Showing Compound Venlafaxine (FDB023588)

Record Information

Version

1.0

Creation date

2011-09-21 00:32:02 UTC

Update date

2015-10-09 22:33:06 UTC

Primary ID

FDB023588

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Venlafaxine

Description

Venlafaxine is an effective antidepressant for many persons; Venlafaxine is a bicyclic antidepressant, and is usually categorized as a serotonin-norepinephrine reuptake inhibitor (SNRI), but it has been referred to as a serotonin-norepinephrine-dopamine reuptake inhibitor. It works by blocking the transporter reuptake proteins for key neurotransmitters affecting mood, thereby leaving more active neurotransmitter in the synapse. The neurotransmitters affected are serotonin (5-hydroxytryptamine) and norepinephrine (noradrenaline) Additionally, in high doses it weakly inhibits the reuptake of dopamine; A comparison of adverse event rates in a fixed dose study comparing venlafaxine 75, 225, and 375 mg/day with placebo revealed a dose dependency for some of the more common adverse events associated with venlafaxine use. The rule for including events was to enumerate those that occurred at an incidence of 5% or more for at least one of the venlafaxine groups and for which the incidence was at least twice the placebo incidence for at least one venlafaxine group. Tests for potential dose relationships for these events (Cochran-Armitage Test, with a criterion of exact 2-sided p-value <= 0.05) suggested a dose-dependency for several adverse events in this list, including chills, hypertension, anorexia, nausea, agitation, dizziness, somnolence, tremor, yawning, sweating, and abnormal ejaculation.[Wyeth Monograph]; Venlafaxine is an effective anti-depressant for many persons; however, it seems to be especially effective for those with treatment resistant depression. Some of these persons have taken two or more antidepressants prior to venlafaxine with no relief. Patients suffering with severe long-term depression typically respond better to venlafaxine than other drugs. However, venlafaxine has been reported to be more difficult to discontinue than other antidepressants. In addition, a September 2004 Consumer Reports study ranked venlafaxine as the most effective among six commonly prescribed antidepressants. However, this should not be considered a definitive finding, since responses to psychiatric medications can vary significantly from individual to individual; however, it seems to be especially effective for those with treatment-resistant depression. Some of these persons have taken two or more antidepressants prior to venlafaxine with no relief. Patients suffering with severe long term depression typically respond better to venlafaxine than other drugs. However, venlafaxine has been reported to be more difficult to discontinue than other antidepressants. In addition, a September 2004 Consumer Reports study ranked venlafaxine as the most effective among six commonly prescribed antidepressants. However, this should not be considered a definitive finding, since responses to psychiatric medications can vary significantly from individual to individual; Venlafaxine hydrochloride is a prescription antidepressant that belongs to the class of antidepressants called serotonin-norepinephrine reuptake inhibitors (SNRI). The chemical structure of venlafaxine is designated (R/S)-1-[2-(dimethylamino)-1-(4 methoxyphenyl)ethyl] cyclohexanol hydrochloride or (+/-)-1-[alpha [alpha- (dimethylamino)methyl] p-methoxybenzyl] cyclohexanol hydrochloride and it has the empirical formula of C17H27NO2. It is a white to off-white crystalline solid. Venlafaxine is structurally and pharmacologically related to the analgesic tramadol, but not to any of the conventional antidepressant drugs, including tricyclic antidepressants, SSRIs, MAOIs, or reversible inhibitors of monoamine oxidase (RIMAs); A Black Box Warning has been issued with Effexor and with other SSRI and SNRI anti-depressants advising of risk of suicide. Thoughts of suicide (suicide ideation) as potential risk of suicide as shown in studies by Wyeth and reported on their datasheet for effexor were twice that of placebo (4% compared to 2%, however, no suicides occurred in these trials). The black box warnings advise physicians to carefully monitor patients for suicide risk at start of usage and whenever the dosage is changed. There is an additional risk if a physician misinterprets patient expression of adverse effects such as panic or akithesia. Careful assessment of patient history and comorbid risk factors such as drug abuse are essential in evaluating the safety of Effexor for individual patients. These cautions are emphasized in Wyeth's detailed information sheet with special precautions if prescribed to children. The extent of this effect and the actual risk are not known as studies may exclude individuals with higher risk. This is another reason why careful patient monitoring at start of use of this medication, as well as at any change of dosage is emphasized. Another risk is Serotonin syndrome. This is a serious effect that can be caused by interactions with other drugs and is potentially fatal. This risk necessitates clear information to patients and proper medical history. For example, the drug abuse by at risk patients of certain non-prescription drugs can cause this serious effect and emphasizes the importance of good medical history sharing between General Practitioners and Psychiatrists as both may prescribe Venlafaxine. Involvement of family in awareness of risk factors is highlighted in Wyeth information sheets on Effexor; The chemical structure of venlafaxine is designated (R/S)-1-[2-(dimethylamino)-1-(4 methoxyphenyl)ethyl] cyclohexanol hydrochloride or (+/-)-1-[alpha [alpha- (dimethylamino)methyl] p-methoxybenzyl] cyclohexanol hydrochloride and it has the empirical formula of C17H27NO2. It is a white to off-white crystalline solid. Venlafaxine is structurally and pharmacologically related to the analgesic tramadol, but not to any of the conventional antidepressant drugs, including tricyclic antidepressants, SSRIs, MAOIs, or reversible inhibitors of monoamine oxidase (RIMAs); Venlafaxine is used primarily for the treatment of depression, generalized anxiety disorder, obsessive compulsive disorder, social anxiety disorder, and panic disorder in adults. It is also used for other general depressive disorders. Although it is not approved for use in children or adolescents, there is a considerable information by Wyeth on cautions if presecribed to this age group. Venlafaxine hydrochloride is a prescription antidepressant first introduced by Wyeth in 1993. It belongs to class of antidepressants called serotonin-norepinephrine reuptake inhibitors (SNRI). As of August 2006, generic venlafaxine is available in the United States. It was previously available only under the brand names Effexor and Effexor XR. [HMDB]

CAS Number

93413-69-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Elafax	ChEBI
Venlafaxina	ChEBI
Venlafaxinum	ChEBI
Efectin	Kegg
Efexor	HMDB, MeSH
Effexor	HMDB, MeSH
Trevilor	HMDB, MeSH
Venlafaxin	HMDB
Venlafexine	HMDB
Cyclohexanol, 1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)-, hydrochloride	MeSH, HMDB
Hydrochloride, venlafaxine	MeSH, HMDB
1-(2-(dimethylamino)-1-(4-Methoxyphenyl)ethyl)cyclohexanol HCL	MeSH, HMDB
Dobupal	MeSH, HMDB
Sila venlafaxine	MeSH, HMDB
Vandral	MeSH, HMDB
Sila-venlafaxine	MeSH, HMDB
Venlafaxine hydrochloride	MeSH, HMDB

Predicted Properties

Property	Value	Source
Water Solubility	0.23 g/L	ALOGPS
logP	2.69	ALOGPS
logP	2.74	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.42	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.7 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.02 m³·mol⁻¹	ChemAxon
Polarizability	32.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H27NO2

IUPAC name

1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol

InChI Identifier

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

InChI Key

PNVNVHUZROJLTJ-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1

Average Molecular Weight

277.4018

Monoisotopic Molecular Weight

277.204179113

Classification

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Anisole
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Cyclohexanol
Monocyclic benzene moiety
1,3-aminoalcohol
Tertiary alcohol
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Amine
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary alcohol (CHEBI:9943 )
tertiary amino compound (CHEBI:9943 )
monomethoxybenzene (CHEBI:9943 )
cyclohexanols (CHEBI:9943 )

Ontology

Physiological effect

Health effect:

Health condition:

Psychiatric disorders:

Depression

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Endogenous

Environmental:

Wastewater

Biological location:

Organ and components:

Subcellular:

Biofluid and excreta:

Role

Environmental role:

Environmental contaminant

Industrial application:

Drug

Pharmaceutical industry:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Venlafaxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9110000000-10fdc1f0eb77f9e8ed4e	Spectrum
Predicted GC-MS	Venlafaxine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-9512000000-579bd169c5d6903163c2	Spectrum
Predicted GC-MS	Venlafaxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Venlafaxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Venlafaxine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0090000000-d413fb5f16658fcc5acb	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-0090000000-182f1032c3f72220679d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00dj-0910000000-c7a4a25a9bc95faa6db1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-7be3d65db3af35be404e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-615322444dcf11a7fb8d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0090000000-d212108d9a8267ed7dad	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0090000000-0c4e12d13e69311b26bf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0bvi-4090000000-8bf2805a95084bfd952a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-9520000000-de599153aa118f97ad81	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ab9-8900000000-6e9f54b654899b486e4d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ab9-9800000000-d762b2d7edeba1e12b28	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ab9-9700000000-2b8ebcefcf1274550d32	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0090000000-c592b4ae2ead9b2bb7ea	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0bvi-4090000000-30b9b5dca017215ebaa4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0a4i-9620000000-ab905f15470a13b750c5	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ab9-8900000000-52ec7a86d35dbbd47681	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ab9-9800000000-7a7cc5b11e1a30499063	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0ab9-9700000000-062f05f9fe2a1540985c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-03di-0090000000-8eb971c1dc9a14696c31	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-0090000000-479240d2112a5b71fa58	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02w9-4190000000-4942ed295b70fa38aa2a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldl-9030000000-2af1eebea0622a8f7757	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-99e5b56ecf6f61518e30	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1390000000-58c1f11113a0c69c42d9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03dl-6930000000-bcbc7b00748a2c2bec30	2016-08-03	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum