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Bicifadine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Bicifadine
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Eliminationhalf-life1.6 hours
Excretionrenal
Identifiers
  • 1-(4-Methylphenyl)-3-azabicyclo[3.1.0]hexane
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.124.957Edit this at Wikidata
Chemical and physical data
FormulaC12H15N
Molar mass173.259 g·mol−1
3D model (JSmol)
  • c1cc(ccc1C)[C@]32CNC[C@@H]2C3
  • InChI=1S/C12H15N/c1-9-2-4-10(5-3-9)12-6-11(12)7-13-8-12/h2-5,11,13H,6-8H2,1H3/t11-,12+/m0/s1 checkY
  • Key:OFYVIGTWSQPCLF-NWDGAFQWSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Bicifadine (DOV-220,075) is aserotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI) discovered atAmerican Cyanamid as ananalgesic drug candidate, and licensed toDOV Pharmaceutical in 1998 after American Cyanamid was acquired byWyeth.[1][2][3]

In January 2007, Dov licensed the rights to bicifadine to XTL Biopharmaceuticals after bicifadine failed in a Phase III clinical trial for chronic lower back pain.[4][5][6] XTL ran a PhaseIIb clinical trial for pain caused bydiabetic neuropathy, which failed in 2008;[7] XTL terminated the agreement in 2010.[8] In 2010 Dov was acquired by Euthymics Bioscience which intended to continue development of other candidates from Dov's portfolio.[9]

Bicifadine has a non-opioid, non-NSAIDmechanism for the treatment of pain, which should have less abuse potential than opioid drugs and less propensity to cause gastric ulcers than NSAID drugs.[10] While the drug is purported to be aserotonin (SERT) andnoradrenaline transporter (NET) inhibitor, it also has effects at thedopamine transporter (DAT), effectively making it a broad-spectrummonoamine transporter inhibitor or "triple reuptake inhibitor."[11]

See also

[edit]

References

[edit]
  1. ^Marks DM, Pae CU, Patkar AA (September 2008)."Triple reuptake inhibitors: a premise and promise".Psychiatry Investigation.5 (3):142–7.doi:10.4306/pi.2008.5.3.142.PMC 2796030.PMID 20046357.
  2. ^SEC Filing: Wyeth-DOV Restated License Agreement Page accessed July 15, 2015]
  3. ^Neubauer DN (2010). "Indiplon". In Monti JM, Pandi-Perumal SR, Möhler H (eds.).GABA and Sleep: Molecular, Functional and Clinical Aspects. Springer Science & Business Media. pp. 453––464.ISBN 9783034602266.
  4. ^Lawrence S, Hansen S (26 July 2010)."Bear Out of Hibernation".BioCentury.
  5. ^"Euthymics: Balancing act"(PDF). BioCentury, The Bernstein Report on Biobusiness. December 5, 2011. p. A13. Archived fromthe original(PDF) on August 13, 2014. RetrievedMay 7, 2012.
  6. ^Caroll J (7 January 2007)."XTL licenses development rights to pain therapy".Fierce Biotech.
  7. ^Fierce Biotech. December 9, 2008Tiny XTL cuts costs, jobs
  8. ^"XTL Form 6-K March, 2013". Archived fromthe original on 2015-07-15. Retrieved2015-07-15.
  9. ^Fierce Biotech July 22, 2010Euthymics lands $24M to fund antidepressant work
  10. ^Wang RI, Johnson RP, Lee JC, Waite EM (April 1982). "The oral analgesic efficacy of bicifadine hydrochloride in postoperative pain".Journal of Clinical Pharmacology.22 (4):160–4.doi:10.1002/j.1552-4604.1982.tb02157.x.PMID 7096604.S2CID 35998284.
  11. ^Basile AS, Janowsky A, Golembiowska K, Kowalska M, Tam E, Benveniste M, et al. (June 2007). "Characterization of the antinociceptive actions of bicifadine in models of acute, persistent, and chronic pain".The Journal of Pharmacology and Experimental Therapeutics.321 (3):1208–25.doi:10.1124/jpet.106.116483.PMID 17325229.S2CID 17215882.
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SSRIsTooltip Selective serotonin reuptake inhibitors
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NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
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MAOATooltip Monoamine oxidase A-selective
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SERTTooltip Serotonin transporter
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