Dirlotapide

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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Contraindications & Blackbox Warnings
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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
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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

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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
  1. Merritt DA, Lynch MP, King VL: Pharmacokinetics of dirlotapide in the dog. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:24-32. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. 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]
  8. 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]
  9. 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]
  10. 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]
KEGG Drug
D03867
ChemSpider
8093509
BindingDB
50204367
RxNav
1592684
ChEMBL
CHEMBL410414
ZINC
ZINC000003988502
Wikipedia
Dirlotapide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1WithdrawnTreatmentObesity1

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
PropertyValueSource
Water Solubility9.05e-05 mg/mLALOGPS
logP7.41ALOGPS
logP8.51Chemaxon
logS-6.9ALOGPS
pKa (Strongest Acidic)8.92Chemaxon
pKa (Strongest Basic)0.85Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area86.93 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity189.73 m3·mol-1Chemaxon
Polarizability69.99 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002e-4290014000-adbe4e433cce48cae7e8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-007c-3921101000-38cc246b3f01e1959ed3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002g-9523044000-a4203bf13f4d9c2dfdfa
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-4825934000-0b5ac5ac531dc34d745f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-006x-9483202000-4ddf1db7d4ae1ebb5a15
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1982731000-5d02f2c86c201a32f6f9
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-246.84685
predicted
DeepCCS 1.0 (2019)
[M+H]+248.74226
predicted
DeepCCS 1.0 (2019)
[M+Na]+254.43553
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:24 / Updated at February 21, 2021 18:53