Loxiglumide | CAS#107097-80-3 | CCK-A receptor antagonist

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

MedKoo CAT#: 317122

CAS#: 107097-80-3

Description: Loxiglumide is a potent, orally active, and selective CCK-A receptor antagonist which stimulates calorie intake and hunger feelings in humans. Loxiglumide inhibits pancreatic secretion of digestive enzymes, and also blocks CCK-induced gastric secretions and emptying. Intravenous administration of loxiglumide antagonized the CCK-induced reduction of gastric emptying in rats, acceleration of intestinal transport in mice, increase in ileal motility in rabbits, gallbladder contraction in guinea pigs and acceleration of gallbladder emptying in mice.

Chemical Structure

Loxiglumide

CAS# 107097-80-3

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317122
Name: Loxiglumide
CAS#: 107097-80-3
Chemical Formula: C21H30Cl2N2O5
Exact Mass: 460.15
Molecular Weight: 461.380
Elemental Analysis: C, 54.67; H, 6.55; Cl, 15.37; N, 6.07; O, 17.34

Price and Availability

Size	Price	Availability
25mg	USD 400	2 weeks
50mg	USD 700	2 weeks
100mg	USD 1150	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: CR-1505; CR 1505; CR1505; Loxiglumide, brand name: Loxizin.

IUPAC/Chemical Name: 4-(3,4-dichlorobenzamido)-5-((3-methoxypropyl)(pentyl)amino)-5-oxopentanoic acid

InChi Key: QNQZBKQEIFTHFZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H30Cl2N2O5/c1-3-4-5-11-25(12-6-13-30-2)21(29)18(9-10-19(26)27)24-20(28)15-7-8-16(22)17(23)14-15/h7-8,14,18H,3-6,9-13H2,1-2H3,(H,24,28)(H,26,27)

SMILES Code: CCCCCN(C(C(NC(C1=CC(Cl)=C(Cl)C=C1)=O)CCC(O)=O)=O)CCCOC

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:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Loxiglumide is a cholecystokinin (CCK-1) receptor antagonist.
In vitro activity:	Exposure of primary mouse duodenal cells to 10 pM sulfated CCK-8 caused a two fold increase in dodecanoic acid fatty acid (FA) uptake. The selective CCK A receptor antagonist loxiglumide (100 μM) completely abolished the CCK-8 induced FA uptake. Reference: Front Physiol. 2017 Sep 1;8:660. https://pubmed.ncbi.nlm.nih.gov/28919867/
In vivo activity:	Eight-week-old Wistar rats were divided into the following groups: preadministration of loxiglumide (40 mg/kg) intravenously at 120, 60, and 0 minutes before endogenous CCK stimulation induced by a single oral administration of camostat (50 mg/kg) or exogenous CCK stimulation by a subcutaneous injection of CCK-8 (6 g/kg body weight). The most significant suppression of the proliferation of the acinar cells was observed in those groups which received loxiglumide 60 minutes before CCK stimulation (P < 0.016). Reference: Pancreas. 2006 Mar;32(2):190-6. https://pubmed.ncbi.nlm.nih.gov/16552340/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	65.02
	DMSO	58.7	127.26
	DMSO:PBS (pH 7.2) (1:7)	0.1	0.26
	Ethanol	33.1	71.68

Preparing Stock Solutions

The following data is based on the product molecular weight 461.38 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. Demenis C, McLaughlin J, Smith CP. Sulfated Cholecystokinin-8 Promotes CD36-Mediated Fatty Acid Uptake into Primary Mouse Duodenal Enterocytes. Front Physiol. 2017 Sep 1;8:660. doi: 10.3389/fphys.2017.00660. PMID: 28919867; PMCID: PMC5586203. 2. Hirata M, Itoh M, Tsuchida A, Ooishi H, Hanada K, Kajiyama G. Cholecystokinin receptor antagonist, loxiglumide, inhibits invasiveness of human pancreatic cancer cell lines. FEBS Lett. 1996 Apr 1;383(3):241-4. doi: 10.1016/0014-5793(96)00245-1. PMID: 8925905. 3. Yucel T, Gonullu D, Orhan Gurer A, Duzman R, Nihat Koksoy F, Yilmaz N, Sit M. The effects on diet, anastomotic type, and loxiglumide on gastric emptying following gastrojejunostomy. Int J Surg. 2009 Apr;7(2):163-7. doi: 10.1016/j.ijsu.2009.01.010. Epub 2009 Feb 13. PMID: 19342323. 4. Kanemitsu D, Sakagami J, Motoyoshi T, Nakajima T, Kataoka K. Effects of the cholecystokinin A receptor antagonist loxiglumide on the proliferation and cell cycle time of pancreatic acinar cells in rats. Pancreas. 2006 Mar;32(2):190-6. doi: 10.1097/01.mpa.0000202960.63977.d1. PMID: 16552340.
In vitro protocol:	1. Demenis C, McLaughlin J, Smith CP. Sulfated Cholecystokinin-8 Promotes CD36-Mediated Fatty Acid Uptake into Primary Mouse Duodenal Enterocytes. Front Physiol. 2017 Sep 1;8:660. doi: 10.3389/fphys.2017.00660. PMID: 28919867; PMCID: PMC5586203. 2. Hirata M, Itoh M, Tsuchida A, Ooishi H, Hanada K, Kajiyama G. Cholecystokinin receptor antagonist, loxiglumide, inhibits invasiveness of human pancreatic cancer cell lines. FEBS Lett. 1996 Apr 1;383(3):241-4. doi: 10.1016/0014-5793(96)00245-1. PMID: 8925905.
In vivo protocol:	1. Yucel T, Gonullu D, Orhan Gurer A, Duzman R, Nihat Koksoy F, Yilmaz N, Sit M. The effects on diet, anastomotic type, and loxiglumide on gastric emptying following gastrojejunostomy. Int J Surg. 2009 Apr;7(2):163-7. doi: 10.1016/j.ijsu.2009.01.010. Epub 2009 Feb 13. PMID: 19342323. 2. Kanemitsu D, Sakagami J, Motoyoshi T, Nakajima T, Kataoka K. Effects of the cholecystokinin A receptor antagonist loxiglumide on the proliferation and cell cycle time of pancreatic acinar cells in rats. Pancreas. 2006 Mar;32(2):190-6. doi: 10.1097/01.mpa.0000202960.63977.d1. PMID: 16552340.

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1: Yucel T, Gonullu D, Orhan Gurer A, Duzman R, Nihat Koksoy F, Yilmaz N, Sit M. The effects on diet, anastomotic type, and loxiglumide on gastric emptying following gastrojejunostomy. Int J Surg. 2009 Apr;7(2):163-7. doi: 10.1016/j.ijsu.2009.01.010. Epub 2009 Feb 13. PubMed PMID: 19342323.

2: Kanemitsu D, Sakagami J, Motoyoshi T, Nakajima T, Kataoka K. Effects of the cholecystokinin A receptor antagonist loxiglumide on the proliferation and cell cycle time of pancreatic acinar cells in rats. Pancreas. 2006 Mar;32(2):190-6. PubMed PMID: 16552340.

3: Katschinski M. Loxiglumide Rotta research. IDrugs. 2002 May;5(5):469-74. PubMed PMID: 15570466.

4: Fanali S, D'Orazio G, Quaglia MG, Rocco A. Use of a hepta-Tyr antibiotic modified silica stationary phase for the enantiomeric resolution of D,L-loxiglumide by electrochromatography and nano-liquid chromatography. J Chromatogr A. 2004 Oct 8;1051(1-2):247-52. PubMed PMID: 15532580.

5: Ishizaki K, Kinbara S, Kawamura M, Kimura K, Shiratori K, Takeuchi T. Effect of cholecystokinin1 receptor antagonist loxiglumide (CR1505) on basal pancreatic exocrine secretion in conscious rats. Pancreas. 2003 Jan;26(1):87-91. PubMed PMID: 12499923.

6: Shiratori K, Takeuchi T, Satake K, Matsuno S; Study Group of Loxiglumide in Japan. Clinical evaluation of oral administration of a cholecystokinin-A receptor antagonist (loxiglumide) to patients with acute, painful attacks of chronic pancreatitis: a multicenter dose-response study in Japan. Pancreas. 2002 Jul;25(1):e1-5. PubMed PMID: 12131781.

7: Ogura Y, Matsuda S, Itho M, Sasaki H, Tanigawa K, Shimomura M. Inhibitory effect of loxiglumide (CR 1505), a cholecystokinin receptor antagonist, on N-nitrosobis(2-oxopropyl) amine-induced biliary carcinogenesis in Syrian hamsters. World J Surg. 2002 Mar;26(3):359-65. Epub 2002 Jan 18. PubMed PMID: 11865375.

8: Beglinger C, Degen L, Matzinger D, D'Amato M, Drewe J. Loxiglumide, a CCK-A receptor antagonist, stimulates calorie intake and hunger feelings in humans. Am J Physiol Regul Integr Comp Physiol. 2001 Apr;280(4):R1149-54. PubMed PMID: 11247838.

9: Ochi K, Harada H, Satake K. Clinical evaluation of cholecystokinin-A- receptor antagonist (loxiglumide) for the treatment of acute pancreatitis. A preliminary clinical trial. Study Group of Loxiglumide in Japan. Digestion. 1999;60 Suppl 1:81-5. PubMed PMID: 10026438.

10: Satake K, Kimura K, Saito T. Therapeutic effects of loxiglumide on experimental acute pancreatitis using various models. Digestion. 1999;60 Suppl 1:64-8. PubMed PMID: 10026435.

11: Kimura K, Tominaga K, Fujii M, Saito T, Kasai H. Effects of loxiglumide on experimental acute pancreatitis in comparison with gabexate mesilate. Arzneimittelforschung. 1998 Jan;48(1):65-9. PubMed PMID: 9522035.

12: Fukamizu Y, Nakajima T, Kimura K, Kanda H, Fujii M, Saito T, Kasai H. Biochemical and pharmacological profiles of loxiglumide, a novel cholecystokinin-A receptor antagonist. Arzneimittelforschung. 1998 Jan;48(1):58-64. PubMed PMID: 9522034.

13: Ninomiya K, Saito T, Wakatsuki K, Saeki M, Kato T, Edano K, Kasai H, Kimura K, Fujii M. Effects of loxiglumide on pancreatic exocrine secretion stimulated by meal in conscious dogs. Arzneimittelforschung. 1998 Jan;48(1):55-7. PubMed PMID: 9522033.

14: Ninomiya K, Saito T, Wakatsuki K, Saeki M, Kato T, Kasai H, Kimura K, Fujii M. Effects of loxiglumide on pancreatic exocrine secretion stimulated by cholecystokinin-8 in conscious dogs. Arzneimittelforschung. 1998 Jan;48(1):52-4. PubMed PMID: 9522032.

15: Saito T, Ukai K, Masuda T, Nakagawa T, Kimura K, Fujii M, Wakatsuki K, Saeki M, Kasai H. General pharmacological profile of the novel cholecystokinin-A antagonist loxiglumide. Arzneimittelforschung. 1997 Dec;47(12):1375-82. PubMed PMID: 9450167.

16: Imoto I, Yamamoto M, Jia DM, Otsuki M. Effect of chronic oral administration of the CCK receptor antagonist loxiglumide on exocrine and endocrine pancreas in normal rats. Int J Pancreatol. 1997 Dec;22(3):177-85. PubMed PMID: 9444548.

17: Schwizer W, Borovicka J, Kunz P, Fraser R, Kreiss C, D'Amato M, Crelier G, Boesiger P, Fried M. Role of cholecystokinin in the regulation of liquid gastric emptying and gastric motility in humans: studies with the CCK antagonist loxiglumide. Gut. 1997 Oct;41(4):500-4. PubMed PMID: 9391249; PubMed Central PMCID: PMC1891533.

18: Wakatsuki K, Saito T, Saeki M, Ninomiya K, Kasai H, Kimura K, Fujii M. Cholecystokinin antagonistic activities of loxiglumide. Arzneimittelforschung. 1997 Oct;47(10):1130-3. PubMed PMID: 9368707.

19: Militello C, Sperti C, Di Prima F, Pedrazzoli S. Clinical evaluation and safety of loxiglumide (CCK-A receptor antagonist) in nonresectable pancreatic cancer patients. Italian Pancreatic Cancer Study Group. Pancreas. 1997 Apr;14(3):222-8. PubMed PMID: 9094151.

20: Beckh K, Dirks A, Koop I, Koop H, Adler G. Impairment of hepatic transport processes in perfused rat liver by the specific CCK receptor antagonist loxiglumide. Res Exp Med (Berl). 1997;197(3):125-35. PubMed PMID: 9406280.

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