Desvenlafaxine (CHEM022356)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:29:46 UTC
Update Date2016-11-09 01:17:28 UTC
Accession NumberCHEM022356
Identification
Common NameDesvenlafaxine
ClassSmall Molecule
DescriptionA tertiary amino compound that is N,N-dimethylethanamine substituted at position 1 by a 1-hydroxycyclohexyl and 4-hydroxyphenyl group. It is a metabolite of the drug venlafaxine.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-[2-(Dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanolChEBI
4-[2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenolChEBI
KhedezlaKegg
O-Desmethylvenlafaxine succinateHMDB
4-(2-(Dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenolHMDB
Succinate, desvenlafaxineHMDB
2-(1-Hydroxycyclohexyl)-2-((4-hydroxyphenyl)ethyl)dimethylammonium 3-carboxypropanoate monohydrateHMDB
O DesmethylvenlafaxineHMDB
O Desmethylvenlafaxine succinateHMDB
O-Desmethylvenlafaxine succinate monohydrateHMDB
Succinate, O-desmethylvenlafaxineHMDB
Desvenlafaxine succinateHMDB
Monohydrate, O-desmethylvenlafaxine succinateHMDB
O Desmethylvenlafaxine succinate monohydrateHMDB
O-DesmethylvenlafaxineHMDB
PristiqHMDB
Succinate monohydrate, O-desmethylvenlafaxineHMDB
O-DesvenlafaxineHMDB
DesvenlafaxineChEBI
Chemical FormulaC16H25NO2
Average Molecular Mass263.375 g/mol
Monoisotopic Mass263.189 g/mol
CAS Registry Number93413-62-8
IUPAC Name4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
Traditional Namedesvenlafaxine
SMILESCN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1
InChI IdentifierInChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3
InChI KeyKYYIDSXMWOZKMP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclohexanols. Cyclohexanols are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexanol
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • 1,3-aminoalcohol
  • Cyclic alcohol
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.4 g/LALOGPS
logP2.6ALOGPS
logP2.29ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.54 m³·mol⁻¹ChemAxon
Polarizability30.32 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9110000000-bddb56f900488038ac8fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ab9-9426000000-d585011517fe757dd5ffSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0090000000-90abc876cc91a398d25dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03y0-0960000000-0219d7d7ea1a46c8cfdfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-529d7fb237a99866f0b4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-ccb6c8906a1ac7d27cd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0290000000-422a5daa0d4bf51308efSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0910000000-03ecfc411d730c35b892Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-d0fa1892dfaae0510ee8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001m-0900000000-7515704132219cf15c78Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0090000000-1a8bdddd358a8706e896Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-c218ef4ab652831ee930Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06r2-4090000000-b1767a9c9c01cb43bca9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9320000000-e38b2ae07ab3cc9b7693Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9600000000-edbb26312a47b22bffb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9800000000-b41801091e3c7132fec9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9800000000-4b30d7e9d71dab81d9d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-5e859f484b6e3a5560c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06r2-4090000000-ef1215dc6fc4eb904b90Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9310000000-dac7bd983af34469bc5fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9600000000-8ea073e198c8a9a9a528Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0090000000-8bdd9e87d70ac30b0f4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i01-3190000000-e9a4354f756616119ea4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1003-9030000000-d873fc36430c62fd51b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-3151e03b6d1268750f4eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1390000000-6f6b5ce6a7122f629702Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9810000000-cf06f7edcabc2b491fb3Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06700
HMDB IDHMDB0015646
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDesvenlafaxine
Chemspider ID111300
ChEBI ID83527
PubChem Compound ID125017
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24493333
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24502274
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24989434
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25086830
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25188033
6. Mason JN, Deecher DC, Richmond RL, Stack G, Mahaney PE, Trybulski E, Winneker RC, Blakely RD: Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter. J Pharmacol Exp Ther. 2007 Nov;323(2):720-9. Epub 2007 Aug 2.
7. Kamath J, Handratta V: Desvenlafaxine succinate for major depressive disorder: a critical review of the evidence. Expert Rev Neurother. 2008 Dec;8(12):1787-97. doi: 10.1586/14737175.8.12.1787.
8. Liebowitz MR, Tourian KA: Efficacy, safety, and tolerability of Desvenlafaxine 50 mg/d for the treatment of major depressive disorder:a systematic review of clinical trials. Prim Care Companion J Clin Psychiatry. 2010;12(3). pii: PCC.09r00845. doi: 10.4088/PCC.09r00845blu.
9. Reddy S, Kane C, Pitrosky B, Musgnung J, Ninan PT, Guico-Pabia CJ: Clinical utility of desvenlafaxine 50 mg/d for treating MDD: a review of two randomized placebo-controlled trials for the practicing physician. Curr Med Res Opin. 2010 Jan;26(1):139-50. doi: 10.1185/03007990903408678.
10. Pae CU, Park MH, Marks DM, Han C, Patkar AA, Masand PS: Desvenlafaxine, a serotonin-norepinephrine uptake inhibitor for major depressive disorder, neuropathic pain and the vasomotor symptoms associated with menopause. Curr Opin Investig Drugs. 2009 Jan;10(1):75-90.
11. Preskorn S, Patroneva A, Silman H, Jiang Q, Isler JA, Burczynski ME, Ahmed S, Paul J, Nichols AI: Comparison of the pharmacokinetics of venlafaxine extended release and desvenlafaxine in extensive and poor cytochrome P450 2D6 metabolizers. J Clin Psychopharmacol. 2009 Feb;29(1):39-43. doi: 10.1097/JCP.0b013e318192e4c1.
12. Oganesian A, Shilling AD, Young-Sciame R, Tran J, Watanyar A, Azam F, Kao J, Leung L: Desvenlafaxine and venlafaxine exert minimal in vitro inhibition of human cytochrome P450 and P-glycoprotein activities. Psychopharmacol Bull. 2009;42(2):47-63.
13. Montgomery SA, Fava M, Padmanabhan SK, Guico-Pabia CJ, Tourian KA: Discontinuation symptoms and taper/poststudy-emergent adverse events with desvenlafaxine treatment for major depressive disorder. Int Clin Psychopharmacol. 2009 Nov;24(6):296-305. doi: 10.1097/YIC.0b013e32832fbb5a.
14. Kornstein SG, Jiang Q, Reddy S, Musgnung JJ, Guico-Pabia CJ: Short-term efficacy and safety of desvenlafaxine in a randomized, placebo-controlled study of perimenopausal and postmenopausal women with major depressive disorder. J Clin Psychiatry. 2010 Aug;71(8):1088-96. doi: 10.4088/JCP.10m06018blu.
15. Ilett KF, Watt F, Hackett LP, Kohan R, Teoh S: Assessment of infant dose through milk in a lactating woman taking amisulpride and desvenlafaxine for treatment-resistant depression. Ther Drug Monit. 2010 Dec;32(6):704-7. doi: 10.1097/FTD.0b013e3181f88f70.
16. Pae CU: Desvenlafaxine in the treatment of major depressive disorder. Expert Opin Pharmacother. 2011 Dec;12(18):2923-8. doi: 10.1517/14656566.2011.636033.
17. Berm EJ, Brummel-Mulder E, Paardekooper J, Hak E, Wilffert B, Maring JG: Determination of venlafaxine and O-desmethylvenlafaxine in dried blood spots for TDM purposes, using LC-MS/MS. Anal Bioanal Chem. 2014 Apr;406(9-10):2349-53. doi: 10.1007/s00216-014-7619-9. Epub 2014 Feb 4.
18. Murrell MD, Cruz DA, Javors MA, Thompson PM: Distribution of venlafaxine, O-desmethylvenlafaxine, and O-desmethylvenlafaxine to venlafaxine ratio in postmortem human brain tissue. J Forensic Sci. 2014 May;59(3):683-9. doi: 10.1111/1556-4029.12393. Epub 2014 Feb 6.
19. ter Horst PG, Larmene-Beld KH, Bosman J, van der Veen EL, Wieringa A, Smit JP: Concentrations of venlafaxine and its main metabolite O-desmethylvenlafaxine during pregnancy. J Clin Pharm Ther. 2014 Oct;39(5):541-4. doi: 10.1111/jcpt.12188. Epub 2014 Jul 3.
20. Vignali C, Morini L, Chen Y, Stramesi C, Groppi A: Distribution of venlafaxine and O-desmethylvenlafaxine in a fatal case. Forensic Sci Int. 2014 Sep;242:e48-e51. doi: 10.1016/j.forsciint.2014.07.011. Epub 2014 Jul 21.
21. Paulzen M, Groppe S, Tauber SC, Veselinovic T, Hiemke C, Grunder G: Venlafaxine and O-desmethylvenlafaxine concentrations in plasma and cerebrospinal fluid. J Clin Psychiatry. 2015 Jan;76(1):25-31. doi: 10.4088/JCP.13m08921.
22. FDA label
23. Wyeth Laboratories Inc. Pristiq® (desvenlafaxine succinate) extended-release tablets prescribing information. Philadelphia, PA; 2010 Sept.
24. PharmGKB: http://www.pharmgkb.org/pathway/PA166014758