Venlafaxine Hydrochloride

HCID 62923

Basic information

CAS
99300-78-4
Standard SMILES
COc1ccc(C(CN(C)C)C2(O)CCCCC2)cc1.Cl
InChIKey
QYRYFNHXARDNFZ-UHFFFAOYSA-N
Molecular formula
C17H28ClNO2
Average molar mass
313.9 g/mol
Monoisotopic mass
313.18085682

Overview

Venlafaxine Hydrochloride is a synthetic ethyl-cyclohexanol derivative used for the treatment of depression, Venlafaxine Hydrochloride is metabolized to O-desmethylvenlafaxine, which potentiates CNS activity. Both venlafaxine and its active metabolite inhibit neuronal reuptake of norepinephrine, dopamine, and serotonin. (NCI04)

Names & identifiers

Preferred name
Venlafaxine Hydrochloride
IUPAC
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol;hydrochloride
English name
Venlafaxine hydrochloride
Molecular formula
C17H28ClNO2
Molecular weight
313.86

Names & synonyms

Venlafaxine hydrochloride99300-78-4VENLAFAXINE HClEffexor XRWy-45030VandralWy 450301-(2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol hydrochlorideWy-45,030DTXSID80473977D7RX5A8MO1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride
Show more names
D,L-VENLAFAXINED,L-VENLAFAXINE, HYDROCHLORIDEVexorVenliftAKOS 92111VENLAFAXINEHCLVenlaffaxine HCLVenlafaxine HCL APIVENLAFAXINE HCI, 99%
NSC-745751Venlafaxine (as hydrochloride)DTXCID6027397Cyclohexanol, 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)-, hydrochlorideCHEBI:9944Sila VenlafaxineVenlafaxine HCL ERRefChem:56206

Database identifiers

CAS
99300-78-4
PubChem CID
62923
DTXSID
DTXSID8047397
ChEMBL
CHEMBL1201066
UNII
7D7RX5A8MO
EC Number
619-421-1

Properties

Computed structural properties

Topological polar surface area
32.7 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
5
Heavy atoms
21

Experimental & physicochemical properties

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physicochemical properties

Melting point
207 · 207-209°C
Flash point
9 ℃ · 9℃
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: >10mg/mL
form
powder
color
white

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.9% (1 of 113) of reports.

Warning

H302 (15.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 113 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (15.9%)

Toxicology

Treatment · 1 item

Treatment should consist of those general measures employed in the management of overdosage with any antidepressant. Ensure an adequate airway, oxygenation, and ventilation. Monitor cardiac rhythm and vital signs. General supportive and symptomatic measures are also recommended. Induction of emesis is not recommended. Gastric lavage with a large bore orogastric tube with appropriate airway protection, if needed, may be indicated if performed soon after ingestion or in symptomatic patients. Activated charcoal should be administered. Due to the large volume of distribution of this drug, forced diuresis, dialysis, hemoperfusion, and exchange transfusion are unlikely to be of benefit. No specific antidotes for venlafaxine are known. (L1712)

Exposure RoutesOral. Venlafaxine is well absorbed. Food does not effect the absorption of venlafaxine or its subsequent metabolism into ODV. Bioavailability is 45% following oral administration. Time to steady state = 3 days.
Toxicity Summary · 1 item

The exact mechanism of action of venlafaxine is unknown, but appears to be associated with the its potentiation of neurotrasmitter 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. 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.

Signs and SymptomsMost patients overdosing with venlafaxine develop only mild symptoms. However, severe toxicity is reported with the most common symptoms being CNS depression, serotonin toxicity, seizure, or cardiac conduction abnormalities.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Venlafaxine hydrochloride

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk
3
rtecs
GV8872760
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29225090
risk_code
36/37/38-36-39/23/24/25-23/24/25-11
Signal word
Danger

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Undergoes extensive first pass metabolism in the liver to its major, active metabolite, 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. Route of Elimination: Renal elimination of venlafaxine and its metabolites is the primary route of excretion. Approximately 87% of a venlafaxine dose is recovered in the urine within 48 hours as either unchanged venlafaxine (5%), unconjugated ODV (29%), conjugated ODV (26%), or other minor inactive metabolites (27%). Half Life: 5 hours

FDA Pharmacological Classification · 6 items

VENLAFAXINE HCL

Norepinephrine Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Serotonin Uptake Inhibitors [MoA]

VENLAFAXINE HCL ER

Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Norepinephrine Uptake Inhibitors [MoA]

VENLAFAXINE HYDROCHLORIDE

Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Norepinephrine Uptake Inhibitors [MoA]

MeSH Pharmacological Classification · 2 items

Drugs that selectively block or suppress the plasma membrane transport of SEROTONIN and NORADRENALINE into axon terminals and are used as ANTIDEPRESSIVE AGENTS.

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake.

Uses & manufacturing

Uses · 1 item

For the management of major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder (social phobia), panic disorder with or without agoraphobia, vasomotor symptoms in women with breast cancer and in postmenopausal women, and neuropathic pain.

Applications · 5 items

DescriptionVenlafaxine hydrochloride, a novel phenethylamine derivative, was introduced in the U.S.A. as an antidepressant. Venlafaxine is reported to be the first in the class of the second-generation of antidepressants with dual serotonidnorepinephrine reuptake inhibitory activity. Venlafaxine lacks any affinity for muscarinic, cholinergic, histaminergic and noradrenergic receptors and therefore, has an unusually favorable side effect profile compared with classical tricyclic antidepressants and shows less cardiotoxicity. In addition, venlafaxine has a rapid onset of action that makes it unique among the antidepressant agents. Other indications for venlafaxine include the treatment of obsessive and panic disorders, and obesity. Both enantiomers of venlafaxine were reported to have similar biological activity.

UsesA selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant

UsesAn inhibitor of ST and SLC6A2.

UsesVenlafaxine hydrochloride is an inhibitor of reuptake of both serotonin (IC50 = 0.21 μM) and norepinephrine (IC50 = 0.64 μM). It is effective in vitro and in vivo and against human as well as rat receptors. As an antidepressant, it is properly placed in the serotonin-norepinephrine reuptake inhibitor class.[Cayman Chemical]

General DescriptionA Certified Snap-N-Spike Solution suitable for many LC/MS and GC/MS applications from forensic or clinical toxicology analysis to urine drug testing. Also known by the brand name Effexor, venlafaxine is an SNRI antidepressant approved for the treatment of major depressive and general anxiety disorders.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Related reactions

12 records

Compound notes

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