General
Preferred name
VENLAFAXINE
Synonyms
VENLAFAXINE HYDROCHLORIDE ()
Effexor ()
Wy 45030 hydrochloride ()
Venlafaxine HCl ()
WY-45030 ()
Wy 45030 ()
Venlafaxine hydrochloride93413-69-5 ()
Venlafaxine (hydrochloride) ()
Wy 453 HCl ()
WY-45,030 ()
Venlafaxine (as hydrochloride) ()
Effexor Xr ()
NSC-745751 ()
Bonilux XL ()
Mentaven XL ()
Efexor XL ()
Venaxx XL ()
Efectin ()
Winfex XL ()
Kanghong ()
Vaxalin XL ()
Ranfaxine XL ()
Alventa XL ()
Velafax ()
Tardcaps XL ()
Tifaxin XL ()
Venladex XL ()
Venlor ()
Depefex XL ()
Sunveniz XL ()
NSC-758676 ()
Venlablue XL ()
Amphero XL ()
Politid XL ()
Trixat XL ()
Trevilor ()
Rodomel XL ()
Vensir XL ()
Venlaneo XL ()
Viepax ()
Efexor ()
Foraven XL ()
Vexarin XL ()
Venlafaxina ()
Venlalic XL ()
Tonpular XL ()
ViePax XL ()
Venlafaxine besylate anhydrous ()
VENLAFAXINE BESYLATE ()
Venlafaxine-d6 (hydrochloride) ()
Venlafaxine-d6 (hydrochloride) (CRM) ()
Venlafaxine (hydrochloride) (CRM) ()
P&D ID
PD010124
CAS
99300-78-4
93413-69-5
540726-98-5
1062606-12-5
Tags
available
drug
Approved by
FDA
First approval
1993
2022
Drug indication
Depression
Antidepressant
Drug Status
approved
Max Phase
4.0
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS
The mechanism of venlafaxine's (and its metabolite, O-desmethylvenlafaxine (ODV)) antidepressant effect is believed to be due to their potentiation of neurotransmitter activity in the central nervous system through the inhibition of the reuptake of serotonin and norepinephrine from within the synapse. Venlafaxine has also been shown to weakly inhibit dopamine reuptake. Neither venlafaxine nor ODV bind to muscarinic, histaminergic, or alpha-1 adrenergic receptors[FDA Label]; pharmacologic activity at these receptors is hypothesized to be associated with the various anticholinergic, sedative, and cardiovascular effects seen with other psychotropic drugs. Hyponatremia has also been shown to occur as a result of treatment with SNRIs, and is associated with the development of the syndrome of inappropriate antidiuretic hormone secretion (SIADH) [FDA Label, A177244]. Venlafaxine also demonstrates a clinically significant and dose-related effect on blood pressure,, likely due to its potentiation of norepinephrine [FDA Label, A177250].
ABSORPTION
Venlafaxine is well absorbed, with at least 92% of a single dose absorbed on the basis of mass balance studies [FDA Label]. Food does not affect the absorption of venlafaxine or its subsequent metabolism into ODV. Bioavailability is 45% following oral administration.; Time to steady state = 3 days.
MOA
The exact mechanism of action of venlafaxine is unknown, but appears to be associated with the potentiation of neurotransmitter activity in the CNS. Venlafaxine and its active metabolite, O-desmethylvenlafaxine (ODV), inhibit the reuptake of both serotonin and norepinephrine with a potency greater for the 5-HT than for the NE reuptake process [A27600]. Both venlafaxine and the ODV metabolite have weak inhibitory effects on the reuptake of dopamine but, unlike the tricyclics and similar to SSRIs, they are not active at histaminergic, muscarinic, or alpha(1)-adrenergic receptors.
INDICATION
Venlafaxine is indicated in the management of major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder (social phobia), and panic disorder with or without agoraphobia. Venlafaxine is also used off-label for prophylaxis of migraine headaches [A177229], for reduction of vasomotor symptoms associated with menopause [A177238], and for management of neuropathic pain (although there is only minimal evidence of efficacy for this condition) [A177232]. It is also considered a second-line option for management of obsessive-compulsive disorder (OCD) [A177226, A177235].
TOXICITY
Overdose of venlafaxine is typically associated with mild symptoms. However, severe toxicity is reported with the most common symptoms being CNS depression, serotonin toxicity, seizure, or cardiac conduction abnormalities. Venlafaxine's toxicity appears to be higher than other SSRIs, with a fatal toxic dose closer to that of the tricyclic antidepressants than the SSRIs. Doses of 900 mg or more are likely to cause moderate toxicity. Deaths have been reported following large doses.
METABOLISM
Undergoes extensive first pass metabolism in the liver to its major, active metabolite, O-desmethylvenlafaxine ODV, and two minor, less active metabolites, N-desmethylvenlafaxine and N,O-didesmethylvenlafaxine. Formation of ODV is catalyzed by cytochrome P450 (CYP) 2D6, whereas N-demethylation is catalyzed by CYP3A4, 2C19 and 2C9. ODV possesses antidepressant activity that is comparable to that of venlfaxine.
DESCRIPTION
Venlafaxine is a selective serotonin-norepinephrine reuptake inhibitor (SNRI); a bicyclic antidepressant. Venlafaxine is a racemic mixture of R (PubChem CID 9795623) and S (PubChem CID 11846746) stereoisomers, which have assay data in PubChem but its is unclear if these apply to the experimentally separated forms. Marketed formulations may contain venlafaxine hydrochloride (PubChem CID 62923).
The major active metabolite of venlafaxine, (O-desmethylvenlafaxine) has also been developed as a drug. (GtoPdb)
The major active metabolite of venlafaxine, (O-desmethylvenlafaxine) has also been developed as a drug. (GtoPdb)
DESCRIPTION
Equilibrative nucleoside transporter 1 (ENT1) inhibitor
(Tocris Bioactive Compound Library)
DESCRIPTION
Dual serotonin/noradrenalin re-uptake inhibitor
(Tocriscreen Plus)
DESCRIPTION
Dual serotonin and norepinephrine reuptake inhibitor. Antidepressant.
(LOPAC library)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
30
Axon Medchem Screening Library
ChEMBL Approved Drugs
ChEMBL Drugs
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
EU-OPENSCREEN Bioactive Compound Library
Guide to Pharmacology
Ki Database
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
NIH Clinical Collections (NCC)
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
Tocris Bioactive Compound Library
Tocriscreen Plus
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
70
Molecular Weight
277.2
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
2
Aromatic Ring Count
1
cLogP
3.04
TPSA
32.7
Fraction CSP3
0.65
Chiral centers
1.0
Largest ring
6.0
QED
0.9
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
Transporters
Selectivity
5-HT and NE
Pathway
GPCR/G protein
Neuroscience
Neuronal Signaling
Target
5-HT
SNRI
Serotonin Transporter
Primary Target
5-HT Transporters
MOA
Inhibitor
5-HT Reuptake Inhibitors
Norepinephrine Reuptake Inhibitors
Member status
member
Therapeutic Indication
Antidepressant
Therapeutic Class
CNS & PNS
Antidepressants
Source data
