クロルプロパミド
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/06/24 01:15:55」(JST)
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Chlorpropamide
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| Systematic (IUPAC) name |
| 4-chloro-N-(propylcarbamoyl)benzenesulfonamide |
| Clinical data |
| Trade names |
Diabinese |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a682479 |
| Licence data |
US FDA:link |
| Pregnancy cat. |
C |
| Legal status |
? |
| Routes |
Oral |
| Pharmacokinetic data |
| Bioavailability |
>90% |
| Protein binding |
90% |
| Metabolism |
<1% |
| Half-life |
36 hours |
| Excretion |
Renal (glomerular filtration → reabsorption → tubular secretion) |
| Identifiers |
| CAS number |
94-20-2 Y |
| ATC code |
A10BB02 |
| PubChem |
CID 2727 |
| DrugBank |
DB00672 |
| ChemSpider |
2626 Y |
| UNII |
WTM2C3IL2X Y |
| KEGG |
D00271 Y |
| ChEBI |
CHEBI:3650 Y |
| ChEMBL |
CHEMBL498 Y |
| Chemical data |
| Formula |
C10H13ClN2O3S |
| Mol. mass |
276.74 g/mol |
SMILES
- O=S(=O)(c1ccc(Cl)cc1)NC(=O)NCCC
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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) Y
Key:RKWGIWYCVPQPMF-UHFFFAOYSA-N Y
|
| Physical data |
| Melt. point |
126–130 °C (259–266 °F) |
| Y (what is this?) (verify) |
Chlorpropamide is a drug in the sulfonylurea class used to treat type 2 diabetes mellitus. It is a long-acting 1st generation sulfonylurea. It has more side effects than other sulfonylureas and its use is no longer recommended.[citation needed]
Contents
- 1 Mechanism of action
- 2 Pharmacokinetics
- 3 Cautions and contraindications
- 4 Chemical properties
- 5 References
Mechanism of action
Like other sulfonylureas, chlorpropamide acts to increase the secretion of insulin, so it is only effective in patients who have some pancreatic beta cell function. It can cause relatively long episodes of hypoglycemia; this is one reason why shorter-acting sulfonylureas such as gliclazide or tolbutamide are used instead. The risk of hypoglycemia makes this drug a poor choice for the elderly and patients with mild to moderate hepatic and renal impairment. Chlorpropamide is also used in partial central diabetes insipidus.[1]
Pharmacokinetics
Maximal plasma concentrations are reached 3 to 5 hours after quick and nearly complete (>90%) resorption from the gut. Plasma half life is 36 hours; the drug is effective for about 24 hours, longer than other sulfonylureas. A stable plasma level is only reached after three days of continuous application. 90% of the drug are bound to plasma proteins; at least two albumin binding sites exist. More than 99% of chlorpropamide are excreted unchanged via the kidneys. It is first filtrated in the glomeruli, then reabsorbed, and finally secreted into the tubular lumen.[1]
Cautions and contraindications
Further information: Sulfonylurea § Side-effects and cautions
Chlorpropamide and other sulfonylureas encourage weight gain, so they are generally not favored for use in very obese patients. Metformin (Glucophage) is considered a better drug for these patients. Sulfonylureas should be used with caution or generally avoided in patients with hepatic and renal impairment, patients with porphyria, patients who are breastfeeding, patients with ketoacidosis, and elderly patients.[1][2]
Other side effects
The most common side effects are skin related, such as rashes, photoallergy and (in rare cases) Stevens-Johnson syndrome.[1] Less common side effects of chlorpropamide include gastrointestinal symptoms such as nausea, vomiting, and diarrhea.[2] It may cause facial flushing after the ingestion of alcohol.[3] In very high doses it can increase secretion of antidiuretic hormone (ADH), which can lead to hyponatremia.[1] It also markedly raises the serum level of alkaline phosphatase.[citation needed]
Chemical properties
Chlorpropamide is a white crystalline powder with no characteristic taste or smell. It exhibits polymorphism. Its acid dissociation constant pKa is 5.0 at 20 °C.[1]
Solubility
| Solvent |
Solubility[1] |
| Water, pH 6 |
1:450 |
| Water, pH 7.3 |
insoluble |
| Acetone |
1:5 |
| Dichlormethane |
1:9 |
| Ethanol |
1:12 |
| Diethylether |
1:200 |
References
- ^ a b c d e f g Dinnendahl, V.; Fricke, U., eds. (2010). Arzneistoff-Profile (in German) 4 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
- ^ a b Drugs.com: Chlorpropamide
- ^ Fitzgerald, M.G. (1962). "Alcohol sensitivity in diabetics receiving chlorpropamide". Diabetes 11: 40–46.
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Oral anti-diabetic drugs and Insulin analogs (A10)
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| Insulin |
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Sensitizers
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Biguanides
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- Metformin#
- Buformin‡
- Phenformin‡
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TZDs/"glitazones" (PPAR)
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- Pioglitazone
- Rivoglitazone†
- Rosiglitazone
- Troglitazone‡
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Dual PPAR agonists
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- Aleglitazar†
- Muraglitazar§
- Saroglitazar
- Tesaglitazar§
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Secretagogues
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K+ ATP
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Sulfonylureas
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- 1st generation: Acetohexamide
- Carbutamide
- Chlorpropamide
- Metahexamide
- Tolbutamide
- Tolazamide
2nd generation: Glibenclamide (Glyburide)#
- Glibornuride
- Glipizide
- Gliquidone
- Glisoxepide
- Glyclopyramide
- Glimepiride
- Gliclazide
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Meglitinides/"glinides"
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- Nateglinide
- Repaglinide
- Mitiglinide
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GLP-1 agonists
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- Exenatide
- Liraglutide
- Taspoglutide†
- Albiglutide†
- Lixisenatide
- Dulaglutide†
- Semaglutide
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DPP-4 inhibitors
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- Alogliptin
- Anagliptin
- Gemigliptin
- Linagliptin
- Saxagliptin
- Sitagliptin
- Teneligliptin
- Vildagliptin
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GPR40 Free fatty acid receptor 1
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Analogs/other insulins
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- fast-acting (Insulin lispro
- Insulin aspart
- Insulin glulisine)
- short-acting (Regular insulin)
- long-acting (Insulin glargine
- Insulin detemir
- NPH insulin)
- ultra-long-acting (Insulin degludec†)
- inhalable Exubera‡
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| Other |
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Alpha-glucosidase inhibitors
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- Acarbose
- Miglitol
- Voglibose
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Amylin analog
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SGLT2 inhibitors
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- Canagliflozin
- Dapagliflozin
- Empagliflozin†
- Remogliflozin§
- Sergliflozin§
- Tofogliflozin†
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Other
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- Bromocriptine
- Benfluorex‡
- Tolrestat‡
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco (d)/cong/tumr, sysi/epon
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proc, drug (A10/H1/H2/H3/H5)
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English Journal
- [Long range results (5 years) in the treatment of stable diabetes with low doses of clorpropamide-metformin (author's transl)].
- Díes H, Lozano Castañeda O, García Viveros M, Schulte J, Figueroa J, Rull JA.
- Revista de investigacion clinica; organo del Hospital de Enfermedades de la Nutricion.Rev Invest Clin.1978 Apr-Jun;30(2):131-4.
- PMID 353940
Related Links
- Clorpropamide - drugs for diabetes, kidney problems, heart disease, blindness, impotency and stroke. ... Clorpropamide helps control high blood sugar and prevents kidney problems, heart disease, blindness, impotency and stroke. It ...
- Clorpropamide [DCIT] - chemical information, properties, structures, articles, patents and more chemical data. Enter your search term above and find: · CAS Numbers · Molecular Formulas · Synonyms · Sites/Web Search · Suppliers
Related Pictures
★リンクテーブル★
[★]
- 同
- スルフォニル尿酸系薬、SU剤、スルホニル尿素系血糖降下薬
- 関
- 糖尿病治療薬、薬理学
分類
スルホンアミド系薬
作用機序
- GOO.1634
- ATP感受性KチャネルのSUR1サブユニットに結合し、チャネルを阻害する。膜が脱分極し、電位依存性Ca2+チャネルが開口する。
薬理作用
動態
適応
- 以下の全てを満たす場合
- 1. NIDDM
- 2. 高度の肥満がない
- 3. 食事療法、運動療法で満足な血糖コントロールが得られない
- 4. 膵インスリン分解能をある程度保持 (尿中Cペプチド>20μg/day)
- 5. 低血糖を理解し対応できる
- 6. 妊婦ではない
注意
禁忌
- 1. IDDM
- 2. 重篤な感染症を繰り返す場合
- 3. 大きな外科手術を受ける場合
- 4. 高度の肝・腎障害がある場合
- 5. 妊婦
- 6. アレルギーなど副作用の発現を満たすもの