Lintitript | CAS#136381-85-6 | CCK1 (CCKA) antagonist

MedKoo Cat#: 529323 | Name: Lintitript

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Description:

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

Lintitript is a CCK1 (CCKA) antagonist potentially for the treatment of pancreatic cancer.

Chemical Structure

Lintitript

CAS#136381-85-6

Theoretical Analysis

MedKoo Cat#: 529323

Name: Lintitript

CAS#: 136381-85-6

Chemical Formula: C20H14ClN3O3S

Exact Mass: 411.0444

Molecular Weight: 411.86

Elemental Analysis: C, 58.33; H, 3.43; Cl, 8.61; N, 10.20; O, 11.65; S, 7.78

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Related CAS #

No Data

Synonym

SR-27897; SR27897; SR 27897; Lintitript;

IUPAC/Chemical Name

2-(2-((4-(2-chlorophenyl)thiazol-2-yl)carbamoyl)-1H-indol-1-yl)acetic acid

InChi Key

ILNRQFBVVQUOLP-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H14ClN3O3S/c21-14-7-3-2-6-13(14)15-11-28-20(22-15)23-19(27)17-9-12-5-1-4-8-16(12)24(17)10-18(25)26/h1-9,11H,10H2,(H,25,26)(H,22,23,27)

SMILES Code

O=C(O)CN1C(C(NC2=NC(C3=CC=CC=C3Cl)=CS2)=O)=CC4=C1C=CC=C4

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

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lintitript (SR 27897) is a cholecystokinin (CCK1) receptor antagonist with an EC50 of 6 nM and a Ki of 0.2 nM.

In vitro activity:

TBD

In vivo activity:

As illustrated in Figure 1a, treatment of fed rats with SR-27,897 (0.3 mg kg−1) raised plasma insulin concentration from 1.9±0.2 to 3.2±0.8 μg dl−1. SR-27,897 significantly increased plasma leptin concentration both in fed and fasted rats from 11.2±2.2 to 25.0±1.3 ng ml−1 (one-way ANOVA, F(1,18)=11.193; P<0.01) and from 5.1±1.4 to 12.9±2.3 ng ml−1 (F(1,16)=9.539; P<0.01), respectively. Reference: Br J Pharmacol. 2003 Oct;140(4):647-52. https://pubmed.ncbi.nlm.nih.gov/14534148/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	60.3	146.40

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 411.86 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

Formulation protocol:

1. Cano V, Ezquerra L, Ramos MP, Ruiz-Gayo M. Regulation of leptin distribution between plasma and cerebrospinal fluid by cholecystokinin receptors. Br J Pharmacol. 2003 Oct;140(4):647-52. doi: 10.1038/sj.bjp.0705477. PMID: 14534148; PMCID: PMC1574067. 2. Gully D, Fréhel D, Marcy C, Spinazzé A, Lespy L, Neliat G, Maffrand JP, Le Fur G. Peripheral biological activity of SR 27897: a new potent non-peptide antagonist of CCKA receptors. Eur J Pharmacol. 1993 Feb 23;232(1):13-9. doi: 10.1016/0014-2999(93)90722-t. PMID: 7681406.

In vitro protocol:

TBD

In vivo protocol:

1: Kreiss C, Schwizer W, Borovicka J, Jansen JB, Bouloux C, Pignol R, Bischof Delaloye A, Fried M. Effect of lintitript, a new CCK-A receptor antagonist, on gastric emptying of a solid-liquid meal in humans. Regul Pept. 1998 Jun 30;74(2-3):143-9. PubMed PMID: 9712175. 2: Gouldson P, Legoux P, Carillon C, Delpech B, Le Fur G, Ferrara P, Shire D. The agonist SR 146131 and the antagonist SR 27897 occupy different sites on the human CCK(1) receptor. Eur J Pharmacol. 2000 Jul 21;400(2-3):185-94. Erratum in: Eur J Pharmacol 2000 Nov 3;407(3):333. PubMed PMID: 10988332. 3: Gouldson P, Legoux P, Carillon C, Delpech B, Le Fur G, Ferrara P, Shire D. Contrasting roles of leu(356) in the human CCK(1) receptor for antagonist SR 27897 and agonist SR 146131 binding. Eur J Pharmacol. 1999 Nov 3;383(3):339-46. PubMed PMID: 10594328. 4: Gouldson P, Legoux P, Carillon C, Dumont X, Le Fur G, Ferrara P, Shire D. Essential role of extracellular charged residues of the human CCK(1) receptor for interactions with SR 146131, SR 27897 and CCK-8S. Eur J Pharmacol. 2000 Feb 18;389(2-3):115-24. PubMed PMID: 10688974. 5: Poncelet M, Arnone M, Heaulme M, Gonalons N, Gueudet C, Santucci V, Thurneyssen O, Keane P, Gully D, Le Fur G, et al. Neurobehavioural effects of SR 27897, a selective cholecystokinin type A (CCK-A) receptor antagonist. Naunyn Schmiedebergs Arch Pharmacol. 1993 Jul;348(1):102-7. PubMed PMID: 8397341. 6: Gouldson P, Legoux P, Carillon C, Delpech B, Le Fur G, Ferrara P, Shire D. Erratum to: "The agonist SR 146131 and the antagonist SR 27897 occupy different sites on the human CCK(1) receptor". Eur J Pharmacol. 2000 Nov 3;407(3):333. PubMed PMID: 11068031. 7: Gully D, Fréhel D, Marcy C, Spinazzé A, Lespy L, Neliat G, Maffrand JP, Le Fur G. Peripheral biological activity of SR 27897: a new potent non-peptide antagonist of CCKA receptors. Eur J Pharmacol. 1993 Feb 23;232(1):13-9. PubMed PMID: 7681406. 8: Cano V, Ezquerra L, Ramos MP, Ruiz-Gayo M. Regulation of leptin distribution between plasma and cerebrospinal fluid by cholecystokinin receptors. Br J Pharmacol. 2003 Oct;140(4):647-52. PubMed PMID: 14534148; PubMed Central PMCID: PMC1574067. 9: Ruiz-Gayo M, Garrido MM, Fuentes JA. Inhibition of the hypothalamic-pituitary-adrenal axis in food-deprived rats by a CCK-A receptor antagonist. Br J Pharmacol. 2000 Mar;129(5):839-42. PubMed PMID: 10696079; PubMed Central PMCID: PMC1571903. 10: Santucci V, Gueudet C, Thurneyssen O, Gully D, Soubrie P, Le Fur G. The CCKA receptor antagonist SR 27897 differentially influences the activity of A9 and A10 dopaminergic neurons in the rat. Ann N Y Acad Sci. 1994 Mar 23;713:364-7. PubMed PMID: 8185189. 11: Lee JH, Kim SY, Kwon YK, Kim BJ, So I. Characteristics of the cholecystokinin-induced depolarization of pacemaking activity in cultured interstitial cells of Cajal from murine small intestine. Cell Physiol Biochem. 2013;31(4-5):542-54. doi: 10.1159/000350075. PubMed PMID: 23571358. 12: Le Dréan G, Le Huërou-Luron I, Gestin M, Desbois C, Romé V, Bernard C, Dufresne M, Moroder L, Gully D, Chayvialle JA, Fourmy D, Guilloteau P. Exogenous CCK and gastrin stimulate pancreatic exocrine secretion via CCK-A but also via CCK-B/gastrin receptors in the calf. Pflugers Arch. 1999 Jun;438(1):86-93. PubMed PMID: 10370091. 13: González AA, Farré R, Monés J, Capellà G, Clavé P. Pharmacological and molecular characterization of muscular cholecystokinin receptors in the human lower oesophageal sphincter. Neurogastroenterol Motil. 2000 Dec;12(6):539-46. PubMed PMID: 11123709. 14: Le Dréan G, Le Huërou-Luron I, Gestin M, Romé V, Bernard C, Chayvialle JA, Fourmy D, Guilloteau P. Pancreatic secretory response to feeding in the calf: CCK-A receptors, but not CCK-B/gastrin receptors are involved. Can J Physiol Pharmacol. 2000 Oct;78(10):813-9. PubMed PMID: 11077982. 15: Sánchez-Fernández C, González MC, Beart PM, Mercer LD, Ruiz-Gayo M, Fernández-Alfonso MS. A novel role for cholecystokinin: regulation of mesenteric vascular resistance. Regul Pept. 2004 Sep 15;121(1-3):145-53. PubMed PMID: 15256285. 16: Storr M, Sattler D, Hahn A, Schusdziarra V, Allescher HD. Endogenous CCK depresses contractile activity within the ascending myenteric reflex pathway of rat ileum. Neuropharmacology. 2003 Mar;44(4):524-32. PubMed PMID: 12646289. 17: Wu W, Zhou HR, He K, Pan X, Sugita-Konishi Y, Watanabe M, Zhang H, Pestka JJ. Role of cholecystokinin in anorexia induction following oral exposure to the 8-ketotrichothecenes deoxynivalenol, 15-acetyldeoxynivalenol, 3-acetyldeoxynivalenol, fusarenon X, and nivalenol. Toxicol Sci. 2014 Apr;138(2):278-89. doi: 10.1093/toxsci/kft335. PubMed PMID: 24385417; PubMed Central PMCID: PMC4246666. 18: Cano V, Merino B, Ezquerra L, Somoza B, Ruiz-Gayo M. A cholecystokinin-1 receptor agonist (CCK-8) mediates increased permeability of brain barriers to leptin. Br J Pharmacol. 2008 Jul;154(5):1009-15. doi: 10.1038/bjp.2008.149. PubMed PMID: 18587446; PubMed Central PMCID: PMC2451056. 19: Gronier B, Debonnel G. Electrophysiological evidence for the implication of cholecystokinin in the modulation of the N-methyl-D-aspartate response by sigma ligands in the rat CA3 dorsal hippocampus. Naunyn Schmiedebergs Arch Pharmacol. 1996 Mar;353(4):382-90. PubMed PMID: 8935704. 20: Archer-Lahlou E, Tikhonova I, Escrieut C, Dufresne M, Seva C, Pradayrol L, Moroder L, Maigret B, Fourmy D. Modeled structure of a G-protein-coupled receptor: the cholecystokinin-1 receptor. J Med Chem. 2005 Jan 13;48(1):180-91. PubMed PMID: 15634012.