Glipizide | CAS#29094-61-9 | Insulin Blocker

MedKoo Cat#: 317972 | Name: Glipizide

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Description:

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

Glipizide is a short-acting, second-generation, blood-glucose-lowering agent belonging to the sulfonylurea class that increases the release of endogenous insulin from β-cells by blocking potassium channels. The drug-formulated version of Glipizide, marketed as Glucotrol or under generic label, is most commonly prescribed to lower blood sugar levels in type 2 diabetes. Glipizide is rapidly absorbed, has a very quick onset of action and a short half-life. This agent is extensively metabolized in the liver and the metabolites as well as the unchanged form are excreted in the urine.

Chemical Structure

Glipizide

CAS#29094-61-9

Theoretical Analysis

MedKoo Cat#: 317972

Name: Glipizide

CAS#: 29094-61-9

Chemical Formula: C21H27N5O4S

Exact Mass: 445.1784

Molecular Weight: 445.54

Elemental Analysis: C, 56.61; H, 6.11; N, 15.72; O, 14.36; S, 7.20

Price and Availability

Size	Price	Availability
5g	USD 150.00	Ready to ship
10g	USD 250.00	Ready to ship
25g	USD 450.00	Ready to ship
50g	USD 750.00	Ready to ship
100g	USD 1,250.00	Ready to ship
200g	USD 2,150.00	Ready to ship

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Synonym

Glipizide; Glucotrol; Minidiab; Glydiazinamide; Melizide; Minodiab; Ozidia; TK 1320; TK1320; TK-1320; CP-28,720; CP28,720; CP 28,720; CP-28720; CP28720; CP 28720;

IUPAC/Chemical Name

N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-5-methylpyrazine-2-carboxamide

InChi Key

ZJJXGWJIGJFDTL-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)

SMILES Code

CC1=NC=C(N=C1)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3

Appearance

White to off-white 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

Certificate of Analysis

View CoA: current batch, Lot#T20Z09C22

QC Data

View QC data: current batch, Lot#T20Z09C22

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Glipizide (CP 2872; K 4024) is a sulfonylurea class anti-diabetic agent that acts by partially blocking ATP-sensitive potassium (KATP) channels among β cells (IC50 = 6.4 nM) of pancreatic islets of Langerhans.

In vitro activity:

To investigate the effect of glipizide on autophagy flux, whole cell lysates were included to western blot analysis. As shown in Figure2A, the protein levels of DR4 and DR5 were unchanged by glipizide at varying concentrations. Nevertheless, LC3-II increased, and p62 expression decreased after glipizide treatment in a dose-dependent manner (Figure2B). Immunocytochemistry results also supported that various concentrations of glipizide decreased p62 protein levels (Figure2C). A TEM assay suggested that numerous autophagic vacuoles and empty vacuoles were appeared in the cells treated with glipizide (Figure2D). The combined treatment with glipizide and TRAIL (tumor necrosis factor–related apoptosis-inducing ligand) enhanced intracellular apoptosis indicators Ac-cas3 and Ac-cas8 expression levels compare with the single treatment with TRAIL or glipizide (Figure2E). These results reveal that glipizide can induce autophagy in A549 cells. Reference: Oncotarget. 2017 Nov 21; 8(59): 100021–100033. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5724999/

In vivo activity:

Given that glipizide is capable of inhibiting angiogenesis in the chick embryo, it was speculated that glipizide may also suppress tumor-induced angiogenesis, thereby mitigating tumor growth and metastasis. To this end, a mouse xenograft model with mouse breast cancer 4T1 cells was employed. Glipizide (5 mg/kg) was administered daily for 14 days after subcutaneous inoculation of 4T1 cells into mouse mammary fat pad. Glipizide was found to significantly inhibit tumor growth (Figure2A) and weight (Figure2B). Compared with the DMSO treatment, the postprandial blood glucose levels of the mice treated with the glipizide significantly decreased 30 min later and returned to normal 12 h later (Supplemental Table S2). Glipizide treatment also significantly reduced lung metastasis when 4T1 cells were intravenously administered as compared with the DMSO or glimepiride group (Figure2C). Furthermore, glipizide was also found capable of inhibiting B16F10 melanoma growth and metastasis (Supplemental Figure S1). In addition, glipizide abolishes the CD31 staining for MVD (Figure2D).These results collectively suggest that glipizide inhibits the tumor growth and metastasis of malignant melanoma and breast cancer by impeding tumor-induced angiogenesis. Reference: Oncotarget. 2014 Oct; 5(20): 9966–9979. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4259451/

	Solvent	mg/mL	mM
Solubility
	DMSO	53.0	118.96

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 445.54 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. Nazim UM, Moon JH, Lee YJ, Seol JW, Kim YJ, Park SY. Glipizide sensitizes lung cancer cells to TRAIL-induced apoptosis via Akt/mTOR/autophagy pathways. Oncotarget. 2017 Oct 9;8(59):100021-100033. doi: 10.18632/oncotarget.21754. PMID: 29245957; PMCID: PMC5724999. 2. Qi C, Bin Li, Yang Y, Yang Y, Li J, Zhou Q, Wen Y, Zeng C, Zheng L, Zhang Q, Li J, He X, Zhou J, Shao C, Wang L. Glipizide suppresses prostate cancer progression in the TRAMP model by inhibiting angiogenesis. Sci Rep. 2016 Jun 13;6:27819. doi: 10.1038/srep27819. PMID: 27292155; PMCID: PMC4904209. 3. Yang G, Zeng G, Wu JP, Jiang O, Zeng YB, Huang SJ, Huang JJ, Wu DQ. Glipizide blocks renal interstitial fibrosis by inhibiting AKT signaling pathway. Eur Rev Med Pharmacol Sci. 2017 Feb;21(4):867-872. PMID: 28272693 4. Qi C, Zhou Q, Li B, Yang Y, Cao L, Ye Y, Li J, Ding Y, Wang H, Wang J, He X, Zhang Q, Lan T, Lee KK, Li W, Song X, Zhou J, Yang X, Wang L. Glipizide, an antidiabetic drug, suppresses tumor growth and metastasis by inhibiting angiogenesis. Oncotarget. 2014 Oct 30;5(20):9966-79. doi: 10.18632/oncotarget.2483. PMID: 25294818; PMCID: PMC4259451.

In vitro protocol:

In vivo protocol:

1. Yang G, Zeng G, Wu JP, Jiang O, Zeng YB, Huang SJ, Huang JJ, Wu DQ. Glipizide blocks renal interstitial fibrosis by inhibiting AKT signaling pathway. Eur Rev Med Pharmacol Sci. 2017 Feb;21(4):867-872. PMID: 28272693. 2. Qi C, Zhou Q, Li B, Yang Y, Cao L, Ye Y, Li J, Ding Y, Wang H, Wang J, He X, Zhang Q, Lan T, Lee KK, Li W, Song X, Zhou J, Yang X, Wang L. Glipizide, an antidiabetic drug, suppresses tumor growth and metastasis by inhibiting angiogenesis. Oncotarget. 2014 Oct 30;5(20):9966-79. doi: 10.18632/oncotarget.2483. PMID: 25294818; PMCID: PMC4259451.

1: Correa R, Quintanilla Rodriguez BS, Nappe TM. Glipizide. 2020 Jul 6. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 29083816. 2: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Glipizide. 2018 Oct 31. PMID: 29999913. 3: Foster RH, Plosker GL. Glipizide. A review of the pharmacoeconomic implications of the extended-release formulation in type 2 diabetes mellitus. Pharmacoeconomics. 2000 Sep;18(3):289-306. doi: 10.2165/00019053-200018030-00008. PMID: 11147395. 4: Ogonowski J. Glipizid--krókodziałajaca pochodna sulfonylomocznika [Glipizide --a short-acting sulphonylurea derivative]. Przegl Lek. 1996;53(9):666-7. Polish. PMID: 8992534. 5: Małecki M. Miejsce glipizydu w leczeniu cukrzycy nieinsulinozaleznej [The role of glipizide in the treatment of non-insulin dependent diabetes]. Przegl Lek. 1996;53(9):663-5. Polish. PMID: 8992533. 6: Ford SL. NIDDM in the cat: treatment with the oral hypoglycemic medication, glipizide. Vet Clin North Am Small Anim Pract. 1995 May;25(3):599-615. doi: 10.1016/s0195-5616(95)50056-7. PMID: 7660535. 7: Shcherbak AV. Klinicheskaia farmakologiia minidiaba (glipizida) (obzor literatury) [The clinical pharmacology of Minidiab (glipizide) (a review of the literature)]. Lik Sprava. 1993 Jan;(1):28-33. Russian. PMID: 8379132. 8: Wensing G. Glipizide: an oral hypoglycemic drug. Am J Med Sci. 1989 Jul;298(1):69-71. doi: 10.1097/00000441-198907000-00012. PMID: 2665487. 9: Kuhn T. The second generation oral sulfonylureas: glyburide and glipizide. Am Pharm. 1988 Oct;NS28(10):55-61. PMID: 3143256. 10: Lebovitz HE. Glipizide: a second-generation sulfonylurea hypoglycemic agent. Pharmacology, pharmacokinetics and clinical use. Pharmacotherapy. 1985 Mar- Apr;5(2):63-77. doi: 10.1002/j.1875-9114.1985.tb03405.x. PMID: 3923454. 11: Prendergast BD. Glyburide and glipizide, second-generation oral sulfonylurea hypoglycemic agents. Clin Pharm. 1984 Sep-Oct;3(5):473-85. PMID: 6435940. 12: Brogden RN, Heel RC, Pakes GE, Speight TM, Avery GS. Glipizide: a review of its pharmacological properties and therapeutic use. Drugs. 1979 Nov;18(5):329-53. doi: 10.2165/00003495-197918050-00001. PMID: 389600. 13: Brunová E. Glipizid--nové perorální antidiabetikum (souborný referát) [Glipizide a new oral antidiabetic agent (comprehensive review)]. Vnitr Lek. 1976 Jun;22(6):595-9. Czech. PMID: 820071.