3,5-diamino-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide

• ChemBase编号: 476
• 分子式: C6H8ClN7O
• 平均质量: 229.62702
• 单一同位素质量: 229.04788559
• SMILES: Clc1nc(c(nc1N)N)C(=O)N=C(N)N
• Canonical SMILES: NC(=NC(=O)c1nc(Cl)c(nc1N)N)N
• InChI: InChI=1S/C6H8ClN7O/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11/h(H4,8,9,13)(H4,10,11,14,15)
• InChIKey: XSDQTOBWRPYKKA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3,5-diamino-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
• IUPAC传统名: amiloride
• 商标名: Amipramidin; Amipramizid; Amipramizide; Amiprazidine; Guanamprazin; Guanamprazine; Midamor
• 别名: Amiloridum [INN-Latin]; Amiloride hydrochloride hydrate; Amiloride hydrochloride; Amiloride HCL; Amilorida [INN-Spanish]; AMR; Amyloride; Amiloride

登记号

• CAS号: 2016-88-8
• PubChem SID: 46508156; 160963939
• PubChem CID: 16231
• CHEBI ID: 2639
• ATC码: C03DB01
• CHEMBL: 945
• Chemspider ID: 15403
• DrugBank ID: DB00594
• IUPHAR配体索引: 2421
• KEGG ID: D07447
• 美国药典/FDA物质标识码: 7M458Q65S3
• 维基百科标题: Amiloride

理论计算性质

JChem

• 里宾斯基五规则: true
• Acid pKa: 16.458862
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -0.89300954
• LogD (pH = 7.4): -0.89040244
• Log P: -0.8903691
• 摩尔折射率: 56.6884 cm^3
• 极化性: 19.736666 Å^3
• 极化表面积: 159.29 Å^2
• 可自由旋转的化学键: 1

ALOGPS 2.1

• 溶解度: 1.22e+00 g/l
• Log P: -0.72
• LOG S: -2.27

分子性质

理化性质

• 溶解度: Slightly soluble
• 疏水性(logP): -0.3

药理学性质

• 给药途径: oral
• 生物利用度: Readily absorbed
• 排泄: unchanged in urine
• 半衰期: 6 to 9 hours
• 代谢: none
• 法定药品分级: Rx-only (US)
• 妊娠期药物分类: B (US)

详细说明

DrugBank - DB00594

• Drug Groups: approved
• Description: A pyrazine compound inhibiting sodium reabsorption through sodium channels in renal epithelial cells. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with diuretics to spare potassium loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705)
• Indication: For use as adjunctive treatment with thiazide diuretics or other kaliuretic-diuretic agents in congestive heart failure or hypertension.
• Pharmacology: Amiloride, an antikaliuretic-diuretic agent, is a pyrazine-carbonyl-guanidine that is unrelated chemically to other known antikaliuretic or diuretic agents. It is an antihypertensive, potassium-sparing diuretic that was first approved for use in 1967 and helps to treat hypertension and congestive heart failure. The drug is often used in conjunction with thiazide or loop diuretics. Due to its potassium-sparing capacities, hyperkalemia (high blood potassium levels) are occasionally observed in patients taking amiloride. The risk is high in concurrent use of ACE inhibitors or spironolactone. Patients are also advised not to use potassium-containing salt replacements.
• Toxicity: No data are available in regard to overdosage in humans. The oral LD₅₀ of amiloride hydrochloride (calculated as the base) is 56 mg/kg in mice and 36 to 85 mg/kg in rats, depending on the strain. The most likely signs and symptoms to be expected with overdosage are dehydration and electrolyte imbalance.
• Affected Organisms: Humans and other mammals
• Biotransformation: Amiloride is not metabolized by the liver but is excreted unchanged by the kidneys.
• Absorption: Readily absorbed following oral administration.
• Half Life: Plasma half-life varies from 6 to 9 hours.
• Elimination: Amiloride HCl is not metabolized by the liver but is excreted unchanged by the kidneys. About 50 percent of a 20 mg dose of amiloride HCl is excreted in the urine and 40 percent in the stool within 72 hours.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com