Opicapone

Identification

Summary

Opicapone is a catechol-O-methyltransferase inhibitor used as an adjunct treatment for Parkinson's Disease in adults currently receiving levodopa and a dopa decarboxylase inhibitor.

Brand Names
Ongentys
Generic Name
Opicapone
DrugBank Accession Number
DB11632
Background

Opicapone is a potent, reversible, and peripherally-acting third-generation inhibitor of catechol-o-methyltransferase (COMT), an enzyme involved in the breakdown of various catecholamines including dopamine.4,5 Many patients with Parkinson’s disease treated with levodopa plus a dopa decarboxylase (DDC) inhibitor (eg carbidopa) experience motor complications over time, which calls for the management of these symptoms through the use of a dopamine agonist, a monoamine oxidase B inhibitor (selegiline, rasagiline), a catechol-O-methyl transferase (COMT) inhibitor, or amantadine, or using a modified-release formulation of levodopa.6

Opicapone is used for adjunct therapy to levodopa and carbidopa in adult patients with Parkinson's disease and end-of-dose motor fluctuations. Opicapone was approved for use by the European Commission in June 2016 7 and the FDA in April 2020.13 It is marketed under the brand name Ongentys as once-daily oral capsules. Exhibiting a long duration of action that exceeds 24 hours, opicapone can be administered once-daily 6 and demonstrates the lowest risk for cytotoxicity compared to other catechol-O-methyltransferase inhibitors.5

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 413.17
Monoisotopic: 411.9977395
Chemical Formula
C15H10Cl2N4O6
Synonyms
  • Opicapona
  • Opicapone
External IDs
  • BIA 9-1067
  • BIA-9-1067
  • BIA-91067

Pharmacology

Indication

Opicapone is indicated as adjunctive therapy in adults with Parkinson’s disease and end-of-dose motor fluctuations or “off” episodes whose symptoms cannot be stabilized on the combination therapy of levodopa and DOPA decarboxylase inhibitor (e.g., carbidopa).10,13

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Adjunct therapy in management ofParkinson's disease•••••••••••••••••••• •• •••• ••••• •••••••••••• •••• •••••• •• •••••••••••••••••
Adjunct therapy in management ofParkinson's disease (pd)•••••••••••••••••••• •••••••• •• ••••••••• ••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Opicapone is a COMT inhibitor that serves to improve the availability and duration of action of levodopa (L-Dopa), a standard pharmacological treatment for Parkinson's Disease. Opicapone works by blocking the peripheral degradation of L-Dopa mediated by COMT.1 Opicapone has a long duration of action: following administration of a 50 mg dose, COMT inhibition lasted for more than 24 hours.10 In clinical trials, opicapone as adjunct therapy to L-Dopa plus a dopa decarboxylase inhibitor significantly improved motor fluctuations than placebo, and the effects were comparable to entacapone.1

Mechanism of action

Levodopa (L-Dopa) is the gold standard for managing motor and some non-motor symptoms associated with Parkinson's Disease; however, only a small fraction of administered L-Dopa actually crosses the blood-brain barrier to exert its therapeutic action and patients face the risk of developing end-of-dose motor fluctuations, which reflects the rapid peripheral metabolism of L-dopa by aromatic L-amino acid decarboxylase and catechol-O-methyltransferase (COMT).1

Opicapone is a peripheral, selective, and reversible catechol-O-methyltransferase (COMT) inhibitor. It displays a high binding affinity that is in sub-picomolar ranges, resulting in a slow complex dissociation rate constant and long duration of action in vivo.10 When opicapone is added to the treatment regimen that contains L-Dopa and DOPA decarboxylase inhibitor, opicapone helps to increase the plasma levels and enhance the therapeutic efficacy of L-Dopa.1

TargetActionsOrganism
ACatechol O-methyltransferase
inhibitor
Humans
Absorption

Orally administered opicapone demonstrates a linear, dose-dependent absorption profile.5 Opicapone is rapidly absorbed,2 with an oral bioavailability of about 20%.10 Following administration of a single 50 mg dose of opicapone, the median Tmax was two hours, ranging from one to four hours. A moderate fat or moderate calorie meal was shown to decrease the Cmax by 62%, the mean overall plasma exposure (AUC) by 31%, and the Tmax by 4 hours.13

Volume of distribution

Following oral administration, the apparent Vd of opicapone at a dose of 50 mg was 29 L with an inter-subject variability of 36%.10 One study showed small systemic accumulation after multiple-dosing.2

Protein binding

Opicapone is >99% bound to plasma proteins, which is independent of the drug concentration.13

Metabolism

According to clinical and in vitro studies, sulphation is the primary metabolic pathway of opicapone, forming the inactive metabolite. Opicapone can also undergo glucuronidation, COMT-mediated methylation, reduction, and glutathione conjugation.10,13

As two major circulating metabolites, BIA 9-1103 (3-O-sulphated opicapone) accounts for 67.1% of the total radioactivity and BIA 9-1104 (4-O-methylated opicapone) accounts for 20.5% of the total radioactivity. Other metabolites are generally unquantifiable in plasma samples.8,10 Opicapone can undergo N-oxide reduction to form BIA 9-1079, which was shown to be an active metabolite in non-clinical studies;3 however, it is generally undetectable in humans.8 Other inactive metabolites include BIA 9-1100, BIA 9-1101, and BIA 9-1106.3

Hover over products below to view reaction partners

Route of elimination

Following administration of a single 100 mg dose of radiolabeled opicapone in healthy subjects, about 70% of the total dose was recovered in feces, where 22% of the recovered dose was excreted as an unchanged parent drug. About 20% of the total dose was recovered in exhaled air and about 5% was recovered in the urine, where less than 1% of the recovered dose was in an unchanged form.13 The primary detectable metabolite in the urine was the glucuronide metabolite.10

Half-life

The mean elimination half-life of opicapone is one to two hours.13 Despite the short half-life, the observed half-life of opicapone-induced COMT inhibition in human red blood cells was 61.6 hours with a standard deviation of 37.6 hours.3

Clearance

Following oral administration of 50 mg opicapone, the apparent total body clearance was 22 L/h, with an inter-subject variability of 45%.10

Adverse Effects
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Toxicity

There is no reported LD50 data of opicapone. As there is no known antidote for opicapone overdose, overdosage should be managed with symptomatic and supportive treatment. Removal of the drug through gastric lavage and/or inactivation by administering activated charcoal should be considered.10,13

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Abaloparatide is combined with Opicapone.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Opicapone.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Opicapone.
AliskirenThe risk or severity of adverse effects can be increased when Aliskiren is combined with Opicapone.
AmbrisentanOpicapone may increase the hypotensive activities of Ambrisentan.
Food Interactions
  • Take separate from meals. Take opicapone at least one hour before or after eating, as a moderate calorie meal decreases Cmax and overall plasma exposure to the drug, and delays Tmax.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
OngentysCapsule50 mgOralBial Portela Cª, s.a.2016-09-08Not applicableEU flag
OngentysCapsule50 mgOralBial Portela Cª, s.a.2016-09-08Not applicableEU flag
OngentysCapsule25 mgOralBial Portela Cª, s.a.2016-09-08Not applicableEU flag
OngentysCapsule25 mg/1OralNeurocrine Biosciences, Inc.2020-04-24Not applicableUS flag
OngentysCapsule50 mgOralBial Portela Cª, s.a.2016-09-08Not applicableEU flag

Categories

ATC Codes
N04BX04 — Opicapone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyloxadiazoles. These are polycyclic aromatic compounds containing a benzene ring linked to a 1,2,4-oxadiazole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxadiazoles
Direct Parent
Phenyloxadiazoles
Alternative Parents
Nitrophenols / Nitrobenzenes / Catechols / Nitroaromatic compounds / Polyhalopyridines / 1-hydroxy-2-unsubstituted benzenoids / Methylpyridines / 1-hydroxy-4-unsubstituted benzenoids / 2-halopyridines / Aryl chlorides
show 12 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2-halopyridine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / C-nitro compound / Catechol
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Y5929UIJ5N
CAS number
923287-50-7
InChI Key
ASOADIZOVZTJSR-UHFFFAOYSA-N
InChI
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
IUPAC Name
2,5-dichloro-3-[5-(3,4-dihydroxy-5-nitrophenyl)-1,2,4-oxadiazol-3-yl]-4,6-dimethylpyridin-1-ium-1-olate
SMILES
CC1=C(C2=NOC(=N2)C2=CC(=C(O)C(O)=C2)[N+]([O-])=O)C(Cl)=[N+]([O-])C(C)=C1Cl

References

General References
  1. Scott LJ: Opicapone: A Review in Parkinson's Disease. Drugs. 2016 Sep;76(13):1293-1300. doi: 10.1007/s40265-016-0623-y. [Article]
  2. Goncalves D, Alves G, Fortuna A, Soares-da-Silva P, Falcao A: Pharmacokinetics of opicapone, a third-generation COMT inhibitor, after single and multiple oral administration: A comparative study in the rat. Toxicol Appl Pharmacol. 2017 May 15;323:9-15. doi: 10.1016/j.taap.2017.03.013. Epub 2017 Mar 16. [Article]
  3. Almeida L, Rocha JF, Falcao A, Palma PN, Loureiro AI, Pinto R, Bonifacio MJ, Wright LC, Nunes T, Soares-da-Silva P: Pharmacokinetics, pharmacodynamics and tolerability of opicapone, a novel catechol-O-methyltransferase inhibitor, in healthy subjects: prediction of slow enzyme-inhibitor complex dissociation of a short-living and very long-acting inhibitor. Clin Pharmacokinet. 2013 Feb;52(2):139-51. doi: 10.1007/s40262-012-0024-7. [Article]
  4. Bonifacio MJ, Palma PN, Almeida L, Soares-da-Silva P: Catechol-O-methyltransferase and its inhibitors in Parkinson's disease. CNS Drug Rev. 2007 Fall;13(3):352-79. doi: 10.1111/j.1527-3458.2007.00020.x. [Article]
  5. Svetel M, Tomic A, Kresojevic N, Kostic V: Pharmacokinetic drug evaluation of opicapone for the treatment of Parkinson's disease. Expert Opin Drug Metab Toxicol. 2018 Mar;14(3):353-360. doi: 10.1080/17425255.2018.1430138. Epub 2018 Jan 24. [Article]
  6. Opicapone:once-daily adjunctive therapy for Parkinson’s disease [Link]
  7. Clinical pharmacology review of opicapone for the treatment of Parkinson's disease [Link]
  8. EMA assessment report [Link]
  9. Opicapone: a short lived and very long acting novel catechol-O-methyltransferase inhibitor following multiple dose administration in healthy subjects [Link]
  10. Summary of Product Characteristics: Ongentys (opicapone) oral capsules [Link]
  11. Pharmacological Profile of Opicapone, a Third Generation Nitrocatechol COMT Inhibitor, in the Rat [Link]
  12. Wikigenes [Link]
  13. FDA Approved Drug Products: ONGENTYS (opicapone) capsules, for oral use [Link]
ChemSpider
24667564
BindingDB
50019329
RxNav
2362167
ChEBI
134699
ChEMBL
CHEMBL1089318
ZINC
ZINC000034602275
PDBe Ligand
DNI
Wikipedia
Opicapone
PDB Entries
7xgi / 7xjb

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentParkinson's Disease (PD)2
4CompletedTreatmentParkinson's Disease (PD)1
4CompletedTreatmentParkinson's Disease With Wearing-off Motor Fluctuations1
4RecruitingTreatmentParkinson's Disease (PD)1
3Active Not RecruitingTreatmentParkinson's Disease (PD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral25 mg/1
CapsuleOral25 MG
CapsuleOral50 MG
CapsuleOral50 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9550759No2017-01-242026-07-26US flag
US9745290No2017-08-292027-10-10US flag
US9630955No2017-04-252032-12-12US flag
US10583130No2020-03-102030-03-31US flag
US8524746No2013-09-032029-07-14US flag
US8168793No2012-05-012029-04-02US flag
US10357468No2019-07-232035-05-27US flag
US10071085No2018-09-112030-03-31US flag
US8907099No2014-12-092027-05-12US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilityminimalhttp://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002790/WC500209538.pdf
Predicted Properties
PropertyValueSource
logP3.05Chemaxon
pKa (Strongest Acidic)6.12Chemaxon
pKa (Strongest Basic)-0.47Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area149.46 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity118.12 m3·mol-1Chemaxon
Polarizability37.42 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0059-0539000000-7474afd576b5551b7ce4
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-189.81471
predicted
DeepCCS 1.0 (2019)
[M+H]+191.95326
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.8658
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
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-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
Molecular Weight
30036.77 Da
References
  1. Scott LJ: Opicapone: A Review in Parkinson's Disease. Drugs. 2016 Sep;76(13):1293-1300. doi: 10.1007/s40265-016-0623-y. [Article]
  2. Tardy B, Lecompte T, Boelhen F, Tardy-Poncet B, Elalamy I, Morange P, Gruel Y, Wolf M, Francois D, Racadot E, Camarasa P, Blouch MT, Nguyen F, Doubine S, Dutrillaux F, Alhenc-Gelas M, Martin-Toutain I, Bauters A, Ffrench P, de Maistre E, Grunebaum L, Mouton C, Huisse MG, Gouault-Heilmann M, Lucke V: Predictive factors for thrombosis and major bleeding in an observational study in 181 patients with heparin-induced thrombocytopenia treated with lepirudin. Blood. 2006 Sep 1;108(5):1492-6. Epub 2006 May 11. [Article]
  3. EMA assessment report [Link]
  4. Opicapone: a short lived and very long acting novel catechol-O-methyltransferase inhibitor following multiple dose administration in healthy subjects [Link]
  5. Summary of Product Characteristics: Ongentys (opicapone) oral capsules [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
Curator comments
Data supporting this enzyme induction is limited to in vitro studies.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Summary of Product Characteristics: Ongentys (opicapone) oral capsules [Link]
  2. Opicapone EMA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Summary of Product Characteristics: Ongentys (opicapone) oral capsules [Link]
  2. Opicapone EMA Label [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
According to the EU prescribing information, opicapone reduces CYP2C9 activity through competitive or mixed type mode of inhibition.
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Summary of Product Characteristics: Ongentys (opicapone) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
In vitro, the reduction in enzyme activity was observed at the highest concentration of opicapone (10 mcg/mL).
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Summary of Product Characteristics: Ongentys (opicapone) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
In vitro, the reduction in enzyme activity was observed at the highest concentration of opicapone (10 mcg/mL).
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Summary of Product Characteristics: Ongentys (opicapone) oral capsules [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. FDA Approved Drug Products: ONGENTYS (opicapone) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. FDA Approved Drug Products: ONGENTYS (opicapone) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. FDA Approved Drug Products: ONGENTYS (opicapone) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name
SLCO2B1
Uniprot ID
O94956
Uniprot Name
Solute carrier organic anion transporter family member 2B1
Molecular Weight
76709.98 Da
References
  1. FDA Approved Drug Products: ONGENTYS (opicapone) capsules, for oral use [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Summary of Product Characteristics: Ongentys (opicapone) oral capsules [Link]

Drug created at October 17, 2016 21:26 / Updated at February 21, 2021 18:53