Bifeprunox mesylate | DU-127090 | CAS#350992-13-1 | 350992-10-8 | dopamine and serotonin agonist

Bifeprunox Mesylate
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 326984

CAS#: 350992-13-1 (mesylate)

Description: Bifeprunox, also known as DU-127090, is a partial dopamine and serotonin agonist potentially for the treatment of schizophrenia. Bifeprunox influences nicotine-seeking behaviour in response to drug-associated stimuli in rats. Bifeprunox suppresses in vivo VTA dopaminergic neuronal activity via D2 and not D3 dopamine autoreceptor activation.

Chemical Structure

Bifeprunox Mesylate

CAS# 350992-13-1 (mesylate)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326984
Name: Bifeprunox Mesylate
CAS#: 350992-13-1 (mesylate)
Chemical Formula: C25H27N3O5S
Exact Mass: 0.00
Molecular Weight: 481.567
Elemental Analysis: C, 62.35; H, 5.65; N, 8.73; O, 16.61; S, 6.66

Price and Availability

Size	Price	Availability
5mg	USD 190	2 weeks
10mg	USD 250	2 weeks
25mg	USD 580	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 350992-10-8 (free base),350992-13-1 (mesylate).

Synonym: Bifeprunox; Bifeprunox Mesylate; DU-127090; DU 127090; DU127090.

IUPAC/Chemical Name: 7-(4-(Biphenyl-3-ylmethyl)piperazin-1-yl)benzoxazol-2(3H)-one methanesulfonate

InChi Key: ONWKHSGOYGLGPO-UHFFFAOYSA-N

InChi Code: InChI=1S/C24H23N3O2.CH4O3S/c28-24-25-21-10-5-11-22(23(21)29-24)27-14-12-26(13-15-27)17-18-6-4-9-20(16-18)19-7-2-1-3-8-19;1-5(2,3)4/h1-11,16H,12-15,17H2,(H,25,28);1H3,(H,2,3,4)

SMILES Code: O=C1OC2=C(N3CCN(CC4=CC(C5=CC=CC=C5)=CC=C4)CC3)C=CC=C2N1.CS(=O)(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	TBD
In vitro activity:	TBD
In vivo activity:	Different groups of experimentally naïve, food-restricted Wistar rats were trained to associate a discriminative stimulus with response-contingent availability of nicotine or sucrose and tested for reinstatement after extinction of nicotine or sucrose-reinforced behaviour. Bifeprunox (4-16 µg/kg, s.c.) dose-dependently attenuated the response-reinstating effects of nicotine-associated cues. Higher doses (64-250 µg/kg, s.c.) reduced spontaneous locomotor activity and suppressed operant responding induced by sucrose-associated cues and by the primary reinforcing properties of nicotine or sucrose. Reference: Addict Biol. 2012 Mar;17(2):274-86. https://pubmed.ncbi.nlm.nih.gov/21521422/

Preparing Stock Solutions

The following data is based on the product molecular weight 481.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Di Clemente A, Franchi C, Orrù A, Arnt J, Cervo L. Bifeprunox: a partial agonist at dopamine D2 and serotonin 1A receptors, influences nicotine-seeking behaviour in response to drug-associated stimuli in rats. Addict Biol. 2012 Mar;17(2):274-86. doi: 10.1111/j.1369-1600.2011.00319.x. Epub 2011 Apr 26. PMID: 21521422. 2. Etievant A, Bétry C, Arnt J, Haddjeri N. Bifeprunox and aripiprazole suppress in vivo VTA dopaminergic neuronal activity via D2 and not D3 dopamine autoreceptor activation. Neurosci Lett. 2009 Aug 21;460(1):82-6. doi: 10.1016/j.neulet.2009.05.035. Epub 2009 May 18. PMID: 19450663.
In vitro protocol:	TBD
In vivo protocol:	1. Di Clemente A, Franchi C, Orrù A, Arnt J, Cervo L. Bifeprunox: a partial agonist at dopamine D2 and serotonin 1A receptors, influences nicotine-seeking behaviour in response to drug-associated stimuli in rats. Addict Biol. 2012 Mar;17(2):274-86. doi: 10.1111/j.1369-1600.2011.00319.x. Epub 2011 Apr 26. PMID: 21521422. 2. Etievant A, Bétry C, Arnt J, Haddjeri N. Bifeprunox and aripiprazole suppress in vivo VTA dopaminergic neuronal activity via D2 and not D3 dopamine autoreceptor activation. Neurosci Lett. 2009 Aug 21;460(1):82-6. doi: 10.1016/j.neulet.2009.05.035. Epub 2009 May 18. PMID: 19450663.

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1: Chattopadhyay A, Frey S, Green G. Bifeprunox versus placebo for schizophrenia. Cochrane Database Syst Rev. 2016 Oct 12;10(10):CD012029. doi: 10.1002/14651858.CD012029.pub2. PMID: 27732740; PMCID: PMC6457956.

2: Chattopadhyay A, Frey S, Green G, Harkness A, McDermott A, Yates A. Bifeprunox vs Placebo for Schizophrenia. Schizophr Bull. 2016 Jul;42(4):881-2. doi: 10.1093/schbul/sbw048. Epub 2016 May 6. PMID: 27153863; PMCID: PMC4903068.

3: Etievant A, Bétry C, Arnt J, Haddjeri N. Bifeprunox and aripiprazole suppress in vivo VTA dopaminergic neuronal activity via D2 and not D3 dopamine autoreceptor activation. Neurosci Lett. 2009 Aug 21;460(1):82-6. doi: 10.1016/j.neulet.2009.05.035. Epub 2009 May 18. PMID: 19450663.

4: Di Clemente A, Franchi C, Orrù A, Arnt J, Cervo L. Bifeprunox: a partial agonist at dopamine D2 and serotonin 1A receptors, influences nicotine-seeking behaviour in response to drug-associated stimuli in rats. Addict Biol. 2012 Mar;17(2):274-86. doi: 10.1111/j.1369-1600.2011.00319.x. Epub 2011 Apr 26. PMID: 21521422.

5: Dahan L, Husum H, Mnie-Filali O, Arnt J, Hertel P, Haddjeri N. Effects of bifeprunox and aripiprazole on rat serotonin and dopamine neuronal activity and anxiolytic behaviour. J Psychopharmacol. 2009 Mar;23(2):177-89. doi: 10.1177/0269881108089586. Epub 2008 May 30. PMID: 18515444.

6: Newman-Tancredi A, Cussac D, Depoortere R. Neuropharmacological profile of bifeprunox: merits and limitations in comparison with other third-generation antipsychotics. Curr Opin Investig Drugs. 2007 Jul;8(7):539-54. PMID: 17659474.

7: De Santis M, Pan B, Lian J, Huang XF, Deng C. Different effects of bifeprunox, aripiprazole, and haloperidol on body weight gain, food and water intake, and locomotor activity in rats. Pharmacol Biochem Behav. 2014 Sep;124:167-73. doi: 10.1016/j.pbb.2014.06.004. Epub 2014 Jun 13. PMID: 24933333.

8: Casey DE, Sands EE, Heisterberg J, Yang HM. Efficacy and safety of bifeprunox in patients with an acute exacerbation of schizophrenia: results from a randomized, double-blind, placebo-controlled, multicenter, dose-finding study. Psychopharmacology (Berl). 2008 Oct;200(3):317-31. doi: 10.1007/s00213-008-1207-7. Epub 2008 Jul 4. PMID: 18597078.

9: Molecule of the month. Bifeprunox mesilate. Drug News Perspect. 2005 Oct;18(8):523. PMID: 16391722.

10: Tadori Y, Kitagawa H, Forbes RA, McQuade RD, Stark A, Kikuchi T. Differences in agonist/antagonist properties at human dopamine D(2) receptors between aripiprazole, bifeprunox and SDZ 208-912. Eur J Pharmacol. 2007 Nov 28;574(2-3):103-11. doi: 10.1016/j.ejphar.2007.07.031. Epub 2007 Aug 10. PMID: 17692841.

11: Cosi C, Carilla-Durand E, Assié MB, Ormiere AM, Maraval M, Leduc N, Newman- Tancredi A. Partial agonist properties of the antipsychotics SSR181507, aripiprazole and bifeprunox at dopamine D2 receptors: G protein activation and prolactin release. Eur J Pharmacol. 2006 Mar 27;535(1-3):135-44. doi: 10.1016/j.ejphar.2006.01.051. Epub 2006 Mar 22. PMID: 16554049.

12: Spiros A, Carr R, Geerts H. Not all partial dopamine D(2) receptor agonists are the same in treating schizophrenia. Exploring the effects of bifeprunox and aripiprazole using a computer model of a primate striatal dopaminergic synapse. Neuropsychiatr Dis Treat. 2010 Sep 7;6:589-603. doi: 10.2147/NDT.S12460. PMID: 20856922; PMCID: PMC2938308.

13: Novi F, Millan MJ, Corsini GU, Maggio R. Partial agonist actions of aripiprazole and the candidate antipsychotics S33592, bifeprunox, N-desmethylclozapine and preclamol at dopamine D(2L) receptors are modified by co-transfection of D(3) receptors: potential role of heterodimer formation. J Neurochem. 2007 Aug;102(4):1410-24. doi: 10.1111/j.1471-4159.2007.04660.x. Epub 2007 May 26. PMID: 17532788.

14: Seeman P. Dopamine D2(High) receptors moderately elevated by bifeprunox and aripiprazole. Synapse. 2008 Dec;62(12):902-8. doi: 10.1002/syn.20557. PMID: 18792990.

15: Assié MB, Carilla-Durand E, Bardin L, Maraval M, Aliaga M, Malfètes N, Barbara M, Newman-Tancredi A. The antipsychotics clozapine and olanzapine increase plasma glucose and corticosterone levels in rats: comparison with aripiprazole, ziprasidone, bifeprunox and F15063. Eur J Pharmacol. 2008 Sep 11;592(1-3):160-6. doi: 10.1016/j.ejphar.2008.06.105. Epub 2008 Jul 4. PMID: 18640111.

16: Pan B, Chen J, Lian J, Huang XF, Deng C. Unique Effects of Acute Aripiprazole Treatment on the Dopamine D2 Receptor Downstream cAMP-PKA and Akt- GSK3β Signalling Pathways in Rats. PLoS One. 2015 Jul 10;10(7):e0132722. doi: 10.1371/journal.pone.0132722. PMID: 26162083; PMCID: PMC4498891.

17: Kant R , Maji S . Recent advances in the synthesis of piperazine based ligands and metal complexes and their applications. Dalton Trans. 2021 Jan 21;50(3):785-800. doi: 10.1039/d0dt03569f. Epub 2021 Jan 8. PMID: 33416816.

18: Wolf W. DU-127090 Solvay/H Lundbeck. Curr Opin Investig Drugs. 2003 Jan;4(1):72-6. PMID: 12625033.

19: Heusler P, Newman-Tancredi A, Loock T, Cussac D. Antipsychotics differ in their ability to internalise human dopamine D2S and human serotonin 5-HT1A receptors in HEK293 cells. Eur J Pharmacol. 2008 Feb 26;581(1-2):37-46. doi: 10.1016/j.ejphar.2007.11.046. Epub 2007 Nov 28. PMID: 18190908.

20: Jones CA, McCreary AC. Serotonergic approaches in the development of novel antipsychotics. Neuropharmacology. 2008 Nov;55(6):1056-65. doi: 10.1016/j.neuropharm.2008.05.025. Epub 2008 Jun 3. PMID: 18621404.

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