Opicapone
- CAS No.
- 923287-50-7
- Chemical Name:
- Opicapone
- Synonyms
- CS-1268;Opicapone;BIA 9-1067;Opicapone-d6;100G,500G,1KG;Opicapone (BIA 9-1067);Inhibitor,inhibit,COMT,Opicapone;5-[3-(2,5-Dichloro-4,6-dimethyl-1-oxido-3-pyridinyl)-1,2,4-oxadiazol-5-yl]-3-nitro-1,2-benzenediol;2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine 1-oxide;1,2-Benzenediol, 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxido-3-pyridinyl)-1,2,4-oxadiazol-5-yl]-3-nitro-
- CBNumber:
- CB82628219
- Molecular Formula:
- C15H10Cl2N4O6
- Molecular Weight:
- 413.17
- MDL Number:
- MFCD19443745
- MOL File:
- 923287-50-7.mol
- MSDS File:
- SDS
| Boiling point | 701.1±70.0 °C(Predicted) |
|---|---|
| Density | 1.80±0.1 g/cm3(Predicted) |
| solubility | DMSO : 100 mg/mL (242.03 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble) |
| form | Powder |
| pka | 4.67±0.38(Predicted) |
| FDA UNII | Y5929UIJ5N |
| ATC code | N04BX04 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H315-H319-H335 |
| Precautionary statements | P261-P305+P351+P338 |
Opicapone price
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| TRC | O669450 | Opicapone | 923287-50-7 | 10mg | $1540 | 2021-12-16 | Buy |
| ChemScene | CS-3109 | Opicapone 99.64% | 923287-50-7 | 5mg | $210 | 2021-12-16 | Buy |
| ChemScene | CS-3109 | Opicapone 99.64% | 923287-50-7 | 10mg | $360 | 2021-12-16 | Buy |
| American Custom Chemicals Corporation | API0014050 | OPICAPONE 95.00% | 923287-50-7 | 5MG | $531.3 | 2021-12-16 | Buy |
| ChemScene | CS-3109 | Opicapone 99.64% | 923287-50-7 | 50mg | $1190 | 2021-12-16 | Buy |
Opicapone Chemical Properties,Uses,Production
Description
Opicapone is a selective and reversible catechol O-methyltransferase (COMT) inhibitor that was developed by the Portuguese pharmaceutical firm Bial and sold to Neurocrine Biosciences. The drug was approved by the USFDA as adjunctive treatment to levodopa (L-Dopa)/ dopa-decarboxylase inhibitor (DDCI) therapy in adults with Parkinson’s disease (PD) and end-of-dose motor fluctuations that cannot be stabilized on those combinations. In 14- to 15- week double-blind multinational trials and in one-year openlabel extension studies in this patient population, opicapone was an effective and generally well-tolerated adjunctive therapy to L-Dopa plus a DDCI and other PD therapies. During the double-blind phase, adjunctive opicapone (50 mg once daily) provided significantly greater improvements in motor fluctuations than placebo, and no new unexpected safety concerns were identified after treatment with opicapone over a 1.4 year period. Furthermore, no serious cases of hepatotoxicity were reported in clinical trials, which represents a significant safety profile improvement over existing standard-of-care COMT inhibitors enticapone, tolcapone, and nebicapone.
Uses
Opicapone, is used for the synthesis of novel nitrocatechol-substituted heterocycles, having the ability to inhibit catechol-O-methyltransferase (COMT), used for the treatment of Parkinson`s diseases.
Definition
ChEBI: Opicapone is a ring assembly and an oxadiazole.
Synthesis
Although several synthetic approaches to opicapone or
opicapone subunits have been disclosed, a synthetic approach
described by Bial was exemplified on a scale capable of
producing 14.4 kg of the active pharmaceutical ingredient
(API). Commercial 2,4-pentanedione (114) was condensed
with cyanoacetamide in warm methanol to give rise to
cyanopyridone 115 in excellent yield. Chlorination
with sulfuryl chloride in chilled acetonitrile followed by
treatment with phosphorus oxychloride resulted in dichloropyridine
117. Next, treatment with hydroxylamine in aqueous
methanol converted nitrile 117 to the corresponding Nhydroxyamidine
118, and this was followed by exposure to
pyridine and acid chloride 119. These operations facilitated a cyclization
reaction, which furnished the key oxadiazole 120 in good yield.
Subjection of 120 to urea hydrogen peroxide (UHP) in
dichloromethane to establish the pyridine N-oxide functionality
within opicapone preceded methyl ether cleavage through the
use of aluminum trichloride in warm pyridine to furnish
opicapone (X) in 53% yield for the two-step sequence.
The preparation of acid chloride 119 involved the nitration
of commercially available benzoic acid 121 followed by thionyl
chloride-mediated conversion of the resulting nitrobenzoic acid
122 to acid chloride 119. Interestingly, although
the nitration step is low-yielding and involves nitric acid, the
authors report an operationally simple isolation method that
has been exemplified on multiple kilogram scale. No yield was
reported for the conversion of 122 to 119.
storage
Store at -20°C
Opicapone Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| career henan chemical co | +86-0371-86658258 | sales@coreychem.com | China | 29914 | 58 |
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| WinWin Chemical CO., Limited | +86-0086-577-64498589 +86-15355981851 | sales@win-winchemical.com | China | 13854 | 58 |
| AFINE CHEMICALS LIMITED | 0571-85134551 | info@afinechem.com | CHINA | 15377 | 58 |
| Nanjing Doge Biomedical Technology Co., Ltd | +86-25-58227606 +86-15305155328 | sales@dogechemical.com | China | 4128 | 58 |
| ZHEJIANG JIUZHOU CHEM CO., LTD | +86-0576225566889 +86-13454675544 | admin@jiuzhou-chem.com；jamie@jiuzhou-chem.com；alice@jiuzhou-chem.com | China | 20000 | 58 |
| Zhengzhou Anbu Chem Co.,Ltd | +86-0371-88006763; +8615988602810 | sales@anbuchem.com | China | 3000 | 58 |
| Changzhou AniKare Pharmatech Co., Ltd. | +86-0519-8359-8696 +8618018249389 | sales@anikare.com | China | 8382 | 58 |
