Hmdb loader
Read more...Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-10-17 08:44:13 UTC
Update Date2022-09-22 17:43:53 UTC
HMDB IDHMDB0005016
Secondary Accession Numbers
  • HMDB05016
Metabolite Identification
Common NameVenlafaxine
Description
Structure
Thumb
Synonyms
Chemical FormulaC17H27NO2
Average Molecular Weight277.4018
Monoisotopic Molecular Weight277.204179113
IUPAC Name1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
Traditional Namevenlafaxine
CAS Registry Number93413-69-5
SMILES
COC1=CC=C(C=C1)C(CN(C)C)C1(O)CCCCC1
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 KeyPNVNVHUZROJLTJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point74 - 76 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM171.630932474
[M+H]+Not Available169.891http://allccs.zhulab.cn/database/detail?ID=AllCCS00000862
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Brain
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.0 (0.02-4.5) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5454
KEGG Compound IDC07187
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVenlafaxine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID9943
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHusbands, George Edward Morris; Yardley, John Patrick; Muth, Eric Anthony. Phenethylamine derivatives and intermediates. Eur. Pat. Appl. (1984), 58 pp. CODEN: EPXXDW EP 112669 A2 19840704 CAN 102:5895 AN 1985:5895
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fogelman SM, Schmider J, Venkatakrishnan K, von Moltke LL, Harmatz JS, Shader RI, Greenblatt DJ: O- and N-demethylation of venlafaxine in vitro by human liver microsomes and by microsomes from cDNA-transfected cells: effect of metabolic inhibitors and SSRI antidepressants. Neuropsychopharmacology. 1999 May;20(5):480-90. [PubMed:10192828 ]
  2. Saletu B, Grunberger J, Anderer P, Linzmayer L, Semlitsch HV, Magni G: Pharmacodynamics of venlafaxine evaluated by EEG brain mapping, psychometry and psychophysiology. Br J Clin Pharmacol. 1992 Jun;33(6):589-601. [PubMed:1389931 ]
  3. Degner D, Grohmann R, Kropp S, Ruther E, Bender S, Engel RR, Schmidt LG: Severe adverse drug reactions of antidepressants: results of the German multicenter drug surveillance program AMSP. Pharmacopsychiatry. 2004 Mar;37 Suppl 1:S39-45. [PubMed:15052513 ]
  4. Invernizzi RW, Garattini S: Role of presynaptic alpha2-adrenoceptors in antidepressant action: recent findings from microdialysis studies. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Aug;28(5):819-27. [PubMed:15363606 ]
  5. Wikell C, Eap CB, Josefsson M, Apelqvist G, Ahlner J, Baumann P, Bengtsson F: Disposition of venlafaxine enantiomers in rats with hepatic encephalopathy after chronic drug treatment. Chirality. 2002 May 5;14(4):347-50. [PubMed:11968077 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6

Transporters

General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165