Banner
targets (3)
for drugs
Identification
Name Amrinone
Accession Number DB01427
Type small molecule
Groups approved
Description

Amrinone (or inamrinone) is a type 3 pyridine phosphodiesterase inhibitor. It is used in the treatment of congestive heart failure.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Amrinona [inn-spanish]
Amrinonum [inn-latin]
Inamrinone
Inamrinone lactate
Salts Not Available
Brand names
Name Company
Amcoral
Cartonic
Cordarex
Cordemcura
Inocor
Wincoram
Brand mixtures Not Available
Categories
  • Vasodilator Agents
  • Phosphodiesterase Inhibitors
  • Cardiotonic Agents
  • Calcium Channel Blockers
CAS number 60719-84-8
Weight Average: 187.198
Monoisotopic: 187.074561925
Chemical Formula C10H9N3O
InChI Key InChIKey=RNLQIBCLLYYYFJ-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
3-amino-5-(pyridin-4-yl)-1,2-dihydropyridin-2-one
SMILES
NC1=CC(=CNC1=O)C1=CC=NC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Pyridines and Derivatives
  • Aminopyridines and Derivatives
  • Pyridines
Substructures
  • Pyridines and Derivatives
  • Aliphatic and Aryl Amines
  • Aminopyridines and Derivatives
  • Pyridines
  • Heterocyclic compounds
  • Aromatic compounds
Pharmacology
Indication Used in the treatment of congestive heart failure.
Pharmacodynamics Amrinone is a positive inotropic cardiotonic with vasodilator properties, phosphodiesterase inhibitory activity, and the ability to stimulate calcium ion influx into the cardiac cell.
Mechanism of action Amrinone is a phosphodiesterase inhibitor (PDE3), resulting in increased cAMP and cGMP which leads to an increase in the calcium influx like that caused by beta-agonists resulting in increased inotropic effect.
Absorption Not Available
Volume of distribution
  • 1.2 L/kg [normal volunteers]
Protein binding 10 to 49%
Metabolism Hepatic.
Route of 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).
Half life 5 to 8 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Baxter healthcare corp anesthesia critical care
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Sanofi aventis us llc
Packagers
Dosage forms
Form Route Strength
Liquid Intravenous bolus
Liquid Intravenous drip
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 295 dec °C PhysProp
Predicted Properties
Property Value Source
water solubility 5.60e+00 g/l ALOGPS
logP 0.27 ALOGPS
logP -0.57 ChemAxon
logS -1.5 ALOGPS
pKa (strongest acidic) 11.01 ChemAxon
pKa (strongest basic) 4.87 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 68.01 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 53.89 ChemAxon
polarizability 18.94 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00231 Link_out
KEGG Compound C13594 Link_out
PubChem Compound 3698 Link_out
PubChem Substance 46504647 Link_out
ChemSpider 3570 Link_out
BindingDB 34651 Link_out
Therapeutic Targets Database DAP001392 Link_out
PharmGKB PA164746803 Link_out
Wikipedia http://en.wikipedia.org/wiki/Amrinone Link_out
ATC Codes
  • C01CE01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions Not Available
Targets

1. cGMP-inhibited 3',5'-cyclic phosphodiesterase A

Pharmacological action: yes
Actions: inhibitor

Hydrolyzes both cyclic AMP (cAMP) and cyclic GMP (cGMP)

Organism class: human
UniProt ID: Q14432 Link_out
Gene: PDE3A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Kobayashi T, Sugawara Y, Ohkubo T, Imamura H, Makuuchi M: Effects of amrinone on hepatic ischemia-reperfusion injury in rats. J Hepatol. 2002 Jul;37(1):31-8. Pubmed
  3. Ko Y, Morita K, Nagahori R, Kinouchi K, Shinohara G, Kagawa H, Hashimoto K: Myocardial cyclic AMP augmentation with high-dose PDEIII inhibitor in terminal warm blood cardioplegia. Ann Thorac Cardiovasc Surg. 2009 Oct;15(5):311-7. Pubmed
  4. Kucuk C, Akcan A, Akyyldyz H, Akgun H, Muhtaroglu S, Sozuer E: Effects of amrinone in an experimental model of hepatic ischemia-reperfusion injury. J Surg Res. 2009 Jan;151(1):74-9. Epub 2008 Mar 13. Pubmed

2. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

Pharmacological action: unknown
Actions: inhibitor

May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents

Organism class: human
UniProt ID: Q07343 Link_out
Gene: PDE4B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Tumor necrosis factor

Pharmacological action: unknown
Actions: inhibitor

Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin 1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation

Organism class: human
UniProt ID: P01375 Link_out
Gene: TNF Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kumar A, Kosuri R, Kandula P, Dimou C, Allen J, Parrillo JE: Effects of epinephrine and amrinone on contractility and cyclic adenosine monophosphate generation of tumor necrosis factor alpha-exposed cardiac myocytes. Crit Care Med. 1999 Feb;27(2):286-92. Pubmed
  2. Bergman MR, Kao RH, McCune SA, Holycross BJ: Myocardial tumor necrosis factor-alpha secretion in hypertensive and heart failure-prone rats. Am J Physiol. 1999 Aug;277(2 Pt 2):H543-50. Pubmed
  3. Haddad JJ, Land SC, Tarnow-Mordi WO, Zembala M, Kowalczyk D, Lauterbach R: Immunopharmacological potential of selective phosphodiesterase inhibition. I. Differential regulation of lipopolysaccharide-mediated proinflammatory cytokine (interleukin-6 and tumor necrosis factor-alpha) biosynthesis in alveolar epithelial cells. J Pharmacol Exp Ther. 2002 Feb;300(2):559-66. Pubmed
  4. Marx D, Tassabehji M, Heer S, Huttenbrink KB, Szelenyi I: Modulation of TNF and GM-CSF release from dispersed human nasal polyp cells and human whole blood by inhibitors of different PDE isoenzymes and glucocorticoids. Pulm Pharmacol Ther. 2002;15(1):7-15. Pubmed
  5. Giroir BP, Beutler B: Effect of amrinone on tumor necrosis factor production in endotoxic shock. Circ Shock. 1992 Mar;36(3):200-7. Pubmed
Comments
Drug created on July 24, 2007 06:34 / Updated on February 08, 2013 16:20