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94-20-2 molecular structure
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1-(4-chlorobenzenesulfonyl)-3-propylurea

ChemBase ID: 554
Molecular Formular: C10H13ClN2O3S
Molecular Mass: 276.73982
Monoisotopic Mass: 276.03354097
SMILES and InChIs

SMILES:
Clc1ccc(S(=O)(=O)NC(=O)NCCC)cc1
Canonical SMILES:
CCCNC(=O)NS(=O)(=O)c1ccc(cc1)Cl
InChI:
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)
InChIKey:
RKWGIWYCVPQPMF-UHFFFAOYSA-N

Cite this record

CBID:554 http://www.chembase.cn/molecule-554.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-(4-chlorobenzenesulfonyl)-3-propylurea
IUPAC Traditional name
1-(4-chlorobenzenesulfonyl)-3-propylurea
chlorpropamide
Brand Name
Chlorpropamide Bp/ Usp
Clorpropamide
Diabaril
Diabechlor
Diabenal
Diabenese
Diabeneza
Diabet-Pages
Diabetoral
Diabinese
Diamel Ex
Dynalase
Glisema
Glucamide
Insulase
Meldian
Melitase
Mellinese
Millinese
Novo-Propamide
Oradian
Stabinol
Adiaben
Apo-Chlorpropamide
Asucrol
Catanil
Chlorodiabina
Chloronase
Chloropropamide
Chlorpropamid
Synonyms
Chlorporpamide
Chlorpropamide
4-Chloro-N-[(propylamino)carbonyl]benzenesulfonamide
Adiaben
Asucrol
Catanil
Chlorodiabina
Chloronase
Chloropropamide
Chlorpropamid
Chlorpropamide
Diabaril
Diabechlor
Diabenal
Diabenese
Glisema
Meldian
Melitase
Millinese
N-(4-Chlorophenylsulfonyl)-N'-propylurea
NSC 44634
NSC 626720
P 607
Stabinol
U 9818
N-(p-Chlorobenzenesulfonyl)-N'-propylurea
N-Propyl-N'-(p-chlorobenzenesulfonyl)urea
Diabinese
4-Chloro-N-(propylcarbamoyl)benzenesulfonamide
Chlorpropamide
1-[p-Chlorobenzenesulfonyl]-3-propylurea
对氯苯磺酰丙脲
氯磺丙脲
CAS Number
94-20-2
EC Number
202-314-5
MDL Number
MFCD00079004
PubChem SID
46506402
160964017
24277701
PubChem CID
2727

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.329167  H Acceptors
H Donor LogD (pH = 5.5) 1.1719515 
LogD (pH = 7.4) 1.0013003  Log P 1.9413904 
Molar Refractivity 65.4326 cm3 Polarizability 26.156296 Å3
Polar Surface Area 75.27 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.15  LOG S -3.25 
Solubility (Water) 1.57e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Solubility at pH 6 is 2.2 mg/ml expand Show data source
Hydrophobicity(logP)
1.8 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
YS6650000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
20/21/22-40 expand Show data source
Safety Statements
22-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H312-H332-H351 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Target
Others expand Show data source
Gene Information
human ... ALB(213), EPHX2(2053), KCNJ1(3758)mouse ... Ephx2(13850) expand Show data source
Mechanism of Action
Augmenting insulin secretion expand Show data source
Purity
≥97% expand Show data source
95+% expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Oral antihyperglycaemic drug expand Show data source
Used to treat non-insulin dependent diabetes mellitus expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank TRC TRC
MP Biomedicals - 02154978 external link
(1-[p-Chlorobenzenesulfonyl]-3-propylurea) Purity: 97%
DrugBank - DB00672 external link
Item Information
Drug Groups approved
Description Chlorpropamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Chlorpropamide is not recommended for the treatment of NIDDM as it increases blood pressure and the risk of retinopathy (UKPDS-33). Up to 80% of the single oral dose of chlorpropramide is metabolized, likely in the liver; 80-90% of the dose is excreted in urine as unchanged drug and metabolites. Renal and hepatic dysfunction may increase the risk of hypoglycemia.
Indication For treatment of NIDDM in conjunction with diet and exercise.
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.
Toxicity IPN-RAT LD50 580 mg/kg
Affected Organisms
Humans and other mammals
Biotransformation Up to 80% of dose is metabolized likely through the liver to to 2-hydroxylchlorpropamide (2-OH CPA), p-chlorobenzenesulfonylurea (CBSU), 3-hydroxylchlorpropamide (3-OH CPA), and p-chlorobenzenesulfonamide (CBSA); CBSA may be produced by decomposition in urine. It is unknown whether chlorpropamide metabolites exert hypoglycemic effects.
Absorption Readily absorbed from the GI tract. Peak plasma concentrations occur within 2-4 hours and the onset of action occurs within one hour. The maximal effect of chlorpropamide is seen 3-6 hours following oral administration.
Half Life Approximately 36 hours with interindividual variation ranging from 25-60 hours. Duration of effect persists for at least 24 hours.
Protein Binding Highly bound to plasma proteins.
Elimination 80-90% of a single oral dose is excreted in the urine as unchaged drug and metabolites within 96 hours.
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - C424800 external link
Chlorpropamide is a sulfonylurea derivative. Chlorpropamide is a long acting hyopglycemic agent. Chlorpropamide is used in the treatment of diabetes metilus type 2. Chlorpropamide acts to increase the secretion of insulin and is not effective in patients

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Turner, R.C. et al.: Diabetes, 27, 241 (1978)
  • • Grinnell, E.H. et al.: Am. J. Med. Sci., 253, 312 (1978)
  • • Taylor, J.A.: Clin. Pharmacol. Therap., 13, 710 (1978)
  • • Marshall, F.J. et al., J.O.C., 1958, 23, 927, (synth)
  • • Bauer, V.J. et al., J.O.C., 1960, 31, 3440, (synth)
  • • McManus, J.M. et al., J. Med. Chem., 1965, 8, 766, (pharmacol)
  • • Jackson, W.P.U., Med. Chem. (Academic Press), 1969, 9, 135, (pharmacol)
  • • Madsen, S.N. et al., Eur. J. Pharmacol., 1971, 13, 374, (metab)
  • • Dave, G.R. et al., Indian Chem. J., 1971, 5, 31, (synth)
  • • Kuhnert-Brandstaetter, M. et al., Sci. Pharm., 1974, 42, 150, (uv)
  • • Koo, C.H. et al., Arch. Pharmacal Res., 1980, 3, 37, (cryst struct)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1573, (synonyms)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 277
  • • Mizuno, T. et al., Synth. Commun., 2000, 30, 3081-3089, (synth, ir, pmr, cmr)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CKK000
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PATENTS

PATENTS

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