Basic information
- CAS
60719-84-8- Standard SMILES
Nc1cc(-c2ccncc2)c[nH]c1=O- InChIKey
RNLQIBCLLYYYFJ-UHFFFAOYSA-N- Molecular formula
- C10H9N3O
- Average molar mass
- 187.2 g/mol
- Monoisotopic mass
- 187.07456192
Overview
Amrinone is 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. It has a role as a cardiovascular drug and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor.
Names & identifiers
- Preferred name
- Amrinone
- IUPAC
- 3-amino-5-pyridin-4-yl-1H-pyridin-2-one
- English name
- Amrinone
- Molecular formula
- C10H9N3O
- Molecular weight
- 187.2
Names & synonyms
Amrinone60719-84-8inamrinoneCartonicAmcoralVesistolAmrinonaAmrinonumWIN 40680DTXSID9022603[3,4'-Bipyridin]-6(1H)-one, 5-amino-5-Amino(3,4'-bipyridin)-6(1H)-one
Show more names
inocorAmrinonwin40680WincoramImrinoneawd08-250Amirinone
NSC-759805CHEBI:2686JUT23379TN(3,4'-BIPYRIDIN)-6(1H)-ONE, 5-AMINO-C01CE013-amino-5-(pyridin-4-yl)pyridin-2-ol5-Amino[3,4'-bipyridin]-6(1H)-oneDTXCID602603
Database identifiers
- CAS
60719-84-8- PubChem CID
- 3698
- DTXSID
DTXSID9022603- ChEMBL
CHEMBL12856- ChEBI
CHEBI:2686- UNII
- JUT23379TN
- EC Number
- 262-390-0
- Nikkaji
- J17.949C
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 68 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 300
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.54
Solubility
5.60e+00 g/L
>28.1 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsPharmaceuticals
Melting Point
294-297
295 °C
Physical DescriptionSolid
Collision Cross Section
142.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID9022603]
139 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
133.57 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- 3
- rtecs
- DW2500000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29333999
- Toxicity
- LD50 orl-rat: 102 mg/kg NDADD8 1,259,83
- risk_code
- 25-36/37/38-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T,Xn
- safety_code
- 28-45-36-26
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P301+P330+P331+P310
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding10 to 49%
PharmacodynamicsAmrinone 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 ActionAmrinone 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.
Biological Half-Life5 to 8 hours
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
A class of drugs that act by selective inhibition of calcium influx through cellular membranes.
Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).
Drugs used to cause dilation of the blood vessels.
Compounds that specifically inhibit PHOSPHODIESTERASE 3.
Absorption, Distribution and Excretion
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).
1.2 L/kg [normal volunteers]
Cellular LocationsCytoplasm
Uses & manufacturing
Related reactions
7 records
Compound notes
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