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Details

Stereochemistry ACHIRAL
Molecular Formula C25H25Cl2N7O.ClH
Molecular Weight 546.88
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OTENABANT HYDROCHLORIDE

SMILES

CCNC1(CCN(CC1)c2c3c(ncn2)n(-c4ccc(cc4)Cl)c(-c5ccccc5Cl)n3)C(=N)O.Cl

InChI

InChIKey=KPYUQCJBZGQHPL-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C25H25Cl2N7O
Molecular Weight 510.4191
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/?term=20211605 | https://www.ncbi.nlm.nih.gov/pubmed/?term=19102698

Otenabant (CP-945,598) is Pfizer developed as a potent and selective cannabinoid receptor CB1 antagonist with Ki of 0.7 nM, which exhibits 10,000-fold greater selectivity against human CB2 receptor, for treatment of obesity. In clinical trial III Pfizer decided to discontinue the development program based on changing regulatory perspectives on the risk/benefit profile of the CB1 class and likely new regulatory requirements for approval.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.699999999999999956 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Discovery of 1-[9-(4-chlorophenyl)-8-(2-chlorophenyl)-9H-purin-6-yl]-4-ethylaminopiperidine-4-carboxylic acid amide hydrochloride (CP-945,598), a novel, potent, and selective cannabinoid type 1 receptor antagonist.
2009 Jan 22
Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis.
2009 Mar
In vitro and in vivo pharmacology of CP-945,598, a potent and selective cannabinoid CB(1) receptor antagonist for the management of obesity.
2010 Apr 2
Patents

Sample Use Guides

Three double-blind, placebo-controlled, three-parallel-group, multicenter phase 3 trials were conducted to assess the efficacy and safety of CP-945,598 (OTENABANT) for weight loss and weight-loss maintenance. In total, 1,253 and 2,536 participants in the two 2-year multinational and North American studies were randomized to 10-mg CP-945,598 (n = 360; 718); 20-mg CP-945,598 (n = 534, 1,084) and placebo (n = 359, 734), respectively; and 975 participants were randomized to 10-mg CP-945,598 (n = 318); 20-mg CP-945,598 (n = 320); and placebo (n = 337) in the 1-year multinational diabetes trial.
Route of Administration: Oral
CP-945,598 (TENABANT) exhibits sub-nanomolar potency at human CB(1) receptors in both binding (K(i)=0.7 nM) and functional assays (K(i)=0.2 nM). The compound has low affinity (K(i)=7600 nM) for human CB(2) receptors.
Substance Class Chemical
Created
by admin
on Sat Jun 26 09:29:39 UTC 2021
Edited
by admin
on Sat Jun 26 09:29:39 UTC 2021
Record UNII
X2166Z319O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OTENABANT HYDROCHLORIDE
USAN  
USAN  
Official Name English
4-PIPERIDINECARBOXAMIDE, 1-(8-(2-CHLOROPHENYL)-9-(4-CHLOROPHENYL)-9H-PURIN-6-YL)-4- (ETHYLAMINO)-, MONOHYDROCHLORIDE
Common Name English
OTENABANT HCL
Common Name English
1-(8-(2-CHLOROPHENYL)-9-(4-CHLOROPHENYL)-9H-PURIN-6-YL)-4-(ETHYLAMINO)PIPERIDINE-4- CARBOXAMIDE MONOHYDROCHLORIDE
Systematic Name English
OTENABANT HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29728
Created by admin on Sat Jun 26 09:29:39 UTC 2021 , Edited by admin on Sat Jun 26 09:29:39 UTC 2021
Code System Code Type Description
DRUG BANK
DBSALT002063
Created by admin on Sat Jun 26 09:29:39 UTC 2021 , Edited by admin on Sat Jun 26 09:29:39 UTC 2021
PRIMARY
CAS
686347-12-6
Created by admin on Sat Jun 26 09:29:39 UTC 2021 , Edited by admin on Sat Jun 26 09:29:39 UTC 2021
PRIMARY
NCI_THESAURUS
C84035
Created by admin on Sat Jun 26 09:29:39 UTC 2021 , Edited by admin on Sat Jun 26 09:29:39 UTC 2021
PRIMARY
FDA UNII
X2166Z319O
Created by admin on Sat Jun 26 09:29:39 UTC 2021 , Edited by admin on Sat Jun 26 09:29:39 UTC 2021
PRIMARY
PUBCHEM
16223963
Created by admin on Sat Jun 26 09:29:39 UTC 2021 , Edited by admin on Sat Jun 26 09:29:39 UTC 2021
PRIMARY
ChEMBL
CHEMBL562668
Created by admin on Sat Jun 26 09:29:39 UTC 2021 , Edited by admin on Sat Jun 26 09:29:39 UTC 2021
PRIMARY
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