Venlafaxine Hydrochloride

HCID 62923CAS 99300-78-4

Grundinformationen

Standard-SMILES
COc1ccc(C(CN(C)C)C2(O)CCCCC2)cc1.Cl
InChIKey
QYRYFNHXARDNFZ-UHFFFAOYSA-N
Summenformel
C17H28ClNO2
Durchschnittliche Molmasse
313,9 g/mol
Monoisotopische Masse
313,18085682

Überblick

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)

Namen und Bezeichner

Bevorzugter Name
Venlafaxine Hydrochloride
IUPAC
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol;hydrochloride
Englischer Name
Venlafaxine hydrochloride
Summenformel
C17H28ClNO2
Molmasse
313.86

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
32,7 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
5
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Schmelzpunkt
207 · 207-209°C
Flammpunkt
9 ℃ · 9℃
storage temp.
2 · 2-8°C
Löslichkeit
2 O: · H2O: >10mg/mL
Aggregatzustand
powder
Farbe
white

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (15.9%)

Toxikologische Informationen

Treatment · 1 Eintrag

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 Eintrag

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 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Venlafaxine hydrochloride

vLess-DILI-concern

7

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Sicherheitsdaten

wgk
3
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29225090
RTECS-Nr.
GV8872760
risk_code
36/37/38-36-39/23/24/25-23/24/25-11
hazard_code
Xi,T,F

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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 Einträge

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 Einträge

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.

Verwendung und Herstellung

Uses · 1 Eintrag

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.

Anwendungen · 2 Einträge

BeschreibungVenlafaxine 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.

VerwendenA selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant

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