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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]}

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

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 pK_a 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.

UpToDate Contents

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1. 中枢性尿崩症の治療 treatment of central diabetes insipidus
2. 糖尿病の治療におけるスルホニル尿素およびメグリチニド sulfonylureas and meglitinides in the treatment of diabetes mellitus
3. 2型糖尿病の治療のためのジペプチジルペプチダーゼ4（DPP-4）阻害剤 dipeptidyl peptidase 4 dpp 4 inhibitors for the treatment of type 2 diabetes mellitus
4. スルホニル尿素剤中毒 sulfonylurea agent poisoning
5. 抗利尿ホルモン不適合分泌（SIADH）症候群の病態生理および病因 pathophysiology and etiology of the syndrome of inappropriate antidiuretic hormone secretion siadh

English Journal

Sulfa drugs inhibit sepiapterin reduction and chemical redox cycling by sepiapterin reductase.

Yang S1, Jan YH1, Mishin V1, Richardson JR1, Hossain MM1, Heindel ND1, Heck DE1, Laskin DL1, Laskin JD2.
The Journal of pharmacology and experimental therapeutics.J Pharmacol Exp Ther.2015 Mar;352(3):529-40. doi: 10.1124/jpet.114.221572. Epub 2014 Dec 30.
Sepiapterin reductase (SPR) catalyzes the reduction of sepiapterin to dihydrobiopterin (BH2), the precursor for tetrahydrobiopterin (BH4), a cofactor critical for nitric oxide biosynthesis and alkylglycerol and aromatic amino acid metabolism. SPR also mediates chemical redox cycling, catalyzing one-
PMID 25550200

The polymorphic phase transformations in the chlorpropamide under pressure.

Kichanov SE1, Kozlenko DP, Wąsicki J, Nawrocik W, Dubrovinsky LS, Liermann HP, Morgenroth W, Savenko BN.
Journal of pharmaceutical sciences.J Pharm Sci.2015 Jan;104(1):81-6. doi: 10.1002/jps.24241. Epub 2014 Nov 12.
The crystal structure and vibrational spectra of the chlorpropamide have been studied by means of the X-ray diffraction and Raman spectroscopy at pressures up to 24.6 and 4.4 GPa, respectively. Two polymorphic phase transitions, between initial orthorhombic form-A and a monoclinic form-AI at P ∼ 1
PMID 25393056

Mortality risk among sulfonylureas: a systematic review and network meta-analysis.

Simpson SH1, Lee J2, Choi S2, Vandermeer B3, Abdelmoneim AS2, Featherstone TR2.
The lancet. Diabetes & endocrinology.Lancet Diabetes Endocrinol.2015 Jan;3(1):43-51. doi: 10.1016/S2213-8587(14)70213-X. Epub 2014 Oct 22.
BACKGROUND: Sulfonylureas are common second-line options for management of type 2 diabetes; however, they are associated with a higher risk of cardiovascular events compared with other antidiabetic drugs. Since tissue selectivity and risk of hypoglycaemia differ among sulfonylureas, we aimed to asse
PMID 25466239

Japanese Journal

吸着式人工腎"REDY"による糖尿病性腎症患者の血液透析

泌尿器科紀要 20(7), 443-448, 1974-07
NAID 120002232828

糖尿病者に於けるChlorpropamide静注試験 (Diabinese-Test) に対する考察

日本内分泌学会雑誌 39(5), 489-499,420, 1963
NAID 130001925902

糖尿病におけるDiabinese(Chlorpropamide p-607)の効果とその限度

治療 43(4), 819-822, 1961-04
NAID 40018056764

Related Pictures

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★リンクテーブル★

リンク元	「クロルプロパミド」

「クロルプロパミド」

Chlorpropamide
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; category	AU: C; US: C (Risk not ruled out);
Legal status	AU: Prescription Only (S4); CA: ℞-only; UK: Prescription-only (POM); US: ℞-only;
Routes of; administration	Oral
Pharmacokinetic data
Bioavailability	>90%
Protein binding	90%
Metabolism	<1%
Biological half-life	36 hours
Excretion	Renal (glomerular filtration → reabsorption → tubular secretion)
Identifiers
CAS Registry Number	94-20-2
ATC code	A10BB02
PubChem	CID: 2727
IUPHAR/BPS	6801
DrugBank	DB00672
ChemSpider	2626
UNII	WTM2C3IL2X
KEGG	D00271
ChEBI	CHEBI:3650
ChEMBL	CHEMBL498
Chemical data
Formula	C10H13ClN2O3S
Molecular mass	276.74 g/mol
	SMILES O=S(=O)(c1ccc(Cl)cc1)NC(=O)NCCC ;
	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) ; Key:RKWGIWYCVPQPMF-UHFFFAOYSA-N ;
Physical data
Melting point	126 to 130 °C (259 to 266 °F)
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　　[★]

英: chlorpropamide
ラ: chlorpropamidum
商: アベマイド、Diabinese
関: 糖尿病治療薬

[Arzneistoff-Profile-1] ^ ^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.

[Drugs.com-2] Drugs.com: Chlorpropamide

[3] Fitzgerald, M.G. (1962). "Alcohol sensitivity in diabetics receiving chlorpropamide". Diabetes 11: 40–46.

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Diabinese