Glipizide
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MedKoo CAT#: 317972

CAS#: 29094-61-9

Description: 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

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Glipizide
CAS# 29094-61-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317972
Name: Glipizide
CAS#: 29094-61-9
Chemical Formula: C21H27N5O4S
Exact Mass: 445.18
Molecular Weight: 445.540
Elemental Analysis: C, 56.61; H, 6.11; N, 15.72; O, 14.36; S, 7.20

Price and Availability

Size Price Availability Quantity
5g USD 150 Ready to ship
10g USD 250 Ready to ship
25g USD 450 Ready to ship
50g USD 750 Ready to ship
100g USD 1250 Ready to ship
200g USD 2150 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:

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 53.0 118.96

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.

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. 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: 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.
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.

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2: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Glipizide. 2018 Oct 31. PMID: 29999913.


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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.


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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.