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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 279
Experimentelle und physikochemische Eigenschaften
Human Drugs
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
- Wasserlöslichkeit
- 100 mMDMSO: · water: 100mMDMSO: 50mM
- Merck
- 14 · 14,9946
- BCS Class
- 1 · 1
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C17H27NO2.ClH/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;1H
- InChIKey
- QYRYFNHXARDNFZ-UHFFFAOYSA-N
- SMILES
- OC1(CCCCC1)C(C1=CC=C(OC)C=C1)CN(C)C.[H]Cl
- CAS Datenbank
- 99300 · 99300-78-4(CAS DataBase Reference)
- EPA chemische Informationen
- 1 · Cyclohexanol, 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]-, hydrochloride (1:1 (99300-78-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
Toxikologische Informationen
Treatment
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)
Toxicity Summary
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.
Drug Induced Liver Injury
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
- safety_code
- 26-37/39-45-36/37-16-7
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Aquatic Chronic 2
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
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
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
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
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
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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