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

• ChemBase ID: 476
• Molecular Formular: C6H8ClN7O
• Molecular Mass: 229.62702
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-diamino-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
• IUPAC Traditional name: amiloride
• Brand Name: Amipramidin; Amipramizid; Amipramizide; Amiprazidine; Guanamprazin; Guanamprazine; Midamor
• Synonyms: Amiloridum [INN-Latin]; Amiloride hydrochloride hydrate; Amiloride hydrochloride; Amiloride HCL; Amilorida [INN-Spanish]; AMR; Amyloride; Amiloride

Database IDs

• CAS Number: 2016-88-8
• PubChem SID: 46508156; 160963939
• PubChem CID: 16231
• CHEBI ID: 2639
• ATC CODE: C03DB01
• CHEMBL: 945
• Chemspider ID: 15403
• DrugBank ID: DB00594
• IUPHAR ligand ID: 2421
• KEGG ID: D07447
• Unique Ingredient Identifier: 7M458Q65S3
• Wikipedia Title: Amiloride

CALCULATED PROPERTIES

JChem

• Lipinski's Rule of Five: true
• Acid pKa: 16.458862
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.89300954
• LogD (pH = 7.4): -0.89040244
• Log P: -0.8903691
• Molar Refractivity: 56.6884 cm^3
• Polarizability: 19.736666 Å^3
• Polar Surface Area: 159.29 Å^2
• Rotatable Bonds: 1

ALOGPS 2.1

• Solubility (Water): 1.22e+00 g/l
• Log P: -0.72
• LOG S: -2.27

PROPERTIES

Physical Property

• Solubility: Slightly soluble
• Hydrophobicity(logP): -0.3

Pharmacology Properties

• Admin Routes: oral
• Bioavailability: Readily absorbed
• Excretion: unchanged in urine
• Half Life: 6 to 9 hours
• Metabolism: none
• Legal Status: Rx-only (US)
• Pregnancy Category: B (US)

DETAILS

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