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MedKoo Cat#: 319794 | Name: Opicapone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Opicapone, also known as BIA 9-1067, is a novel potent and selective catechol-O-methyltransferase inhibitor (COMT inhibitor) under clinical evaluation as an adjunct to L-Dopa therapy of Parkinson's disease. Opicapone, a novel third generation COMT inhibitor, when compared to entacapone, provides a superior response upon the bioavailability of levodopa associated to more pronounced, long-lasting, and sustained COMT inhibition.

Chemical Structure

Opicapone
Opicapone
CAS#923287-50-7

Theoretical Analysis

MedKoo Cat#: 319794

Name: Opicapone

CAS#: 923287-50-7

Chemical Formula: C15H10Cl2N4O6

Exact Mass: 411.9977

Molecular Weight: 413.17

Elemental Analysis: C, 43.61; H, 2.44; Cl, 17.16; N, 13.56; O, 23.23

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
No Data
Synonym
BIA 9-1067; BIA 91067; BIA-91067; BIA91067; Opicapone
IUPAC/Chemical Name
2,5-dichloro-3-(5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl)-4,6-dimethylpyridine 1-oxide
InChi Key
ASOADIZOVZTJSR-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H10Cl2N4O6/c1-5-10(13(17)20(24)6(2)11(5)16)14-18-15(27-19-14)7-3-8(21(25)26)12(23)9(22)4-7/h3-4,22-23H,1-2H3
SMILES Code
OC1=CC(C2=NC(C3=C(Cl)[N+]([O-])=C(C)C(Cl)=C3C)=NO2)=CC([N+]([O-])=O)=C1O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Opicapone (BIA 9-1067) is a potent third-generation catechol-O-methyltransferase (COMT) inhibitor.
In vitro activity:
The purpose of this study is to systemically investigate the effects of opicapone on human UGTs activities, and also to assess the potential risk of drug-drug interactions (DDIs) associated with opicapone. The results indicated that opicapone is a broad-spectrum inhibitor of UGTs. Particularly, opicapone exhibited potent inhibition against UGT1A1, 1A7, 1A8, 1A9, and 1A10, with a range of inhibition constant Ki values of 1.31-10.58 µM. Reference: Toxicol Lett. 2022 Aug 15;367:3-8. https://pubmed.ncbi.nlm.nih.gov/35810997/
In vivo activity:
Opicapone inhibited rat peripheral COMT with ED50 values below 1.4 mg⋅kg(-1) up to 6 h post-administration. The effect was sustained over the first 8 h and by 24 h COMT had not returned to control values. A single administration of opicapone resulted in increased and sustained plasma levodopa levels with a concomitant reduction in 3-O-methyldopa from 2 h up to 24 h post-administration, while tolcapone produced significant effects only at 2 h post-administration. The effects of opicapone on brain catecholamines after levodopa administration were sustained up to 24 h post-administration. Reference: Br J Pharmacol. 2015 Apr;172(7):1739-52. https://pubmed.ncbi.nlm.nih.gov/25409768/
Solvent mg/mL mM
Solubility
DMF 30.0 72.61
DMSO 57.1 138.22
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 413.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Wang Z, Wang Z, Wang X, Lv X, Yin H, Fan X, Yan M, Jia Y, Jiang L, Xia Y, Li W, Liu Y. In vitro effects of opicapone on activity of human UDP-glucuronosyltransferases isoforms. Toxicol Lett. 2022 Aug 15;367:3-8. doi: 10.1016/j.toxlet.2022.07.003. Epub 2022 Jul 8. PMID: 35810997. 2. Wang J, Zheng B, Yang S, Zheng H, Wang J. Opicapone Protects Against Hyperhomocysteinemia-Induced Increase in Blood-Brain Barrier Permeability. Neurotox Res. 2021 Dec;39(6):2018-2028. doi: 10.1007/s12640-021-00429-8. Epub 2021 Oct 28. PMID: 34709593. 3. Bonifácio MJ, Torrão L, Loureiro AI, Palma PN, Wright LC, Soares-da-Silva P. Pharmacological profile of opicapone, a third-generation nitrocatechol catechol-O-methyl transferase inhibitor, in the rat. Br J Pharmacol. 2015 Apr;172(7):1739-52. doi: 10.1111/bph.13020. Epub 2015 Jan 20. PMID: 25409768; PMCID: PMC4376453.
In vitro protocol:
1. Wang Z, Wang Z, Wang X, Lv X, Yin H, Fan X, Yan M, Jia Y, Jiang L, Xia Y, Li W, Liu Y. In vitro effects of opicapone on activity of human UDP-glucuronosyltransferases isoforms. Toxicol Lett. 2022 Aug 15;367:3-8. doi: 10.1016/j.toxlet.2022.07.003. Epub 2022 Jul 8. PMID: 35810997.
In vivo protocol:
1. Wang J, Zheng B, Yang S, Zheng H, Wang J. Opicapone Protects Against Hyperhomocysteinemia-Induced Increase in Blood-Brain Barrier Permeability. Neurotox Res. 2021 Dec;39(6):2018-2028. doi: 10.1007/s12640-021-00429-8. Epub 2021 Oct 28. PMID: 34709593. 2. Bonifácio MJ, Torrão L, Loureiro AI, Palma PN, Wright LC, Soares-da-Silva P. Pharmacological profile of opicapone, a third-generation nitrocatechol catechol-O-methyl transferase inhibitor, in the rat. Br J Pharmacol. 2015 Apr;172(7):1739-52. doi: 10.1111/bph.13020. Epub 2015 Jan 20. PMID: 25409768; PMCID: PMC4376453.
1: Kwak N, Kang HY, Lee MJ, Lee H. Cost-Effectiveness Analysis of COMT- Inhibitors as Adjuvant Treatments to Levodopa in Patients with Advanced Parkinson's Disease. Clin Ther. 2024 Jul 31:S0149-2918(24)00191-7. doi: 10.1016/j.clinthera.2024.06.016. Epub ahead of print. PMID: 39089982. 2: Bacchin R, Liccari M, Catalan M, Antonutti L, Manganotti P, Malaguti MC, Giometto B. Disease Stage and Motor Fluctuation Duration Predict Drug Tolerability: A Real-Life, Prospective Italian Multicenter Study on the Use of Opicapone in Parkinson's Disease. Drugs Real World Outcomes. 2024 Jul 2. doi: 10.1007/s40801-024-00442-1. Epub ahead of print. PMID: 38954191. 3: Männistö PT, Keränen T, Reinikainen KJ, Hanttu A, Pollesello P. The Catechol O-Methyltransferase Inhibitor Entacapone in the Treatment of Parkinson's Disease: Personal Reflections on a First-in-Class Drug Development Programme 40 Years On. Neurol Ther. 2024 Aug;13(4):1039-1054. doi: 10.1007/s40120-024-00629-2. Epub 2024 May 29. PMID: 38809484; PMCID: PMC11263458. 4: Hauser RA, Videnovic A, Soares-da-Silva P, Liang GS, Olson K, Jen E, Rocha JF, Klepitskaya O. OFF-times before, during, and after nighttime sleep periods in Parkinson's disease patients with motor fluctuations and the effects of opicapone: A post hoc analysis of diary data from BIPARK-1 and -2. Parkinsonism Relat Disord. 2024 Jun;123:106971. doi: 10.1016/j.parkreldis.2024.106971. Epub 2024 Apr 9. PMID: 38631081. 5: Lee JY, Ma HI, Ferreira JJ, Rocha JF, Sung YH, Song IU, Ahn TB, Kwon DY, Cheon SM, Kim JM, Lee CS, Lee PH, Park JH, Lee JH, Park MY, Kim SJ, Baik JS, Choi SM, Shin HW, Lee HW, Kang SY, Jeon B. Opicapone to Treat Early Wearing-off in Parkinson's Disease Patients: The Korean ADOPTION Trial. Mov Disord Clin Pract. 2024 Jun;11(6):655-665. doi: 10.1002/mdc3.14030. Epub 2024 Apr 9. PMID: 38594812; PMCID: PMC11145137. 6: Wu W, Lu X, Zhang L, Hong D. Effectiveness and safety of different catechol- o-methyl transferase inhibitors for patients with parkinson's disease: Systematic review and network meta-analysis. Clin Neurol Neurosurg. 2024 Apr;239:108189. doi: 10.1016/j.clineuro.2024.108189. Epub 2024 Feb 23. PMID: 38437773. 7: Ikenaka K, Kajiyama Y, Aguirre C, Choong CJ, Taniguchi S, Doi J, Wang N, Ajiki T, Ogawa K, Kakuda K, Kimura Y, Mochizuki H. Decreased hepatic enzymes reflect the decreased vitamin B6 levels in Parkinson's disease patients. Pharmacol Res Perspect. 2024 Feb;12(1):e1174. doi: 10.1002/prp2.1174. PMID: 38287715; PMCID: PMC10825373. 8: Rebouta J, Dória L, Coelho A, Fonseca MM, Castilla-Fernández G, Pires NM, Vieira-Coelho MA, Loureiro AI. HR/MS-based lipidome analysis of rat brain modulated by tolcapone. J Pharm Biomed Anal. 2024 Apr 15;241:115971. doi: 10.1016/j.jpba.2024.115971. Epub 2024 Jan 10. PMID: 38266454. 9: Li J, Zelmat Y, Storck W, Laforgue EJ, Yrondi A, Balcerac A, Sommet A, Montastruc F. Drug-induced depressive symptoms: An update through the WHO pharmacovigilance database. J Affect Disord. 2024 Apr 1;350:452-467. doi: 10.1016/j.jad.2024.01.119. Epub 2024 Jan 18. PMID: 38244800. 10: Bologna M, Guerra A, Colella D, Birreci D, Costa D, Cannavacciuolo A, Angelini L, Paparella G, Antonini A, Berardelli A, Fabbrini G. Correction to: Objective assessment of the effects of opicapone in Parkinson's disease through kinematic analysis. Neurol Sci. 2024 May;45(5):2405. doi: 10.1007/s10072-023-07294-7. Erratum for: Neurol Sci. 2024 May;45(5):2035-2046. doi: 10.1007/s10072-023-07233-6. PMID: 38153679; PMCID: PMC11021286. 11: Bologna M, Guerra A, Colella D, Birreci D, Costa D, Cannavacciuolo A, Angelini L, Paparella G, Antonini A, Berardelli A, Fabbrini G. Objective assessment of the effects of opicapone in Parkinson's disease through kinematic analysis. Neurol Sci. 2024 May;45(5):2035-2046. doi: 10.1007/s10072-023-07233-6. Epub 2023 Dec 13. Erratum in: Neurol Sci. 2024 May;45(5):2405. doi: 10.1007/s10072-023-07294-7. PMID: 38091213; PMCID: PMC11021230. 12: Koch J. Management of OFF condition in Parkinson disease. Ment Health Clin. 2023 Dec 1;13(6):289-297. doi: 10.9740/mhc.2023.12.289. PMID: 38058599; PMCID: PMC10696172. 13: Opicapone for Parkinson's disease. Aust Prescr. 2023 Aug;46(2):42. doi: 10.18773/austprescr.2023.012. PMID: 38053568; PMCID: PMC10664095. 14: Metta V, Ibrahim H, Muralidharan N, Rodriguez K, Masagnay T, Mohan J, Lacsina A, Ahmed A, Benamer HTS, Chung-Faye G, Mrudula R, Falup-Pecurariu C, Rodriguez-Blazquez C, Borgohain R, Goyal V, Bhattacharya K, Chaudhuri KR. A 12-month prospective real-life study of opicapone efficacy and tolerability in Emirati and non-White subjects with Parkinson's disease based in United Arab Emirates. J Neural Transm (Vienna). 2024 Jan;131(1):25-30. doi: 10.1007/s00702-023-02700-y. Epub 2023 Oct 5. PMID: 37798410; PMCID: PMC10769978. 15: Antonini A, Barone P, Calabresi P, Lopiano L, Morgante F, Pontieri FE, Sensi M, Stocchi F. The role of opicapone in the management of Parkinson's disease: an Italian consensus through a combined Nominal Group Technique and Delphi approach. Eur Rev Med Pharmacol Sci. 2023 Sep;27(18):8850-8859. doi: 10.26355/eurrev_202309_33805. PMID: 37782207. 16: Serbin M, Marras C, Mansfield C, Leach C, Yonan C, Sheehan M, Donnelly A, Klepitskaya O. Patients' Preferences for Adjunctive Parkinson's Disease Treatments: A Discrete-Choice Experiment. Patient Prefer Adherence. 2023 Sep 13;17:2263-2277. doi: 10.2147/PPA.S420051. PMID: 37724313; PMCID: PMC10505378. 17: Harrison-Jones G, Marston XL, Morgante F, Chaudhuri KR, Castilla-Fernández G, Di Foggia V. Opicapone versus entacapone: Head-to-head retrospective data- based comparison of healthcare resource utilization in people with Parkinson's disease new to catechol-O-methyltransferase (COMT) inhibitor treatment. Eur J Neurol. 2023 Oct;30(10):3132-3141. doi: 10.1111/ene.15990. Epub 2023 Aug 19. PMID: 37489574. 18: Takebe K, Suzuki M, Kuwada-Kusunose T, Shirai S, Fukuzawa K, Takamiya T, Uzawa N, Iijima H. Structural and Computational Analyses of the Unique Interactions of Opicapone in the Binding Pocket of Catechol O-Methyltransferase: A Crystallographic Study and Fragment Molecular Orbital Analyses. J Chem Inf Model. 2023 Jul 24;63(14):4468-4476. doi: 10.1021/acs.jcim.3c00331. Epub 2023 Jul 12. PMID: 37436881. 19: Leta V, van Wamelen DJ, Aureli F, Metta V, Trivedi D, Cortelli P, Rodriguez- Blazquez C, Rizos A, Ray Chaudhuri K. The real-life effect of catechol-O- methyltransferase inhibition on non-motor symptoms in levodopa-treated Parkinson's disease: opicapone versus entacapone. J Neural Transm (Vienna). 2023 Jul;130(7):925-930. doi: 10.1007/s00702-023-02603-y. Epub 2023 Apr 10. PMID: 37036498; PMCID: PMC10293442. 20: Regensburger M, Ip CW, Kohl Z, Schrader C, Urban PP, Kassubek J, Jost WH. Clinical benefit of MAO-B and COMT inhibition in Parkinson's disease: practical considerations. J Neural Transm (Vienna). 2023 Jun;130(6):847-861. doi: 10.1007/s00702-023-02623-8. Epub 2023 Mar 24. PMID: 36964457; PMCID: PMC10199833.

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