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CHLORPROPAMIDE

CHLORPROPAMIDE Structure
CHLORPROPAMIDE
  • CAS No.94-20-2
  • Chemical Name:CHLORPROPAMIDE
  • CBNumber:CB8677954
  • Molecular Formula:C10H13ClN2O3S
  • Formula Weight:276.74
  • MOL File:94-20-2.mol
CHLORPROPAMIDE Property
  • Melting point: :128 °C
  • Boiling point: :302°C (rough estimate)
  • Density  :1.3046 (rough estimate)
  • refractive index  :1.6300 (estimate)
  • storage temp.  :Sealed in dry,Room Temperature
  • pka :pKa 4.8 (Uncertain)
  • form  :neat
  • Water Solubility  :Soluble in ethanol (1:12), acetone (1:5), chloroform (1:9) and solutions of alkali hydroxides. Does not mix well with water.
  • Merck  :14,2186
  • Stability: :Stable. Combustible.
  • CAS DataBase Reference :94-20-2(CAS DataBase Reference)
  • FDA UNII :WTM2C3IL2X
  • NCI Drug Dictionary :chlorpropamide
  • EPA Substance Registry System :Chloropropamide (94-20-2)
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H312+H332-H351-H312-H332-H302
  • Precautionary statements P261-P280-P201-P301+P312a-P308+P313-P405-P501a
CHLORPROPAMIDE Price More Price(12)
  • Brand: Sigma-Aldrich
  • Product number: C1290
  • Product name : Chlorpropamide
  • Purity: ≥97%
  • Packaging: 25g
  • Price: $79.9
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: C1905000
  • Product name : Chlorpropamide
  • Purity: European Pharmacopoeia (EP) Reference Standard
  • Packaging: 
  • Price: $190
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 1126009
  • Product name : Chlorpropamide
  • Purity: 
  • Packaging: 200mg
  • Price: $366
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: C1220
  • Product name : 1-(4-Chlorophenylsulfonyl)-3-propylurea
  • Purity: >99.0%(T)
  • Packaging: 25g
  • Price: $54
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Alfa Aesar
  • Product number: J64110
  • Product name : Chlorpropamide
  • Purity: 
  • Packaging: 25g
  • Price: $71.2
  • Updated: 2021/03/22
  • Buy: Buy

CHLORPROPAMIDE Chemical Properties,Usage,Production

  • Chemical Properties white crystalline powder
  • Originator Diabinese ,Pfizer, US,1958
  • Uses 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 who do not have pancreatic beta cell function.
  • Uses antidiabetic
  • Uses For treatment of NIDDM in conjunction with diet and exercise.
  • Definition ChEBI: An N-sulfonylurea that is urea in which a hydrogen attached to one of the nitrogens is substituted by 4-chlorobenzenesulfonyl group and a hydrogen attached to the other nitrogen is substituted by propyl group. Chlorpropamide is a hypogly aemic agent used in the treatment of type 2 (non-insulin-dependent) diabetes mellitus not responding to dietary modification.
  • Manufacturing Process A solution of 54 g (0.64 mol) of propyl isocyanate in 60 ml of anhydrous
    dimethylformamide was added to a cold, well-stirred suspension of 81 g (0.42 mol) of dry p-chlorobenzenesulfonamide in 210 ml of anhydrous triethylamine during the course of 20 to 30 minutes. The mildly exothermic reaction was completed by allowing it to stand at room temperature for about 5 hours. The reaction mixture was then slowly added to 3 liters of cold 20% acetic acid during the course of about one hour, constant agitation being maintained throughout the addition.
    After the addition was complete, the desired product, which had crystallized out, was filtered and washed well with about 2 liters of cold water. The crude material was then dissolved in 1 liter of cold 5% sodium carbonate and the resulting solution was immediately filtered from an insoluble gum. The product was then reprecipitated, by slowly adding the filtrate to 3 liters of 20% acetic acid. The precipitate, which is very nearly pure N-(p-chlorobenzenesulfonyl)- N'-propylurea, was then dried and subsequently recrystallized from about 800 ml of benzene to give a 59% yield of pure product, MP 129.2 to 129.8°C.
  • brand name Diabinese (Pfizer); Glucamide (Teva).
  • Therapeutic Function Oral hypoglycemic
  • General Description Chlorpropamide is 4-chloro-N-[(propylamino)carbonyl]benzenesulfonamide; or 1-[(p-chlorophenyl)sulfonyl]-3-propylurea; or 1-(p-chlorobenzenesulfonyl)-3-propylurea(Diabinese, generic). The p-chlorophenyl moiety is quite resistantto P450-mediated hydroxylations; hence, blood levelsof the drug are sustained for a markedly long length of time,as aliphatic hydroxylation constitutes most of the clearance,and this happens relatively slowly. Although the -hydroxyland (ω–1)-hydroxyl metabolites (the latter formed in muchgreater portion) exert hypoglycemic potencies not much lessthan does the parent drug, elimination of these by conversion to the corresponding glucuronides occurs more rapidly thanhydroxylation of chlorpropamide, so blood levels of thesemetabolites remain low, and thus they probably do not makean appreciable contribution to the hypoglycemic action ofthis drug in clinical application. Removal of the entire propylside chain (oxidative N-dealkylation) also occurs to a significantextent (up to 20% of an orally administered dose), creatingthe inactive metabolite p-chlorobenzenesulfonylurea,about 10% of which degrades to the corresponding benzenesulfonamide.
  • General Description Chlorpropamide, 1-[(p-chlorophenyl)-sulfonyl]-3-propylurea (Diabinese), is a white, crys-talline powder, practically insoluble in water, soluble in alcohol,and sparingly soluble in chloroform. It will form watersolublesalts in basic solutions. This drug is more resistant toconversion to inactive metabolites than is tolbutamide and, asa result, has a much longer duration of action. One studyshowed that about half of the drug is excreted as metabolites,with the principal one being hydroxylated in the 2-position ofthe propyl side chain.After control of the blood sugar level,the maintenance dose is usually on a once-a-day schedule.
  • General Description White crystalline powder with a slight odor.
  • Air & Water Reactions Insoluble in water.
  • Reactivity Profile A halogenated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).
  • Fire Hazard Flash point data for CHLORPROPAMIDE are not available; however, CHLORPROPAMIDE is probably combustible.
  • Veterinary Drugs and Treatments While chlorpropamide could potentially be of benefit in the adjunctive treatment of diabetes mellitus in small animals, its use has been primarily for adjunctive therapy in diabetes insipidus in dogs and cats.
  • Purification Methods Crystallise the urea from aqueous EtOH. [Beilstein 11 IV 119.]
CHLORPROPAMIDE Preparation Products And Raw materials
Raw materials
Preparation Products
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94-20-2, CHLORPROPAMIDERelated Search:
  • n-(p-chlorobenzenesulfonyl)-n’-propylurea
  • N-(p-Chlorobenzenesulfonyl)-N'-propylurea
  • NCI-C01752
  • n-Propyl-N'-(p-chlorobenzenesulfonyl)urea
  • n-propyl-n’-(p-chlorobenzenesulfonyl)urea
  • n-propyl-n’-p-chlorphenylsulfonylcarbamide
  • n-Propyl-N'-p-chlorophenylsulfonylcarbamide
  • Oradian
  • p607
  • P-607
  • prodiaben
  • Stabinol
  • u-3818
  • Chloropropamide USP
  • CHLORPROPAMIDE USP
  • 1-(p-chlorobenzenesulfonyl)-3-propylure
  • CHLORPROPRAMIDE
  • 4-chloro-N-(propylcarbamoyl)benzenesulfonamide
  • Chlorpropamide (200 mg)
  • ChlorproMaMide
  • 1-(4-Chlorophenylsulfonyl)-3-propylurea , 99.0%(T)
  • u-9818
  • Urea, 1-[(p-chlorophenyl)sulfonyl]-3-propyl-
  • 1-(4-CHLOROPHENYLSULFONYL)-3-PROPYLUREA
  • 1-[P-CHLOROBENZENESULFONYL]-3-PROPYLUREA
  • CHLOROPROPAMIDE
  • CHLORPROPAMIDE
  • 1-((p-chloropenyl)sulfonyl)-3-propyl-ure
  • 1-((p-chlorophenyl)sulfonyl)-3-propyl-ure
  • 1-(p-Chlorophenylsulfonyl)-3-propylurea
  • 1-Chloro-4-(([(propylamino)carbonyl]amino)sulfonyl)benzene
  • 1-p-Chlorophenyl-3-(propylsulfonyl)urea
  • 1-Propyl-3-(p-chlorobenzenesulfonyl)urea
  • 4-Chloro-4-((propylamino)carbonyl)benzenesulfonamide
  • 4-chloro-n-((propylamino)carbonyl)-benzenesulfonamid
  • 4-chloro-n-[(propylamino)carbonyl]-benzenesulfonamid
  • 4-chloro-n-[(propylamino)carbonyl]benzenesulfonamide
  • 4-Chloro-N-[(propylamino)-carbonyl]benzenesulfonamide
  • 4-Chloro-N-[(propylamino)carbonyl]benzene-sul-fonamide
  • Adiaben
  • Asucrol
  • Benzenesulfonamide, 4-chloro-N-[(propylamino)carbonyl]-
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