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Amilorid

Amiloride

HCID 16231
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
2016-88-8
Standard-SMILES
NC(N)=NC(=O)c1nc(Cl)c(N)nc1N
InChIKey
XSDQTOBWRPYKKA-UHFFFAOYSA-N
Summenformel
C6H8ClN7O
Durchschnittliche Molmasse
229,63 g/mol
Monoisotopische Masse
229,0478856

Überblick

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+).

Namen und Bezeichner

Bevorzugter Name
Amiloride
IUPAC
3,5-diamino-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
Lokaler Name
Amilorid
Englischer Name
AMILORIDE
Summenformel
C6H8ClN7O
Molmasse
229.63

Namen und Synonyme

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
Weitere Namen anzeigen
MK-870AMILORIDE ImpurityN-amidino-3,5-diamino-6-chloropyrazine-2-carboxamide3,5-Diamino-6-chloro-N-(diaminomethylene)pyrazinecarboxamide3,5-Diamino-6-chloro-N-(aminoiminomethyl)-2-pyrazinecarboxamide2-Pyrazinecarboxamide, 3,5-diamino-N-(aminoiminomethyl)-6-chloro-
DTXSID90438537DZO8EB0Z3Pyrazinecarboxamide, 3,5-diamino-N-(aminoiminomethyl)-6-chloro-CHEBI:2639DTXCID7023853Trom, AmiduretRefChem:57770C03DB01

Datenbank-Bezeichner

CAS
2016-88-8、2609-46-3

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,7
Polarare Oberfläche (TPSA)
159 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
1
Schwere Atome
15
Formalladung
0
Komplexität
279

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Diuretics

Pharmaceuticals

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 Einträge

-0.3

-0.86

Solubility · 2 Einträge

Slightly soluble

1.22e+00 g/L

Human Drugs · 3 Einträge

Breast Feeding; Lactation; Milk, Human; Diuretics

Pharmaceuticals

Diuretics

Melting Point · 2 Einträge

240.5-241.5

240 °C

Physical DescriptionSolid
Dissociation Constants8.7
Collision Cross Section · 2 Einträge

157.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2024452]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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

Gefahrenhinweise

Regulatory Information · 2 Einträge

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 · 2 Einträge

Acute Tox. 2 (12.5%)

Not Classified

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

C - Cardiovascular system

QC - Cardiovascular system

C03DB01

Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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 · 6 Einträge

7DZO8EB0Z3

AMILORIDE

Physiologic Effects [PE] - Decreased Renal K+ Excretion

Physiologic Effects [PE] - Increased Diuresis

Established Pharmacologic Class [EPC] - Potassium-sparing Diuretic

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
16231
DTXSID
DTXSID9043853
ChEMBL
CHEMBL945
ChEBI
CHEBI:2639
UNII
7DZO8EB0Z3
EC Number
220-024-7、926-801-3
Nikkaji
J9.514A

151.08 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
240.5 · 240.5-241.5°
Dichte
2.11 · 2.11±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
Soluble in DMSO
pka
8.7 · pKa 8.7 (Uncertain)
Aggregatzustand
Solid
Farbe
Off-white to light yellow
Wasserlöslichkeit
659 g/L · 659g/L(25 ºC)
CAS Datenbank
2609 · 2609-46-3(CAS DataBase Reference)
Adverse Effects · 1 Eintrag

Amiloride is generally well tolerated, with few significant adverse effects other than the risk of hyperkalemia. The most common adverse drug reactions of amiloride include nausea, vomiting, diarrhea, and headache. Other adverse drug reactions are listed below.

Toxicity Summary · 1 Eintrag

The most toxic effect of amiloride is hyperkalemia. A rapid increase in the extracellular potassium leads to an increase in cardiac conduction velocity, which lowers the threshold for rapid phase Na-dependent depolarization. Furthermore, after the initial increase in cardiac conduction velocity, there will be a prolongation of phase 4 diastolic depolarization and a shortening of the action potential, which leads to a delay in the conduction in the atrioventricular node and His-Purkinje system. On ECG, it manifests as a peaked "tented" T wave. The QRS complex will widen as the condition worsens, resulting in the so-called ''sine wave''. Therefore, hyperkalemia can lead to increased cardiac excitability or decreased cardiac excitability. Increased cardiac excitation can lead to ventricular tachycardia and ventricular fibrillation, while a decrease in cardiac depression leads to various degrees of heart block and asystole. Hyperkalemia can also cause an absence of the P wave on ECG. Moreover, patients with hyperkalemia may present with fatigue, dizziness, and weakness.

Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

amiloride

DILI Positive

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals · 6 Einträge

Amiloride

0.1

0.5

If it is necessary to use amiloride HCl tablets alone, the starting dosage should be one 5 mg tablet daily. This dosage may be increased to 10 mg per day, if necessary.

Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 5 mg/day, Lowest Therapeutic Dose (LTD): 0.1 mg/kg-day, and Screening Dose: 0.00002 mg/kg-day.

21-Dec-21

Sicherheitsdaten

Alarmwort
Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H300

Amiloride is a Potassium-sparing Diuretic. The physiologic effect of amiloride is by means of Decreased Renal K+ Excretion and Increased Diuresis.

MeSH Pharmacological Classification · 3 Einträge

Agents that promote the excretion of urine through their effects on kidney function.

A subclass of sodium channel blockers that are specific for ACID-SENSING SODIUM CHANNELS.

A subclass of sodium channel blockers that are specific for EPITHELIAL SODIUM CHANNELS.

Absorption, Distribution and Excretion · 2 Einträge

Readily absorbed following oral administration.

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.

Cellular LocationsExtracellular
Metabolite PathwaysAmiloride Action Pathway

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >100
Use ClassificationPharmaceuticals

Anwendungen

BeschreibungAmyloride is also a potassium sparing diuretic that exhibits moderate activity. It is not an antagonist of aldosterone. It inhibits reabsorption of sodium ions and reduces excretion of potassium ions.

VerwendenAmiloride is an epithelial sodium channel blocker.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

HydrogenchloridNatriumGUANIDINEAmmoniak, wasserfreiSulfuryldichlorid

Nachgelagerte Produkte

Methyl-3,5-diamino-6-chlorpyrazincarboxylat

Anbieter15 Anbieter

上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
Musechem+1-800-259-7612 · [email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
成都圣美凯生物科技有限公司028-85157043 15882256948 · [email protected]
范德(北京)生物科技有限责任公司15911056312 · [email protected]
兰州康寓信生物科技有限公司0943-8293106 · [email protected]
海蔚化学86-21-51086038 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
湖北诺纳科技有限公司027-59209883 17386138556 · [email protected]
湖北云镁科技有限公司59206672 18327059871 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A monocarboxylic acid amide that is N-carbamimidoylpyrazine-2-carboxamide substituted by amino groups at positions 3 and 5 and a chloro group at position 6.