Repaglinide | CAS#135062-02-1

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

MedKoo CAT#: 318659

CAS#: 135062-02-1

Description: Repaglinide is an antidiabetic drug in the class of medications known as meglitinides, and was invented in 1983. Repaglinide is an oral medication used in addition to diet and exercise for blood sugar control in type 2 diabetes mellitus. The mechanism of action of repaglinide involves promoting insulin release from β-islet cells of the pancreas.

Chemical Structure

Repaglinide

CAS# 135062-02-1

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318659
Name: Repaglinide
CAS#: 135062-02-1
Chemical Formula: C27H36N2O4
Exact Mass: 452.27
Molecular Weight: 452.590
Elemental Analysis: C, 71.65; H, 8.02; N, 6.19; O, 14.14

Price and Availability

Size	Price	Availability	Quantity
1g	USD 150
2g	USD 250
5g	USD 550
10g	USD 950
25g	USD 1450
50g	USD 2450
100g	USD 3950
500g	USD 5650
1kg	USD 9650
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.

Related CAS #: 147852-26-4

Synonym: Repaglinide; AG-EE 388 ZW; AG-EE388 ZW; AG-EE-388 ZW; AG-EE 623 ZW, AG-EE623 ZW, AG-EE-623 ZW, Prandin, GlucoNorm, Surepost, NovoNorm

IUPAC/Chemical Name: 2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid

InChi Key: FAEKWTJYAYMJKF-QHCPKHFHSA-N

InChi Code: InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1

SMILES Code: O=C(O)C1=CC=C(CC(N[C@H](C2=CC=CC=C2N3CCCCC3)CC(C)C)=O)C=C1OCC

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:	Repaglinide is a metaglitinide antidiabetic agent that blocks ATP-dependent potassium (Kir6) channels in pancreatic β-cells (Kd = 0.42 nM for the sulphonylurea receptor SUR1 when co-expressed with Kir6.2). In vivo, repaglinide lowers blood glucose in fasted rats and dogs (ED50s = 10 and 28.3 μg/kg, respectively).
In vitro activity:	Silencing the FOXO3/LUM axis by repaglinide shows a promising strategy for therapeutic interventions in neuroblastoma and other FOXO3-dependent tumors. Reference: Cells. 2019 Dec 18;9(1):1. https://pubmed.ncbi.nlm.nih.gov/31861249/
In vivo activity:	Repaglinide modulates the downstream regulatory element antagonist modulator-endoplasmic reticulum stress BiP/ATF6/CHOP cascade, increases mitophagy/autophagy, inhibits apoptosis, and lessens oxidative stress, astrocyte/microglial activation, and neuroinflammation in PD. Reference: ACS Chem Neurosci. 2023 Jan 4;14(1):180-194. https://pubmed.ncbi.nlm.nih.gov/36538285/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	30.0	66.29
	DMF	30.0	66.29
	Ethanol	25.0	55.24

Preparing Stock Solutions

The following data is based on the product molecular weight 452.59 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. Salcher S, Spoden G, Huber JM, Golderer G, Lindner H, Ausserlechner MJ, Kiechl-Kohlendorfer U, Geiger K, Obexer P. Repaglinide Silences the FOXO3/Lumican Axis and Represses the Associated Metastatic Potential of Neuronal Cancer Cells. Cells. 2019 Dec 18;9(1):1. doi: 10.3390/cells9010001. PMID: 31861249; PMCID: PMC7017090. 2. Kalehoei E, Azadbakht M. The beneficial effect of repaglinide on in vitro maturation and development ability of immature mouse oocytes. In Vitro Cell Dev Biol Anim. 2017 Aug;53(7):626-631. doi: 10.1007/s11626-017-0152-3. Epub 2017 Apr 21. PMID: 28432599. 3. Motawi TK, Al-Kady RH, Senousy MA, Abdelraouf SM. Repaglinide Elicits a Neuroprotective Effect in Rotenone-Induced Parkinson's Disease in Rats: Emphasis on Targeting the DREAM-ER Stress BiP/ATF6/CHOP Trajectory and Activation of Mitophagy. ACS Chem Neurosci. 2023 Jan 4;14(1):180-194. doi: 10.1021/acschemneuro.2c00656. Epub 2022 Dec 20. PMID: 36538285. 4. Kim CH, Park SH, Sim YB, Kim SS, Kim SJ, Lim SM, Jung JS, Suh HW. Effects of nateglinide and repaglinide administered intracerebroventricularly on the CA3 hippocampal neuronal cell death and hyperglycemia induced by kainic acid in mice. Brain Res Bull. 2014 May;104:36-41. doi: 10.1016/j.brainresbull.2014.02.003. Epub 2014 Apr 2. PMID: 24704461.
In vitro protocol:	1. Salcher S, Spoden G, Huber JM, Golderer G, Lindner H, Ausserlechner MJ, Kiechl-Kohlendorfer U, Geiger K, Obexer P. Repaglinide Silences the FOXO3/Lumican Axis and Represses the Associated Metastatic Potential of Neuronal Cancer Cells. Cells. 2019 Dec 18;9(1):1. doi: 10.3390/cells9010001. PMID: 31861249; PMCID: PMC7017090. 2. Kalehoei E, Azadbakht M. The beneficial effect of repaglinide on in vitro maturation and development ability of immature mouse oocytes. In Vitro Cell Dev Biol Anim. 2017 Aug;53(7):626-631. doi: 10.1007/s11626-017-0152-3. Epub 2017 Apr 21. PMID: 28432599.
In vivo protocol:	1. Motawi TK, Al-Kady RH, Senousy MA, Abdelraouf SM. Repaglinide Elicits a Neuroprotective Effect in Rotenone-Induced Parkinson's Disease in Rats: Emphasis on Targeting the DREAM-ER Stress BiP/ATF6/CHOP Trajectory and Activation of Mitophagy. ACS Chem Neurosci. 2023 Jan 4;14(1):180-194. doi: 10.1021/acschemneuro.2c00656. Epub 2022 Dec 20. PMID: 36538285. 2. Kim CH, Park SH, Sim YB, Kim SS, Kim SJ, Lim SM, Jung JS, Suh HW. Effects of nateglinide and repaglinide administered intracerebroventricularly on the CA3 hippocampal neuronal cell death and hyperglycemia induced by kainic acid in mice. Brain Res Bull. 2014 May;104:36-41. doi: 10.1016/j.brainresbull.2014.02.003. Epub 2014 Apr 2. PMID: 24704461.

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1: Yin J, Deng H, Qin S, Tang W, Zeng L, Zhou B. Comparison of repaglinide and metformin versus metformin alone for type 2 diabetes: a meta-analysis of randomized controlled trials. Diabetes Res Clin Pract. 2014 Sep;105(3):e10-5. doi: 10.1016/j.diabres.2014.06.009. Epub 2014 Jun 23. Review. PubMed PMID: 25005849.

2: Khamaisi M. Severe hypoglycaemia from repaglinide-brotizolam drug interaction: a case report and literature review. Diabet Med. 2012 Sep;29(9):1214-5. doi: 10.1111/j.1464-5491.2012.03631.x. Review. PubMed PMID: 22414218.

3: Scott LJ. Repaglinide: a review of its use in type 2 diabetes mellitus. Drugs. 2012 Jan 22;72(2):249-72. doi: 10.2165/11207600-000000000-00000. Review. Erratum in: Drugs. 2012 Mar 26;72(5):744-5. PubMed PMID: 22268393.

4: Rawat MK, Jain A, Mishra A, Muthu MS, Singh S. Development of repaglinide loaded solid lipid nanocarrier: selection of fabrication method. Curr Drug Deliv. 2010 Jan;7(1):44-50. Review. PubMed PMID: 20044909.

5: Johansen OE, Birkeland KI. Defining the role of repaglinide in the management of type 2 diabetes mellitus: a review. Am J Cardiovasc Drugs. 2007;7(5):319-35. Review. PubMed PMID: 17953471.

6: Plosker GL, Figgitt DP. Repaglinide : a pharmacoeconomic review of its use in type 2 diabetes mellitus. Pharmacoeconomics. 2004;22(6):389-411. Review. PubMed PMID: 15099124.

7: [symbol: see text] Nateglinide and [symbol: see text] repaglinide for type 2 diabetes? Drug Ther Bull. 2003 Jul;41(7):52-4. Review. PubMed PMID: 12879789.

8: Matsuda M, Kaku K. [Repaglinide (NN-623)]. Nihon Rinsho. 2002 Sep;60 Suppl 9:555-8. Review. Japanese. PubMed PMID: 12387050.

9: Culy CR, Jarvis B. Repaglinide: a review of its therapeutic use in type 2 diabetes mellitus. Drugs. 2001;61(11):1625-60. Review. PubMed PMID: 11577798.

10: Moses R. A review of clinical experience with the prandial glucose regulator, repaglinide, in the treatment of type 2 diabetes. Expert Opin Pharmacother. 2000 Dec;1(7):1455-67. Review. PubMed PMID: 11249478.

11: Moses R. Combination therapy in type 2 diabetes: the role of repaglinide. J Assoc Physicians India. 2001 Jan 25;49 Spec No:62-8. Review. PubMed PMID: 11235608.

12: Menon PS. Current understanding regarding the role of repaglinide in post-prandial hyperglycemia. J Assoc Physicians India. 2001 Jan 25;49 Spec No:50-3. Review. PubMed PMID: 11235606.

13: Owens DR, McDougall A. Repaglinide: prandial glucose regulation in clinical practice. Diabetes Obes Metab. 2000 Mar;2 Suppl 1:S43-8. Review. PubMed PMID: 11225759.

14: Massi-Benedetti M, Damsbo P. Pharmacology and clinical experience with repaglinide. Expert Opin Investig Drugs. 2000 Apr;9(4):885-98. Review. PubMed PMID: 11060717.

15: Schatz H. Preclinical and clinical studies on safety and tolerability of repaglinide. Exp Clin Endocrinol Diabetes. 1999;107 Suppl 4:S144-8. Review. PubMed PMID: 10522841.

16: Malaisse WJ. Repaglinide, a new oral antidiabetic agent: a review of recent preclinical studies. Eur J Clin Invest. 1999 Jun;29 Suppl 2:21-9. Review. PubMed PMID: 10383607.

17: Guay DR. Repaglinide, a novel, short-acting hypoglycemic agent for type 2 diabetes mellitus. Pharmacotherapy. 1998 Nov-Dec;18(6):1195-204. Review. PubMed PMID: 9855316.

18: Balfour JA, Faulds D. Repaglinide. Drugs Aging. 1998 Aug;13(2):173-80. Review. Erratum in: Drugs Aging 1999 Jul;15(1):28. PubMed PMID: 9739505.

19: Raskin P. Oral combination therapy: repaglinide plus metformin for treatment of type 2 diabetes. Diabetes Obes Metab. 2008 Dec;10(12):1167-77. doi: 10.1111/j.1463-1326.2008.00907.x. Epub 2008 May 20. Review. PubMed PMID: 18494804.

20: Scheen AJ. Drug-drug and food-drug pharmacokinetic interactions with new insulinotropic agents repaglinide and nateglinide. Clin Pharmacokinet. 2007;46(2):93-108. Review. PubMed PMID: 17253883.

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