Identification

Name
Desvenlafaxine
Accession Number
DB06700
Type
Small Molecule
Groups
Approved, Investigational
Description

Desvenlafaxine (O-desmethylvenlafaxine) the major active metabolite of venlafaxine, is an antidepressant from the serotonin-norepinephrine reuptake inhibitor (SNRI class). Desvenlafaxine may be used to treat major depressive disorder and is being studied for use in the management of vasomotor symptoms in postmenopausal women. It is formulated as an extended release tablet. FDA approved in 2008.

Structure
Thumb
Synonyms
  • Desvenlafaxine
  • O-desmethylvenlafaxine
  • ODV
Product Ingredients
IngredientUNIICASInChI Key
Desvenlafaxine fumarateATX24E9M6L93414-04-1SQTJDJZCPOSWSC-WLHGVMLRSA-N
Desvenlafaxine fumarate monohydrateR5JHD7L72A313471-75-9YETWCSLOYUZBLK-JITBQSAISA-N
Desvenlafaxine succinateZB22ENF0XR386750-22-7ORUUBRMVQCKYHB-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DesvenlafaxineTablet, extended release50 mg/1OralSun Pharmaceutical Industries Limited2013-03-05Not applicableUs63304 0191 30 nlmimage10 aa405562
DesvenlafaxineTablet, extended release50 mg/1OralSun Pharma Global FZE2014-01-302017-02-04Us
DesvenlafaxineTablet, extended release100 mg/1OralSun Pharmaceutical Industries Limited2013-03-05Not applicableUs63304 0192 30 nlmimage10 9544ca96
DesvenlafaxineTablet, extended release100 mg/1OralSun Pharma Global FZE2014-01-302017-02-04Us
KHEDEZLA Extended-releaseTablet, extended release100 mg/1OralPar Pharmaceutical2013-07-102015-05-31Us
KHEDEZLA Extended-releaseTablet, extended release100 mg/1OralPernix Therapeutics2013-07-10Not applicableUs
KHEDEZLA Extended-releaseTablet, extended release50 mg/1OralPar Pharmaceutical2013-07-102015-05-31Us
KHEDEZLA Extended-releaseTablet, extended release50 mg/1OralPernix Therapeutics2013-07-10Not applicableUs
PristiqTablet, extended release50 mgOralPfizer2009-03-05Not applicableCanada
PristiqTablet, extended release100 mgOralPfizer2009-03-06Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-desvenlafaxineTablet, extended release100 mgOralApotex Corporation2017-10-20Not applicableCanada
Apo-desvenlafaxineTablet, extended release50 mgOralApotex Corporation2017-10-20Not applicableCanada
DesvenlafaxineTablet, extended release100 mg/1OralZydus Pharmaceuticals Usa, Inc.2018-05-08Not applicableUs
DesvenlafaxineTablet, film coated, extended release50 mg/1OralMylan Pharmaceuticals2017-03-01Not applicableUs
DesvenlafaxineTablet, extended release100 mg/1OralActavis Pharma Company2017-03-01Not applicableUs
DesvenlafaxineTablet, extended release25 mg/1OralActavis Pharma Company2017-03-01Not applicableUs
DesvenlafaxineTablet, film coated, extended release50 mg/1Oralbryant ranch prepack2017-03-01Not applicableUs
DesvenlafaxineTablet, extended release100 mg/1Oralbryant ranch prepack2017-03-01Not applicableUs
DesvenlafaxineTablet, extended release100 mg/1OralGolden State Medical Supply2018-01-01Not applicableUs
DesvenlafaxineTablet, film coated, extended release100 mg/1OralWest-Ward Pharmaceuticals Corp.2017-03-01Not applicableUs
International/Other Brands
Pristiq / Zyven-OD
Categories
UNII
NG99554ANW
CAS number
93413-62-8
Weight
Average: 263.3752
Monoisotopic: 263.188529049
Chemical Formula
C16H25NO2
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

Pharmacology

Indication

Desvenlafaxine is indicated for the treatment of major depressive disorder in adults.

Associated Conditions
Pharmacodynamics

Desvenlafaxine is a selective serotonin and norepinephrine reuptake inhibitor. It lacks significant activity on muscarinic-cholinergic, H1-histaminergic, or α1-adrenergic receptors in vitro. Desvenlafaxine does not appear to exert activity against calcium, chloride, potassium and sodium ion channels and also lacks monoamine oxidase (MAO) inhibitory activity. It was also shown to lack significant activity again the cardiac potassium channel, hERG, in vitro. Compared to other SNRIs, desvenlafaxine undergoes simple metabolism, has a low risk of drug-drug interactions and does not have to be extensively titrated to reach a therapeutic dose. Some of the limitations of desvenlafaxine include moderate efficacy in the treatment of major depressive disorder, similar safety and tolerability profile to other SNRIs and possible transient discontinuation symptoms upon cessation of therapy.

Mechanism of action

Desvenlafaxine, the major active metabolite of venlafaxine, is a selective serotonin and norepinephrine reuptake inhibitor. The clinical effect of desvenlafaxine is thought to occur via potentiation of serotonin and norepinephrine in the central nervous system. Unlike venlafaxine, desvenlafaxine is thought to have a differential serotonergic and noradrenergic activity profile.

TargetActionsOrganism
ASodium-dependent serotonin transporter
inhibitor
Human
ASodium-dependent noradrenaline transporter
inhibitor
Human
Absorption

Absolute bioavailability is approximately 80% and is unaffected by food. Peak plasma concentration is reached in 7.5 hours.

Volume of distribution

3.4 L/kg, distribution into nonvascular compartments

Protein binding

~ 30%, protein binding is independent of drug concentration.

Metabolism

The primary route of metabolism is via conjugation mediated by UGT isoforms. Desvenlafaxine also undergoes oxidative N-demethylation via cytochrome P450 3A4 to a minor extent. CYP2D6 is not involved with the metabolism of desvenlafaxine.

Route of elimination

Excreted in the urine. Approximately 45% of the total oral dose is excreted unchanged in urine. Approximately 19% of the total oral dose is excreted as the glucuronide metabolite and < 5% is excreted as the oxidative metabolite, N,O-didesmethylvenlafaxine. Excreted in human milk.

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.

Clearance
Not Available
Toxicity

The safety and tolerability of desvenlafaxine is similar to other SNRIs. Common side effects upon initiation or dose increase include increased blood pressure and heart rate, agitation, tremor, sweating, nausea, headache, and sleep disturbances. May cause sexual dysfunction and weight loss in some patients. May cause increases in fasting serum total cholesterol, LDL cholesterol, and triglycerides. Withdrawal effects may occur and thus, the dose of desvenlafaxine should be titrated down prior to discontinuation.

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Venlafaxine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with (S)-Warfarin.
2,4-thiazolidinedioneDesvenlafaxine may increase the hypoglycemic activities of 2,4-thiazolidinedione.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Desvenlafaxine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Desvenlafaxine.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Desvenlafaxine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Desvenlafaxine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Desvenlafaxine.
AbciximabDesvenlafaxine may increase the antiplatelet activities of Abciximab.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Karel Pospisilik, Lambertus Thijs, "Process for making desvenlafaxine." U.S. Patent US20070299283, issued December 27, 2007.

US20070299283
General References
  1. 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. [PubMed:20926994]
  2. 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. [PubMed:19086875]
  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. [PubMed:20797382]
  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. [PubMed:20944767]
  5. 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. [PubMed:17673606]
  6. Montgomery SA, Fava M, Padmanabhan SK, Guico-Pabia CJ, Tourian KA: Discontinuation symptoms and taper/poststudy-emergent adverse events with desvenlafaxine treatment for major depressive disorder. Int Clin Psychopharmacol. 2009 Nov;24(6):296-305. doi: 10.1097/YIC.0b013e32832fbb5a. [PubMed:19779354]
  7. Oganesian A, Shilling AD, Young-Sciame R, Tran J, Watanyar A, Azam F, Kao J, Leung L: Desvenlafaxine and venlafaxine exert minimal in vitro inhibition of human cytochrome P450 and P-glycoprotein activities. Psychopharmacol Bull. 2009;42(2):47-63. [PubMed:19629022]
  8. Pae CU, Park MH, Marks DM, Han C, Patkar AA, Masand PS: Desvenlafaxine, a serotonin-norepinephrine uptake inhibitor for major depressive disorder, neuropathic pain and the vasomotor symptoms associated with menopause. Curr Opin Investig Drugs. 2009 Jan;10(1):75-90. [PubMed:19127490]
  9. 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. [PubMed:19919295]
  10. 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. [PubMed:22098230]
  11. Preskorn S, Patroneva A, Silman H, Jiang Q, Isler JA, Burczynski ME, Ahmed S, Paul J, Nichols AI: Comparison of the pharmacokinetics of venlafaxine extended release and desvenlafaxine in extensive and poor cytochrome P450 2D6 metabolizers. J Clin Psychopharmacol. 2009 Feb;29(1):39-43. doi: 10.1097/JCP.0b013e318192e4c1. [PubMed:19142106]
  12. Link [Link]
External Links
Human Metabolome Database
HMDB0015646
KEGG Drug
D02570
PubChem Compound
125017
PubChem Substance
99443254
ChemSpider
111300
BindingDB
86748
ChEBI
83527
ChEMBL
CHEMBL1118
PharmGKB
PA165958374
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Desvenlafaxine
ATC Codes
N06AX23 — Desvenlafaxine
AHFS Codes
  • 28:16.04.16 — Selective Serotonin and Norepinephrine-reuptake Inhibitors
FDA label
Download (379 KB)
MSDS
Download (86.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceMajor Depressive Disorder (MDD)1
1CompletedOtherHealthy Volunteers3
1CompletedTreatmentHealthy Volunteers2
1CompletedTreatmentMajor Depressive Disorder (MDD)3
1Unknown StatusBasic ScienceHealthy Volunteers1
1WithdrawnOtherHepatic Impairment1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection2
2CompletedTreatmentMajor Depressive Disorder (MDD)1
2, 3TerminatedTreatmentCancers / Cardiovascular Disease (CVD) / Diabetes Mellitus (DM) / Major Depressive Disorder (MDD)1
3CompletedTreatmentDepression1
3CompletedTreatmentMajor Depressive Disorder (MDD)5
3Unknown StatusTreatmentMajor Depressive Disorder (MDD) / Menopausal Staging and Vasomotor Symptoms (for Females)1
4CompletedBasic ScienceCYP3A4 Protein, Human / Cytochrome P-450 CYP2D6 / Pharmacokinetics1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedTreatmentChronic Depressive Disorder / Dysthymic Disorder1
4CompletedTreatmentDepression / Methadone Treatment / Opioid Dependence1
4CompletedTreatmentMajor Depressive Disorder (MDD)2
4CompletedTreatmentSocial Anxiety Disorder (SAD)1
4RecruitingOtherAnhedonia / Depression1
4RecruitingTreatmentGeneralized Anxiety Disorder (GAD)1
4RecruitingTreatmentMenopausal Hot Flushes / Neoplasms, Breast1
4RecruitingTreatmentVascular Depression1
4TerminatedNot AvailableMajor Depressive Disorder (MDD) / Vasomotor Symptoms1
4Unknown StatusBasic ScienceMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)1
Not AvailableCompletedNot AvailableAcute Kidney Injury (AKI) / Depression1
Not AvailableCompletedTreatmentDysthymic Disorder1
Not AvailableCompletedTreatmentMajor Depressive Disorder (MDD)1
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableNot Yet RecruitingNot AvailableMajor Depressive Disorder (MDD)1

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
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral100 mg
Tablet, extended releaseOral50 mg
Tablet, extended releaseOral50 mg/1
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)
CA2436668No2009-05-262022-02-11Canada
US6673838No2002-03-012022-03-01Us
US8269040No2007-07-052027-07-05Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySoluble FDA label
logP0.21FDA label
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
Polarizability30.29 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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
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

Taxonomy

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-hydroxy-2-unsubstituted benzenoid / Cyclohexanol / Phenol / Aralkylamine / Monocyclic benzene moiety / Benzenoid / 1,3-aminoalcohol / Cyclic alcohol / Tertiary alcohol / Tertiary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amino compound, phenols, cyclohexanols (CHEBI:83527)

Targets

Kind
Protein
Organism
Human
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. [PubMed:16675639]
  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. [PubMed:17673606]
  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. [PubMed:19698900]
  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. [PubMed:19086875]
  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. [PubMed:20944767]
  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. [PubMed:19919295]
Kind
Protein
Organism
Human
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. [PubMed:16675639]
  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. [PubMed:17673606]
  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. [PubMed:19698900]
  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. [PubMed:19086875]
  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. [PubMed:20944767]
  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. [PubMed:19919295]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. [PubMed:22098230]
  2. Pfizer Pristiq [Link]

Drug created on May 06, 2010 10:22 / Updated on September 22, 2018 22:42