CAS 2016-88-8|3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride|Amiloride hydrochloride|amiloride hydrochloride|Midamor|Colectril|Amipramizide|amilorida hydrochloride|3,5-diam...

General Information

Structure

Molecular Formula

C₆H₉Cl₂N₇O

Molecular Mass

266.08796

Exact Mass

265.0245633

Charge

InChI

InChI=1S/C6H8ClN7O.ClH/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);1H

InChIKey

ACHKKGDWZVCSNH-UHFFFAOYSA-N

Canonic Smiles

NC(=N)NC(=O)c1nc(Cl)c(nc1N)N.Cl

Isomeric Smiles

c1(c(nc(c(n1)C(=O)NC(=N)N)N)N)Cl.Cl

Calculated Properties

JChem

Acid pKa

11.426196

H Acceptors

H Donor

LogD (pH = 5.5)

-0.7251268

LogD (pH = 7.4)

-0.4992728

Log P

-0.49543247

Molar Refractivity

67.1812

Polarizability

19.563002

Polar Surface Area

156.79

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC name

3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride

Synonyms

Amiloride hydrochlorideMidamorColectrilAmipramizide3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochlorideGuanamprazineAmiloride hydrochlorideAmiprazidineAmipramizidGuanamprazinAmipramidinN-Amidino-3,5-diamino-6-chlorocyrazinecarboxamide MonohydrochlorideAmiprazideN-Amidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride3,5-Diamino-N-(aminoiminomethyl)-6-chloro-2-pyrazinecarboxamide HydrochlorideAmipramidine3,5-Diamino-N-(aminomethyl)-6-chloropyrazinecarboxamideAMILORIDENiluridN-Amidino-3,5-diamino-6-chloropyrazinamide Hydrochloride

IUPAC Traditional name

amiloride hydrochloride amilorida hydrochloride 3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride

Names and Identifiers

Registration numbers

CAS Number

PubChem CID

PubChem SID

EC Number

Registration numbers

Properties

Product Information

Safety Information

Pharmacology Properties

Mechanism of Action

Amiloride exerts its potassium sparing effect through the inhibition of sodium reabsorption at the distal convoluted tubule, cortical collecting tubule and collecting duct;

This promotes the loss of sodium and water from the body, but without depleting potassium.

Amiloride is not an aldosterone antagonist and its effects are seen even in the absence of aldosterone.

this decreases the net negative potential of the tubular lumen and reduces both potassium and hydrogen secretion and their subsequent excretion.

Inhibitor of sodium reabsorption in the distal convoluted tubules and collecting ducts in the kidneys by binding to the amiloride-sensitive sodium channels.

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S1811

Research Area: Metabolic Disease
Biological Activity:
Amiloride hydrochloride(Midamor), a pyrazine compound inhibit 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. [1]

MP Biomedicals

02153537

Hydrochloride
A sodium ion channel inhibitor.

TRC

A578700

Sodium channel blocker. Diuretic.

Molecule Details

References

PubChem Literature

From Data Sources

• http://www.drugbank.ca/drugs/DB00594

• Frank, S., et al.: J. Pharm. Sci., 64, 1585 (1968)

• Khan, K., et al.: J. Pharm. Pharmacol., 27, 48 (1968)

• Vidt, D., et al.: Pharmacotherapy, 1, 179 (1968)

• Paterson, J., et al.: Br. Med. J., 1, 422 (1968)

• Hyams, D.E., Int. Congr. Symp. Ser. R. Soc. Med., 1981, 44, 65, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 445, (synonyms)

• Buono, R.A. et al., J.A.C.S., 1994, 116, 1502, (conformn)

• Mazzo, D.J., Anal. Profiles Drug Subst., 1986, 15, 1, (rev)

• Smith, R.L. et al., J.A.C.S., 1979, 101, 191, (pmr, cmr, N-15 nmr, tautom)

• Burns, D.T. et al., Anal. Chim. Acta, 1980, 118, 185, (detn, ClO(-))

• Amiloride and its Analogs, (eds. Cragoe, E.J. et al), VCH, New York, 1992, (book)

• Cragoe, E.J. et al., J. Med. Chem., 1967, 10, 66, (synth, pharmacol)

• Laragh, J.H., Curr. Ther. Res., 1982, 32, 173, (rev)

• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 2304

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride

Synonyms

IUPAC Traditional name

amiloride hydrochloride amilorida hydrochloride 3,5-diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide hydrochloride

Registration numbers

CAS Number

PubChem CID

PubChem SID

EC Number

Molecule Details

S1811

Hydrochloride
A sodium ion channel inhibitor.

TRC

A578700

Sodium channel blocker. Diuretic.

References

PubChem Literature

From Data Sources

• http://www.drugbank.ca/drugs/DB00594

• Frank, S., et al.: J. Pharm. Sci., 64, 1585 (1968)

• Khan, K., et al.: J. Pharm. Pharmacol., 27, 48 (1968)

• Vidt, D., et al.: Pharmacotherapy, 1, 179 (1968)

• Paterson, J., et al.: Br. Med. J., 1, 422 (1968)

• Hyams, D.E., Int. Congr. Symp. Ser. R. Soc. Med., 1981, 44, 65, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 445, (synonyms)

• Buono, R.A. et al., J.A.C.S., 1994, 116, 1502, (conformn)

• Mazzo, D.J., Anal. Profiles Drug Subst., 1986, 15, 1, (rev)

• Smith, R.L. et al., J.A.C.S., 1979, 101, 191, (pmr, cmr, N-15 nmr, tautom)

• Burns, D.T. et al., Anal. Chim. Acta, 1980, 118, 185, (detn, ClO(-))

• Amiloride and its Analogs, (eds. Cragoe, E.J. et al), VCH, New York, 1992, (book)

• Cragoe, E.J. et al., J. Med. Chem., 1967, 10, 66, (synth, pharmacol)

• Laragh, J.H., Curr. Ther. Res., 1982, 32, 173, (rev)

• Martindale, The Extra Pharmacopoeia, 28th/29th edn., Pharmaceutical Press, 1982, 2304

Bioactivity

PubChem BioAssay

Properties

Product Information

Safety Information

Pharmacology Properties

Mechanism of Action

Amiloride exerts its potassium sparing effect through the inhibition of sodium reabsorption at the distal convoluted tubule, cortical collecting tubule and collecting duct;

This promotes the loss of sodium and water from the body, but without depleting potassium.

Amiloride is not an aldosterone antagonist and its effects are seen even in the absence of aldosterone.

this decreases the net negative potential of the tubular lumen and reduces both potassium and hydrogen secretion and their subsequent excretion.

Inhibitor of sodium reabsorption in the distal convoluted tubules and collecting ducts in the kidneys by binding to the amiloride-sensitive sodium channels.

Molecule

ID:72807