Explore a selection of our essential drug information below, or:
Overview
- Description
- A drug used to treat severe and persistent fever and pain.
- Description
- A drug used to treat severe and persistent fever and pain.
- DrugBank ID
- DB04817
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 3
- Phase 2
- 8
- Phase 3
- 11
- Phase 4
- 20
- Mechanism of Action
- Prostaglandin G/H synthase 1Inhibitor
- Prostaglandin G/H synthase 1
Identification
- Summary
Metamizole is an antipyretic and analgesic drug used to relieve severe and persistent fever and pain.
- Generic Name
- Metamizole
- DrugBank Accession Number
- DB04817
- Background
Metamizole (dipyrone) is a pyrazolone derivative that belongs to the group of nonacid nonopioids. It is considered a potent analgesic and antipyretic with favourable gastrointestinal tolerability.2 Metamizole was formerly marketed in the US as Dimethone tablets and injection, Protemp oral liquid, and other drug products, and was withdrawn due to its association with potentially fatal agranulocytosis. Approvals of the NDA's for metamizole drug products were withdrawn on June 27, 1977 (see the Federal Register of June 17, 1977, 42 FR 30893).9 In 1963, metamizole was withdrawn from the Canadian market and banned in the UK, France, Sweden, Norway and Australia.1 Metamizole is still used in certain countries in Europe, Asia and South America.1
- Type
- Small Molecule
- Groups
- Approved, Investigational, Withdrawn
- Structure
- Weight
- Average: 311.36
Monoisotopic: 311.093977213 - Chemical Formula
- C13H17N3O4S
- Synonyms
- Dipyrone
- Metamizol
Pharmacology
- Indication
Metamizole is banned in several countries, where it was previously used as a powerful analgesic and fever reducer. In countries where it is still available, metamizole is indicated for acute severe pain after injuries or surgeries, colic, tumor pain, and acute or severe pain symptoms, as well as high fever if other treatments are unsuccessful.1
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with evidence-based and structured datasets.See howBuild, train, & validate predictive machine-learning models with structured datasets.See how- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Severe pain •••••••••••• Symptomatic treatment of Severe fever •••••••••••• - 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.Learn moreAvoid life-threatening adverse drug events with our Clinical APILearn more- Pharmacodynamics
Metamizole is a strong analgesic and antipyretic with spasmolytic properties. It has weak anti-inflammatory or antithrombotic properties and does not follow the same mechanism of action as conventional non-steroidal anti-inflammatory drugs (NSAIDs).1 Metamizole can lead to agranulocytosis, a life-threatening side effect where a patient’s neutrophil count falls below 500 cells per microliter.1 It has been shown that metamizole-induced agranulocytosis is caused by the development of drug-dependent anti-neutrophil antibodies requiring covalent binding of neutrophils to metamizole and its metabolites.2
- Mechanism of action
The mechanism of action of metamizole is not fully understood. Its active metabolites, 4-methyl-amino-antipyrine (MAA) and 4-amino-antipyrine (AA), inhibit prostaglandin E2 (PGE2)-induced hyperalgesia.7 It has been suggested that the anti-hyperalgesic effect of MAA is mediated by guanosine 3',5'-cyclic monophosphate (cGMP) activation and ATP-sensitive potassium channel opening, while the effects of AA are associated with the activation of cannabinoid receptor type 1 (CB1).7 Metamizole is classified in some sources as a weak non-steroidal anti-inflammatory drug (NSAID);2 however, evidence suggests that its analgesic effects do not depend on its anti-inflammatory properties.7 Although the inhibition of cyclooxygenase (COX) 2 may play a role in the central nervous system effects of metamizole,7 reports suggest that metamizole inhibits COX-3 with a higher affinity compared to COX-1 or COX-2.6,8
Target Actions Organism AProstaglandin G/H synthase 1 inhibitorHumans - Absorption
Metamizole is hydrolyzed to 4-methyl-amino-antipyrine (MAA) in gastric juice and is mostly absorbed in this form. MAA bioavailability differs based on the administration route. In patients given metamizole tablets, the bioavailability of MAA is 85%, in patients given drops, 89%, in patients given suppositories, 54%, and in patients given an intramuscular injection, 87%.3 There is a linear relationship between metamizole oral dose and MAA Cmax. After oral doses ranging between 0.75 and 3 g, the tmax is reached at 1.4-2.0 hours.3
- Volume of distribution
Metamizole is quickly metabolized into 4-methyl-amino-antipyrine (MAA), its active metabolite. MAA has a volume of distribution of 1.15 L/kg.3
- Protein binding
The protein binding of metamizole and its metabolites is low, with an average of 60% for the metabolites 4-methyl-amino-antipyrine, 4-formyl-amino-antipyrine, 4-amino-antipyrine and 4-acetyl-amino-antipyrine.3,4
- Metabolism
Metamizole undergoes rapid hydrolysis to the active moiety 4-methyl-amino-antipyrine (MAA). MAA is then metabolized to 4-formyl-amino-antipyrine (FAA) via c-oxidation and 4-amino-antipyrine (AA) via N-demethylation. The N-demethylation of MAA is mainly mediated by CYP3A4, although CYP2B6, CYP2C8 and CYP2C9 may also be involved.2 FAA is an end metabolite, while AA is acetylated by N-acetyl-transferase to form 4-acetyl-amino-antipyrine (AAA).3 The unchanged drug may be present in plasma following the intravenous administration of metamizole; however, following oral administration, it cannot be detected in plasma or urine.3
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- Route of elimination
After intravenous or oral administration, 90% of metamizole is recovered in urine, while 10% is recovered in feces.3 Approximately 60% of four metamizole metabolites (4-methyl-amino-antipyrine, 4-formyl-amino-antipyrine, 4-amino-antipyrine and 4-acetyl-amino-antipyrine) are excreted through urine.3
- Half-life
In vitro, the half-life of metamizole is 16 minutes. The half-life of 4-methyl-amino-antipyrine (MAA), its active metabolite, ranges from 2.6 to 3.5 hours.3
- Clearance
The clearance of 4-methyl-amino-antipyrine (MAA), the active metabolite of metamizole, ranges from 110 mL/min to 180 mL/min after oral administration.3
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including:blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!See the dataImprove decision support & research outcomes with our structured adverse effects data.See a data sample- Toxicity
A metamizole overdose (7.5 g) may lead to gastrointestinal toxicity. If less than an hour has passed since metamizole ingestion, gastrointestinal decontamination and supportive measures are suggested as overdose treatment.5 Metamizole can also cause myelotoxicity, leading to drug-induced agranulocytosis.2,6
- 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 Metamizole may decrease the excretion rate of Abacavir which could result in a higher serum level. Acebutolol Metamizole may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of nephrotoxicity can be increased when Metamizole is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Metamizole is combined with Acemetacin. Acetaminophen Metamizole may decrease the excretion rate of Acetaminophen which could result in a higher serum level. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.Access nowAccess drug product information from over 10 global regions.Access now- Product Ingredients
Ingredient UNII CAS InChI Key Metamizole magnesium MS15642725 6150-97-6 NHMUJYOBLYTIKO-UHFFFAOYSA-L Metamizole sodium VSU62Z74ON 68-89-3 DJGAAPFSPWAYTJ-UHFFFAOYSA-M Metamizole sodium monohydrate 6429L0L52Y 5907-38-0 UNZIDPIPYUMVPA-UHFFFAOYSA-M - International/Other Brands
- Algocalmin /Algozone /Analgin /Dimethone /Dipirona /Neo-Melubrina /Novalgin /Optalgin /Protemp /Pyralgin
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ANALSIK Metamizole sodium(500 mg) +Diazepam(2 mg) Tablet, film coated Oral Sanbe Farma 2019-08-20 2024-06-02 Indonesia 
ANTIALGINA® Metamizole sodium(300 mg) +Caffeine(30 mg) +Isometheptene mucate(30 mg) Tablet, film coated Oral TECNOQUIMICAS S.A. 2007-04-24 Not applicable Colombia 
ANTIALGINA® Metamizole sodium(300 mg) +Caffeine(30 mg) +Isometheptene(50 mg) Solution Oral TECNOFAR TQ S.A.S 2007-03-06 2015-02-27 Colombia BUSCAPINA® COMPOSITUM AMPOLLAS Metamizole sodium(2.5 g) +Butylscopolamine bromide(0.02 g) Solution Intramuscular; Intravenous BOEHRINGER INGELHEIM ESPAŃA S.A. 2006-11-10 2020-06-01 Colombia CAFETRIN ® Metamizole(300 mg) +Caffeine(30 mg) +Isometheptene mucate(30 mg) Tablet, coated Oral LABORATORIOS RICH MONDS S.A.S 2018-05-11 Not applicable Colombia
Categories
- ATC Codes
- N02BB72 — Metamizole sodium, combinations with psycholepticsN02BB02 — Metamizole sodiumN02BB52 — Metamizole sodium, combinations excl. psycholeptics
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Aminopyrine
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Antipyretics
- Cytochrome P-450 CYP2B6 Inducers
- Cytochrome P-450 CYP2B6 Inducers (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Nephrotoxic agents
- Nervous System
- Peripheral Nervous System Agents
- Pyrazoles
- Pyrazolones
- Sensory System Agents
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 934T64RMNJ
- CAS number
- 50567-35-6
- InChI Key
- LVWZTYCIRDMTEY-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H17N3O4S/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,18,19,20)
- IUPAC Name
- [(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)(methyl)amino]methanesulfonic acid
- SMILES
- CN(CS(O)(=O)=O)C1=C(C)N(C)N(C1=O)C1=CC=CC=C1
References
- General References
- Cascorbi I: The Uncertainties of Metamizole Use. Clin Pharmacol Ther. 2021 Jun;109(6):1373-1375. doi: 10.1002/cpt.2258. [Article]
- Lutz M: Metamizole (Dipyrone) and the Liver: A Review of the Literature. J Clin Pharmacol. 2019 Nov;59(11):1433-1442. doi: 10.1002/jcph.1512. Epub 2019 Aug 21. [Article]
- Levy M, Zylber-Katz E, Rosenkranz B: Clinical pharmacokinetics of dipyrone and its metabolites. Clin Pharmacokinet. 1995 Mar;28(3):216-34. doi: 10.2165/00003088-199528030-00004. [Article]
- Zylber-Katz E, Granit L, Levy M: Plasma protein binding of dipyrone metabolites in man. Eur J Clin Pharmacol. 1985;29(1):67-71. doi: 10.1007/BF00547371. [Article]
- Bentur Y, Cohen O: Dipyrone overdose. J Toxicol Clin Toxicol. 2004;42(3):261-5. doi: 10.1081/clt-120037425. [Article]
- Jasiecka A, Maslanka T, Jaroszewski JJ: Pharmacological characteristics of metamizole. Pol J Vet Sci. 2014;17(1):207-14. doi: 10.2478/pjvs-2014-0030. [Article]
- dos Santos GG, Dias EV, Teixeira JM, Athie MC, Bonet IJ, Tambeli CH, Parada CA: The analgesic effect of dipyrone in peripheral tissue involves two different mechanisms: neuronal K(ATP) channel opening and CB(1) receptor activation. Eur J Pharmacol. 2014 Oct 15;741:124-31. doi: 10.1016/j.ejphar.2014.07.019. Epub 2014 Jul 21. [Article]
- Chandrasekharan NV, Dai H, Roos KL, Evanson NK, Tomsik J, Elton TS, Simmons DL: COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13926-31. Epub 2002 Sep 19. [Article]
- FDA Federal Register: List of Drug Products That Have Been Withdrawn or Removed From the Market for Reasons of Safety or Effectiveness [Link]
- External Links
- KEGG Drug
- D08188
- PubChem Compound
- 522325
- PubChem Substance
- 46509035
- ChemSpider
- 3000
- BindingDB
- 235671
- RxNav
- 3523
- ChEBI
- 62088
- ChEMBL
- CHEMBL461522
- ZINC
- ZINC000001782155
- Therapeutic Targets Database
- DNC000568
- PharmGKB
- PA166128206
- Wikipedia
- Metamizole
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 Completed Not Available Anesthesia Morbidity/Obesity, Morbid/Opioids Use/Pharmacological Action (PA)/Postoperative pain 1 somestatus stop reason just information to hide Not Available Completed Not Available Anesthetics Adverse Reaction/Anxiety/Craniotomy/Postoperative pain 1 somestatus stop reason just information to hide Not Available Completed Not Available Postoperative pain 1 somestatus stop reason just information to hide Not Available Completed Basic Science Platelet Aggregation 1 somestatus stop reason just information to hide Not Available Completed Diagnostic Lumbar Disc Disease 1 somestatus stop reason just information to hide Unlock 75,000+ rows when you subscribe
Explore data packages curated & structured to speed up your pharmaceutical research
View Sample Data
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Zhejiang Haisen Pharmaceutical Co. Ltd.
- Dosage Forms
Form Route Strength Injection, solution Intramuscular; Intravenous 2.5 g/5ml Injection, solution Parenteral 1000 mg Syrup Oral 50 mg/mL Syrup Oral 250 mg/5ml Tablet Oral Solution Oral Solution Intramuscular 1.000 g Tablet Oral 500.00 mg Solution Parenteral 1.0000 g Solution / drops Oral 15 ml Tablet Oral 500 mg/1 Suppository Rectal 1000 MG Solution Parenteral 20.000 mg Solution Parenteral Suppository Rectal Solution Intramuscular; Intravenous Solution Intravenous Syrup Oral 3 g Tablet Oral 5 g Injection, solution Intramuscular; Intravenous Solution Intramuscular; Intravenous Solution Parenteral 2.5 g Injection Parenteral 1 g Solution Intramuscular 1 g Tablet, coated Oral 500 mg Solution Parenteral 2000 mg Injection Intramuscular; Intravenous 2 g Solution Intramuscular; Intravenous 2 g Solution Parenteral 2 g Solution Intramuscular; Intravenous 1 g Solution Intramuscular; Intravenous; Subcutaneous 2.5 g Injection Intramuscular; Intravenous 2500 mg Tablet Oral 0.5 g Solution Parenteral 2.50 g Solution Intramuscular 1.0 g Tablet Oral Injection Parenteral Capsule, coated Oral Tablet, coated Oral Tablet Oral 5.00 g Injection, solution Intramuscular; Intravenous 1000 mg/2ml Syrup Oral Tablet Oral 10 mg Injection Intravenous Solution Oral 0.5 g Solution Intramuscular 200.000 mg Solution Intramuscular 2.5 g Solution Intravenous; Parenteral 2.5 g Solution Parenteral 1 g Solution Parenteral 2.000 g Injection, solution Parenteral 1.0 g Tablet, film coated Oral 1000 mg Solution Oral 500 MG/ML Injection, solution Parenteral 500 mg/ml Tablet, film coated Oral 500 MG Injection, solution Parenteral 7.5 mg Injection Injection 500 mg Solution / drops Oral Tablet, film coated Oral 2 mg Tablet Oral 5 mg Tablet Oral 25.000 g Tablet Oral 5.000 g Solution Intramuscular Solution Oral 300 mg Solution Oral 96 mg Tablet, film coated Oral 50 mg Tablet Tablet, film coated Oral 500 mg Tablet; tablet, film coated Oral Injection Intramuscular; Intravenous 1 gr/2ml Injection Intramuscular; Intravenous 2.5 gr/5ml Solution / drops; suspension / drops 250 mg/ml Ointment Injection, solution Intramuscular; Intravenous 1 gr/2ml Injection 500 mg/ml Suppository Rectal 300 mg Injection, solution Intramuscular; Intravenous 500 mg/ml Injection, solution Parenteral 2.5 G Syrup Oral 250 mg/ml Injection, solution Intramuscular; Intravenous 1 G/2ML Solution / drops Oral 500 MG/ML Suppository Rectal 1 G Tablet Oral 500 MG Solution Intramuscular; Intravenous 2.5 g Solution Oral 500 MG Injection, solution Parenteral 1 G/2ML Injection Intramuscular; Intravenous Injection Intramuscular; Intravenous 1 g/2ml Solution Parenteral 50.000 mg Solution Oral 5.0 g Tablet Oral 500.000 mg Tablet, coated Oral 850 mg Solution Parenteral 0.020 g Injection 1 g Injection 2 g Solution Parenteral 0.02 g Solution Oral 500.000 mg Solution Oral 500.00000 mg Tablet, film coated Oral Tablet, sugar coated Oral Solution Parenteral 500 mg Solution Parenteral 1.000 g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.53 mg/mL ALOGPS logP -0.4 ALOGPS logP -0.82 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) -1.4 Chemaxon pKa (Strongest Basic) -0.54 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 81.16 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 80.04 m3·mol-1 Chemaxon Polarizability 31.41 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7868 Blood Brain Barrier + 0.8896 Caco-2 permeable - 0.5869 P-glycoprotein substrate Non-substrate 0.8148 P-glycoprotein inhibitor I Non-inhibitor 0.828 P-glycoprotein inhibitor II Non-inhibitor 0.8107 Renal organic cation transporter Non-inhibitor 0.921 CYP450 2C9 substrate Non-substrate 0.8588 CYP450 2D6 substrate Non-substrate 0.7959 CYP450 3A4 substrate Substrate 0.6035 CYP450 1A2 substrate Non-inhibitor 0.7153 CYP450 2C9 inhibitor Non-inhibitor 0.7064 CYP450 2D6 inhibitor Non-inhibitor 0.8562 CYP450 2C19 inhibitor Non-inhibitor 0.6768 CYP450 3A4 inhibitor Non-inhibitor 0.9297 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8506 Ames test AMES toxic 0.7763 Carcinogenicity Carcinogens 0.8197 Biodegradation Ready biodegradable 0.7192 Rat acute toxicity 2.6224 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8411 hERG inhibition (predictor II) Non-inhibitor 0.6724
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-1009000000-431728299201b0fb868d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0019000000-b8d7405e368fa22b6915 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01q9-9004000000-79f614717a7a99cafbbd Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0390000000-eb45759e184b23c05705 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001l-9220000000-2c0ed857809190b300d8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000f-3930000000-f710a44ca4cfcfa52e2a 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]- 172.57713 predictedDeepCCS 1.0 (2019) [M+H]+ 174.93513 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.58745 predictedDeepCCS 1.0 (2019)
Targets
insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
- Specific Function
- heme binding
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- 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
- Saussele T, Burk O, Blievernicht JK, Klein K, Nussler A, Nussler N, Hengstler JG, Eichelbaum M, Schwab M, Zanger UM: Selective induction of human hepatic cytochromes P450 2B6 and 3A4 by metamizole. Clin Pharmacol Ther. 2007 Sep;82(3):265-74. doi: 10.1038/sj.clpt.6100138. Epub 2007 Mar 7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- 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
- Saussele T, Burk O, Blievernicht JK, Klein K, Nussler A, Nussler N, Hengstler JG, Eichelbaum M, Schwab M, Zanger UM: Selective induction of human hepatic cytochromes P450 2B6 and 3A4 by metamizole. Clin Pharmacol Ther. 2007 Sep;82(3):265-74. doi: 10.1038/sj.clpt.6100138. Epub 2007 Mar 7. [Article]
Drug created at September 11, 2007 20:09 / Updated at March 26, 2025 14:34