CHEBI:9943 - venlafaxine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name venlafaxine
ChEBI ID CHEBI:9943
Definition A tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-methoxyphenyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB2724915, eMolecules:509860, ZINC000000097471
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Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin–norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic disorder, and social anxiety disorder. Studies have shown that venlafaxine improves post-traumatic stress disorder (PTSD). It may also be used for chronic neuropathic pain. It is taken orally (swallowed by mouth). It is also available as the salt venlafaxine besylate (venlafaxine benzenesulfonate monohydrate) in an extended-release formulation (Venbysi XR). Common side effects include loss of appetite, constipation, dry mouth, dizziness, sweating, insomnia, drowsiness and sexual problems. Severe side effects include an increased risk of suicide, mania, and serotonin syndrome. Antidepressant withdrawal syndrome may occur if stopped. There are concerns that use during the later part of pregnancy can harm the baby. How it works is not entirely clear, but it seems to be related to the potentiation of the activity of some neurotransmitters in the brain. Venlafaxine was approved for medical use in the United States in 1993. It is available as a generic medication. In 2022, it was the 44th most commonly prescribed medication in the United States, with more than 13 million prescriptions.
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Formula C17H27NO2
Net Charge 0
Average Mass 277.40182
Monoisotopic Mass 277.20418
InChI InChI=1S/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3
InChIKey PNVNVHUZROJLTJ-UHFFFAOYSA-N
SMILES COc1ccc(cc1)C(CN(C)C)C1(O)CCCCC1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
dopamine uptake inhibitor
A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
dopamine uptake inhibitor
A dopaminergic agent that blocks the transport of dopamine into axon terminals or into storage vesicles within terminals. Most of the adrenergic uptake inhibitors also inhibit dopamine uptake.
analgesic
An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
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ChEBI Ontology
Outgoing venlafaxine (CHEBI:9943) has role adrenergic uptake inhibitor (CHEBI:35640)
venlafaxine (CHEBI:9943) has role analgesic (CHEBI:35480)
venlafaxine (CHEBI:9943) has role antidepressant (CHEBI:35469)
venlafaxine (CHEBI:9943) has role dopamine uptake inhibitor (CHEBI:51039)
venlafaxine (CHEBI:9943) has role environmental contaminant (CHEBI:78298)
venlafaxine (CHEBI:9943) has role serotonin uptake inhibitor (CHEBI:50949)
venlafaxine (CHEBI:9943) has role xenobiotic (CHEBI:35703)
venlafaxine (CHEBI:9943) is a cyclohexanols (CHEBI:23480)
venlafaxine (CHEBI:9943) is a monomethoxybenzene (CHEBI:25235)
venlafaxine (CHEBI:9943) is a tertiary alcohol (CHEBI:26878)
venlafaxine (CHEBI:9943) is a tertiary amino compound (CHEBI:50996)
Incoming venlafaxine hydrochloride (CHEBI:9944) has part venlafaxine (CHEBI:9943)
IUPAC Name
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol
INNs Sources
venlafaxina WHO MedNet
venlafaxine WHO MedNet
venlafaxine ChemIDplus
venlafaxinum WHO MedNet
Synonyms Sources
Elafax ChemIDplus
Venlafaxine KEGG COMPOUND
Manual Xrefs Databases
2813 DrugCentral
C07187 KEGG COMPOUND
D08670 KEGG DRUG
DB00285 DrugBank
HMDB0005016 HMDB
LSM-1616 LINCS
Venlafaxine Wikipedia
View more database links
Registry Numbers Types Sources
4234848 Reaxys Registry Number Reaxys
93413-69-5 CAS Registry Number KEGG COMPOUND
93413-69-5 CAS Registry Number ChemIDplus
Citations Types Sources
11098420 PubMed citation Europe PMC
12409680 PubMed citation Europe PMC
18321472 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag