Dirlotapide | CAS#481658-94-0 | MTTP Inhibitor

MedKoo Cat#: 524967 | Name: Dirlotapide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dirlotapide is a gut-selective microsomal triglyceride transfer protein (MTTP or MTP) inhibitor. This blocks the assembly and release of lipoproteins into the bloodstream, thereby reducing fat absorption. It also elicits a satiety signal from lipid-filled cells lining the intestine. Dirlotapide is a drug used to treat obesity in dogs.

Chemical Structure

Dirlotapide

CAS#481658-94-0

Theoretical Analysis

MedKoo Cat#: 524967

Name: Dirlotapide

CAS#: 481658-94-0

Chemical Formula: C40H33F3N4O3

Exact Mass: 674.2505

Molecular Weight: 674.71

Elemental Analysis: C, 71.21; H, 4.93; F, 8.45; N, 8.30; O, 7.11

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Dirlotapide; Slentrol; CP 742033; CP-742033; CP742033; CP-742,033.

IUPAC/Chemical Name

(S)-N-(2-(benzyl(methyl)amino)-2-oxo-1-phenylethyl)-1-methyl-5-(4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamido)-1H-indole-2-carboxamide

InChi Key

TUOSYWCFRFNJBS-BHVANESWSA-N

InChi Code

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

SMILES Code

O=C(C(N1C)=CC2=C1C=CC(NC(C3=CC=CC=C3C4=CC=C(C(F)(F)F)C=C4)=O)=C2)N[C@@H](C5=CC=CC=C5)C(N(C)CC6=CC=CC=C6)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 674.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: German AJ, Titcomb JM, Holden SL, Queau Y, Morris PJ, Biourge V. Cohort Study of the Success of Controlled Weight Loss Programs for Obese Dogs. J Vet Intern Med. 2015 Nov-Dec;29(6):1547-55. doi: 10.1111/jvim.13629. Epub 2015 Oct 1. PubMed PMID: 26426704; PubMed Central PMCID: PMC4895666. 2: Ables GP, Yang KJ, Vogel S, Hernandez-Ono A, Yu S, Yuen JJ, Birtles S, Buckett LK, Turnbull AV, Goldberg IJ, Blaner WS, Huang LS, Ginsberg HN. Intestinal DGAT1 deficiency reduces postprandial triglyceride and retinyl ester excursions by inhibiting chylomicron secretion and delaying gastric emptying. J Lipid Res. 2012 Nov;53(11):2364-79. doi: 10.1194/jlr.M029041. Epub 2012 Aug 21. PubMed PMID: 22911105; PubMed Central PMCID: PMC3466005. 3: 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. PubMed PMID: 22094027. 4: 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. PubMed PMID: 21684740. 5: Bessire AJ, Vaz AD, Walker GS, Wang WW, Sharma R. The use of 18O-exchange and base-catalyzed N-dealkylation with liquid chromatography/tandem mass spectrometry to identify carbinolamide metabolites. Rapid Commun Mass Spectrom. 2010 Jul 30;24(14):2151-61. doi: 10.1002/rcm.4595. PubMed PMID: 20552706. 6: Wren JA, Ramudo AA, Campbell SL, King VL, Eagleson JS, Gossellin J, Sunderland SJ. Efficacy and safety of dirlotapide in the management of obese dogs evaluated in two placebo-controlled, masked clinical studies in North America. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:81-9. PubMed PMID: 17567518. 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. PubMed PMID: 17567517. 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. PubMed PMID: 17567516. 9: 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. PubMed PMID: 17567515. 10: 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. PubMed PMID: 17567514. 11: 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. PubMed PMID: 17567513. 12: Merritt DA, Lynch MP, King VL. Pharmacokinetics of dirlotapide in the dog. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:24-32. PubMed PMID: 17567512. 13: 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. PubMed PMID: 17567511. 14: 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. Review. PubMed PMID: 17567510. 15: Gossellin J, Wren JA, Sunderland SJ. Canine obesity: an overview. J Vet Pharmacol Ther. 2007 Aug;30 Suppl 1:1-10. Review. PubMed PMID: 17567509. 16: Klonoff DC. Dirlotapide, a U.S. Food and Drug Administration-approved first-in-class obesity drug for dogs-will humans be next? J Diabetes Sci Technol. 2007 May;1(3):314-6. PubMed PMID: 19885086; PubMed Central PMCID: PMC2769592. 17: Li J, Bronk BS, Dirlam JP, Blize AE, Bertinato P, Jaynes BH, Hickman A, Miskell C, Pillai UA, Tibbitts JS, Haven ML, Kolosko NL, Barry CJ, Manion TB. 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. Bioorg Med Chem Lett. 2007 Apr 1;17(7):1996-9. Epub 2007 Jan 17. PubMed PMID: 17276061.