Desvenlafaxine

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
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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofHot flashes••• •••••••••••••••••••••••••• •••••••• •••••••
Treatment ofMajor depressive disorder•••••••••••••••••••••••• •••••••• •••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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

TargetActionsOrganism
ASodium-dependent noradrenaline transporter
inhibitor
Humans
ASodium-dependent serotonin transporter
inhibitor
Humans
USodium-dependent dopamine transporter
inhibitor
Humans
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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Toxicity

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
PathwayCategory
Venlafaxine Metabolism PathwayDrug 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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Desvenlafaxine.
AbacavirAbacavir may decrease the excretion rate of Desvenlafaxine which could result in a higher serum level.
AbametapirThe serum concentration of Desvenlafaxine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Desvenlafaxine can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Desvenlafaxine is combined with Abciximab.
Food Interactions
  • Avoid alcohol.
  • Avoid St. John's Wort.
  • Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Desvenlafaxine fumarateATX24E9M6L93414-04-1SQTJDJZCPOSWSC-WLHGVMLRSA-N
Desvenlafaxine fumarate monohydrateR5JHD7L72A313471-75-9YETWCSLOYUZBLK-JITBQSAISA-N
Desvenlafaxine hydrochloride3TP4E4F972300827-87-6IMWPSXHIEURNKZ-UHFFFAOYSA-N
Desvenlafaxine succinateZB22ENF0XR386750-22-7PWPDEXVGKDEKTE-UHFFFAOYSA-N
Product Images
International/Other Brands
Khedezla / Zyven-OD
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DesvenlafaxineTablet, extended release100 mg/1OralSun Pharmaceutical Industries, Inc.2013-03-05Not applicableUS flag
DesvenlafaxineTablet, extended release50 mg/1OralAlembic Pharmaceuticals Limited2013-03-05Not applicableUS flag
DesvenlafaxineTablet, extended release100 mgOralSanis Health Inc2023-05-25Not applicableCanada flag
DesvenlafaxineTablet, extended release100 mg/1OralSun Pharma Global FZE2014-01-302017-02-04US flag
DesvenlafaxineTablet, extended release50 mg/1OralSun Pharmaceutical Industries, Inc.2013-03-05Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-desvenlafaxineTablet, extended release100 mgOralAngita Pharma Inc.2023-05-12Not applicableCanada flag
Ag-desvenlafaxineTablet, extended release50 mgOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Apo-desvenlafaxineTablet, extended release100 mgOralApotex Corporation2017-10-20Not applicableCanada flag
Apo-desvenlafaxineTablet, extended release50 mgOralApotex Corporation2017-10-20Not applicableCanada flag
Apo-desvenlafaxine Extended-release TabletsTablet, extended release100 mgOralApotex Corporation2022-04-26Not applicableCanada flag

Categories

ATC Codes
N06AX23 — Desvenlafaxine
Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
  8. 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]
  9. 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]
  10. 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]
  11. FDA Drug Approval Package for Desvenlafaxine [Link]
  12. FDA Approved Drug Products: DESVENLAFAXINE extended-release tablets, for oral use (August 2023) [Link]
  13. The Absolute Bioavailability of Desvenlafaxine in Healthy Subjects [Link]
Human Metabolome Database
HMDB0015646
KEGG Drug
D07793
PubChem Compound
125017
PubChem Substance
99443254
ChemSpider
111300
BindingDB
86748
RxNav
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

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, extended releaseOral25 mg/1
Tablet, film coated, extended releaseOral100 mg/1
Tablet, film coated, extended releaseOral25 mg/1
Tablet, film coated, extended releaseOral50 mg/1
Capsule, extended releaseOral150 mg
TabletOral50.000 mg
TabletOral100.0000 mg
Tablet, extended releaseOral100 mg/1
TabletOral151.770 mg
Tablet, extended releaseOral
Tablet, extended releaseOral50 mg/1
Tablet, extended releaseOral100 mg
TabletOral75.870 mg
TabletOral50.00 mg
TabletOral151.677 mg
TabletOral75.87 mg
Tablet, extended releaseOral50 mg
Prices
Unit descriptionCostUnit
Pristiq 100 mg extended-release tablet4.46USD tablet
Pristiq 50 mg extended-release tablet4.31USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2436668No2009-05-262022-02-11Canada flag
US6673838No2004-01-062022-03-01US flag
US8269040No2012-09-182027-07-05US flag

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.4 mg/mLALOGPS
logP2.6ALOGPS
logP2.29Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.11Chemaxon
pKa (Strongest Basic)8.87Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area43.7 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity78.54 m3·mol-1Chemaxon
Polarizability30.32 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9772
Blood Brain Barrier+0.7722
Caco-2 permeable+0.8404
P-glycoprotein substrateSubstrate0.6918
P-glycoprotein inhibitor INon-inhibitor0.7835
P-glycoprotein inhibitor IIInhibitor0.5921
Renal organic cation transporterNon-inhibitor0.5894
CYP450 2C9 substrateNon-substrate0.7837
CYP450 2D6 substrateSubstrate0.7753
CYP450 3A4 substrateSubstrate0.6997
CYP450 1A2 substrateNon-inhibitor0.6816
CYP450 2C9 inhibitorNon-inhibitor0.757
CYP450 2D6 inhibitorInhibitor0.6334
CYP450 2C19 inhibitorNon-inhibitor0.7811
CYP450 3A4 inhibitorNon-inhibitor0.8646
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8888
Ames testNon AMES toxic0.8084
CarcinogenicityNon-carcinogens0.7648
BiodegradationNot ready biodegradable0.9927
Rat acute toxicity2.4429 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6046
hERG inhibition (predictor II)Inhibitor0.5603
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-9110000000-bddb56f900488038ac8f
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03di-0090000000-90abc876cc91a398d25d
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03y0-0960000000-0219d7d7ea1a46c8cfdf
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-014i-0900000000-529d7fb237a99866f0b4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0090000000-ccb6c8906a1ac7d27cd6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0290000000-422a5daa0d4bf51308ef
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0910000000-03ecfc411d730c35b892
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-d0fa1892dfaae0510ee8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001m-0900000000-7515704132219cf15c78
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0090000000-1a8bdddd358a8706e896
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0090000000-c218ef4ab652831ee930
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-06r2-4090000000-b1767a9c9c01cb43bca9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9320000000-e38b2ae07ab3cc9b7693
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9600000000-edbb26312a47b22bffb7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9800000000-b41801091e3c7132fec9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9800000000-4b30d7e9d71dab81d9d7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03di-0090000000-5e859f484b6e3a5560c4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-06r2-4090000000-ef1215dc6fc4eb904b90
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9310000000-dac7bd983af34469bc5f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9600000000-8ea073e198c8a9a9a528
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9800000000-f8db755a9bb1f788394e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-9700000000-b50718dbaca8fdae5401
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0090000000-7ed75e3f487ccd4f981d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0bta-6090000000-c41286a6446e8e51aab6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9100000000-e80f225fbf61adb457b7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-9200000000-81250c46509f91e0409b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9400000000-b6e08db8ef3bea2640a3
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9500000000-6ece9a9beebd1cd99bfd
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9400000000-5411c26ee28734211eb5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-2090000000-134bece44509731dae98
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-9150000000-383ebf283bfe27d5b20f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-08fr-5190000000-9ed6fdc774a9eecbca3c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-253cde3650467552e3a5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9260000000-0daef94f80448c8f85dc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1290000000-0e083fe2d602a8094427
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-6940000000-e287c8462172697f03dc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-022a-5940000000-9ddb03d4f08fce66797e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-171.0775649
predicted
DarkChem Lite v0.1.0
[M-H]-173.8004649
predicted
DarkChem Lite v0.1.0
[M-H]-163.10936
predicted
DeepCCS 1.0 (2019)
[M+H]+171.8260649
predicted
DarkChem Lite v0.1.0
[M+H]+174.3121649
predicted
DarkChem Lite v0.1.0
[M+H]+165.46736
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.2289649
predicted
DarkChem Lite v0.1.0
[M+Na]+173.9138649
predicted
DarkChem Lite v0.1.0
[M+Na]+171.56052
predicted
DeepCCS 1.0 (2019)

Targets

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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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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
Substrate
Inhibitor
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
  1. 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]
  2. 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]
  3. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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 March 18, 2024 16:48