Tìm theo
Chlorpropamide
Các tên gọi khác (13 ) :
  • 1-(P-Chlorobenzenesulfonyl)-3-propylurea
  • 1-(P-Chlorophenylsulfonyl)-3-propylurea
  • 1-Propyl-3-(P-chlorobenzenesulfonyl)urea
  • 4-chloro-N-((Propylamino)carbonyl)benzenesulfonamide
  • 4-chloro-N-[(Propylamino)carbonyl]benzenesulfonamide
  • Chlorpropamid
  • Chlorpropamide
  • Chlorpropamidum
  • Clorpropamida
  • N-(4-Chlorophenylsulfonyl)-n'-propylurea
  • N-(P-Chlorobenzenesulfonyl)-n'-propylurea
  • N-Propyl-n'-(P-chlorobenzenesulfonyl)urea
  • N-Propyl-n'-P-chlorophenylsulfonylcarbamide
Hormon, Nội tiết tố
Thuốc Gốc
Small Molecule
CAS: 94-20-2
ATC: A10BB02
ĐG : Central Texas Community Health Centers , http://www.chcsct.com
CTHH: C10H13ClN2O3S
PTK: 276.74
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.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C10H13ClN2O3S
Phân tử khối
276.74
Monoisotopic mass
276.033540689
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)
InChI Key
InChIKey=RKWGIWYCVPQPMF-UHFFFAOYSA-N
IUPAC Name
1-[(4-chlorobenzene)sulfonyl]-3-propylurea
Traditional IUPAC Name
1-(4-chlorobenzenesulfonyl)-3-propylurea
SMILES
CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1
Độ tan chảy
129.2-129.8
Độ hòa tan
258 mg/L (at 37 °C)
logP
2.27
logS
-3.03
pKa (strongest acidic)
4.33
PSA
75.27 Å2
Refractivity
65.43 m3·mol-1
Polarizability
27.06 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
3
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
1
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
5.13
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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. Sulfonylureas such as chlorpropamide bind to ATP-sensitive potassium channels 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.
Dược Động Học :
▧ 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.
▧ Protein binding :
Highly bound to plasma proteins.
▧ Metabolism :
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.
▧ Route of Elimination :
80-90% of a single oral dose is excreted in the urine as unchaged drug and metabolites within 96 hours.
▧ Half Life :
Approximately 36 hours with interindividual variation ranging from 25-60 hours. Duration of effect persists for at least 24 hours.
Độc Tính : IPN-RAT LD50 580 mg/kg
Chỉ Định : For treatment of NIDDM in conjunction with diet and exercise.
Tương Tác Thuốc :
  • Acebutolol Acebutolol may decrease symptoms of hypoglycemia and increase the time required for the body to compensate for hypoglycemia.
  • Acetylsalicylic acid Acetylsalicylic acid may increase the effect of the sulfonylurea, chlorpropamide.
  • Atenolol The beta-blocker, atenolol, may decrease symptoms of hypoglycemia.
  • Betaxolol The beta-blocker, betaxolol, may decrease symptoms of hypoglycemia.
  • Bevantolol The beta-blocker, bevantolol, may decrease symptoms of hypoglycemia.
  • Bisoprolol The beta-blocker, bisoprolol, may decrease symptoms of hypoglycemia.
  • Carteolol The beta-blocker, carteolol, may decrease symptoms of hypoglycemia.
  • Carvedilol The beta-blocker, carvedilol, may decrease symptoms of hypoglycemia.
  • Chloramphenicol Chloramphenicol may increase the effect of sulfonylurea, chlorpropamide.
  • Clofibrate Clofibrate may increase the effect of sulfonylurea, chlorpropamide.
  • Diazoxide Antagonism.
  • Dicoumarol Dicumarol may increase the effect of sulfonylurea, chlorpropamide.
  • Esmolol The beta-blocker, esmolol, may decrease symptoms of hypoglycemia.
  • Glucosamine Possible hyperglycemia
  • Labetalol The beta-blocker, labetalol, may decrease symptoms of hypoglycemia.
  • Metoprolol The beta-blocker, metoprolol, may decrease symptoms of hypoglycemia.
  • Nadolol The beta-blocker, nadolol, may decrease symptoms of hypoglycemia.
  • Oxprenolol The beta-blocker, oxprenolol, may decrease symptoms of hypoglycemia.
  • Penbutolol The beta-blocker, penbutolol, may decrease symptoms of hypoglycemia.
  • Phenylbutazone Phenylbutazone increases the effect of the hypoglycemic agent
  • Pindolol The beta-blocker, pindolol, may decrease symptoms of hypoglycemia.
  • Practolol The beta-blocker, practolol, may decrease symptoms of hypoglycemia.
  • Propranolol The beta-blocker, propranolol, may decrease symptoms of hypoglycemia.
  • Rifampicin Rifampin may decrease the effect of sulfonylurea, chlorpropamide.
  • Salsalate The salicylate, salsalate, increases the effect of the sulfonylurea, chlorpropamide.
  • Somatropin recombinant Somatropin may antagonize the hypoglycemic effect of chlorpropamide. Monitor for changes in fasting and postprandial blood sugars.
  • Sotalol The beta-blocker, sotalol, may decrease 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, timolol, may decrease symptoms of hypoglycemia.
  • Trisalicylate-choline The salicylate, trisalicylate-choline, increases the effect of the sulfonylurea, chlorpropamide.
  • Voriconazole Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Liều Lượng & Cách Dùng : Tablet - Oral - 100 mg
Tablet - Oral - 250 mg
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Kobayashi Kako
    Sản phẩm biệt dược : Abemide
  • Công ty : Hoechst
    Sản phẩm biệt dược : Chloronase
  • Công ty : Mylan
    Sản phẩm biệt dược : Chlorpropamide
  • Công ty : Pfizer
    Sản phẩm biệt dược : Dabinese
  • Sản phẩm biệt dược : Diabeedol
  • Công ty : Guidotti
    Sản phẩm biệt dược : Diabemide
  • Công ty : Prince
    Sản phẩm biệt dược : Diabezin
  • Công ty : Pfizer
    Sản phẩm biệt dược : Diabinese
  • Công ty : Plantex-Ikapharm
    Sản phẩm biệt dược : Diabitex
  • Công ty : Pharmasant
    Sản phẩm biệt dược : Dibecon
  • Công ty : Siam Bheasach
    Sản phẩm biệt dược : Glycemin
  • Công ty : Aspen Pharmacare
    Sản phẩm biệt dược : Hypomide
  • Công ty : Ming Ta
    Sản phẩm biệt dược : Litangen
  • Công ty : Atlantic
    Sản phẩm biệt dược : Propamide
  • Công ty : Omega
    Sản phẩm biệt dược : Trane
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00672
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=2727
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506402
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00271
ChemSpider
http://www.chemspider.com/Chemical-Structure.2626.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0378-0197-01
PharmGKB
http://www.pharmgkb.org/drug/PA448966
Wikipedia
http://en.wikipedia.org/wiki/Chlorpropamide
RxList
http://www.rxlist.com/cgi/generic2/chlorpro.htm
Drugs.com
http://www.drugs.com/cdi/chlorpropamide.html
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