Dirlotapide
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- Dirlotapide
- DrugBank Accession Number
- DB11399
- Background
Dirlotapide is a drug employed in the treatment of obesity in dogs. It is marketed by Pfizer and Zoetis under the brand name, Slentrol, and is not intended for human use.
- Type
- Small Molecule
- Groups
- Investigational, Vet approved
- Structure
- Weight
- Average: 674.724
Monoisotopic: 674.250475428 - Chemical Formula
- C40H33F3N4O3
- Synonyms
- Dirlotapide
- External IDs
- CP 742033
- CP-742,033
- CP-742033
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Slentrol
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-acyl-alpha amino acids and derivatives
- Alternative Parents
- Alpha amino acid amides / Biphenyls and derivatives / Indolecarboxamides and derivatives / Trifluoromethylbenzenes / Phenylacetamides / N-alkylindoles / Benzamides / Indoles / 2-heteroaryl carboxamides / Benzoyl derivatives show 13 more
- Substituents
- 2-heteroaryl carboxamide / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Aromatic heteropolycyclic compound / Azacycle / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 578H0RMP25
- CAS number
- 481658-94-0
- InChI Key
- TUOSYWCFRFNJBS-BHVANESWSA-N
- InChI
- 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
- IUPAC Name
- N-[(S)-[benzyl(methyl)carbamoyl](phenyl)methyl]-1-methyl-5-[4'-(trifluoromethyl)-[1,1'-biphenyl]-2-amido]-1H-indole-2-carboximidic acid
- SMILES
- CN(CC1=CC=CC=C1)C(=O)[C@@H](NC(=O)C1=CC2=C(C=CC(NC(=O)C3=CC=CC=C3C3=CC=C(C=C3)C(F)(F)F)=C2)N1C)C1=CC=CC=C1
References
- General References
- Merritt DA, Lynch MP, King VL: Pharmacokinetics of dirlotapide in the dog. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:24-32. [Article]
- Wren JA, King VL, Krautmann MJ, Gossellin J, Kerlin RL, Hickman MA, Schmahai TJ: The safety of dirlotapide in dogs. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:43-54. [Article]
- Merritt DA, Bessire AJ, Vaz AD, Sams JP, Lynch MP: Absorption, distribution, metabolism, and excretion of dirlotapide in the dog. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:17-23. [Article]
- Wren JA, Gossellin J, Sunderland SJ: Dirlotapide: a review of its properties and role in the management of obesity in dogs. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:11-6. [Article]
- Gossellin J, Peachey S, Sherington J, Rowan TG, Sunderland SJ: Evaluation of dirlotapide for sustained weight loss in overweight Labrador retrievers. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:55-65. [Article]
- Sun H, Bessire AJ, Vaz A: Dirlotapide as a model substrate to refine structure-based drug design strategies on CYP3A4-catalyzed metabolism. Bioorg Med Chem Lett. 2012 Jan 1;22(1):371-6. doi: 10.1016/j.bmcl.2011.10.121. Epub 2011 Nov 6. [Article]
- Gossellin J, McKelvie J, Sherington J, Wren JA, Eagleson JS, Rowan TG, Sunderland SJ: An evaluation of dirlotapide to reduce body weight of client-owned dogs in two placebo-controlled clinical studies in Europe. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:73-80. [Article]
- Kirk CA, Boucher JF, Sunderland SJ, Wren JA: Influence of dirlotapide, a microsomal triglyceride transfer protein inhibitor, on the digestibility of a dry expanded diet in adult dogs. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:66-72. [Article]
- Robinson RP, Bartlett JA, Bertinato P, Bessire AJ, Cosgrove J, Foley PM, Manion TB, Minich ML, Ramos B, Reese MR, Schmahai TJ, Swick AG, Tess DA, Vaz A, Wolford A: Discovery of microsomal triglyceride transfer protein (MTP) inhibitors with potential for decreased active metabolite load compared to dirlotapide. Bioorg Med Chem Lett. 2011 Jul 15;21(14):4150-4. doi: 10.1016/j.bmcl.2011.05.099. Epub 2011 Jun 2. [Article]
- Wren JA, King VL, Campbell SL, Hickman MA: Biologic activity of dirlotapide, a novel microsomal triglyceride transfer protein inhibitor, for weight loss in obese dogs. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:33-42. [Article]
- External Links
- KEGG Drug
- D03867
- ChemSpider
- 8093509
- BindingDB
- 50204367
- 1592684
- ChEMBL
- CHEMBL410414
- ZINC
- ZINC000003988502
- Wikipedia
- Dirlotapide
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 9.05e-05 mg/mL ALOGPS logP 7.41 ALOGPS logP 8.51 Chemaxon logS -6.9 ALOGPS pKa (Strongest Acidic) 8.92 Chemaxon pKa (Strongest Basic) 0.85 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 86.93 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 189.73 m3·mol-1 Chemaxon Polarizability 69.99 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 246.84685 predictedDeepCCS 1.0 (2019) [M+H]+ 248.74226 predictedDeepCCS 1.0 (2019) [M+Na]+ 254.43553 predictedDeepCCS 1.0 (2019)
Drug created at February 25, 2016 18:24 / Updated at February 21, 2021 18:53