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Desvenlafaxine

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Also known as D-venizDesvenlafaxinaKhedezlaMdd-xrNewvenO-desmethylvenlafaxineO-desmethylvenlafaxine (odv)OdvDesvenlafaxine succinateÊDesvenlafaxine succinateÂDESVENLAFAXINE SUCCINATE

Summary

Desvenlafaxine (CHEMBL1118) is an approved small-molecule antidepressant (ATC N06AX23) targeting SLC6A2, SLC6A3, and SLC6A4; indicated across 4 conditions including major depressive disorder and depressive disorder.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N06AX23
  • Targets: 3 (SLC6A2, SLC6A3, SLC6A4)
  • Indications: 4 conditions
  • Clinical trials: 31
  • Chemistry: 263.37 Da · C16H25NO2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1118
NameDesvenlafaxine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID125017
ChEBICHEBI:83527
ATCN06AX23
Molecular formulaC16H25NO2
Molecular weight263.37
InChIKeyKYYIDSXMWOZKMP-UHFFFAOYSA-N

SMILES: CN(C)CC(C1=CC=C(C=C1)O)C2(CCCCC2)O

IUPAC name: 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol

ChEBI definition: A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-hydroxyphenyl group. It is a metabolite of the drug venlafaxine.

Pharmacological roles (ChEBI): antidepressant.

Other ChEBI roles (chemical / environmental): marine xenobiotic metabolite, drug metabolite.

Also known as: D-veniz, Desvenlafaxina, Desvenlafaxine, Khedezla, Mdd-xr, Newven, O-desmethylvenlafaxine, O-desmethylvenlafaxine (odv), Odv, o-desmethylvenlafaxine, DESVENLAFAXINE, Desvenlafaxine succinateÊ

Parent form; salt/anhydrous children: CHEMBL1201728, CHEMBL3989861, CHEMBL5723329

Patent coverage: 1,699 distinct patent families (6,152 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
SLC6A2NETInhibition6.190.4%P23975
SLC6A3DATInhibition6.070.2%Q01959
SLC6A4SERTInhibition7.820.7%P31645

Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Sodium-dependent noradrenaline transporter, Sodium-dependent serotonin transporter, Mu-type opioid receptor, Sodium-dependent dopamine transporter, Sodium-dependent serotonin transporter, Alpha-1A adrenergic receptor.

Bioactivity

ChEMBL activities: 11 potent at pChembl ≥ 5 of 14 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
SLC6A48.39Ki4.1nMCHEMBL_ACT_27603299
SLC6A47.82Ki15nMCHEMBL_ACT_13325670
SLC6A47.77IC5017nMCHEMBL_ACT_13325589
SLC6A47.35AC5044.8nMCHEMBL_ACT_25151160
SLC6A47.28IC5053nMCHEMBL_ACT_18566488
P431407.22IC5060nMCHEMBL_ACT_737822
P316526.75IC50180nMCHEMBL_ACT_737824
SLC6A26.27IC50538nMCHEMBL_ACT_18566490
SLC6A26.17Ki668nMCHEMBL_ACT_27603293
SLC6A25.82IC501500nMCHEMBL_ACT_13325584
SLC6A35.43Ki3726nMCHEMBL_ACT_27603296

Target pathways

Aggregated over 3 target gene(s): SLC6A2, SLC6A3, SLC6A4.

Top Reactome pathways

15 total, by targets touching each:

PathwayTargetsGenes
SLC-mediated transport of neurotransmitters3SLC6A2, SLC6A3, SLC6A4
Neurotransmitter clearance2SLC6A3, SLC6A4
Transmission across Chemical Synapses2SLC6A3, SLC6A4
Neuronal System2SLC6A3, SLC6A4
Disease2SLC6A2, SLC6A3
Transport of small molecules2SLC6A2, SLC6A3
R-HSA-4253662SLC6A2, SLC6A3
SLC-mediated transmembrane transport2SLC6A2, SLC6A3
SLC transporter disorders2SLC6A2, SLC6A3
Disorders of transmembrane transporters2SLC6A2, SLC6A3
Dopamine clearance from the synaptic cleft1SLC6A3
Serotonin clearance from the synaptic cleft1SLC6A4
Defective neurotransmitter clearance by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS)1SLC6A3
Defective SLC6A2 causes orthostatic intolerance (OI)1SLC6A2
Defective transport of neurotransmitters by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS)1SLC6A3

Dominant GO biological processes

GO termTargets
neurotransmitter transport3
amino acid transport3
response to xenobiotic stimulus3
obsolete monoamine transport3
sodium ion transmembrane transport3
transmembrane transport3
dopamine uptake involved in synaptic transmission2
norepinephrine uptake2
neurotransmitter reuptake2
chemical synaptic transmission1
obsolete norepinephrine transport1
response to pain1
neuron cellular homeostasis1
catecholamine uptake1
chloride transmembrane transport1

Indications & clinical

Indications

2 approved indications. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

IndicationPhaseMONDOEFO
major depressive disorder4MONDO:0002009MONDO:0002009
depressive disorder4MONDO:0002050MONDO:0002050

2 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)PhaseMONDOEFO
fibromyalgia2MONDO:0005546EFO:0005687
chronic hepatitis C virus infection2MONDO:0005354EFO:0004220

Clinical trials

Total trials: 31.

Phase distribution

PhaseTrials
PHASE410
Not specified10
PHASE36
PHASE14
PHASE2/PHASE31

Top trials by phase / activity

NCTPhaseStatusTitle
NCT05273996PHASE4ACTIVE_NOT_RECRUITINGPredictors of Cognitive Outcomes in Geriatric Depression
NCT01492621PHASE4UNKNOWNEffect of Antidepressants on White Matter Structure
NCT01537068PHASE4COMPLETEDDesvenlafaxine vs. Placebo Treatment of Chronic Depression
NCT01974934PHASE4UNKNOWNEfficacy and Safety Study of Desvenlafaxine in the Treatment of Vascular Depression
NCT01975480PHASE4COMPLETEDEfficacy of SNRI Treatment on Prefrontality in Patients With GAD and Other Comorbities
NCT02200406PHASE4COMPLETEDDesvenlafaxine in Opioid-Dependent Patients
NCT02330679PHASE4UNKNOWNPrediction of Antidepressant Treatment Response Using Machine Learning Classification Analysis
NCT02819921PHASE4TERMINATEDDesvenlafaxine for Treatment of Hot Flashes in Women With Breast Cancer Taking Tamoxifen
NCT02859103PHASE4COMPLETEDDimensional Approach to Evaluate Reward Processing in Major Depressive Disorder Pre- and Post-Desvenlafaxine Treatment
NCT04448431PHASE4COMPLETEDComparison of Vortioxetine and Desvenlafaxine in Adult Patients Suffering From Depression
NCT00300378PHASE3COMPLETEDStudy Evaluating the Efficacy and Safety of Desvenlafaxine Tablets in Adult Outpatients With Major Depressive Disorder
NCT00888862PHASE3UNKNOWNDesvenlafaxine Succinate (DVS) for Major Depressive Disorder (MDD) in Midlife Men and Women
NCT01309542PHASE3COMPLETEDLong-Term Safety Of DVS-233 SR In Patients With Major Depressive Disorder
NCT01527786PHASE3COMPLETEDFunctional Outcome in Postpartum Depression in Women Treated With Desvenlafaxine
NCT01803711PHASE2/PHASE3TERMINATEDOmega 3 FA Supplements as Augmentation in the Treatment of Depression
NCT04345471PHASE3COMPLETEDA Study of MD-120 in Patients With Depression
NCT04476030PHASE3COMPLETEDA Comparative Study of Sage-217 Plus an Antidepressant (ADT) Versus Placebo Plus an ADT in Adults With Major Depressive Disorder
NCT01101152PHASE1UNKNOWNEffectiveness of the Dual Serotonin Norepinephrine Reuptake Inhibitor Desvenlafaxine Succinate in Healthy Volunteers
NCT01443208PHASE1COMPLETEDPharmacokinetics and Safety of Desvenlafaxine in Korean Healthy Subjects Following Single and Multiple Oral Doses of Desvenlafaxine Succinate Sustained Release Tablet
NCT03155893PHASE1COMPLETEDA Study to Evaluate the Cardiac Safety of a Single Dose of AL-335 Administered on a Background of Simeprevir and Odalasvir and of Repeated Doses of Odalasvir Administered Alone in Healthy Participants
NCT03277755PHASE1WITHDRAWNA Study to Investigate the Pharmacokinetics, Safety, and Tolerability of Odalasvir and AL-335 Alone and in Combination With Simeprevir in Participants With Moderately Impaired Hepatic Function
NCT06049797Not specifiedACTIVE_NOT_RECRUITINGA Study Following Women in Menopause Treated With a Non-hormonal Therapy for Hot Flashes and Night Sweats
NCT07359248Not specifiedACTIVE_NOT_RECRUITINGDesvenlafaxine for Preventive Treatment of Frequent Episodic Tension-type Headache
NCT07385755Not specifiedACTIVE_NOT_RECRUITINGDesvenlafaxine for Preventive Treatment of Frequent Migraines
NCT01353963Not specifiedTERMINATEDDesvenlafaxine Succinate (Pristiq): Postmarketing Surveillance Study Among Filipino Patients
NCT01468610Not specifiedCOMPLETEDNeurocognition and Work Productivity in Major Depressive Disorder (MDD)
NCT01948895Not specifiedCOMPLETEDDesvenlafaxine Monotherapy in Dysthymia
NCT02320240Not specifiedCOMPLETEDSerotonin-norepinephrine Reuptake Inhibitors and Acute Kidney Injury
NCT02893371Not specifiedTERMINATEDLongitudinal Comparative Effectiveness of Bipolar Disorder Therapies
NCT03432221Not specifiedUNKNOWNSwitching From SSRI to Desvenlafaxine on Cognitive Functioning
NCT04446039Not specifiedCOMPLETEDNon-interventional, Retrospective Cohort Study to Explore Antidepressant Treatment in Korea

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (2) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of CPIC Guideline for desvenlafaxine, duloxetine, fluoxetinCPICHTR2A
Annotation of CPIC Guideline for citalopram, desvenlafaxine, duloxetinCPICSLC6A4

PharmGKB also curates 0 clinical and 17 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

664 molecules share ≥1 primary target. Top 100 by shared-target count:

MoleculeSourceStatusShared targets
AfatinibChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
AMITRIPTYLINEChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
GENTIAN VIOLETChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
IdelalisibChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
OlodaterolChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
PIMAVANSERINChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
REGORAFENIBChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
TadalafilChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
TAFENOQUINEChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
UMECLIDINIUMChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
VORAPAXARChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ACETOPHENAZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
AMIODARONEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
AMOXAPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ARIPIPRAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ASENAPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ASTEMIZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ATOMOXETINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
AZELASTINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BAZEDOXIFENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BENFLUOREXChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BENZPHETAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BENZTROPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BENZYDAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BEPRIDILChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BOSUTINIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BREXPIPRAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BROMHEXINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BROMODIPHENHYDRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BROMPERIDOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BROMPHENIRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
BUPROPIONChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CABERGOLINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CALCITRIOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CARBINOXAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CARVEDILOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CELECOXIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CETIRIZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORHEXIDINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORPHENIRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORPHENTERMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORPROMAZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CHLORPROTHIXENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CINACALCETChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CINNARIZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CITALOPRAMChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CLEMASTINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CLOMIPHENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CLOMIPRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CLOTRIMAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
COBIMETINIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
COCAINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
CYPROHEPTADINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DANAZOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DAUNORUBICINChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DEQUALINIUMChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DESIPRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DESLORATADINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DESOGESTRELChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DEXBROMPHENIRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DEXCHLORPHENIRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DEXTROAMPHETAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DIPHENHYDRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DOBUTAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DOMPERIDONEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DOTHIEPINChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DOXAZOSINChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DRONEDARONEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
DULOXETINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
EBASTINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ECONAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
EPALRESTATChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ERDAFITINIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ETHINYL ESTRADIOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
FEDRATINIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
FENOLDOPAMChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
FENOTEROLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
FIPEXIDEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
FLUOXETINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
FLUPHENAZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
FLUSPIRILENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
FLUVOXAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
GUANABENZChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
HALOPERIDOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
HALOPROGINChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
HEXAFLUORENIUMChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
HEXETIDINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
IDARUBICINChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ILOPERIDONEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
IMIPRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
INDACATEROLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
INDOCYANINE GREEN ACID FORMChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
ISOCONAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
KETOCONAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
LABETALOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
LASOFOXIFENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
LEVOMILNACIPRANChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4
LOFEPRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3, SLC6A4

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.4
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot