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Identification
- Summary
Brivaracetam is an anticonvulsant used for the treatment of partial-onset seizures that functions by binding to synaptic vesicle glycoprotein 2A (SV2A) in the brain.
- Brand Names
- Briviact
- Generic Name
- Brivaracetam
- DrugBank Accession Number
- DB05541
- Background
Brivaracetam is a racetam derivative of levetiracetam used in the treatment of partial-onset seizures. Brivaracetam binds SV2A with 20 times higher affinity than levetiracetam 2. It is available under the brand name Briviact made by UCB. Briviact received FDA approval on February 19, 2016 7.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Brivaracetam (DB05541)
- Weight
- Average: 212.2887
Monoisotopic: 212.152477894 - Chemical Formula
- C11H20N2O2
- Synonyms
- Brivaracetam
- External IDs
- UCB 34714
- UCB-34714
Pharmacology
- Indication
Used as adjunctive therapy for partial-onset seizures in patients 16 years of age or older.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Partial-onset seizures •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Brivaracetam binds SV2A with high affinity 2. SV2A is known to play a role in epileptogenesis through modulation of synaptic GABA release 3. It is thought that brivaracetam exerts its anti-epileptogenic effects through its binding to SV2A. Brivaracetam is also known to inhibit Na+ channels which may also contribute to its anti-epileptogenic action 4.
- Mechanism of action
The precise mechanism of brivaracetam's anti-epileptogenic activity is unknown.
Target Actions Organism ASynaptic vesicle glycoprotein 2A unknownHumans ASodium channel protein inhibitorHumans - Absorption
Nearly 100% oral bioavailability 1.
- Volume of distribution
0.5L/kg Label.
- Protein binding
<20% bound to plasma proteins Label.
- Metabolism
Primarily metabolized by hydrolysis of the acetamide moeity to form a carboxylic acid metabolite 6. Another metabolite is created via oxidation of the propyl side chain by CYP2C8 as well as CYP3A4, CYP2C19, and CYP2B6. Some conjugation with glucuronic acid and taurine account for a small amount of metabolism.
- Route of elimination
>95% excreted in urine with <10% of the parent compound unchanged. <1% excreted in feces Label.
- Half-life
7-8h 1.
- Clearance
CL/F of 0.7-1.07 mL/min kg 5. Clearance is primarily metabolic with less than 10% of the parent drug excreted unchanged.
- Adverse Effects
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No carcinogenesis or fertility impairment found. Overdose is associated with somnolence and dizziness Label.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C19 CYP2C19*2A Not Available 681G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*2B Not Available 681G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*3 Not Available 636G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*4 Not Available 1A>G Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*5 Not Available 1297C>T Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*6 Not Available 395G>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*7 Not Available 19294T>A Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*22 Not Available 557G>C / 991A>G Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*24 Not Available 99C>T / 991A>G … show all Effect Inferred Poor drug metabolizer. Details Cytochrome P450 2C19 CYP2C19*35 Not Available 12662A>G Effect Inferred Poor drug metabolizer. Details
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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Brivaracetam is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Brivaracetam which could result in a higher serum level. Abametapir The serum concentration of Brivaracetam can be increased when it is combined with Abametapir. Abatacept The metabolism of Brivaracetam can be increased when combined with Abatacept. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Brivaracetam. - Food Interactions
- Avoid alcohol. Taking Brivaracetam with alcohol may increase alcohol's effects on attention, memory, and psychomotor functioning.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Rikelta (UCB)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Briviact Tablet, film coated 10 mg Oral Ucb Pharma S.A. 2016-09-08 Not applicable EU 
Briviact Tablet, film coated 75 mg Oral Ucb Pharma S.A. 2016-09-08 Not applicable EU Briviact Tablet, film coated 50 mg Oral Ucb Pharma S.A. 2016-09-08 Not applicable EU Briviact Tablet, film coated 100 mg Oral Ucb Pharma S.A. 2016-09-08 Not applicable EU Briviact Tablet, film coated 25 mg Oral Ucb Pharma S.A. 2016-09-08 Not applicable EU - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BRIVAXON Brivaracetam (100 mg) + Brivaracetam (25 mg) + Brivaracetam (50 mg) Tablet, coated Oral TECNOFARMA COLOMBIA S.A.S 2020-07-31 2025-08-19 Colombia 
BRIVAXON Brivaracetam (100 mg) + Brivaracetam (25 mg) + Brivaracetam (50 mg) Tablet, coated Oral TECNOFARMA COLOMBIA S.A.S 2020-07-31 2025-08-19 Colombia BRIVAXON Brivaracetam (100 mg) + Brivaracetam (25 mg) + Brivaracetam (50 mg) Tablet, coated Oral TECNOFARMA COLOMBIA S.A.S 2020-07-31 2025-08-19 Colombia
Categories
- ATC Codes
- N03AX23 — Brivaracetam
- Drug Categories
- Anticonvulsants
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Epoxide Hydrolase Inhibitors
- Miscellaneous Anticonvulsants
- Nervous System
- Pyrrolidines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acids and derivatives
- Alternative Parents
- Pyrrolidine-2-ones / N-alkylpyrrolidines / Fatty amides / Tertiary carboxylic acid amides / Primary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides show 2 more
- Substituents
- 2-pyrrolidone / Aliphatic heteromonocyclic compound / Alpha-amino acid or derivatives / Azacycle / Carbonyl group / Carboxamide group / Fatty acyl / Fatty amide / Hydrocarbon derivative / Lactam show 12 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- U863JGG2IA
- CAS number
- 357336-20-0
- InChI Key
- MSYKRHVOOPPJKU-BDAKNGLRSA-N
- InChI
- InChI=1S/C11H20N2O2/c1-3-5-8-6-10(14)13(7-8)9(4-2)11(12)15/h8-9H,3-7H2,1-2H3,(H2,12,15)/t8-,9+/m1/s1
- IUPAC Name
- (2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
- SMILES
- CCC[C@H]1CN([C@@H](CC)C(N)=O)C(=O)C1
References
- General References
- Rolan P, Sargentini-Maier ML, Pigeolet E, Stockis A: The pharmacokinetics, CNS pharmacodynamics and adverse event profile of brivaracetam after multiple increasing oral doses in healthy men. Br J Clin Pharmacol. 2008 Jul;66(1):71-5. doi: 10.1111/j.1365-2125.2008.03158.x. Epub 2008 Mar 13. [Article]
- Gillard M, Fuks B, Leclercq K, Matagne A: Binding characteristics of brivaracetam, a selective, high affinity SV2A ligand in rat, mouse and human brain: relationship to anti-convulsant properties. Eur J Pharmacol. 2011 Aug 16;664(1-3):36-44. doi: 10.1016/j.ejphar.2011.04.064. Epub 2011 May 8. [Article]
- Tokudome K, Okumura T, Shimizu S, Mashimo T, Takizawa A, Serikawa T, Terada R, Ishihara S, Kunisawa N, Sasa M, Ohno Y: Synaptic vesicle glycoprotein 2A (SV2A) regulates kindling epileptogenesis via GABAergic neurotransmission. Sci Rep. 2016 Jun 6;6:27420. doi: 10.1038/srep27420. [Article]
- Zona C, Pieri M, Carunchio I, Curcio L, Klitgaard H, Margineanu DG: Brivaracetam (ucb 34714) inhibits Na(+) current in rat cortical neurons in culture. Epilepsy Res. 2010 Jan;88(1):46-54. doi: 10.1016/j.eplepsyres.2009.09.024. Epub 2009 Nov 13. [Article]
- Sargentini-Maier ML, Rolan P, Connell J, Tytgat D, Jacobs T, Pigeolet E, Riethuisen JM, Stockis A: The pharmacokinetics, CNS pharmacodynamics and adverse event profile of brivaracetam after single increasing oral doses in healthy males. Br J Clin Pharmacol. 2007 Jun;63(6):680-8. Epub 2007 Jan 12. [Article]
- Sargentini-Maier ML, Espie P, Coquette A, Stockis A: Pharmacokinetics and metabolism of 14C-brivaracetam, a novel SV2A ligand, in healthy subjects. Drug Metab Dispos. 2008 Jan;36(1):36-45. Epub 2007 Oct 1. [Article]
- Briviact FDA Approval [Link]
- External Links
- KEGG Drug
- D08879
- PubChem Compound
- 9837243
- PubChem Substance
- 347827736
- ChemSpider
- 8012964
- BindingDB
- 50422531
- 1739745
- ChEBI
- 133013
- ChEMBL
- CHEMBL607400
- ZINC
- ZINC000003979899
- PharmGKB
- PA166153491
- PDBe Ligand
- VLX
- Wikipedia
- Brivaracetam
- PDB Entries
- 8k77 / 8yf1
- FDA label
- Download (1.46 MB)
- MSDS
- Download (170 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Available Not Available Epilepsy 1 somestatus stop reason just information to hide Not Available Completed Not Available Breastfeeding 1 somestatus stop reason just information to hide Not Available Completed Not Available Epilepsy 1 somestatus stop reason just information to hide 3 Active Not Recruiting Treatment Epilepsy 1 somestatus stop reason just information to hide 3 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Epilepsy 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Oral Injection, suspension Intravenous 50 mg/5mL Solution Intravenous 50.000 mg Solution Oral 1.0000 g Solution Oral 10 mg/1mL Tablet Oral 10.000 mg Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, film coated Oral 75 mg/1 Solution Intravenous 50 mg Tablet, coated Oral 100 mg Tablet, film coated Oral Injection, solution Intravenous 10 mg/ml Solution Oral 1000 mg Solution Intravenous 10 mg / mL Solution Oral 10 mg / mL Tablet Oral 10 mg Tablet Oral 100 mg Tablet Oral 25 mg Tablet Oral 50 mg Tablet Oral 75 mg Solution Oral 10 MG/ML Tablet, film coated Oral 10 MG Tablet, film coated Oral 100 MG Tablet, film coated Oral 25 MG Tablet, film coated Oral 50 MG Tablet, film coated Oral 75 MG - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6911461 No 2005-06-28 2021-02-21 US 
US6784197 No 2004-08-31 2021-02-21 US US8492416 No 2013-07-23 2021-02-21 US US10729653 No 2020-08-04 2030-04-09 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 46.8 mg/mL ALOGPS logP 0.86 ALOGPS logP 0.66 Chemaxon logS -0.66 ALOGPS pKa (Strongest Acidic) 16.29 Chemaxon pKa (Strongest Basic) -1.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 63.4 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 57.75 m3·mol-1 Chemaxon Polarizability 23.77 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9904 Blood Brain Barrier + 0.9812 Caco-2 permeable - 0.5912 P-glycoprotein substrate Substrate 0.5307 P-glycoprotein inhibitor I Inhibitor 0.5318 P-glycoprotein inhibitor II Non-inhibitor 0.7691 Renal organic cation transporter Non-inhibitor 0.766 CYP450 2C9 substrate Non-substrate 0.9026 CYP450 2D6 substrate Non-substrate 0.8221 CYP450 3A4 substrate Substrate 0.5486 CYP450 1A2 substrate Non-inhibitor 0.9103 CYP450 2C9 inhibitor Non-inhibitor 0.7784 CYP450 2D6 inhibitor Non-inhibitor 0.9115 CYP450 2C19 inhibitor Non-inhibitor 0.8035 CYP450 3A4 inhibitor Non-inhibitor 0.9584 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.953 Ames test Non AMES toxic 0.8836 Carcinogenicity Non-carcinogens 0.8866 Biodegradation Not ready biodegradable 0.9479 Rat acute toxicity 2.2355 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9434 hERG inhibition (predictor II) Non-inhibitor 0.8922
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00ko-9600000000-ff6fdfd2af8595903280 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0390000000-062c25bf40f9ae7ba867 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0190000000-0cc5906d47db48d609ca Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0059-4910000000-52f5ea00ad4e31e0d36a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01tc-7910000000-38a52df6df4321e70da0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9400000000-a8112355b2b49354cbb3 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9200000000-414d654ad393bbd2266f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 152.30127 predictedDeepCCS 1.0 (2019) [M+H]+ 154.65927 predictedDeepCCS 1.0 (2019) [M+Na]+ 160.75243 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Unknown
- General Function
- Plays a role in the control of regulated secretion in neural and endocrine cells, enhancing selectively low-frequency neurotransmission. Positively regulates vesicle fusion by maintaining the readily releasable pool of secretory vesicles (By similarity)
- Specific Function
- Protein kinase binding
- Gene Name
- SV2A
- Uniprot ID
- Q7L0J3
- Uniprot Name
- Synaptic vesicle glycoprotein 2A
- Molecular Weight
- 82694.665 Da
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient (PubMed:14672992). Plays a key role in brain, probably by regulating the moment when neurotransmitters are released in neurons. Involved in sensory perception of mechanical pain: activation in somatosensory neurons induces pain without neurogenic inflammation and produces hypersensitivity to mechanical, but not thermal stimuli
- Specific Function
- Voltage-gated monoatomic ion channel activity involved in regulation of presynaptic membrane potential
Components:
References
- Zona C, Pieri M, Carunchio I, Curcio L, Klitgaard H, Margineanu DG: Brivaracetam (ucb 34714) inhibits Na(+) current in rat cortical neurons in culture. Epilepsy Res. 2010 Jan;88(1):46-54. doi: 10.1016/j.eplepsyres.2009.09.024. Epub 2009 Nov 13. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Sargentini-Maier ML, Espie P, Coquette A, Stockis A: Pharmacokinetics and metabolism of 14C-brivaracetam, a novel SV2A ligand, in healthy subjects. Drug Metab Dispos. 2008 Jan;36(1):36-45. Epub 2007 Oct 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
References
- Sargentini-Maier ML, Espie P, Coquette A, Stockis A: Pharmacokinetics and metabolism of 14C-brivaracetam, a novel SV2A ligand, in healthy subjects. Drug Metab Dispos. 2008 Jan;36(1):36-45. Epub 2007 Oct 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
- Specific Function
- Anandamide 11,12 epoxidase activity
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Sargentini-Maier ML, Espie P, Coquette A, Stockis A: Pharmacokinetics and metabolism of 14C-brivaracetam, a novel SV2A ligand, in healthy subjects. Drug Metab Dispos. 2008 Jan;36(1):36-45. Epub 2007 Oct 1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Brivaracetam FDA Label [File]
Drug created at November 18, 2007 18:25 / Updated at December 05, 2023 12:31