CAS 60719-84-8|Amcoral|Wincoram|Cordemcura|Inamrinone|Amrinona [inn-spanish]|Amrinone|3-amino-5-(pyridin-4-yl)-1,2-dihydropyridin-2-one|Inamrinone lactate|Inocor|Amrinonum [inn-latin]|Cartonic|Corda...

General Information

Structure

Molecular Formula

C₁₀H₉N₃O

Molecular Mass

187.19796

Exact Mass

187.07456192

Charge

InChI

InChI=1S/C10H9N3O/c11-9-5-8(6-13-10(9)14)7-1-3-12-4-2-7/h1-6H,11H2,(H,13,14)

InChIKey

RNLQIBCLLYYYFJ-UHFFFAOYSA-N

Canonic Smiles

O=c1[nH]cc(cc1N)c1ccncc1

Isomeric Smiles

O=c1[nH]cc(c2ccncc2)cc1N

Calculated Properties

JChem

LogD (pH = 7.4)

-0.57

LogD (pH = 5.5)

-0.65

Log P

-0.57

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.87

Polar Surface Area

68.01

Polarizability

18.93

Molar Refractivity

53.89

LOG S

-1.95

Data Source

Names and Identifiers

Synonyms

Amrinonum [inn-latin]Amrinona [inn-spanish]AmrinoneInamrinone lactateInamrinoneAmrinone5-Amino-(3,4′-bipyridin)-6(1H)-one5-Amino-[3,4'-bipyridin]-6(1H)-oneCartonic3-Amino-5-(4-pyridinyl)-1,2-dihydro-2-pyridone5-Amino-1,6-dihydro-6-oxo-[3,4'-bipyridine]WincoramInocorAWD 08-250Win 40680Vesistol5-Amino-[3,4'-bipyridin]-6(1H)-oneCordemcuraamrinone

Brand Name

InocorAmcoralCordarexWincoramCordemcuraCartonic

IUPAC Traditional name

amrinone 3-amino-5-(pyridin-4-yl)-1,2-dihydropyridin-2-one

IUPAC name

3-amino-5-(pyridin-4-yl)-1,2-dihydropyridin-2-one 5-amino-1,6-dihydro-[3,4'-bipyridin]-6-one

API Name

Amrinone

International Nonproprietary Name (INN)

amrinone

Names and Identifiers

Registration numbers

PubChem SID

2489074146504647160964695332875312

CAS Number

MDL Number

EC Number

PubChem CID

DrugBank ID

MetaboLights Database

MTBLS2633MTBLS2291

PubMed Citation Links

184686272390832816154150150643312816621715892406

BRENDA Database

3.1.4.353.1.5.B13.1.4.17

SureChEMBL Database

Wikipedia Title

ACToR Database

CompTox Database

BKMS React Database

KEGG ID

CHEBI ID

CHEBI:95269CHEBI:2686

BRENDA Ligand Database

LINCS Database

CHEMBL

KEGG DRUG Database

BindingDB Database

Registration numbers

Properties

Pharmacology Properties

rat ... Pde3a(50678)

cAMP agonist

Phosphodiesterase inhibitor

Physical Property

Brown Solid

DMSO

Methanol (Sparingly)

>240°C (dec.)

Product Information

Download link

Cardiac inotropic agent

95+%

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01427

Drug Groups

approved

Description

Amrinone (or inamrinone) is a type 3 pyridine phosphodiesterase inhibitor. It is used in the treatment of congestive heart failure.

Indication

Used in the treatment of congestive heart failure.

Pharmacology

Amrinone is a positive inotropic cardiotonic with vasodilator properties, phosphodiesterase inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Half Life

5 to 8 hours

Protein Binding

10 to 49%

Elimination

The primary route of excretion in man is via the urine as both inamrinone and several metabolites (N-glycolyl, N-acetate, O-glucuronide and N-glucuronide).

Distribution

* 1.2 L/kg [normal volunteers]

External Links

• [Wikipedia]

Sigma Aldrich

A4056

Biochem/physiol Actions
Simple, non-glycoside cardiotonic agent, possibly via its phosphodiesterase III (PDE-III) inhibitory action.1
Simple, non-glycoside cardiotonic agent, possibly via its phosphodiesterase III (PDE-III) inhibitory action.1 Independent of its cardiac effects, amrinone provides protection against ischemia-reperfusion injury in kidney,2 liver,3 and heart.4

TRC

A635000

A selective cAMP phosphodiesterase (PDE-3) inhibitor with positive inotropic and vasodilatory activity. Cardiotonic.

ChEBI

CHEBI:2686

A 3,4'-bipyridine substituted at positions 5 and 6 by an amino group and a keto function respectively. A pyridine phosphodiesterase 3 inhibitor, it is a drug that may improve the prognosis in patients with congestive heart failure.

Molecule Details

References

PubChem Literature

From Data Sources

• Benotti, J.R., et al.: N. Engl. J. Med., 21, 1373 (1978)

• Bottorff, M.B., et al.: Pharmacotherapy, 5, 227 (1978)

• Ward, A., et al.: Drugs, 26, 468 (1978)

• U.S. Pat., 1978, 4 107 315; CA, 90, 103844r, (synth)

• Landmann, H. et al., Arch. Toxicol., Suppl., 1988, 418, (tox, rev)

• Niedrich, H. et al., Pharmazie, 1986, 41, 173; 176; 181, (synth, cryst struct, tautom)

• Perry, R.S., Drugs of Today (Barcelona), 1984, 20, 381, (rev)

• Robertson, D.W. et al., J. Med. Chem., 1986, 29, 635, (cryst struct)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 663

• Ward, A. et al., Drugs, 1983, 26, 468, (rev, pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AOD375

• Alousi, A.A. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 120, (rev, pharmacol)

• Gomez-Parra, V. et al., Arch. Pharm. (Weinheim, Ger.), 1984, 317, 183, (synth)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Brand Name

InocorAmcoralCordarexWincoramCordemcuraCartonic

IUPAC Traditional name

amrinone 3-amino-5-(pyridin-4-yl)-1,2-dihydropyridin-2-one

IUPAC name

3-amino-5-(pyridin-4-yl)-1,2-dihydropyridin-2-one 5-amino-1,6-dihydro-[3,4'-bipyridin]-6-one

API Name

Amrinone

International Nonproprietary Name (INN)

amrinone

Registration numbers

PubChem SID

2489074146504647160964695332875312

CAS Number

MDL Number

EC Number

PubChem CID

DrugBank ID

MetaboLights Database

MTBLS2633MTBLS2291

PubMed Citation Links

184686272390832816154150150643312816621715892406

BRENDA Database

3.1.4.353.1.5.B13.1.4.17

SureChEMBL Database

Wikipedia Title

ACToR Database

CompTox Database

BKMS React Database

KEGG ID

CHEBI ID

CHEBI:95269CHEBI:2686

BRENDA Ligand Database

LINCS Database

CHEMBL

KEGG DRUG Database

BindingDB Database

Molecule Details

DB01427

Drug Groups

approved

Description

Amrinone (or inamrinone) is a type 3 pyridine phosphodiesterase inhibitor. It is used in the treatment of congestive heart failure.

Indication

Used in the treatment of congestive heart failure.

Pharmacology

Amrinone is a positive inotropic cardiotonic with vasodilator properties, phosphodiesterase inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic.

Half Life

5 to 8 hours

Protein Binding

10 to 49%

Elimination

The primary route of excretion in man is via the urine as both inamrinone and several metabolites (N-glycolyl, N-acetate, O-glucuronide and N-glucuronide).

Distribution

* 1.2 L/kg [normal volunteers]

External Links

• [Wikipedia]

Sigma Aldrich

A4056

TRC

A635000

A selective cAMP phosphodiesterase (PDE-3) inhibitor with positive inotropic and vasodilatory activity. Cardiotonic.

ChEBI

CHEBI:2686

Bioactivity