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MedKoo Cat#: 317122 | Name: Loxiglumide
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Description:

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

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
Loxiglumide
CAS#107097-80-3

Theoretical Analysis

MedKoo Cat#: 317122

Name: Loxiglumide

CAS#: 107097-80-3

Chemical Formula: C21H30Cl2N2O5

Exact Mass: 460.1532

Molecular Weight: 461.38

Elemental Analysis: C, 54.67; H, 6.55; Cl, 15.37; N, 6.07; O, 17.34

Price and Availability

Size Price Availability Quantity
25mg USD 400.00 2 weeks
50mg USD 700.00 2 weeks
100mg USD 1,150.00 2 weeks
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Related CAS #
No Data
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/
Solvent mg/mL 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
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 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.

Recalculate based on batch purity %
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.
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.