Entacapone
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Basic Info
| Common Name | Entacapone(F04758) |
| 2D Structure | |
| Description | Entacapone is a selective, reversible catechol-O-methyl transferase (COMT) inhibitor for the treatment of Parkinson's disease. It is a member of the class of nitrocatechols. When administered concomittantly with levodopa and a decarboxylase inhibitor (e.g., carbidopa), increased and more sustained plasma levodopa concentrations are reached as compared to the administration of levodopa and a decarboxylase inhibitor. |
| FRCD ID | F04758 |
| CAS Number | 130929-57-6 |
| PubChem CID | 5281081 |
| Formula | C14H15N3O5 |
| IUPAC Name | (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide |
| InChI Key | JRURYQJSLYLRLN-BJMVGYQFSA-N |
| InChI | InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+ |
| Canonical SMILES | CCN(CC)C(=O)C(=CC1=CC(=C(C(=C1)O)O)[N+](=O)[O-])C#N |
| Isomeric SMILES | CCN(CC)C(=O)/C(=C/C1=CC(=C(C(=C1)O)O)[N+](=O)[O-])/C#N |
| Wikipedia | Entacapone |
| Synonyms |
Entacapona [INN-Spanish]
ENTACAPONE
130929-57-6
Comtan
Comtess
Entacaponum
Entacapona
OR-611
Entacaponum [INN-Latin]
Entacom
|
| Classifies |
Predicted: Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Cinnamic acids and derivatives |
| Subclass | Hydroxycinnamic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Hydroxycinnamic acids and derivatives |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Hydroxycinnamic acid or derivatives - Nitrophenol - Nitrobenzene - Nitroaromatic compound - Catechol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Tertiary carboxylic acid amide - Carboxamide group - C-nitro compound - Organic nitro compound - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Carboxylic acid derivative - Carbonitrile - Nitrile - Organic oxoazanium - Organic 1,3-dipolar compound - Organic nitrogen compound - Organic zwitterion - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organopnictogen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. These are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 305.29 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Complexity | 500 |
| Monoisotopic Mass | 305.101 |
| Exact Mass | 305.101 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 22 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Tolcapone in Parkinson's disease: liver toxicity and clinical efficacy. | Expert Opin Drug Saf | 2005 Jan | 15709899 |
Targets
- General Function:
- O-methyltransferase activity
- Specific Function:
- Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
- Gene Name:
- COMT
- Uniprot ID:
- P21964
- Molecular Weight:
- 30036.77 Da
- Mechanism of Action:
- The mechanism of action of entacapone is believed to be through its ability to inhibit COMT and alter the plasma pharmacokinetics of levodopa. When entacapone is given in conjunction with levodopa and an aromatic amino acid decarboxylase inhibitor, such as carbidopa, plasma levels of levodopa are greater and more sustained than after administration of levodopa and an aromatic amino acid decarboxylase inhibitor alone. It is believed that at a given frequency of levodopa administration, these more sustained plasma levels of levodopa result in more constant dopaminergic stimulation in the brain, leading to greater effects on the signs and symptoms of Parkinson's disease.
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]