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Identification
- Summary
Prasugrel is a P2Y12 platelet inhibitor used to reduce risk of thrombotic cardiovascular events in unstable angina or non-ST-elevation myocardial infarction (NSTEMI), and in patients with STEMI when managed with either primary or delayed PCI.
- Brand Names
- Effient, Efient
- Generic Name
- Prasugrel
- DrugBank Accession Number
- DB06209
- Background
Prasugrel, a thienopyridine derivative, is a platelet activation and aggregation inhibitor structurally and pharmacologically related to clopidogrel and ticlopidine. Similar to clopidogrel, prasugrel is a prodrug that requires enzymatic transformation in the liver to its active metabolite, R-138727. R-138727 irreversibly binds to P2Y12 type ADP receptors on platelets thus preventing activation of the GPIIb/IIIa receptor complex. As a result, inhibition of ADP-mediated platelet activation and aggregation occurs. Prasugrel was developed by Daiichi Sankyo Co. and is currently marketed in the United States and Canada in cooperation with Eli Lilly and Company for acute coronary syndromes planned for percutaneous coronary intervention (PCI). FDA approved in 2009.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Prasugrel (DB06209)
- Weight
- Average: 373.441
Monoisotopic: 373.114792406 - Chemical Formula
- C20H20FNO3S
- Synonyms
- Prasugrel
- External IDs
- CS-747
- LY-640315
Pharmacology
- Indication
Indicated in combination with acetylsalicylic acid (ASA) to prevent atherothrombotic events in patients with acute coronary syndrome (ACS) who are to be managed with percutaneous coronary intervention (PCI). May be used in patients with unstable angina (UA), non-ST elevation myocardial infarction (NSTEMI), ST-elevation myocardial infarction (STEMI) who are to be managed with PCI. Prasugrel is not recommended in patients 75 years of age or greater, those that weigh<60kg, and patients with a history of stroke or transient ischemic attack due to increased risk of fatal and intracranial bleeding.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Cardiovascular event •••••••••••• Prevention of Cardiovascular event •••••••••••• Prevention of Cardiovascular event •••••••••••• - Contraindications & Blackbox Warnings
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Prasugrel is a thienopyridine ADP receptor inhibitors which inhibits platelet aggregation by irreversibly binding to P2Y12 receptors.
- Mechanism of action
Prasugrel is an thienopyridine and a prodrug which inhibits ADP receptors by irreversibly acting on the P2Y12 receptor on platelets. The active metabolite of prasugrel prevents binding of adenosine diphosphate (ADP) to its platelet receptor, impairing the ADP-mediated activation of the glycoprotein GPIIb/IIIa complex. Prasugrel is proposed to have a similar mechanism of action to clopidogrel.
Target Actions Organism AP2Y purinoceptor 12 antagonistHumans - Absorption
79% or greater of the dose is absorbed after oral administration. Absorption and metabolism occur rapidly and peak plasma concentrations (Cmax) are reached approximately 30 minutes following oral administration. Administration with a high fat, high calorie meal did not affect the AUC of the active metabolite in healthy individuals, but the Cmax was decreased by ~49% and the Tmax was increased to 0.5 to 1.5 hours. Prasugrel may be administered with or without food.
- Volume of distribution
44-68L
- Protein binding
Approximately 98% of the active metabolite was bound to human serum albumin in a 4% buffered solution. The major inactive metabolites are also highly bound to human plasma proteins.
- Metabolism
Prasugrel is not detected in plasma following oral administration. It is rapidly hydrolyzed in the intestine to thiolactone by human carboxylesterase (hCE) 2. This intermediate is further metabolized to its active metabolite, R-138727, in a single step by cytochrome P450 enzymes in the liver (primarily CYP3A4 and CYP2B6 and to a lesser extent by CYP2C9 and CYP2C19). The active metabolite is further metabolized by S-methylation or cysteine conjugation to two inactive metabolites.
Unlike clopidogrel, transformation of prasugrel to its active metabolite does not appear to be affected by cytochrome P450 polymorphisms.
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- Route of elimination
Approximately 68% of the orally administered dose is excreted in urine and 27% in the feces, as inactive metabolites. The active metabolite is not expected to be removed by dialysis.
- Half-life
The active metabolite has an elimination half-life of about 7.4 hours (range 2-15 hours).
- Clearance
Apparent clearance = 112 - 166 L/hr
- Adverse Effects
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LD50 (rat) 1,000 - 2,000 mg/kg; LD50 (rabbit) > 1,000 mg/kg
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Prasugrel which could result in a higher serum level. Abametapir The serum concentration of Prasugrel can be increased when it is combined with Abametapir. Abatacept The metabolism of Prasugrel can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Prasugrel. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Prasugrel is combined with Abrocitinib. - Food Interactions
- Avoid herbs and supplements with anticoagulant/antiplatelet activity. Examples include garlic, ginger, bilberry, danshen, piracetam, and ginkgo biloba.
- 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.- Product Ingredients
Ingredient UNII CAS InChI Key Prasugrel besylate 7KYD4NE018 952340-40-8 UFXQKLQPHZRPDV-UHFFFAOYSA-N Prasugrel hydrochloride G89JQ59I13 389574-19-0 JALHGCPDPSNJNY-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Prasita (Daiichi Sankyo Co.)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Effient Tablet, coated 5 mg/1 Oral Cosette Pharmaceuticals, Inc. 2022-09-01 Not applicable US 
Effient Tablet, coated 5 mg/1 Oral Daiichi Sankyo, Inc. 2009-07-10 2023-12-31 US Effient Tablet, film coated 5 mg/1 Oral Eli Lilly and Company 2009-07-10 2022-02-28 US Effient Tablet, film coated 10 mg/1 Oral Physicians Total Care, Inc. 2011-03-15 Not applicable US Effient Tablet 10 mg Oral Eli Lilly & Co. Ltd. 2010-05-17 2020-02-10 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Jamp Prasugrel Tablet 10 mg Oral Jamp Pharma Corporation 2021-05-14 Not applicable Canada Prasugrel Tablet, film coated 10 mg/1 Oral Accord Healthcare Inc. 2019-01-16 Not applicable US Prasugrel Tablet, film coated 5 mg/1 Oral Aurobindo Pharma Limited 2017-10-16 Not applicable US Prasugrel Tablet, film coated 10 mg/1 Oral A-S Medication Solutions 2018-06-22 Not applicable US Prasugrel Tablet, film coated 10 mg/1 Oral Mylan Pharmaceuticals Inc. 2017-08-15 Not applicable US
Categories
- ATC Codes
- B01AC22 — Prasugrel
- Drug Categories
- Anticoagulants
- Antiplatelet agents
- Blood and Blood Forming Organs
- 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
- Decreased Platelet Aggregation
- Drugs that are Mainly Renally Excreted
- Hematologic Agents
- P2Y12 Platelet Inhibitor
- Piperazines
- Platelet Aggregation Inhibitors Excl. Heparin
- Purinergic P2Y Receptor Antagonists
- Sulfur Compounds
- Thiophenes
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as thienopyridines. These are heterocyclic compounds containing a thiophene ring fused to a pyridine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Thienopyridines
- Sub Class
- Not Available
- Direct Parent
- Thienopyridines
- Alternative Parents
- 2,3,5-trisubstituted thiophenes / Aralkylamines / Fluorobenzenes / Pyridines and derivatives / Aryl fluorides / Alpha-amino ketones / Heteroaromatic compounds / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives show 6 more
- Substituents
- 2,3,5-trisubstituted thiophene / Alpha-aminoketone / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tertiary amino compound, acetate ester, cyclopropanes, ketone, monofluorobenzenes, thienopyridine (CHEBI:87723)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 34K66TBT99
- CAS number
- 150322-43-3
- InChI Key
- DTGLZDAWLRGWQN-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H20FNO3S/c1-12(23)25-18-10-14-11-22(9-8-17(14)26-18)19(20(24)13-6-7-13)15-4-2-3-5-16(15)21/h2-5,10,13,19H,6-9,11H2,1H3
- IUPAC Name
- 5-[2-cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-4H,5H,6H,7H-thieno[3,2-c]pyridin-2-yl acetate
- SMILES
- CC(=O)OC1=CC2=C(CCN(C2)C(C(=O)C2CC2)C2=CC=CC=C2F)S1
References
- Synthesis Reference
Teruhiko Inoue, Kazuyoshi Nakamura, Masahiko Hagihara, Hiroyuki Miyata, Yukinori Wada, Naoyuki Yokota, "Process for Producing High-Purity Prasugrel and Acid Addition Salt Thereof." U.S. Patent US20090203729, issued August 13, 2009.
US20090203729- General References
- Dovlatova NL, Jakubowski JA, Sugidachi A, Heptinstall S: The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. J Thromb Haemost. 2008 Jul;6(7):1153-9. doi: 10.1111/j.1538-7836.2008.03020.x. Epub 2008 Jul 1. [Article]
- Tagarakis GI: Ticagrelor and prasugrel: two novel, most-promising antiplatelet agents. Recent Pat Cardiovasc Drug Discov. 2010 Nov;5(3):208-11. [Article]
- Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [Article]
- Jeong YH, Tantry US, Gurbel PA: Importance of potent P2Y(12) receptor blockade in acute myocardial infarction: focus on prasugrel. Expert Opin Pharmacother. 2012 Aug;13(12):1771-96. doi: 10.1517/14656566.2012.704909. Epub 2012 Jul 12. [Article]
- External Links
- Human Metabolome Database
- HMDB0015625
- KEGG Drug
- D05597
- PubChem Compound
- 6918456
- PubChem Substance
- 99443238
- ChemSpider
- 5293653
- 613391
- ChEBI
- 87723
- ChEMBL
- CHEMBL1201772
- PharmGKB
- PA154410481
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Prasugrel
- FDA label
- Download (1000 KB)
- MSDS
- Download (134 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 Active Not Recruiting Treatment Chronic Coronary Syndromes / Non-STEMI Acute Coronary Syndrome 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Treatment Migraine / Patent Foramen Ovale (PFO) 1 somestatus stop reason just information to hide Not Available Completed Not Available Acute Coronary Syndrome (ACS) 1 somestatus stop reason just information to hide Not Available Completed Not Available Acute Myocardial Infarction (AMI) 1 somestatus stop reason just information to hide Not Available Completed Not Available Antiplatelets 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 10 mg Tablet, coated Oral 10 mg/1 Tablet, coated Oral 5 mg/1 Tablet, film coated Oral 10 mg/1 Tablet, film coated Oral 4.12 Mg Tablet, film coated Oral 5.49 Mg Tablet, coated Oral 10 mg Tablet, coated Oral 5 mg Tablet Oral 5 mg Tablet, film coated Oral 5 mg/1 Tablet, film coated Oral 10 MG Tablet, film coated Oral 5 MG Tablet, film coated Oral - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6693115 No 2004-02-17 2021-07-03 US CA2077695 No 2002-08-20 2012-09-08 Canada US8404703 Yes 2013-03-26 2023-07-02 US US8569325 Yes 2013-10-29 2023-07-02 US US5288726 Yes 1994-02-22 2017-10-14 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 3.536 MSDS - Predicted Properties
Property Value Source Water Solubility 0.00237 mg/mL ALOGPS logP 3.67 ALOGPS logP 4.31 Chemaxon logS -5.2 ALOGPS pKa (Strongest Acidic) 15.34 Chemaxon pKa (Strongest Basic) 5.12 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 46.61 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 96.81 m3·mol-1 Chemaxon Polarizability 37.7 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9352 Caco-2 permeable + 0.5325 P-glycoprotein substrate Substrate 0.767 P-glycoprotein inhibitor I Inhibitor 0.6555 P-glycoprotein inhibitor II Non-inhibitor 0.7365 Renal organic cation transporter Inhibitor 0.5312 CYP450 2C9 substrate Non-substrate 0.7508 CYP450 2D6 substrate Non-substrate 0.7371 CYP450 3A4 substrate Substrate 0.5402 CYP450 1A2 substrate Non-inhibitor 0.5288 CYP450 2C9 inhibitor Non-inhibitor 0.5706 CYP450 2D6 inhibitor Non-inhibitor 0.7051 CYP450 2C19 inhibitor Inhibitor 0.7083 CYP450 3A4 inhibitor Non-inhibitor 0.7432 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8719 Ames test Non AMES toxic 0.6616 Carcinogenicity Non-carcinogens 0.9521 Biodegradation Not ready biodegradable 0.9961 Rat acute toxicity 2.4834 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7927 hERG inhibition (predictor II) Non-inhibitor 0.6438
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 198.0351359 predictedDarkChem Lite v0.1.0 [M-H]- 170.83142 predictedDeepCCS 1.0 (2019) [M+H]+ 198.1982359 predictedDarkChem Lite v0.1.0 [M+H]+ 173.18944 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.0999359 predictedDarkChem Lite v0.1.0 [M+Na]+ 180.20473 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Receptor for ADP and ATP coupled to G-proteins that inhibit the adenylyl cyclase second messenger system. Not activated by UDP and UTP. Required for normal platelet aggregation and blood coagulation
- Specific Function
- G protein-coupled adenosine receptor activity
- Gene Name
- P2RY12
- Uniprot ID
- Q9H244
- Uniprot Name
- P2Y purinoceptor 12
- Molecular Weight
- 39438.355 Da
References
- Dovlatova NL, Jakubowski JA, Sugidachi A, Heptinstall S: The reversible P2Y antagonist cangrelor influences the ability of the active metabolites of clopidogrel and prasugrel to produce irreversible inhibition of platelet function. J Thromb Haemost. 2008 Jul;6(7):1153-9. doi: 10.1111/j.1538-7836.2008.03020.x. Epub 2008 Jul 1. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (PubMed:9169443). Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine (PubMed:9169443). Hydrolyzes aspirin, substrates with large alcohol group and small acyl group and endogenous lipids such as triacylglycerol (PubMed:28677105). Converts monoacylglycerides to free fatty acids and glycerol. Hydrolyzes of 2-arachidonoylglycerol and prostaglandins (PubMed:21049984)
- Specific Function
- carboxylesterase activity
- Gene Name
- CES2
- Uniprot ID
- O00748
- Uniprot Name
- Cocaine esterase
- Molecular Weight
- 61806.41 Da
References
- Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [Article]
- 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
- Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [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
- 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
- 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
- Angiolillo DJ: The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs. 2012 Nov 12;72(16):2087-116. doi: 10.2165/11640880-000000000-00000. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
Drug created at March 19, 2008 16:17 / Updated at August 02, 2024 07:30