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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:05:47
Primary Accession Number DB00672
Secondary Accession Number
  • APRD00029
Name Chlorpropamide
Drug Type
  • Approved
  • Small Molecule
Description A sulfonylurea hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. (From Martindale, The Extra Pharmacopoeia, 30th ed, p277)
Synonyms Not Available
Brand Names
  1. Adiaben
  2. Apo-Chlorpropamide
  3. Asucrol
  4. Catanil
  5. Chlorodiabina
  6. Chloronase
  7. Chloropropamide
  8. Chlorpropamid
  9. Chlorpropamide Bp/ Usp
  10. Clorpropamide
  11. Diabaril
  12. Diabechlor
  13. Diabenal
  14. Diabenese
  15. Diabeneza
  16. Diabet-Pages
  17. Diabetoral
  18. Diabinese
  19. Diamel Ex
  20. Dynalase
  21. Glisema
  22. Glucamide
  23. Insulase
  24. Meldian
  25. Melitase
  26. Mellinese
  27. Millinese
  28. Novo-Propamide
  29. Oradian
  30. Stabinol
Brand Mixtures Not Available
Chemical IUPAC Name 1-(4-chlorophenyl)sulfonyl-3-propylurea
Chemical Formula C10H13ClN2O3S
Chemical Structure Structure
CAS Registry Number 94-20-2
InChI Identifier InChI=1/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)/f/h12-13H
InChI Key RKWGIWYCVPQPMF-BAINRFMOCW
KEGG Drug D00271 Link Image
KEGG Compound Not Available
PubChem Compound 2727 Link Image
PubChem Substance 150222 Link Image
ChEBI ID Not Available
PharmGKB ID PA448966 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 00156728 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/chlorpro.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Chlorpropamide Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 276.7400
Monoisotopic Molecular Weight 276.0335
State Solid
Melting Point 127 - 129 oC
Experimental Water Solubility Solubility at pH 6 is 2.2 mg/ml Source: PhysProp
Predicted Water Solubility 1.57e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.8 Source: PhysProp
Predicted LogP 2.15 Calculated using ALOGPS
Experimental LogS -3.03 [ADME Research, USCD]
Predicted LogS -3.25 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1
Canonical SMILES CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1
Drug Category
  • Hypoglycemic Agents
  • Sulfonylureas
ATC Codes
AHFS Codes
  • 68:20.20
Indication For managing hyperglycemia in Non-insulin-dependent diabetes mellitus (NIDDM).
Pharmacology Chlorpropamide, a second-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Chlorpropamide is twice as potent as the related second-generation agent glipizide.
Mechanism of Action Sulfonylureas such as Chlorpropamide likely bind to ATP-sensitive potassium-channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin.
Absorption Not Available
Toxicity IPN-RAT LD50 580 mg/kg
Protein Binding Not Available
Biotransformation Not Available
Half Life 36 hours
Dosage Forms
Form Route
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acebutolol The beta-blocker decreases the symptoms of hypoglycemia
Aspirin The salicylate increases the effect of sulfonylurea
Atenolol The beta-blocker decreases the symptoms of hypoglycemia
Betaxolol The beta-blocker decreases the symptoms of hypoglycemia
Bevantolol The beta-blocker decreases the symptoms of hypoglycemia
Bismuth The salicylate increases the effect of sulfonylurea
Bisoprolol The beta-blocker decreases the symptoms of hypoglycemia
Carteolol The beta-blocker decreases the symptoms of hypoglycemia
Carvedilol The beta-blocker decreases the symptoms of hypoglycemia
Chloramphenicol The agent increases the effect of sulfonylurea
Clofibrate The agent increases the effect of sulfonylurea
Diazoxide Diazoxyde/sulfonylurea: antagonism of action
Dicumarol The agent increase the effect of sulfonylurea
Esmolol The beta-blocker decreases the symptoms of hypoglycemia
Glucosamine Possible hyperglycemia
Isocarboxazid The MAO inhibitor increases the effect of hypoglycemic agent
Labetalol The beta-blocker decreases the symptoms of hypoglycemia
Metoprolol The beta-blocker decreases the symptoms of hypoglycemia
Nadolol The beta-blocker decreases the symptoms of hypoglycemia
Oxprenolol The beta-blocker decreases the symptoms of hypoglycemia
Penbutolol The beta-blocker decreases the symptoms of hypoglycemia
Phenelzine The MAO inhibitor increases the effect of hypoglycemic agent
Phenylbutazone Phenylbutazone increases the effect of the hypoglycemic agent
Pindolol The beta-blocker decreases the symptoms of hypoglycemia
Practolol The beta-blocker decreases the symptoms of hypoglycemia
Propranolol The beta-blocker decreases the symptoms of hypoglycemia
Repaglinide Similar mode of action-questionable association
Rifampin Rifampin decreases the effect of sulfonylurea
Salsalate The salicylate increases the effect of sulfonylurea
Sotalol The beta-blocker decreases the symptoms of hypoglycemia
Sulfacytine Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfadiazine Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfadoxine Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfamerazine Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfamethazine Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfamethizole Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfamethoxazole Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfapyridine Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfasalazine Sulfonamide/sulfonylurea: possible hypoglycemia
Sulfisoxazole Sulfonamide/sulfonylurea: possible hypoglycemia
Timolol The beta-blocker decreases the symptoms of hypoglycemia
Tranylcypromine The MAO inhibitor increases the effect of hypoglycemic agent
Trisalicylate-choline The salicylate increases the effect of sulfonylurea
Food Interactions
  • Avoid alcohol.
  • Food reduces the rate of absorption.
  • Take without regard to meals.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2D6 (CYP2D6)
Targets
  1. ATP-sensitive inward rectifier potassium channel 1
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2D6 (CYP2D6)
Enzyme 1 Gene Name CYP2D6
Enzyme 1 SwissProt ID P10635 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P10635|CP2D6_HUMAN Cytochrome P450 2D6 (EC 1.14.14.1) 
MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVDFQNTPYCFDQ
LRRRFGDVFSLQLAWTPVVVLNGLAAVREALVTHGEDTADRPPVPITQILGFGPRSQGVF
LARYGPAWREQRRFSVSTLRNLGLGKKSLEQWVTEEAACLCAAFANHSGRPFRPNGLLDK
AVSNVIASLTCGRRFEYDDPRFLRLLDLAQEGLKEESGFLREVLNAVPVLLHIPALAGKV
LRFQKAFLTQLDELLTEHRMTWDPAQPPRDLTEAFLAEMEKAKGNPESSFNDENLRIVVA
DLFSAGMVTTSTTLAWGLLLMILHPDVQRRVQQEIDDVIGQVRRPEMGDQAHMPYTTAVI
HEVQRFGDIVPLGMTHMTSRDIEVQGFRIPKGTTLITNLSSVLKDEAVWEKPFRFHPEHF
LDAQGHFVKPEAFLPFSAGRRACLGEPLARMELFLFFTSLLQHFSFSVPTGQPRPSHHGV
FAFLVSPSPYELCAVPR
Drug Target 1 [top]
Target 1 ID 709
Target 1 Name ATP-sensitive inward rectifier potassium channel 1
Target 1 Synonyms
  1. ATP-regulated potassium channel ROM-K
  2. Kir1.1
  3. Potassium channel, inwardly rectifying subfamily J member 1
Target 1 Gene Name KCNJ1
Target 1 Protein Sequence >ATP-sensitive inward rectifier potassium channel 1 
MNASSRNVFDTLIRVLTESMFKHLRKWVVTRFFGHSRQRARLVSKDGRCNIEFGNVEAQS
RFIFFVDIWTTVLDLKWRYKMTIFITAFLGSWFFFGLLWYAVAYIHKDLPEFHPSANHTP
CVENINGLTSAFLFSLETQVTIGYGFRCVTEQCATAIFLLIFQSILGVIINSFMCGAILA
KISRPKKRAKTITFSKNAVISKRGGKLCLLIRVANLRKSLLIGSHIYGKLLKTTVTPEGE
TIILDQININFVVDAGNENLFFISPLTIYHVIDHNSPFFHMAAETLLQQDFELVVFLDGT
VESTSATCQVRTSYVPEEVLWGYRFAPIVSKTKEGKYRVDFHNFSKTVEVETPHCAMCLY
NEKDVRARMKRGYDNPNFILSEVNETDDTKM
Target 1 Number of Residues 397
Target 1 Molecular Weight 44795
Target 1 Theoretical pI 9.04
Target 1 GO Classification
Function
transporter activity
ion transporter activity
ion channel activity
voltage-gated ion channel activity
voltage-gated potassium channel activity
inward rectifier potassium channel activity
Process
physiological process
cellular physiological process
transport
ion transport
cation transport
monovalent inorganic cation transport
potassium ion transport
Component
cell
membrane
Target 1 General Function Involved in inward rectifier potassium channel activity
Target 1 Specific Function In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 78-102
  • 156-177
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 529313 Link Image
Target 1 UniProtKB/Swiss-Prot ID P48048 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name IRK1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1176 bp 
ATGAATGCTTCCAGTCGGAATGTGTTTGACACGTTGATCAGGGTGTTGACAGAAAGTATG
TTCAAACATCTTCGGAAATGGGTCGTCACTCGCTTTTTTGGGCATTCTCGGCAAAGAGCA
AGGCTAGTCTCCAAAGATGGAAGGTGCAACATAGAATTTGGCAATGTGGAGGCACAGTCA
AGGTTTATATTCTTTGTGGACATCTGGACAACGGTACTTGACCTCAAGTGGAGATACAAA
ATGACCATTTTCATCACAGCCTTCTTGGGGAGTTGGTTTTTCTTTGGTCTCCTGTGGTAT
GCAGTAGCGTACATTCACAAAGACCTCCCGGAATTCCATCCTTCTGCCAATCACACTCCC
TGTGTGGAGAATATTAATGGCTTGACCTCAGCTTTTCTGTTTTCTCTGGAGACTCAAGTG
ACCATTGGATATGGATTCAGGTGTGTGACAGAACAGTGTGCCACTGCCATTTTTCTGCTT
ATCTTTCAGTCTATACTTGGAGTTATAATCAATTCTTTCATGTGTGGGGCCATCTTAGCC
AAGATCTCCAGGCCCAAAAAACGTGCCAAGACCATTACGTTCAGCAAGAACGCAGTGATC
AGCAAACGGGGAGGGAAGCTTTGCCTCCTAATCCGAGTGGCTAATCTCAGGAAGAGCCTT
CTTATTGGCAGTCACATTTATGGAAAGCTTCTGAAGACCACAGTCACTCCTGAAGGAGAG
ACCATTATTTTGGACCAGATCAATATCAACTTTGTAGTTGACGCTGGGAATGAAAATTTA
TTCTTCATCTCCCCATTGACAATTTACCATGTCATTGATCACAACAGCCCTTTCTTCCAC
ATGGCAGCGGAGACCCTTCTCCAGCAGGACTTTGAATTAGTGGTGTTTTTAGATGGCACA
GTGGAGTCCACCAGTGCTACCTGCCAAGTCCGGACATCCTATGTCCCAGAGGAGGTGCTT
TGGGGCTACCGTTTTGCTCCCATAGTATCCAAGACAAAGGAAGGGAAATACCGAGTGGAT
TTCCATAACTTTAGCAAGACAGTGGAAGTGGAGACCCCTCACTGTGCCATGTGCCTTTAT
AATGAGAAAGATGTTAGAGCCAGGATGAAGAGAGGCTATGACAACCCCAACTTCATCTTG
TCAGAAGTCAATGAAACAGATGACACCAAAATGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID KCNJ1 Link Image
Target 1 GenAtlas ID KCNJ1 Link Image
Target 1 HGNC ID HGNC:6255 Link Image
Target 1 Chromosome Location 11
Target 1 Locus 11q24
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Krishnan SN, Desai T, Ward DC, Haddad GG: Isolation and chromosomal localization of a human ATP-regulated potassium channel. Hum Genet. 1995 Aug;96(2):155-60. [PubMed Link Image]
  2. Shuck ME, Bock JH, Benjamin CW, Tsai TD, Lee KS, Slightom JL, Bienkowski MJ: Cloning and characterization of multiple forms of the human kidney ROM-K potassium channel. J Biol Chem. 1994 Sep 30;269(39):24261-70. [PubMed Link Image]
  3. Yano H, Philipson LH, Kugler JL, Tokuyama Y, Davis EM, Le Beau MM, Nelson DJ, Bell GI, Takeda J: Alternative splicing of human inwardly rectifying K+ channel ROMK1 mRNA. Mol Pharmacol. 1994 May;45(5):854-60. [PubMed Link Image]
  4. Mutations in the gene encoding the inwardly-rectifying renal potassium channel, ROMK, cause the antenatal variant of Bartter syndrome: evidence for genetic heterogeneity. International Collaborative Study Group for Bartter-like Syndromes. Hum Mol Genet. 1997 Jan;6(1):17-26. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.