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）』「2017/07/14 00:32:30」(JST)
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Not to be confused with Chlorpromazine.
Chlorpropamide
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| Clinical data |
| Trade names |
Diabinese |
| AHFS/Drugs.com |
Monograph |
| MedlinePlus |
a682479 |
| License data |
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Pregnancy
category |
- AU: C
- US: C (Risk not ruled out)
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Routes of
administration |
Oral |
| ATC code |
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| Legal status |
| Legal status |
- AU: S4 (Prescription only)
- CA: ℞-only
- UK: POM (Prescription only)
- US: ℞-only
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| Pharmacokinetic data |
| Bioavailability |
>90% |
| Protein binding |
90% |
| Metabolism |
<1% |
| Biological half-life |
36 hours |
| Excretion |
Renal (glomerular filtration → reabsorption → tubular secretion) |
| Identifiers |
IUPAC name
- 4-chloro-N-(propylcarbamoyl)benzenesulfonamide
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| CAS Number |
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| PubChem CID |
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| IUPHAR/BPS |
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| DrugBank |
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| ChemSpider |
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| UNII |
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| KEGG |
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| ChEBI |
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| ChEMBL |
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| ECHA InfoCard |
100.002.104 |
| Chemical and physical data |
| Formula |
C10H13ClN2O3S |
| Molar mass |
276.74 g/mol |
| 3D model (Jmol) |
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| Melting point |
126 to 130 °C (259 to 266 °F) |
SMILES
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O=S(=O)(c1ccc(Cl)cc1)NC(=O)NCCC
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InChI
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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
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Key:RKWGIWYCVPQPMF-UHFFFAOYSA-N Y
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| (verify) |
Chlorpropamide is a drug in the sulfonylurea class used to treat diabetes mellitus type 2. It is a long-acting first-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 See also
- 6 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] Chlorpropamide, while effective in the treatment of diabetics in patients of Chinese descent, should never be used in people of Mongolian descent.[citation needed]
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 |
See also
- Tolbutamide
- Tolazamide
- Glyburide
- Glipizide
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, insulins and insulin analogs, and other drugs used in diabetes (A10)
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| Insulin |
| Sensitizers |
| Biguanides |
- Buformin‡
- Metformin#
- Phenformin‡
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| TZDs/"glitazones" (PPAR) |
- Ciglitazone§
- Darglitazone§
- Englitazone§
- Lobeglitazone
- Netoglitazone§
- Pioglitazone
- Rivoglitazone†
- Rosiglitazone
- Troglitazone‡
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| Dual PPAR agonists |
- Aleglitazar†
- Muraglitazar§
- Saroglitazar
- Tesaglitazar§
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| Secretagogues |
| K+ATP |
| Sulfonylureas |
- 1st generation: Acetohexamide
- Carbutamide
- Chlorpropamide
- Glycyclamide
- Metahexamide
- Tolazamide
- Tolbutamide
- 2nd generation: Glibenclamide (glyburide)#
- Glibornuride
- Glicaramide
- Gliclazide
- Glimepiride
- Glipizide
- Gliquidone
- Glisoxepide
- Glyclopyramide
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| Meglitinides/"glinides" |
- Mitiglinide
- Nateglinide
- Repaglinide
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| GLP-1 agonists |
- Albiglutide†
- Dulaglutide
- Exenatide
- Liraglutide
- Lixisenatide
- Semaglutide†
- Taspoglutide†
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| DPP-4 inhibitors/"gliptins" |
- Alogliptin
- Anagliptin
- Evogliptin
- Gemigliptin
- Linagliptin
- Omarigliptin
- Saxagliptin
- Sitagliptin
- Teneligliptin
- Trelagliptin
- Vildagliptin
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| Free fatty acid receptor 1 (GPR40) |
|
|
| Analogs/other insulins |
- fast-acting (Insulin aspart
- Insulin glulisine
- Insulin lispro)
- short-acting (Regular insulin)
- long-acting (Insulin detemir
- Insulin glargine
- NPH insulin)
- ultra-long-acting (Insulin degludec)
- inhalable (Exubera‡
- Afrezza)
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| Other |
| Aldose reductase inhibitors |
- Epalrestat
- Fidarestat§
- Ranirestat†
- Tolrestat‡
- Zenarestat§
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| Alpha-glucosidase inhibitors |
- Acarbose
- Miglitol
- Voglibose
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| Amylin analog |
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| Sodium glucose transporter (SGLT2) inhibitors/"gliflozins" |
- Canagliflozin
- Dapagliflozin
- Empagliflozin
- Ipragliflozin
- Remogliflozin§
- Sergliflozin§
- Tofogliflozin†
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| Other |
- Benfluorex‡
- Bromocriptine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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English Journal
- AuthorsEuwema M1, Swanson T2.
- Open/close author information list" class="jig-ncbitoggler" href="#
- PMID 28722879
- Quantification and modeling of nanomechanical properties of chlorpropamide α, β, and γ conformational polymorphs.
- Janković B1, Joksimović T2, Stare J3, Losev E4, Zemtsova V4, Srčič S5, Boldyreva E6.
- European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.Eur J Pharm Sci.2017 Jun 10. pii: S0928-0987(17)30347-0. doi: 10.1016/j.ejps.2017.06.013. [Epub ahead of print]
- PMID 28606802
- Potentially inappropriate prescribing and associated factors in elderly patients at hospital discharge in Brazil: a cross-sectional study.
- Mori AL1, Carvalho RC1, Aguiar PM2, de Lima MG1, Rossi MD1, Carrillo JF1, Dórea EL3, Storpirtis S1.
- International journal of clinical pharmacy.Int J Clin Pharm.2017 Apr;39(2):386-393. doi: 10.1007/s11096-017-0433-7. Epub 2017 Feb 10.
- PMID 28188508
Japanese Journal
- HPLC Determination of Chlorpropamide in Human Serum by Fluorogenic Derivatization Based on the Suzuki Coupling Reaction with Phenylboronic Acid
- Kishikawa Naoya,Hammad Sherin Farouk,Ohyama Kaname,Kubo Kimiko,Mabrouk Mokhtar Mohamed,Nakashima Kenichiro,Kuroda Naotaka
- Chromatographia 76(11-12), 703-706, 2013-06
- … A fluorogenic derivatization method for the determination of chlorpropamide in human serum was developed by means of high-performance liquid chromatography (HPLC) with fluorescence detection. … The Suzuki coupling reaction with a non-fluorescent reagent, phenylboronic acid (PBA), was employed to convert chlorpropamide into highly fluorescent biphenyl derivative. …
- NAID 120005303651
- Prominent Inhibitory Effect of 2-Hydroxybutyl-β-cyclodextrin on Solution-mediated Polymorphic Transition of Chlorpropamide
- ISHIGURO Takako,HIRAYAMA Fumitoshi,IOHARA Daisuke,UEKAMA Kaneto
- Chemistry letters 37(8), 816-817, 2008-08-05
- NAID 10024281162
- Prominent Inhibitory Effect of 2-Hydroxybutyl-.BETA.-cyclodextrin on Solution-mediated Polymorphic Transition of Chlorpropamide
- , , ,
- Chemistry Letters 37(8), 816-817, 2008
- … The effects of cyclodextrins on crystallization of chlorpropamide from aqueous solutions were investigated. …
- NAID 130004425233
Related Links
- chlor·prop·a·mide / klɔrˈprɒp əˌmaɪd, -ˈproʊ pə-, kloʊr-/ Show Spelled [klawr-prop-uh-mahyd, - proh-p uh-, klohr-] Show IPA noun Pharmacology. an oral hypoglycemic substance, C 10 H 13 ClN 2 O 3 S, used to augment insulin ...
- Chlorpropamide is an oral diabetes medicine that helps control blood sugar levels. This medication helps your pancreas produce insulin. Chlorpropamide is used together with diet and exercise to treat type 2 diabetes. Other diabetes ...
Related Pictures
★リンクテーブル★
[★]
- 英
- chlorpropamide
- ラ
- chlorpropamidum
- 商
- アベマイド、Diabinese
- 関
- 糖尿病治療薬