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78415-72-2 molecular structure
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6-methyl-2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridine-3-carbonitrile

ChemBase ID: 120
Molecular Formular: C12H9N3O
Molecular Mass: 211.21936
Monoisotopic Mass: 211.07456192
SMILES and InChIs

SMILES:
O=c1[nH]c(c(c2ccncc2)cc1C#N)C
Canonical SMILES:
N#Cc1cc(c2ccncc2)c([nH]c1=O)C
InChI:
InChI=1S/C12H9N3O/c1-8-11(9-2-4-14-5-3-9)6-10(7-13)12(16)15-8/h2-6H,1H3,(H,15,16)
InChIKey:
PZRHRDRVRGEVNW-UHFFFAOYSA-N

Cite this record

CBID:120 http://www.chembase.cn/molecule-120.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
6-methyl-2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridine-3-carbonitrile
IUPAC Traditional name
milrinone
Brand Name
Corotrop
Corotrope
Milrila
Primacor
Synonyms
Milrinone Lactate
Milrinone
1,6-Dihydro-2-methyl-6-oxo-3,4-bipyridine-5-carbonitrile
Primacor
1,6-Dihydro-2-methyl-6-oxo-(3,4′-bipyridine)-5-carbonitrile
1,6-Dihydro-2-methyl-6-oxo-[3,4'-bipyridine]-5-carbonitrile
Corotrope
Milrila
Win 47203
Milrinone
CAS Number
78415-72-2
EC Number
278-903-6
MDL Number
MFCD00133539
PubChem SID
160963583
24278060
46507838
PubChem CID
4197

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.536811  H Acceptors
H Donor LogD (pH = 5.5) 0.2525552 
LogD (pH = 7.4) 0.12443696  Log P 0.3290194 
Molar Refractivity 61.1381 cm3 Polarizability 22.2292 Å3
Polar Surface Area 65.78 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.04  LOG S -3.0 
Solubility (Water) 2.09e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
DMSO: >10 mg/mL expand Show data source
H2O: insoluble expand Show data source
Slightly soluble expand Show data source
Apperance
off-white powder expand Show data source
Off-White Solid expand Show data source
Melting Point
305-308°C (dec.) expand Show data source
Density
0.87 g/ml expand Show data source
Hydrophobicity(logP)
0.4 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
RTECS
DW1762000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
23/24/25 expand Show data source
R:25 expand Show data source
Safety Statements
36/37/39-45 expand Show data source
S:28-29-36/37/39-45 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H311-H331 expand Show data source
GHS Precautionary statements
P261-P280-P301 + P310-P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... PDE3A(5139), PDE3B(5140), PDE4B(5142), PDE5A(8654), PTPRA(5786)rat ... Pde3a(50678) expand Show data source
Purity
≥97% (TLC) expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC Selleck Chemicals Selleck Chemicals
DrugBank - DB00235 external link
Item Information
Drug Groups approved
Description A positive inotropic cardiotonic agent with vasodilator properties. It inhibits cAMP phosphodiesterase activity in myocardium and vascular smooth muscle. Milrinone is a derivative of amrinone and has 20-30 times the ionotropic potency of amrinone. [PubChem]
Indication Indicated for the treatment of congestive heart failure.
Pharmacology Milrinone, a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine, is used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.
Toxicity LD50 = 0.3 mg/L in rats
Affected Organisms
Humans and other mammals
Biotransformation There are five metabolites but the O-glucuronide represents the major pathway of biotransformation.
Absorption Milrinone is rapidly and almost completely absorbed after oral administration. Bioavailability is 92% (in healthy volunteers).
Half Life 2.3 hours
Protein Binding 70 to 80%
Elimination The primary route of excretion of milrinone in man is via the urine.
Distribution * 0.38 liters/kg [intravenous injections of 12.5 mcg/kg to 125 mcg/kg to congestive heart failure patients]
* 0.45 liters/kg [intravenous infusions of 0.20 mcg/kg/min to 0.70 mcg/kg/min to congestive heart failure patients]
Clearance * 0.13 L/kg/hr [congestive heart failure patients, following IV injections of 12.5 mcg/kg to 125 mcg/kg]
* 0.14 L/kg/hr [congestive heart failure patients, following infusions of 0.2 mcg/kg/min to 0.7 mcg/kg/min]
External Links
Wikipedia
RxList
Drugs.com
MP Biomedicals - 02158962 external link
Purity: 97%
Specifically inhibits cGMP-inhibited phosphodiesterase. Strong cardiotonic positive inotropic vasodilator.
Sigma Aldrich - M4659 external link
Biochem/physiol Actions
Phosphodiesterase type III inhibitor; cAMP-specific, cGMP-inhibitable; potent cardiotonic, positive inotropic vasodilator.
Toronto Research Chemicals - M344680 external link
Selective phosphodiesterase inhibitor with vasodilating and positive inotropic activity. Cardiotonic.
Selleck Chemicals - S2484 external link
Research Area: Cardiovascular Disease
Biological Activity:
Milrinone(Primacor) is a a potent and selective phosphodiesterase 3 inhibitor with an IC50 of 0.42 µM for the inhibition of FIII PDE. [1] It potentiates the effect of cyclic adenosine monophosphate (cAMP). It also enhances relaxation of the left ventricle by increasing Ca2+-ATPase activity on the cardiac sarcoplasmic reticulum. This increases calcium ion uptake.It has positive inotropic, vasodilating and minimal chronotropic effects. It is used in the management of heart failure only when conventional treatment with vasodilators and diuretics has proven insufficient. This is due to the potentially fatal adverse effects of milrinone, including ventricular arrhythmias. [2]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Ito M et al. Biochem Pharmacol. 1988 May 15;37(10)
  • • Harrison, S.A., et al., Mol. Pharmacol. , 29 : 506 (1986).
  • • Ahn, S., et al., Biochem. Pharmacol. , 35 : 1113 (1986).
  • • Alousi, A.A., et al., J. Cardiovas. Pharmacol. , 5 : 792 (1983).
  • • Alousi, A.A., et al.: J. Cardiovasc Pharmacol., 5, 792 (1983)
  • • Maskin, C.S., et al.: Circulation, 67, 1065 (1983)
  • • Sinoway, L.S., et al.: J. Am. Coll. Cardiol., 2, 327 (1983)
  • • Baim, D.S., et al.: N. Engl. J. Med., 309, 748 (1983)
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PATENTS

PATENTS

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INTERNET

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