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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 5 mg 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
- 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
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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 UcAMP-specific 3',5'-cyclic phosphodiesterase 3 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
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
- ChEBI
- 2686
- ChEMBL
- CHEMBL12856
- 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 5 mg - 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]
4. cAMP-specific 3',5'-cyclic phosphodiesterase 3
Unknown
Inhibitor
References
- Weishaar RE, Kobylarz-Singer DC, Steffen RP, Kaplan HR: Subclasses of cyclic AMP-specific phosphodiesterase in left ventricular muscle and their involvement in regulating myocardial contractility. Circ Res. 1987 Oct;61(4):539-47. [PubMed:2820608]
Drug created on July 24, 2007 06:34 / Updated on June 04, 2019 05:17