Venlafaxine besylate monohydrateProduct ingredient for Venlafaxine

Name
Venlafaxine besylate monohydrate
Drug Entry
Venlafaxine

Venlafaxine is an antidepressant and a serotonin and norepinephrine reuptake inhibitor (SNRI). Its active metabolite, desvenlafaxine, works by blocking the reuptake of serotonin and norepinephrine, which are key neurotransmitters in mood regulation. Venlafaxine is officially approved to treat major depressive disorder (MDD), generalized anxiety disorder (GAD), social anxiety disorder, and panic disorder in adults.17 The immediate formulation of the drug, marketed as Effexor, was first approved by the FDA in 1993 and the extended-release formulation, Effexor XR, was later introduced in 1997.11

Venlafaxine has been used as a first-line treatment for MDD, GAD, social anxiety disorder, and panic disorder in Canada for many years. It was also considered a second-line treatment for obsessive-compulsive disorder (OCD).2,5 Venlafaxine was also investigated in off-label uses for the prophylaxis of migraine headaches,1,3 for reduction of vasomotor symptoms associated with menopause,6 and for the management of neuropathic pain (although there is only minimal evidence of efficacy for this condition).4

Accession Number
DBSALT003481
Structure
Synonyms
CYCLOHEXANOL, 1-(2-(DIMETHYLAMINO)-1-(4-METHOXYPHENYL)ETHYL)-, BENZENESULFONATE (SALT), MONOHYDRATE / CYCLOHEXANOL, 1-(2-(DIMETHYLAMINO)-1-(4-METHOXYPHENYL)ETHYL)-, BENZENESULFONATE, HYDRATE (1:1:1)
UNII
18XP3YT5NH
CAS Number
609345-59-7
Weight
Average: 453.59
Monoisotopic: 453.218509025
Chemical Formula
C23H35NO6S
InChI Key
XHPQSXIKZWZGIP-UHFFFAOYSA-N
InChI
InChI=1S/C17H27NO2.C6H6O3S.H2O/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14;7-10(8,9)6-4-2-1-3-5-6;/h7-10,16,19H,4-6,11-13H2,1-3H3;1-5H,(H,7,8,9);1H2
IUPAC Name
1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol benzenesulfonic acid hydrate
SMILES
O.OS(=O)(=O)C1=CC=CC=C1.COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1
ChemSpider
68007187
Predicted Properties
PropertyValueSource
logP2.74Chemaxon
pKa (Strongest Acidic)14.42Chemaxon
pKa (Strongest Basic)9.01Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area32.7 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity83.02 m3·mol-1Chemaxon
Polarizability32.33 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleYesChemaxon