U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H25ClF3N3O2
Molecular Weight 515.955
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TARANABANT

SMILES

C[C@H](NC(=O)C(C)(C)OC1=CC=C(C=N1)C(F)(F)F)[C@@H](CC2=CC=C(Cl)C=C2)C3=CC=CC(=C3)C#N

InChI

InChIKey=QLYKJCMUNUWAGO-GAJHUEQPSA-N
InChI=1S/C27H25ClF3N3O2/c1-17(34-25(35)26(2,3)36-24-12-9-21(16-33-24)27(29,30)31)23(14-18-7-10-22(28)11-8-18)20-6-4-5-19(13-20)15-32/h4-13,16-17,23H,14H2,1-3H3,(H,34,35)/t17-,23+/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H25ClF3N3O2
Molecular Weight 515.955
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19597516

Taranabant is a highly selective cannabinoid-1 (CB1) receptor inverse agonist developed by Merck & Co for the treatment of obesity. The Phase III taranabant study involved about 2,400 patients and was to be conducted for two years. In March 2008, after completion of 52 weeks of the study, Merck reported positive results of the drug in conjunction with diet and exercise in obese patients. The patients experienced double the amount of weight loss by taking 2mg of taranabant when compared to the patients treated with placebo. However, in October 2008, the company discontinued the Phase III programme and clinical development of taranabant because of its side effects. The drug showed gastrointestinal and psychiatric side effects such as increased anxiety, depression and irritability. Merck had previously planned to file for regulatory approval with the US Food and Drug Administration in 2008, but subsequently withdrew it.

Originator

Curator's Comment: # Merck & Co

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.3 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
49.99 nM
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
58.24 nM
7.5 mg 1 times / day steady-state, oral
dose: 7.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
85.62 nM
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
147.55 nM
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
265.2 nM × h
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
298.3 nM × h
7.5 mg 1 times / day steady-state, oral
dose: 7.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
416.4 nM × h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
806.3 nM × h
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
90.5 h
5 mg 1 times / day steady-state, oral
dose: 5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
93.3 h
7.5 mg 1 times / day steady-state, oral
dose: 7.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
97.4 h
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
103.6 h
25 mg 1 times / day steady-state, oral
dose: 25 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TARANABANT plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
weak [IC50 >20.0 uM]
yes [IC50 0.59 uM]
yes [IC50 0.93 uM]
yes [IC50 >20.0 uM]
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
The endocannabinoid system as a target for obesity treatment.
2008
Patents

Patents

Sample Use Guides

0.5 mg capsule, 1 mg capsule, 2 mg capsule once daily. Treatment for 52 weeks.
Route of Administration: Oral
In vitro, taranabant (10(-10) -10(-7) mol/L) increased contractile responses in mouse ileum and blocked the effect of the CB agonist WIN 55,212-2.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:47:02 UTC 2023
Edited
by admin
on Sat Dec 16 16:47:02 UTC 2023
Record UNII
X9U622S114
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TARANABANT
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
MK-0364
Code English
TARANABANT [USAN]
Common Name English
Taranabant [WHO-DD]
Common Name English
MK0364
Code English
N-[(1S,2S)-3-(4-Chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-[[5-(trifluoromethyl)pyridin-2-yl]oxy]propanamide
Systematic Name English
PROPANAMIDE, N-((1S,2S)-3-(4-CHLOROPHENYL)-2-(3-CYANOPHENYL)-1-METHYLPROPYL)-2-METHYL-2-((5-(TRIFLUOROMETHYL)-2-PYRIDINYL)OXY)-
Systematic Name English
taranabant [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29728
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID60220464
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL220360
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
CAS
701977-09-5
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
USAN
SS-80
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
DRUG BANK
DB06624
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
PUBCHEM
11226090
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
SMS_ID
100000091898
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
INN
8848
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
FDA UNII
X9U622S114
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
NCI_THESAURUS
C81420
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
EVMPD
SUB25601
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
WIKIPEDIA
TARANABANT
Created by admin on Sat Dec 16 16:47:02 UTC 2023 , Edited by admin on Sat Dec 16 16:47:02 UTC 2023
PRIMARY
Related Record Type Details
TARGET->INVERSE AGONIST
Related Record Type Details
ACTIVE MOIETY