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MedKoo Cat#: 317518 | Name: Chlorpropamide
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Description:

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

Chlorpropamide is a drug in the sulfonylurea class used to treat type 2 diabetes mellitus. It is a long-acting 1st generation sulfonylurea. Chlorpropamide acts to increase the secretion of insulin, so it is only effective in patients who have some pancreatic beta cell function.

Chemical Structure

Chlorpropamide
Chlorpropamide
CAS#94-20-2

Theoretical Analysis

MedKoo Cat#: 317518

Name: Chlorpropamide

CAS#: 94-20-2

Chemical Formula: C10H13ClN2O3S

Exact Mass: 0.0000

Molecular Weight: 276.74

Elemental Analysis: C, 43.40; H, 4.73; Cl, 12.81; N, 10.12; O, 17.34; S, 11.59

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
10g USD 400.00 2 Weeks
25g USD 750.00 2 Weeks
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Synonym
Chlorpropamide; Chloropropamide; Diabinese; Chlorpropamid; Meldian; Apo-Chlorpropamide; Apotex Brand of Chlorpropamide; Byk Gulden Brand of Chlorpropamide; Chlorpropamide; Clorpropamid; Diabinese; Farmasierra Brand of Chlorpropamide; Glucamide; Insogen; Meldian; Pfizer Brand of Chlorpropamide;
IUPAC/Chemical Name
1-(4-chlorophenyl)sulfonyl-3-propylurea
InChi Key
RKWGIWYCVPQPMF-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)
SMILES Code
CCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)Cl
Appearance
White crystalline 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

Preparing Stock Solutions

The following data is based on the product molecular weight 276.74 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
1: Kichanov SE, Kozlenko DP, Wąsicki J, Nawrocik W, Dubrovinsky LS, Liermann HP, Morgenroth W, Savenko BN. The polymorphic phase transformations in the chlorpropamide under pressure. J Pharm Sci. 2015 Jan;104(1):81-6. doi: 10.1002/jps.24241. Epub 2014 Nov 12. PubMed PMID: 25393056. 2: Seryotkin YV, Drebushchak TN, Boldyreva EV. A high-pressure polymorph of chlorpropamide formed on hydrostatic compression of the α-form in saturated ethanol solution. Acta Crystallogr B. 2013 Feb;69(Pt 1):77-85. doi: 10.1107/S0108768112051142. Epub 2013 Jan 19. PubMed PMID: 23364463. 3: Drebushchak TN, Drebushchak VA, Boldyreva EV. Solid-state transformations in the β-form of chlorpropamide on cooling to 100 K. Acta Crystallogr B. 2011 Apr;67(Pt 2):163-76. doi: 10.1107/S0108768111004290. Epub 2011 Mar 10. PubMed PMID: 21422615. 4: Ishiguro T, Hirayama F, Iohara D, Arima H, Uekama K. Crystallization and polymorphic transitions of chlorpropamide in aqueous 2-hydroxybutyl-beta-cyclodextrin solution. Eur J Pharm Sci. 2010 Feb 19;39(4):248-55. doi: 10.1016/j.ejps.2009.12.008. Epub 2009 Dec 29. PubMed PMID: 20036739. 5: Drebushchak TN, Chesalov YA, Boldyreva EV. A conformational polymorphic transition in the high-temperature epsilon-form of chlorpropamide on cooling: a new epsilon'-form. Acta Crystallogr B. 2009 Dec;65(Pt 6):770-81. doi: 10.1107/S010876810903290X. Epub 2009 Oct 27. PubMed PMID: 19923705. 6: Wasicki J, Kozlenko DP, Pankov SE, Bilski P, Pajzderska A, Hancock BC, Medek A, Nawrocik W, Savenko BN. NMR search for polymorphic phase transformations in chlorpropamide form-A at high pressures. J Pharm Sci. 2009 Apr;98(4):1426-37. doi: 10.1002/jps.21471. PubMed PMID: 18623194. 7: Drebushchak TN, Chukanov NV, Boldyreva EV. A new gamma-polymorph of chlorpropamide: 4-chloro-N-(propylaminocarbonyl)benzenesulfonamide. Acta Crystallogr C. 2007 Jun;63(Pt 6):o355-7. Epub 2007 May 11. PubMed PMID: 17551203. 8: Barzegar-Jalali M, Dastmalchi S. Kinetic analysis of chlorpropamide dissolution from solid dispersions. Drug Dev Ind Pharm. 2007 Jan;33(1):63-70. PubMed PMID: 17192252. 9: Boldyreva EV, Dmitriev V, Hancock BC. Effect of pressure up to 5.5GPa on dry powder samples of chlorpropamide form-A. Int J Pharm. 2006 Dec 11;327(1-2):51-7. Epub 2006 Jul 16. PubMed PMID: 16920295. 10: Nunes FB, Alves-Filho JC, Alves Bastos CM, Tessele PM, Caberlon E, Moreira KB, Ferreira TM, de Oliveira JR. Effect of the chlorpropamide and fructose-1,6-bisphosphate of soluble TNF receptor II levels. Pharmacol Res. 2004 May;49(5):449-53. PubMed PMID: 14998554. 11: Sládek NE, Rekha GK, Lee MJ, Nagasawa HT. Inhibition of ALDH3A1-catalyzed oxidation by chlorpropamide analogues. Chem Biol Interact. 2001 Jan 30;130-132(1-3):135-49. Corrected and republished in: Chem Biol Interact. 2001 Nov 28;138(2):201-15. PubMed PMID: 11306038. 12: Gribaldo L, Malerba I, Collotta A, Casati S, Pessina A. Inhibition of CFU-E/BFU-E by 3'-azido-3'-deoxythymidine, chlorpropamide, and protoporphirin IX zinc (II): a comparison between direct exposure of progenitor cells and long-term exposure of bone marrow cultures. Toxicol Sci. 2000 Nov;58(1):96-101. PubMed PMID: 11053545. 13: Durr JA, Hensen J, Ehnis T, Blankenship MS. Chlorpropamide upregulates antidiuretic hormone receptors and unmasks constitutive receptor signaling. Am J Physiol Renal Physiol. 2000 May;278(5):F799-808. PubMed PMID: 10807592. 14: Crespo Valadés E, Ortega Gómez A, Alvarado Izquierdo MI, Magro Ledesma D. [Hepatotoxic reaction associated with metformin and chlorpropamide treatment]. Rev Clin Esp. 1999 Feb;199(2):118-9. Spanish. PubMed PMID: 10216414. 15: Kosior A. Influence of a carrier and basis upon liberation of chlorpropamide from rectal suppositories with an active substance in the dispersion system. Acta Pol Pharm. 1998 Sep-Oct;55(5):353-7. PubMed PMID: 9921114. 16: Chua HC, Stewart B, Lim BH, Lee HK. Screening of chlorpropamide in horse plasma by high-performance liquid chromatography with ultraviolet absorbance detection, and confirmation by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1998 Aug 7;712(1-2):243-52. PubMed PMID: 9698247. 17: Rekha GK, Devaraj VR, Sreerama L, Lee MJ, Nagasawa HT, Sladek NE. Inhibition of human class 3 aldehyde dehydrogenase, and sensitization of tumor cells that express significant amounts of this enzyme to oxazaphosphorines, by chlorpropamide analogues. Biochem Pharmacol. 1998 Feb 15;55(4):465-74. Erratum in: Biochem Pharmacol 1998 May 15;55(10):1739. PubMed PMID: 9514081. 18: Devaraj VR, Sreerama L, Lee MJ, Nagasawa HT, Sladek NE. Yeast aldehyde dehydrogenase sensitivity to inhibition by chlorpropamide analogues as an indicator of human aldehyde dehydrogenase sensitivity to these agents. Adv Exp Med Biol. 1997;414:155-69. PubMed PMID: 9059617. 19: Kaminski CA, Angueira E. Chlorpropamide-induced cholestatic liver failure resulting in death. Endocr Pract. 1996 May-Jun;2(3):191-2. PubMed PMID: 15251538. 20: Kimura T, Ota K, Shoji M, Funyu T, Ohta M, Sato K, Yamamoto T, Mori T, Sahata T, Sugimura K, et al. Chlorpropamide-induced ADH release, hyponatremia and central pontine myelinolysis in diabetes mellitus. Tohoku J Exp Med. 1995 Dec;177(4):303-13. PubMed PMID: 8928190.