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Details

Stereochemistry ABSOLUTE
Molecular Formula C34H31F3N2O3
Molecular Weight 572.6167
Optical Activity ( + )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of USISTAPIDE

SMILES

COC(=O)[C@H](N1CCC(CC1)C2=CC=C(NC(=O)C3=CC=CC=C3C4=CC=C(C=C4)C(F)(F)F)C=C2)C5=CC=CC=C5

InChI

InChIKey=WSYALRNYQFNNGP-WJOKGBTCSA-N
InChI=1S/C34H31F3N2O3/c1-42-33(41)31(26-7-3-2-4-8-26)39-21-19-24(20-22-39)23-13-17-28(18-14-23)38-32(40)30-10-6-5-9-29(30)25-11-15-27(16-12-25)34(35,36)37/h2-18,24,31H,19-22H2,1H3,(H,38,40)/t31-/m1/s1

HIDE SMILES / InChI
Molecular Formula C34H31F3N2O3
Molecular Weight 572.6167
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Johnson and Johnson was developing usistapide, a microsomal triglyceride transfer protein (MTTP) inhibitor, for the treatment of obesity and type 2 diabetes. Usistapide, also known as JNJ-16269110 and R256918, has been used in trials studying the treatment of obesity, overweight, metabolic diseases, nutrition disorders, and nutritional and metabolic diseases. Usistapide was removed from the company pipeline and appears to have been discontinued.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
PubMed

PubMed

TitleDatePubMed
American Society for Clinical Pharmacology and Therapeutics (ASCPT)-111th annual meeting. 17-20 March 2010, Atlanta, GA, USA.
2010-05
Patents

Patents

20120071660
1
8461341
1
WO2010136526A1
1
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:08:03 GMT 2025
Edited
by admin
on Mon Mar 31 19:08:03 GMT 2025
Record UNII
73YSY3U094
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
JNJ-16269110
Preferred Name English
USISTAPIDE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
JNJ16269110
Code English
METHYL (2S)-2-PHENYL-2-(4-(4-(((4'-(TRIFLUOROMETHYL)BIPHENYL-2-YL)CARBONYL)AMINO)PHENYL)PIPERIDIN-1-YL)ACETATE
Systematic Name English
R-256918
Code English
USISTAPIDE [USAN]
Common Name English
JNJ-16269110-AAA
Code English
R256918
Code English
Usistapide [WHO-DD]
Common Name English
1-PIPERIDINEACETIC ACID, .ALPHA.-PHENYL-4-(4-(((4'-(TRIFLUOROMETHYL)(1,1'-BIPHENYL)-2- YL)CARBONYL)AMINO)PHENYL)-, METHYL ESTER, (+)-
Common Name English
usistapide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29728
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
NCI_THESAURUS C29711
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
Code System Code Type Description
USAN
WW-160
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
INN
9364
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
CAS
403989-79-7
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
NCI_THESAURUS
C152809
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
EPA CompTox
DTXSID30193393
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
FDA UNII
73YSY3U094
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
DRUG BANK
DB12414
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
SMS_ID
100000177637
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
ChEMBL
CHEMBL2103860
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
PUBCHEM
56842069
Created by admin on Mon Mar 31 19:08:03 GMT 2025 , Edited by admin on Mon Mar 31 19:08:03 GMT 2025
PRIMARY
Related Record Type Details
LIVER CARBOXYLESTERASE 1
METABOLIC ENZYME -> SUBSTRATE
MICROSOMAL TRIGLYCERIDE TRANSFER PROTEIN LARGE SUBUNIT
TARGET -> INHIBITOR
Differential stability of the ester functionality towards intestinal versus liver esterases. Inhibits intesinal transferase.
Related Record Type Details
Structure of (+)-(R)-?-Phenyl-4-[4-[[[4?-(trifluoromethyl)[1,1?-biphenyl]-2-yl]carbonyl]amino]phenyl]-1-piperidineacetic acid
METABOLITE INACTIVE -> PARENT
Formed in Liver
Related Record Type Details
Structure of USISTAPIDE
ACTIVE MOIETY
Treatment of obesity and type 2 diabetes. Soft drug
NIH
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