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

Details

Stereochemistry ABSOLUTE
Molecular Formula C40H33F3N4O3
Molecular Weight 674.7117
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIRLOTAPIDE

SMILES

CN(Cc1ccccc1)C(=O)[C@]([H])(c2ccccc2)N=C(c3cc4cc(ccc4n3C)NC(=O)c5ccccc5-c6ccc(cc6)C(F)(F)F)O

InChI

InChIKey=TUOSYWCFRFNJBS-BHVANESWSA-N
InChI=1S/C40H33F3N4O3/c1-46(25-26-11-5-3-6-12-26)39(50)36(28-13-7-4-8-14-28)45-38(49)35-24-29-23-31(21-22-34(29)47(35)2)44-37(48)33-16-10-9-15-32(33)27-17-19-30(20-18-27)40(41,42)43/h3-24,36H,25H2,1-2H3,(H,44,48)(H,45,49)/t36-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including: https://www.vetdepot.com/product-labels/slentrol.pdf | https://www.ncbi.nlm.nih.gov/pubmed/17276061 | https://www.ncbi.nlm.nih.gov/pubmed/17567511

Dirlotapide is indicated for the management of obesity in dogs. Dirlotapide is a microsomal triglyceride transfer protein (MTP) inhibitor. It mainly acts locally in the gut to reduce appetite, increase fecal fat and produce weight loss in dogs. The adverse reactions associated with treatment with Dirlotapide include vomiting, loose stools/diarrhea, lethargy, and anorexia.

CNS Activity

Originator

Curator's Comment:: https://www.google.com/patents/WO2003002533A1 # Pfizer Inc.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SLENTROL

Approved Use

SLENTROL (dirlotapide) Oral Solution is indicated for the management of obesity in dogs.

Launch Date

1.16786882E12
PubMed

PubMed

TitleDatePubMed
In vitro and in vivo profile of 5-[(4'-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid benzylmethyl carbamoylamide (dirlotapide), a novel potent MTP inhibitor for obesity.
2007 Apr 1
Efficacy and safety of dirlotapide in the management of obese dogs evaluated in two placebo-controlled, masked clinical studies in North America.
2007 Aug
Influence of dirlotapide, a microsomal triglyceride transfer protein inhibitor, on the digestibility of a dry expanded diet in adult dogs.
2007 Aug
Canine obesity: an overview.
2007 Aug
The use of 18O-exchange and base-catalyzed N-dealkylation with liquid chromatography/tandem mass spectrometry to identify carbinolamide metabolites.
2010 Jul 30
Low-energy nanoemulsification to design veterinary controlled drug delivery devices.
2010 Oct 21
Patents

Sample Use Guides

The initial dosage of SLENTROL is 0.01 mL/kg (0.0045 mL/lb) body weight, administered once daily, for the first 14 days. After the first 14 days of treatment, the dose volume of SLENTROL should be doubled to 0.02 mL/kg (0.009 mL/lb) of body weight, administered once daily for the next 14 days (days 15 to 28 of treatment). Dogs should be weighed monthly and the dose volume adjusted every month, as necessary, to maintain a target percent weight loss of ≥0.7% per week.
Route of Administration: Oral
In a murine model investigating intestinal triglyceride transfer protein (MTP) inhibition, dirlotapide demonstrated potent inhibition of intestinal fat absorption with an ED25 of 0.16 mg/kg. In contrast, it was a poor inhibitor of hepatic MTP as demonstrated in a murine model of triglyceride lowering, where it had an ED25 of 6 mg/kg.
Name Type Language
DIRLOTAPIDE
GREEN BOOK   INN   MI   USAN  
INN   USAN  
Official Name English
CP-742,033
Code English
1H-INDOLE-2-CARBOXAMIDE, 1-METHYL-N-((1S)-2-(METHYL(PHENYLMETHYL)AMINO)-2-OXO-1-PHENYLETHYL)-5-(((4'-(TRIFLUOROMETHYL)(1,1'-BIPHENYL)-2-YL)CARBONYL)AMINO)-
Common Name English
CP-742033
Code English
DIRLOTAPIDE [GREEN BOOK]
Common Name English
SLENTROL
Brand Name English
DIRLOTAPIDE [INN]
Common Name English
N-((1S)-2-(BENZYLMETHYLAMINO)-2-OXO-1-PHENYLETHYL)-1-METHYL-5-(((4'-(TRIFLUOROMETHYL)BIPHENYL-2-YL)CARBONYL)AMINO)-1H-INDOLE-2-CARBOXAMIDE
Common Name English
DIRLOTAPIDE [USAN]
Common Name English
DIRLOTAPIDE [EMA EPAR VETERINARY]
Common Name English
DIRLOTAPIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29728
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
WHO-VATC QA08AB91
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
CFR 21 CFR 520.666
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
EMA VETERINARY ASSESSMENT REPORTS SLENTROL [WITHDRAWN]
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C77329
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
MESH
C521290
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
FDA UNII
578H0RMP25
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
WIKIPEDIA
DIRLOTAPIDE
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
PUBCHEM
9917862
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
MERCK INDEX
M4665
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB11399
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
CAS
481658-94-0
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
ChEMBL
CHEMBL410414
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
INN
8468
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY
RXCUI
1592684
Created by admin on Sat Jun 26 02:52:08 UTC 2021 , Edited by admin on Sat Jun 26 02:52:08 UTC 2021
PRIMARY RxNorm