Otenabant HCl

• CAS: 686347-12-6
• Catalog Number: ACM686347126
• Category: Antagonists
• Molecular Weight: 546.88
• Molecular Formula: C25H26Cl3N7O
• Description: Otenabant, also known as CP-945,598, is a drug which acts as a potent and highly selective CB1 antagonist. It was developed by Pfizer for the treatment of obesity, but development for this application has been discontinued following the problems seen during clinical use of the similar drug rimonabant. (source: http://en.wikipedia.org/wiki/Otenabant).
• Synonyms: CP945598; CP-945598; CP 945598; CP945,598; CP-945,598; CP 945,598; Otenabant HCl
• IUPAC Name: 1-(8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl)-4-(ethylamino)piperidine-4-carboxamide hydrochloride
• Canonical SMILES: O=C(C1(NCC)CCN(C2=C3N=C(C4=CC=CC=C4Cl)N(C5=CC=C(Cl)C=C5)C3=NC=N2)CC1)N.[H]Cl
• InChI: InChI=1S/C25H25Cl2N7O.ClH/c1-2-31-25(24(28)35)11-13-33(14-12-25)22-20-23(30-15-29-22)34(17-9-7-16(26)8-10-17)21(32-20)18-5-3-4-6-19(18)27;/h3-10,15,31H,2,11-14H2,1H3,(H2,28,35);1H
• InChI Key: KPYUQCJBZGQHPL-UHFFFAOYSA-N
• Solubility: Soluble in DMSO, not in water
• Appearance: White solid powder
• Shelf Life: >5 years if stored properly
• Storage: Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
• Alternative CAS: 686347-12-6 (HCl); 686344-29-6 (free base)
• Biological Target: Otenabant Hydrochloride is a potent and selective cannabinoid receptor CB1 antagonist with Ki of 0.7 nM.
• Drug Formulation: This drug may be formulated in DMSO
• Elemental Analysis: C, 54.91; H, 4.79; Cl, 19.45; N, 17.93; O, 2.93
• HS Tariff Code: 2934.99.9001
• In Vitro Activity: The metabolic turnover of 32 drugs known to be largely metabolized by CYP3A was examined in human liver microsomes (HLMs) from CYP3A5 expressers (*1/*1 genotype) and nonexpressers (*3/*3 genotype) in the presence and absence of ketoconazole and CYP3cide (a selective CYP3A4 inactivator) to calculate the contribution of CYP3A5 to metabolism. Drugs with the highest contribution of CYP3A5 included atazanavir, vincristine, midazolam, vardenafil, otenabant, verapamil, and tacrolimus, whereas 17 of the 32 tested showed negligible CYP3A5 contribution. For otenabant, there is a considerable contribution by CYP3A5 in the *1/*1 donor microsomes, and this contribution is illustrated by the difference in lability between the ketoconazole and CYP3cide-containing incubations. Otenabant had comparable contributions of CYP3A4 and CYP3A5. There were a few drugs for which CYP3A5 was estimated to contribute more than 40% in liver microsomes but for which the ratio of CLint values in recombinant 3A5 and 3A4 was not greater than two (e.g. otenabant).; Drug Metabolism and Disposition July 2014, 42 (7) 1163-1173. https://dmd.aspetjournals.org/content/42/7/1163.full?casa_token=0bFzj47rEgAAAAA:ZqAN9CW_qtnEpJnXC8rMFdo5BCm1lhNbavCmN13j5SIe4JPppW-RhqRbkwJ4sOS8Z_YtidNmHEawQg
• In Vivo Activity: CP-945,598 (1-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-4-ethylamino piperidine-4-carboxylic acid amide hydrochloride) is a recently discovered selective, high affinity, competitive CB1 receptor antagonist that inhibits both basal and cannabinoid agonist-mediated CB1 receptor signaling in vitro and in vivo. CP-945,598 exhibits sub-nanomolar potency at human CB1 receptors in both binding (Ki = 0.7 nM) and functional assays (Ki = 0.2 nM). The compound has low affinity (Ki = 7600 nM) for human CB2 receptors. In vivo, CP-945,598 reverses four cannabinoid agonist-mediated CNS-driven responses (hypo-locomotion, hypothermia, analgesia, and catalepsy) to a synthetic cannabinoid receptor agonist. CP-945,598 exhibits dose and concentrationdependent anorectic activity in two models of acute food intake in rodents, fast-induced re-feeding and spontaneous, nocturnal feeding. CP-945,598 also acutely stimulates energy expenditure in rats and decreases the respiratory quotient indicating a metabolic switch to increased fat oxidation. CP-945,598 at 10 mg/kg promoted a 9%, vehicle adjusted weight loss in a 10 day weight loss study in diet-induced obese mice. Concentration/effect relationships combined with ex vivo brain CB1 receptor occupancy data were used to evaluate efficacy in behavioral, food intake, and energy expenditure studies. Together, these in vitro, ex vivo, and in vivo data indicate that CP-945,598 is a novel CB1 receptor competitive antagonist that may further our understanding of the endocannabinoid system.; Biochem Biophys Res Commun. 2010 Apr 2;394(2):366-71. https://www.sciencedirect.com/science/article/abs/pii/S0006291X10004523?via%3Dihub
• Shipping: 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.
• Stock Solution Storage: 0-4 °C for short term (days to weeks), or -20 °C for long term (months).