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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyAmrinone
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
Structure for Amrinone (DB01427)
- Synonyms
- Amrinona
- Amrinone
- Amrinonum
- Inamrinone
- External IDs
- C01CE01 / WIN 40680 / WIN-40680
- Product Ingredients
Ingredient UNII CAS InChI Key Amrinone lactate I229274Y5B 75898-90-7 DOSIONJFGDSKCQ-UHFFFAOYSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataInocor Liq 5mg/ml Liquid Intravenous Sanofi 1984-12-31 2000-07-24 Canada 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataInamrinone Injection 5 mg/1mL Intravenous Bedford Pharmaceuticals 2000-07-01 2009-10-31 US 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- International/Other Brands
- Amcoral / Inocor
- Categories
- Amines
- Aminopyridines
- Calcium-Regulating Hormones and Agents
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Cardiotonic Agents
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Membrane Transport Modulators
- Phosphodiesterase 3 Inhibitors
- Phosphodiesterase Inhibitors
- Protective Agents
- Pyridines
- Vasodilating Agents
- UNII
- JUT23379TN
- CAS number
- 60719-84-8
- Weight
- Average: 187.198
Monoisotopic: 187.074561925 - Chemical Formula
- C10H9N3O
- InChI Key
- 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)
- IUPAC Name
- 3-amino-5-(pyridin-4-yl)-1,2-dihydropyridin-2-one
- SMILES
- NC1=CC(=CNC1=O)C1=CC=NC=C1
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.
Target Actions Organism AcGMP-inhibited 3',5'-cyclic phosphodiesterase A inhibitorHumans UcAMP-specific 3',5'-cyclic phosphodiesterase 4B inhibitorHumans UTumor necrosis factor inhibitorHumans UcGMP-inhibited 3',5'-cyclic phosphodiesterase B inhibitorHumans - 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
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Abacavir may decrease the excretion rate of Amrinone which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Amrinone which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Amrinone which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Amrinone which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Amrinone which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Amrinone which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Amrinone which could result in a higher serum level. Aclidinium Amrinone may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Amrinone may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Amrinone which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Not Available
References
- Synthesis Reference
Lesher,G.Y. and Opalka, C.J.; US. Patent 4,004,012; January 18,1977; assigned to Sterling Drug Inc. Lesher, G.Y. and Opalka, C.J.; U.S. Patent 4,107,315; August 15,1978; assigned to Sterling Drug Inc.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015496
- KEGG Drug
- D00231
- KEGG Compound
- C13594
- PubChem Compound
- 3698
- PubChem Substance
- 46504647
- ChemSpider
- 3570
- BindingDB
- 34651
- RxNav
- 738
- ChEBI
- 2686
- ChEMBL
- CHEMBL12856
- ZINC
- ZINC000008673078
- Therapeutic Targets Database
- DAP001392
- PharmGKB
- PA164746803
- Wikipedia
- Amrinone
- ATC Codes
- C01CE01 — Amrinone
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bedford Labs
- Ben Venue Laboratories Inc.
- Taylor Pharmaceuticals
- Dosage forms
Form Route Strength Injection Intravenous 5 mg/1mL Liquid Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 294-297 Lesher,G.Y. and Opalka, C.J.; US. Patent 4,004,012; January 18,1977; assigned to Sterling Drug Inc. Lesher, G.Y. and Opalka, C.J.; U.S. Patent 4,107,315; August 15,1978; assigned to Sterling Drug Inc. - Predicted Properties
Property Value Source Water Solubility 5.6 mg/mL 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 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 53.89 m3·mol-1 ChemAxon Polarizability 18.94 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9522 Blood Brain Barrier + 0.9525 Caco-2 permeable + 0.8867 P-glycoprotein substrate Non-substrate 0.6469 P-glycoprotein inhibitor I Non-inhibitor 0.9338 P-glycoprotein inhibitor II Non-inhibitor 0.9946 Renal organic cation transporter Non-inhibitor 0.9258 CYP450 2C9 substrate Non-substrate 0.8642 CYP450 2D6 substrate Non-substrate 0.8389 CYP450 3A4 substrate Non-substrate 0.6443 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.5328 CYP450 2D6 inhibitor Non-inhibitor 0.9651 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.6534 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5933 Ames test Non AMES toxic 0.8492 Carcinogenicity Non-carcinogens 0.9116 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.9371 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9923 hERG inhibition (predictor II) Non-inhibitor 0.7418
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-00lr-3900000000-f6b4ee8cb119f30be206
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Bipyridines and oligopyridines
- Direct Parent
- Bipyridines and oligopyridines
- Alternative Parents
- Pyridinones / Dihydropyridines / Aminopyridines and derivatives / Heteroaromatic compounds / Lactams / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organooxygen compounds / Organic oxides show 1 more
- Substituents
- Bipyridine / Aminopyridine / Dihydropyridine / Pyridinone / Hydropyridine / Heteroaromatic compound / Lactam / Azacycle / Amine / Primary amine show 8 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
- Gene Name
- PDE3A
- Uniprot ID
- Q14432
- Uniprot Name
- cGMP-inhibited 3',5'-cyclic phosphodiesterase A
- Molecular Weight
- 124978.06 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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:12076859]
- 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:19901885]
- 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. doi: 10.1016/j.jss.2008.02.008. Epub 2008 Mar 13. [PubMed:18468627]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging f...
- Gene Name
- PDE4B
- Uniprot ID
- Q07343
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4B
- Molecular Weight
- 83342.695 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- 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:17016423]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Tumor necrosis factor receptor binding
- Specific Function
- 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 ac...
- Gene Name
- TNF
- Uniprot ID
- P01375
- Uniprot Name
- Tumor necrosis factor
- Molecular Weight
- 25644.15 Da
References
- 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:10075051]
- 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:10444479]
- 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:11805217]
- 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:11969359]
- Giroir BP, Beutler B: Effect of amrinone on tumor necrosis factor production in endotoxic shock. Circ Shock. 1992 Mar;36(3):200-7. [PubMed:1611705]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Protein kinase b binding
- Specific Function
- Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. May play a role in fat metab...
- Gene Name
- PDE3B
- Uniprot ID
- Q13370
- Uniprot Name
- cGMP-inhibited 3',5'-cyclic phosphodiesterase B
- Molecular Weight
- 124332.145 Da
References
- Rao YJ, Xi L: Pivotal effects of phosphodiesterase inhibitors on myocyte contractility and viability in normal and ischemic hearts. Acta Pharmacol Sin. 2009 Jan;30(1):1-24. doi: 10.1038/aps.2008.1. Epub 2008 Dec 8. [PubMed:19060915]
- Yan C, Miller CL, Abe J: Regulation of phosphodiesterase 3 and inducible cAMP early repressor in the heart. Circ Res. 2007 Mar 2;100(4):489-501. doi: 10.1161/01.RES.0000258451.44949.d7. [PubMed:17332439]
- Zywert A, Szkudelska K, Szkudelski T: Inhibition of phosphodiesterase 3B in insulin-secreting cells of normal and streptozocin-nicotinamide-induced diabetic rats: implications for insulin secretion. J Physiol Pharmacol. 2014 Jun;65(3):425-33. [PubMed:24930515]
Drug created on July 24, 2007 06:34 / Updated on March 01, 2020 23:30
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