基本情報
- CAS
2016-88-8- 標準SMILES
NC(N)=NC(=O)c1nc(Cl)c(N)nc1N- InChIKey
XSDQTOBWRPYKKA-UHFFFAOYSA-N- 分子式
- C6H8ClN7O
- 平均分子量
- 229.63 g/mol
- 単同位体質量
- 229.0478856
概要
Amiloride is a member of the class of pyrazines resulting from the formal monoacylation of guanidine with the carboxy group of 3,5-diamino-6-chloropyrazine-2-carboxylic acid. It has a role as a diuretic and a sodium channel blocker. It is a member of guanidines, an aromatic amine, an organochlorine compound and a member of pyrazines. It is a conjugate base of an amiloride(1+).
名称と識別子
- 優先名称
- Amiloride
- IUPAC
- 3,5-diamino-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
- 現地名
- アミロライド
- 英語名
- AMILORIDE
- 分子式
- C6H8ClN7O
- 分子量
- 229.63
名称と別名
AMILORIDE2609-46-3AmipramidinGuanamprazinAmiloridaAmipramizid3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamideAmiloridumMidamorAmiclaranN-Amidino-3,5-diamino-6-chloropyrazinecarboxamide3,5-diamino-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
名称をさらに表示
アミロライド3,5-ジアミノ-N-(アミノイミノメチル)-6-クロロ-2-ピラジンカルボアミド3,5-ジアミノ-6-クロロ-N-(アミノイミノメチル)-2-ピラジンカルボキサミドN-(ジアミノメチレン)-3,5-ジアミノ-6-クロロピラジン-2-カルボアミド3,5-ジアミノ-6-クロロ-N-(アミノイミノメチル)ピラジン-2-カルボアミドグアナムプラジンアミプラミジン3,5-ジアミノ-6-クロロ-N-(ジアミノメチレン)ピラジンカルボアミドアミロリド3,5-ジアミノ-N-(アミノイミノメチル)-6-クロロピラジン-2-カルボアミドN-(アミノイミノメチル)-3,5-ジアミノ-6-クロロピラジン-2-カルボアミド3,5-ジアミノ-N-カルバムイミドイル-6-クロロピラジン-2-カルボキサミドMK-870AMILORIDE ImpurityN-amidino-3,5-diamino-6-chloropyrazine-2-carboxamide3,5-Diamino-6-chloro-N-(diaminomethylene)pyrazinecarboxamide
物性
構造計算による物性
- XLogP
- -0.7
- 極性表面積
- 159 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 5
- 回転可能結合数
- 1
- 重原子数
- 15
- 形式電荷
- 0
- 複雑度
- 279
実験および物理化学的性質
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Diuretics
Pharmaceuticals
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP
-0.3
-0.86
Solubility
Slightly soluble
1.22e+00 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Diuretics
Pharmaceuticals
Diuretics
Melting Point
240.5-241.5
240 °C
Physical DescriptionSolid
Dissociation Constants8.7
Collision Cross Section
157.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2024452]
151.08 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H300 (12.5%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P316, P301+P317, P302+P352, P305+P351+P338, P305+P354+P338, P317, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Not Classified
危険有害性情報
Regulatory Information
REACH registered substance: Amiloride (EC: 220-024-7)
REACH registered substance: N-amidino-3,5-diamino-6-chloropyrazinecarboxamide (EC: 926-801-3)
Other Safety InformationIMAP assessments - Pyrazinecarboxamide, 3,5-diamino-N-(aminoiminomethyl)-6-chloro-: Environment tier I assessment
Hazard Classes and Categories
Acute Tox. 2 (12.5%)
Not Classified
毒性情報
Hepatotoxicity
Amiloride therapy has not been associated with serum aminotransferase elevations. Idiosyncratic, clinically apparent liver injury from amiloride is rare, but several instances have been reported as isolated case reports in which the combination of amiloride with hydrochlorothiazide was used (Case 1). The numbers of cases have been too few to characterize the clinical features, but the latency to onset was ranged from 2 to 12 months and the pattern of injury either hepatocellular or mixed. Immunoallergic features and autoantibodies have not been associated with the liver injury from amiloride.
Adverse Effects
化学と産業
薬理情報
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
C03DB01
Pharmacodynamics
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.
Mechanism of Action
Amiloride works by inhibiting sodium reabsorption in the distal convoluted tubules and collecting ducts in the kidneys by binding to the amiloride-sensitive sodium channels. This promotes the loss of sodium and water from the body, but without depleting potassium. Amiloride exerts its potassium sparing effect through the inhibition of sodium reabsorption at the distal convoluted tubule, cortical collecting tubule and collecting duct; this decreases the net negative potential of the tubular lumen and reduces both potassium and hydrogen secretion and their subsequent excretion. Amiloride is not an aldosterone antagonist and its effects are seen even in the absence of aldosterone.
Biological Half-LifePlasma half-life varies from 6 to 9 hours.
Metabolism/MetabolitesAmiloride is not metabolized by the liver but is excreted unchanged by the kidneys.
FDA Pharmacological Classification
7DZO8EB0Z3
AMILORIDE
Physiologic Effects [PE] - Decreased Renal K+ Excretion
Physiologic Effects [PE] - Increased Diuresis
Established Pharmacologic Class [EPC] - Potassium-sparing Diuretic
Amiloride is a Potassium-sparing Diuretic. The physiologic effect of amiloride is by means of Decreased Renal K+ Excretion and Increased Diuresis.
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