1-(4-chlorobenzenesulfonyl)-3-propylurea

• ChemBase ID: 554
• Molecular Formular: C10H13ClN2O3S
• Molecular Mass: 276.73982
• Monoisotopic Mass: 276.03354097
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 94-20-2
• EC Number: 202-314-5
• MDL Number: MFCD00079004
• PubChem SID: 46506402; 160964017; 24277701
• PubChem CID: 2727

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.329167
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.1719515
• LogD (pH = 7.4): 1.0013003
• Log P: 1.9413904
• Molar Refractivity: 65.4326 cm^3
• Polarizability: 26.156296 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.15
• LOG S: -3.25
• Solubility (Water): 1.57e-01 g/l

PROPERTIES

Physical Property

• Solubility: Solubility at pH 6 is 2.2 mg/ml
• Hydrophobicity(logP): 1.8

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: YS6650000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-40
• Safety Statements: 22-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H312-H332-H351
• GHS Precautionary statements: P280
• 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

Pharmacology Properties

• Target: Others
• Gene Information: human ... ALB(213), EPHX2(2053), KCNJ1(3758)mouse ... Ephx2(13850)
• Mechanism of Action: Augmenting insulin secretion

Product Information

• Purity: ≥97%; 95+%; 97%
• Salt Data: Free Base
• Application(s): Oral antihyperglycaemic drug; Used to treat non-insulin dependent diabetes mellitus

DETAILS

MP Biomedicals - 02154978

(1-[p-Chlorobenzenesulfonyl]-3-propylurea) Purity: 97%

DrugBank - DB00672

• 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

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

• 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