Pharmaceuticals Limited 2013-03-05 Not applicable US Desvenlafaxine Tablet, extended release 100 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2013-03-05 Not applicable US 
Desvenlafaxine Tablet, extended release 100 mg Oral Sanis Health Inc 2023-05-25 Not applicable Canada 
Desvenlafaxine Tablet, extended release 50 mg/1 Oral Alembic Pharmaceuticals Limited 2013-03-05 Not applicable US Desvenlafaxine Tablet, extended release 50 mg Oral Sanis Health Inc 2023-05-25 Not applicable Canada Desvenlafaxine Tablet, extended release 50 mg/1 Oral Sun Pharmaceutical Industries, Inc. 2013-03-05 Not applicable US 
Intelli-desvenlafaxine Tablet, extended release 100 mg Oral Intellipharmaceutics Corp Not applicable Not applicable Canada Intelli-desvenlafaxine Tablet, extended release 50 mg Oral Intellipharmaceutics Corp Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ag-desvenlafaxine Tablet, extended release 100 mg Oral Angita Pharma Inc. 2023-05-12 Not applicable Canada Ag-desvenlafaxine Tablet, extended release 50 mg Oral Angita Pharma Inc. Not applicable Not applicable Canada Apo-desvenlafaxine Tablet, extended release 100 mg Oral Apotex Corporation 2017-10-20 Not applicable Canada Apo-desvenlafaxine Tablet, extended release 50 mg Oral Apotex Corporation 2017-10-20 Not applicable Canada Apo-desvenlafaxine Extended-release Tablets Tablet, extended release 100 mg Oral Apotex Corporation 2022-04-26 Not applicable Canada Apo-desvenlafaxine Extended-release Tablets Tablet, extended release 50 mg Oral Apotex Corporation 2022-04-26 Not applicable Canada Desvenlafaxine Tablet, film coated, extended release 50 mg/1 Oral Mylan Pharmaceuticals Inc. 2017-03-01 2020-01-31 US Desvenlafaxine Tablet, extended release 100 mg/1 Oral Actavis Pharma, Inc. 2017-03-01 Not applicable US Desvenlafaxine Tablet, extended release 50 mg/1 Oral Lake Erie Medical DBA Quality Care Products LLC 2018-01-05 2019-10-11 US Desvenlafaxine Tablet, film coated, extended release 50 mg/1 Oral bryant ranch prepack 2017-03-01 Not applicable US
Categories
- ATC Codes
- N06AX23 — Desvenlafaxine
- Drug Categories
- Agents producing tachycardia
- Agents that reduce seizure threshold
- Alcohols
- Antidepressive Agents
- Antidepressive Agents Indicated for Depression
- Benzene Derivatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Combined Inhibitors of Serotonin/Norepinephrine Reuptake
- Cyclohexanes
- Cyclohexanols
- Cycloparaffins
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (moderate)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Fatty Alcohols
- Hexanols
- Hypoglycemia-Associated Agents
- Lipids
- Membrane Transport Modulators
- Nervous System
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Norepinephrine Uptake Inhibitors
- Phenols
- Psychoanaleptics
- Psychotropic Drugs
- Selective Serotonin Reuptake Inhibitors
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin and Noradrenaline Reuptake Inhibitors
- Serotonin Modulators
- UGT1A1 Substrates
- UGT1A3 substrates
- UGT2B17 substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cyclohexanols. These are compounds containing an alcohol group attached to a cyclohexane ring.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Alcohols and polyols
- Direct Parent
- Cyclohexanols
- Alternative Parents
- Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Tertiary alcohols / 1,3-aminoalcohols / Trialkylamines / Cyclic alcohols and derivatives / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 1,3-aminoalcohol / 1-hydroxy-2-unsubstituted benzenoid / Amine / Aralkylamine / Aromatic homomonocyclic compound / Benzenoid / Cyclic alcohol / Cyclohexanol / Hydrocarbon derivative / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary amino compound, phenols, cyclohexanols (CHEBI:83527)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- NG99554ANW
- CAS number
- 93413-62-8
- InChI Key
- KYYIDSXMWOZKMP-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3
- IUPAC Name
- 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
- SMILES
- CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1
References
- Synthesis Reference
Karel Pospisilik, Lambertus Thijs, "Process for making desvenlafaxine." U.S. Patent US20070299283, issued December 27, 2007.
US20070299283- General References
- Pae CU: Desvenlafaxine in the treatment of major depressive disorder. Expert Opin Pharmacother. 2011 Dec;12(18):2923-8. doi: 10.1517/14656566.2011.636033. [Article]
- Ilett KF, Watt F, Hackett LP, Kohan R, Teoh S: Assessment of infant dose through milk in a lactating woman taking amisulpride and desvenlafaxine for treatment-resistant depression. Ther Drug Monit. 2010 Dec;32(6):704-7. doi: 10.1097/FTD.0b013e3181f88f70. [Article]
- Kornstein SG, Jiang Q, Reddy S, Musgnung JJ, Guico-Pabia CJ: Short-term efficacy and safety of desvenlafaxine in a randomized, placebo-controlled study of perimenopausal and postmenopausal women with major depressive disorder. J Clin Psychiatry. 2010 Aug;71(8):1088-96. doi: 10.4088/JCP.10m06018blu. [Article]
- Liebowitz MR, Tourian KA: Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Prim Care Companion J Clin Psychiatry. 2010;12(3). pii: PCC.09r00845. doi: 10.4088/PCC.09r00845blu. [Article]
- Reddy S, Kane C, Pitrosky B, Musgnung J, Ninan PT, Guico-Pabia CJ: Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. Curr Med Res Opin. 2010 Jan;26(1):139-50. doi: 10.1185/03007990903408678. [Article]
- Jasiak NM, Bostwick JR: Risk of QT/QTc prolongation among newer non-SSRI antidepressants. Ann Pharmacother. 2014 Dec;48(12):1620-8. doi: 10.1177/1060028014550645. Epub 2014 Sep 9. [Article]
- Johnson ED, Carroll DG: Venlafaxine and desvenlafaxine in the management of menopausal hot flashes. Pharm Pract (Granada). 2011 Jul;9(3):117-21. Epub 2011 Sep 14. [Article]
- Calleja S, Zubiaur P, Ochoa D, Villapalos-Garcia G, Mejia-Abril G, Soria-Chacartegui P, Navares-Gomez M, de Miguel A, Roman M, Martin-Vilchez S, Abad-Santos F: Impact of polymorphisms in CYP and UGT enzymes and ABC and SLCO1B1 transporters on the pharmacokinetics and safety of desvenlafaxine. Front Pharmacol. 2023 Feb 2;14:1110460. doi: 10.3389/fphar.2023.1110460. eCollection 2023. [Article]
- Sopko MA Jr, Ehret MJ, Grgas M: Desvenlafaxine: another "me too" drug? Ann Pharmacother. 2008 Oct;42(10):1439-46. doi: 10.1345/aph.1K563. Epub 2008 Aug 12. [Article]
- Seo HJ, Sohi MS, Patkar AA, Masand PS, Pae CU: Desvenlafaxine succinate: a newer antidepressant for the treatment of depression and somatic symptoms. Postgrad Med. 2010 Jan;122(1):125-38. doi: 10.3810/pgm.2010.01.2106. [Article]
- FDA Drug Approval Package for Desvenlafaxine [Link]
- FDA Approved Drug Products: DESVENLAFAXINE extended-release tablets, for oral use (August 2023) [Link]
- The Absolute Bioavailability of Desvenlafaxine in Healthy Subjects [Link]
- External Links
- Human Metabolome Database
- HMDB0015646
- KEGG Drug
- D07793
- PubChem Compound
- 125017
- PubChem Substance
- 99443254
- ChemSpider
- 111300
- BindingDB
- 86748
- 734064
- ChEBI
- 83527
- ChEMBL
- CHEMBL1118
- PharmGKB
- PA165958374
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Desvenlafaxine
- FDA label
- Download (1.02 MB)
- MSDS
- Download (24.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Basic Science CYP3A4 Protein, Human / Cytochrome P-450 CYP2D6 / Pharmacokinetics 1 4 Completed Basic Science Pharmacokinetics 1 4 Completed Other Anhedonia / Depression 1 4 Completed Other Healthy Controls / Major Depressive Disorder (MDD) 1 4 Completed Treatment Chronic Depressive Disorder / Persistent Depressive Disorder (Dysthymia) 1 4 Completed Treatment Depression / Methadone Treatment / Opioid Dependence 1 4 Completed Treatment Generalized Anxiety Disorder 1 4 Completed Treatment Major Depressive Disorder (MDD) 5 4 Completed Treatment Social Anxiety Disorder (SAD) 1 4 Recruiting Other Alteration of Cognitive Function / Major Depressive Disorder (MDD) / Neuroticism / Stress (Psychology) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, extended release Oral 25 mg/1 Tablet, film coated, extended release Oral 100 mg/1 Tablet, film coated, extended release Oral 25 mg/1 Tablet, film coated, extended release Oral 50 mg/1 Capsule, extended release Oral 150 mg Tablet Oral 50.000 mg Tablet, extended release Oral 100 mg/1 Tablet Oral 151.770 mg Tablet, extended release Oral Tablet, extended release Oral 50 mg/1 Tablet, extended release Oral 100 mg Tablet Oral 50.00 mg Tablet, extended release Oral 50 mg - Prices
Unit description Cost Unit Pristiq 100 mg extended-release tablet 4.46USD tablet Pristiq 50 mg extended-release tablet 4.31USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2436668 No 2009-05-26 2022-02-11 Canada US6673838 No 2004-01-06 2022-03-01 US US8269040 No 2012-09-18 2027-07-05 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.4 mg/mL ALOGPS logP 2.6 ALOGPS logP 2.29 Chemaxon logS -2.3 ALOGPS pKa (Strongest Acidic) 10.11 Chemaxon pKa (Strongest Basic) 8.87 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 43.7 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 78.54 m3·mol-1 Chemaxon Polarizability 30.32 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9772 Blood Brain Barrier + 0.7722 Caco-2 permeable + 0.8404 P-glycoprotein substrate Substrate 0.6918 P-glycoprotein inhibitor I Non-inhibitor 0.7835 P-glycoprotein inhibitor II Inhibitor 0.5921 Renal organic cation transporter Non-inhibitor 0.5894 CYP450 2C9 substrate Non-substrate 0.7837 CYP450 2D6 substrate Substrate 0.7753 CYP450 3A4 substrate Substrate 0.6997 CYP450 1A2 substrate Non-inhibitor 0.6816 CYP450 2C9 inhibitor Non-inhibitor 0.757 CYP450 2D6 inhibitor Inhibitor 0.6334 CYP450 2C19 inhibitor Non-inhibitor 0.7811 CYP450 3A4 inhibitor Non-inhibitor 0.8646 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8888 Ames test Non AMES toxic 0.8084 Carcinogenicity Non-carcinogens 0.7648 Biodegradation Not ready biodegradable 0.9927 Rat acute toxicity 2.4429 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6046 hERG inhibition (predictor II) Inhibitor 0.5603
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Norepinephrine:sodium symporter activity
- Specific Function
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Deecher DC, Beyer CE, Johnston G, Bray J, Shah S, Abou-Gharbia M, Andree TH: Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. Epub 2006 May 4. [Article]
- Mason JN, Deecher DC, Richmond RL, Stack G, Mahaney PE, Trybulski E, Winneker RC, Blakely RD: Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter. J Pharmacol Exp Ther. 2007 Nov;323(2):720-9. Epub 2007 Aug 2. [Article]
- Perry R, Cassagnol M: Desvenlafaxine: a new serotonin-norepinephrine reuptake inhibitor for the treatment of adults with major depressive disorder. Clin Ther. 2009 Jun;31 Pt 1:1374-404. doi: 10.1016/j.clinthera.2009.07.012. [Article]
- Kamath J, Handratta V: Desvenlafaxine succinate for major depressive disorder: a critical review of the evidence. Expert Rev Neurother. 2008 Dec;8(12):1787-97. doi: 10.1586/14737175.8.12.1787. [Article]
- Liebowitz MR, Tourian KA: Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Prim Care Companion J Clin Psychiatry. 2010;12(3). pii: PCC.09r00845. doi: 10.4088/PCC.09r00845blu. [Article]
- Reddy S, Kane C, Pitrosky B, Musgnung J, Ninan PT, Guico-Pabia CJ: Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. Curr Med Res Opin. 2010 Jan;26(1):139-50. doi: 10.1185/03007990903408678. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serotonin:sodium symporter activity
- Specific Function
- Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
- Gene Name
- SLC6A4
- Uniprot ID
- P31645
- Uniprot Name
- Sodium-dependent serotonin transporter
- Molecular Weight
- 70324.165 Da
References
- Deecher DC, Beyer CE, Johnston G, Bray J, Shah S, Abou-Gharbia M, Andree TH: Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. Epub 2006 May 4. [Article]
- Mason JN, Deecher DC, Richmond RL, Stack G, Mahaney PE, Trybulski E, Winneker RC, Blakely RD: Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter. J Pharmacol Exp Ther. 2007 Nov;323(2):720-9. Epub 2007 Aug 2. [Article]
- Perry R, Cassagnol M: Desvenlafaxine: a new serotonin-norepinephrine reuptake inhibitor for the treatment of adults with major depressive disorder. Clin Ther. 2009 Jun;31 Pt 1:1374-404. doi: 10.1016/j.clinthera.2009.07.012. [Article]
- Kamath J, Handratta V: Desvenlafaxine succinate for major depressive disorder: a critical review of the evidence. Expert Rev Neurother. 2008 Dec;8(12):1787-97. doi: 10.1586/14737175.8.12.1787. [Article]
- Liebowitz MR, Tourian KA: Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Prim Care Companion J Clin Psychiatry. 2010;12(3). pii: PCC.09r00845. doi: 10.4088/PCC.09r00845blu. [Article]
- Reddy S, Kane C, Pitrosky B, Musgnung J, Ninan PT, Guico-Pabia CJ: Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. Curr Med Res Opin. 2010 Jan;26(1):139-50. doi: 10.1185/03007990903408678. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Liebowitz MR, Tourian KA: Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Prim Care Companion J Clin Psychiatry. 2010;12(3). pii: PCC.09r00845. doi: 10.4088/PCC.09r00845blu. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Pae CU: Desvenlafaxine in the treatment of major depressive disorder. Expert Opin Pharmacother. 2011 Dec;12(18):2923-8. doi: 10.1517/14656566.2011.636033. [Article]
- Calleja S, Zubiaur P, Ochoa D, Villapalos-Garcia G, Mejia-Abril G, Soria-Chacartegui P, Navares-Gomez M, de Miguel A, Roman M, Martin-Vilchez S, Abad-Santos F: Impact of polymorphisms in CYP and UGT enzymes and ABC and SLCO1B1 transporters on the pharmacokinetics and safety of desvenlafaxine. Front Pharmacol. 2023 Feb 2;14:1110460. doi: 10.3389/fphar.2023.1110460. eCollection 2023. [Article]
- Pfizer Pristiq [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- FDA Drug Approval Package for Desvenlafaxine [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Calleja S, Zubiaur P, Ochoa D, Villapalos-Garcia G, Mejia-Abril G, Soria-Chacartegui P, Navares-Gomez M, de Miguel A, Roman M, Martin-Vilchez S, Abad-Santos F: Impact of polymorphisms in CYP and UGT enzymes and ABC and SLCO1B1 transporters on the pharmacokinetics and safety of desvenlafaxine. Front Pharmacol. 2023 Feb 2;14:1110460. doi: 10.3389/fphar.2023.1110460. eCollection 2023. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
References
- Calleja S, Zubiaur P, Ochoa D, Villapalos-Garcia G, Mejia-Abril G, Soria-Chacartegui P, Navares-Gomez M, de Miguel A, Roman M, Martin-Vilchez S, Abad-Santos F: Impact of polymorphisms in CYP and UGT enzymes and ABC and SLCO1B1 transporters on the pharmacokinetics and safety of desvenlafaxine. Front Pharmacol. 2023 Feb 2;14:1110460. doi: 10.3389/fphar.2023.1110460. eCollection 2023. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
- Gene Name
- UGT2B4
- Uniprot ID
- P06133
- Uniprot Name
- UDP-glucuronosyltransferase 2B4
- Molecular Weight
- 60512.035 Da
References
- Calleja S, Zubiaur P, Ochoa D, Villapalos-Garcia G, Mejia-Abril G, Soria-Chacartegui P, Navares-Gomez M, de Miguel A, Roman M, Martin-Vilchez S, Abad-Santos F: Impact of polymorphisms in CYP and UGT enzymes and ABC and SLCO1B1 transporters on the pharmacokinetics and safety of desvenlafaxine. Front Pharmacol. 2023 Feb 2;14:1110460. doi: 10.3389/fphar.2023.1110460. eCollection 2023. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
- Gene Name
- UGT2B15
- Uniprot ID
- P54855
- Uniprot Name
- UDP-glucuronosyltransferase 2B15
- Molecular Weight
- 61035.815 Da
References
- Calleja S, Zubiaur P, Ochoa D, Villapalos-Garcia G, Mejia-Abril G, Soria-Chacartegui P, Navares-Gomez M, de Miguel A, Roman M, Martin-Vilchez S, Abad-Santos F: Impact of polymorphisms in CYP and UGT enzymes and ABC and SLCO1B1 transporters on the pharmacokinetics and safety of desvenlafaxine. Front Pharmacol. 2023 Feb 2;14:1110460. doi: 10.3389/fphar.2023.1110460. eCollection 2023. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. The major substrates of this isozyme are eugenol > 4-methylumbe...
- Gene Name
- UGT2B17
- Uniprot ID
- O75795
- Uniprot Name
- UDP-glucuronosyltransferase 2B17
- Molecular Weight
- 61094.915 Da
References
- Calleja S, Zubiaur P, Ochoa D, Villapalos-Garcia G, Mejia-Abril G, Soria-Chacartegui P, Navares-Gomez M, de Miguel A, Roman M, Martin-Vilchez S, Abad-Santos F: Impact of polymorphisms in CYP and UGT enzymes and ABC and SLCO1B1 transporters on the pharmacokinetics and safety of desvenlafaxine. Front Pharmacol. 2023 Feb 2;14:1110460. doi: 10.3389/fphar.2023.1110460. eCollection 2023. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Calleja S, Zubiaur P, Ochoa D, Villapalos-Garcia G, Mejia-Abril G, Soria-Chacartegui P, Navares-Gomez M, de Miguel A, Roman M, Martin-Vilchez S, Abad-Santos F: Impact of polymorphisms in CYP and UGT enzymes and ABC and SLCO1B1 transporters on the pharmacokinetics and safety of desvenlafaxine. Front Pharmacol. 2023 Feb 2;14:1110460. doi: 10.3389/fphar.2023.1110460. eCollection 2023. [Article]
Drug created at May 06, 2010 16:22 / Updated at November 29, 2023 23:14