Bicifadine

Bicifadine
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	US: Unscheduled;
Pharmacokinetic data
Elimination half-life	1.6 hours
Excretion	renal
Identifiers
	IUPAC name 1-(4-Methylphenyl)-3-azabicyclo[3.1.0]hexane;
CAS Number	71195-57-8 ;
PubChem CID	47953;
ChemSpider	9889978 ;
UNII	B0SV3N7J3H;
ChEMBL	ChEMBL511099 ;
CompTox Dashboard (EPA)	DTXSID20867995 ;
ECHA InfoCard	100.124.957
Chemical and physical data
Formula	C12H15N
Molar mass	173.259 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1cc(ccc1C)[C@]32CNC[C@@H]2C3;
	InChI 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 ; Key:OFYVIGTWSQPCLF-NWDGAFQWSA-N ;
	(what is this?) (verify)

Bicifadine (DOV-220,075) is a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI) discovered at American Cyanamid as an analgesic drug candidate, and licensed to DOV Pharmaceutical in 1998 after American Cyanamid was acquired by Wyeth.^[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 by diabetic 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-NSAID mechanism 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 a serotonin (SERT) and noradrenaline transporter (NET) inhibitor, it also has effects at the dopamine transporter (DAT), effectively making it a broad-spectrum monoamine transporter inhibitor or "triple reuptake inhibitor."^[11]

References

^ 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.
^ SEC Filing: Wyeth-DOV Restated License Agreement Page accessed July 15, 2015]
^ 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.
^ Lawrence S, Hansen S (26 July 2010). "Bear Out of Hibernation". BioCentury.
^ "Euthymics: Balancing act" (PDF). BioCentury, The Bernstein Report on Biobusiness. December 5, 2011. p. A13. Archived from the original (PDF) on August 13, 2014. Retrieved May 7, 2012.
^ Caroll J (7 January 2007). "XTL licenses development rights to pain therapy". Fierce Biotech.
^ Fierce Biotech. December 9, 2008 Tiny XTL cuts costs, jobs
^ "XTL Form 6-K March, 2013". Archived from the original on 2015-07-15. Retrieved 2015-07-15.
^ Fierce Biotech July 22, 2010 Euthymics lands $24M to fund antidepressant work
^ 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.
^ 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.

[Marks-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]

[Neubauer-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 from the original (PDF) on August 13, 2014. Retrieved May 7, 2012.

[6] Caroll J (7 January 2007). "XTL licenses development rights to pain therapy". Fierce Biotech.

[7] Fierce Biotech. December 9, 2008 Tiny XTL cuts costs, jobs

[8] "XTL Form 6-K March, 2013". Archived from the original on 2015-07-15. Retrieved 2015-07-15.

[9] Fierce Biotech July 22, 2010 Euthymics lands $24M to fund antidepressant work

[Wang-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.

[Basile-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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Bicifadine

See also

References

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