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Desvenlafaxine

July 24, 2017
Common Name

Desvenlafaxine Description

Desvenlafaxine, the major active metabolite of venlafaxine, is an antidepressant from the serotonin-norepinephrine reuptake inhibitor (SNRI class). Desvenlafaxine may be used to treat major depressive disorder and is being studied for use in the management of vasomotor symptoms in postmenopausal women. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 1-[2-(dimethylamino)-1-(4-Hydroxyphenyl)ethyl]cyclohexanolChEBI 4-[2-(dimethylamino)-1-(1-Hydroxycyclohexyl)ethyl]phenolChEBI O-Desmethylvenlafaxine succinateMeSH 4-(2-(dimethylamino)-1-(1-Hydroxycyclohexyl)ethyl)phenolMeSH Succinate, desvenlafaxineMeSH 2-(1-Hydroxycyclohexyl)-2-((4-hydroxyphenyl)ethyl)dimethylammonium 3-carboxypropanoate monohydrateMeSH O DesmethylvenlafaxineMeSH O Desmethylvenlafaxine succinateMeSH O-Desmethylvenlafaxine succinate monohydrateMeSH Succinate, O-desmethylvenlafaxineMeSH Desvenlafaxine succinateMeSH Monohydrate, O-desmethylvenlafaxine succinateMeSH O Desmethylvenlafaxine succinate monohydrateMeSH O-DesmethylvenlafaxineMeSH PristiqMeSH Succinate monohydrate, O-desmethylvenlafaxineMeSH

Chemical Formlia

C16H25NO2 Average Molecliar Weight

263.3752 Monoisotopic Molecliar Weight

263.188529049 IUPAC Name

4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol Traditional Name

desvenlafaxine CAS Registry Number

93413-62-8 SMILES

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

InChI Identifier

InChI=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 Key

KYYIDSXMWOZKMP-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as cyclohexanols. These are compounds containing an alcohol group attached to a cyclohexane ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic oxygen compounds Sub Class

Organooxygen compounds Direct Parent

Cyclohexanols Alternative Parents

  • Aralkylamines
  • 1-hydroxy-2-unsubstituted benzenoids
  • Benzene and substituted derivatives
  • Tertiary alcohols
  • 1,3-aminoalcohols
  • Trialkylamines
  • Cyclic alcohols and derivatives
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • tertiary amino compound (CHEBI:83527 )
  • phenols (CHEBI:83527 )
  • cyclohexanols (CHEBI:83527 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antidepressants
  • Antidepressive Agents
  • Serotonin and Norepinephrine Reuptake Inhibitors (SNRIs)

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility1.4 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity78.54 m3·mol-1ChemAxon Polarizability30.29 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-03di-0090000000-90abc876cc91a398d25dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-03y0-0960000000-0219d7d7ea1a46c8cfdfView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , negativesplash10-014i-0900000000-529d7fb237a99866f0b4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-03di-0090000000-ccb6c8906a1ac7d27cd6View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0002-0290000000-422a5daa0d4bf51308efView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001i-0910000000-03ecfc411d730c35b892View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001i-0900000000-d0fa1892dfaae0510ee8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-001m-0900000000-7515704132219cf15c78View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0002-0090000000-1a8bdddd358a8706e896View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-03di-0090000000-c218ef4ab652831ee930View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-06r2-4090000000-b1767a9c9c01cb43bca9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-9320000000-e38b2ae07ab3cc9b7693View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-9600000000-edbb26312a47b22bffb7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-9800000000-b41801091e3c7132fec9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-9800000000-4b30d7e9d71dab81d9d7View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-03di-0090000000-5e859f484b6e3a5560c4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-06r2-4090000000-ef1215dc6fc4eb904b90View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-9310000000-dac7bd983af34469bc5fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-9600000000-8ea073e198c8a9a9a528View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06700

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06700

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06700 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    111300 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Desvenlafaxine NuGOwiki Link

    HMDB15646 Metagene Link

    HMDB15646 METLIN ID

    Not Available PubChem Compound

    125017 PDB ID

    Not Available ChEBI ID

    261281

    Product: Cyclamic acid

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. 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. [PubMed:17673606 ]
    2. 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. [PubMed:19086875 ]
    3. 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. [PubMed:20944767 ]
    4. 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. [PubMed:19919295 ]
    5. 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. [PubMed:19127490 ]
    6. 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. [PubMed:19142106 ]
    7. 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. [PubMed:19629022 ]
    8. 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. [PubMed:19779354 ]
    9. 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. [PubMed:20797382 ]
    10. 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. [PubMed:20926994 ]
    11. 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. [PubMed:22098230 ]
    12. (). FDA label . .
    13. (). Wyeth Laboratories Inc. Pristiq® (desvenlafaxine succinate) extended-release tablets prescribing information. Philadelphia, PA; 2010 Sept.. .
    14. PharmGKB [Link]

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585

    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
    References
    1. Deecher DC, Beyer CE, Johnston G, Bray J, Shah S, Abou-Gharbia M, Andree TH: Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. Epub 2006 May 4. [PubMed:16675639 ]
    2. 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. [PubMed:17673606 ]
    3. Perry R, Cassagnol M: Desvenlafaxine: a new serotonin-norepinephrine reuptake inhibitor for the treatment of adults with major depressive disorder. Clin Ther. 2009 Jun;31 Pt 1:1374-404. doi: 10.1016/j.clinthera.2009.07.012. [PubMed:19698900 ]
    4. 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. [PubMed:19086875 ]
    5. 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. [PubMed:20944767 ]
    6. 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. [PubMed:19919295 ]
    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
    References
    1. Deecher DC, Beyer CE, Johnston G, Bray J, Shah S, Abou-Gharbia M, Andree TH: Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther. 2006 Aug;318(2):657-65. Epub 2006 May 4. [PubMed:16675639 ]
    2. 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. [PubMed:17673606 ]
    3. Perry R, Cassagnol M: Desvenlafaxine: a new serotonin-norepinephrine reuptake inhibitor for the treatment of adults with major depressive disorder. Clin Ther. 2009 Jun;31 Pt 1:1374-404. doi: 10.1016/j.clinthera.2009.07.012. [PubMed:19698900 ]
    4. 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. [PubMed:19086875 ]
    5. 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. [PubMed:20944767 ]
    6. 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. [PubMed:19919295 ]

    PMID: 23071308

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