Drinabant | AVE1625 | CAS#358970-97-5 | CB1 receptor antagonist

MedKoo Cat#: 319868 | Name: Drinabant

Featured

Description:

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

Drinabant, also known as AVE1625, is a selective CB1 receptor antagonist under investigation varyingly as a treatment for obesity, schizophrenia, Alzheimer's disease, Parkinson's disease, and nicotine dependence. AVE1625 may be useful to treat the cognitive deficits in schizophrenia and as a co-treatment with currently available antipsychotics. In addition, an improved side-effect profile was seen, with potential to ameliorate the EPS and weight gain issues with currently available treatments.

Chemical Structure

Drinabant

CAS#358970-97-5

Theoretical Analysis

MedKoo Cat#: 319868

Name: Drinabant

CAS#: 358970-97-5

Chemical Formula: C23H20Cl2F2N2O2S

Exact Mass: 496.0591

Molecular Weight: 497.38

Elemental Analysis: C, 55.54; H, 4.05; Cl, 14.25; F, 7.64; N, 5.63; O, 6.43; S, 6.45

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

AVE1625; AVE 1625; AVE-1625; Drinabant.

IUPAC/Chemical Name

N-(1-(bis(4-chlorophenyl)methyl)azetidin-3-yl)-N-(3,5-difluorophenyl)methanesulfonamide

InChi Key

IQQBRKLVEALROM-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H20Cl2F2N2O2S/c1-32(30,31)29(21-11-19(26)10-20(27)12-21)22-13-28(14-22)23(15-2-6-17(24)7-3-15)16-4-8-18(25)9-5-16/h2-12,22-23H,13-14H2,1H3

SMILES Code

CS(=O)(N(C1CN(C(C2=CC=C(Cl)C=C2)C3=CC=C(Cl)C=C3)C1)C4=CC(F)=CC(F)=C4)=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, not in water

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

Though initially studied as a potential treatment for a variety of different medical conditions, Sanofi-Aventis eventually narrowed down the therapeutic indications of the compound to just appetite suppression. Drinabant reached phase IIb clinical trials for this purpose in the treatment of obesity but was shortly thereafter discontinued, likely due to the observation of severe psychiatric side effects including anxiety, depression, and thoughts of suicide in patients treated with the now-withdrawn rimonabant, another CB1 antagonist that was also under development by Sanofi-Aventis.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Drinabant (AVE1625) is an orally active CB1 receptor antagonist.

In vitro activity:

TBD

In vivo activity:

AVE1625 (1, 3, and 10 mg/kg ip), reversed abnormally persistent LI induced by MK-801 or neonatal nitric oxide synthase inhibition in rodents, and improved both working and episodic memory. These preclinical data suggest that AVE1625 may be useful to treat the cognitive deficits in schizophrenia and as a co-treatment with currently available antipsychotics. Reference: Psychopharmacology (Berl). 2011 May;215(1):149-63. https://pubmed.ncbi.nlm.nih.gov/21181124/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	30.16
	DMSO	32.4	65.08
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.60
	Ethanol	0.2	0.30

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 497.38 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. Black MD, Stevens RJ, Rogacki N, Featherstone RE, Senyah Y, Giardino O, Borowsky B, Stemmelin J, Cohen C, Pichat P, Arad M, Barak S, De Levie A, Weiner I, Griebel G, Varty GB. AVE1625, a cannabinoid CB1 receptor antagonist, as a co-treatment with antipsychotics for schizophrenia: improvement in cognitive function and reduction of antipsychotic-side effects in rodents. Psychopharmacology (Berl). 2011 May;215(1):149-63. doi: 10.1007/s00213-010-2124-0. Epub 2010 Dec 22. PMID: 21181124. 2. Liebig M, Gossel M, Pratt J, Black M, Haschke G, Elvert R, Juretschke HP, Neumann-Haefelin C, Kramer W, Herling AW. Profiling of energy metabolism in olanzapine-induced weight gain in rats and its prevention by the CB1-antagonist AVE1625. Obesity (Silver Spring). 2010 Oct;18(10):1952-8. doi: 10.1038/oby.2010.17. Epub 2010 Feb 18. PMID: 20168311.

In vitro protocol:

TBD

In vivo protocol:

1: Black MD, Stevens RJ, Rogacki N, Featherstone RE, Senyah Y, Giardino O, Borowsky B, Stemmelin J, Cohen C, Pichat P, Arad M, Barak S, De Levie A, Weiner I, Griebel G, Varty GB. AVE1625, a cannabinoid CB1 receptor antagonist, as a co-treatment with antipsychotics for schizophrenia: improvement in cognitive function and reduction of antipsychotic-side effects in rodents. Psychopharmacology (Berl). 2011 May;215(1):149-63. doi: 10.1007/s00213-010-2124-0. Epub 2010 Dec 22. PubMed PMID: 21181124. 2: Bertalovitz AC, Ahn KH, Kendall DA. Ligand Binding Sensitivity of the Extracellular Loop Two of the Cannabinoid Receptor 1. Drug Dev Res. 2010 Nov 1;71(7):404-411. PubMed PMID: 21170298; PubMed Central PMCID: PMC3003262. 3: Liebig M, Gossel M, Pratt J, Black M, Haschke G, Elvert R, Juretschke HP, Neumann-Haefelin C, Kramer W, Herling AW. Profiling of energy metabolism in olanzapine-induced weight gain in rats and its prevention by the CB1-antagonist AVE1625. Obesity (Silver Spring). 2010 Oct;18(10):1952-8. doi: 10.1038/oby.2010.17. Epub 2010 Feb 18. PubMed PMID: 20168311. 4: Janero DR, Makriyannis A. Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis. Expert Opin Emerg Drugs. 2009 Mar;14(1):43-65. doi: 10.1517/14728210902736568 . Review. PubMed PMID: 19249987. 5: Zuurman L, Roy C, Schoemaker RC, Amatsaleh A, Guimaeres L, Pinquier JL, Cohen AF, van Gerven JM. Inhibition of THC-induced effects on the central nervous system and heart rate by a novel CB1 receptor antagonist AVE1625. J Psychopharmacol. 2010 Mar;24(3):363-71. doi: 10.1177/0269881108096509. Epub 2008 Sep 18. PubMed PMID: 18801827. 6: Herling AW, Gossel M, Haschke G, Stengelin S, Kuhlmann J, Müller G, Schmoll D, Kramer W. CB1 receptor antagonist AVE1625 affects primarily metabolic parameters independently of reduced food intake in Wistar rats. Am J Physiol Endocrinol Metab. 2007 Sep;293(3):E826-32. Epub 2007 Jun 26. PubMed PMID: 17595216.