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Details

Stereochemistry ACHIRAL
Molecular Formula C25H25Cl2N7O
Molecular Weight 510.418
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OTENABANT

SMILES

CCNC1(CCN(CC1)C2=NC=NC3=C2N=C(N3C4=CC=C(Cl)C=C4)C5=CC=CC=C5Cl)C(N)=O

InChI

InChIKey=UNAZAADNBYXMIV-UHFFFAOYSA-N
InChI=1S/C25H25Cl2N7O/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)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including 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
0.7 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OTENABANT serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
42 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
N-DESETHYL OTENABANT serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.01 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OTENABANT serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3966 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
N-DESETHYL OTENABANT serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
159 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
OTENABANT serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
139 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
N-DESETHYL OTENABANT serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
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.
Name Type Language
OTENABANT
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
CP-945,598
Code English
OTENABANT [USAN]
Common Name English
4-PIPERIDINECARBOXAMIDE, 1-(8-(2-CHLOROPHENYL)-9-(4-CHLOROPHENYL)-9H-PURIN-6-YL)-4- (ETHYLAMINO)-
Systematic Name English
CP-945598
Code English
otenabant [INN]
Common Name English
Otenabant [WHO-DD]
Common Name English
1-(8-(2-CHLOROPHENYL)-9-(4-CHLOROPHENYL)-9H-PURIN-6-YL)-4-(ETHYLAMINO)PIPERIDINE-4- CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29728
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID20988316
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL562668
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
FDA UNII
J8211Y53EF
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PRIMARY
SMS_ID
100000127535
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
EVMPD
SUB33607
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
PUBCHEM
10052040
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
CAS
686344-29-6
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
USAN
TT-97
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
DRUG BANK
DB11745
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
NCI_THESAURUS
C84034
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
WIKIPEDIA
OTENABANT
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY
INN
9009
Created by admin on Sat Dec 16 18:01:29 GMT 2023 , Edited by admin on Sat Dec 16 18:01:29 GMT 2023
PRIMARY