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Identification
- Summary
Chlorphenesin is a phenol ether used to treat painful muscular conditions.
- Generic Name
- Chlorphenesin
- DrugBank Accession Number
- DB00856
- Background
Not Available
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Chlorphenesin (DB00856)
- Weight
- Average: 202.635
Monoisotopic: 202.039671925 - Chemical Formula
- C9H11ClO3
- Synonyms
- 3-(4-chlorophenoxy)-1,2-propanediol
- 3-(p-chlorophenoxy)-1,2-propanediol
- 3-(p-chlorophenoxy)propane-1,2-diol
- Chlorphenesin
- Chlorphénésine
- Chlorphenesinum
- Clorfenesina
- glycerol α-p-chlorophenyl ether
- p-chlorophenyl-α-glyceryl ether
Pharmacology
- Indication
Used, along with rest and physical therapy, to treat injuries and other painful muscular conditions. Investigated for use in trigeminal neuralgia (tic douloureux), a neuropathic disorder characterized by severe facial pain. Was investigated as a modulator of histamine release.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used as adjunct for symptomatic treatment of Muscle spasm ••• ••• - Contraindications & Blackbox Warnings
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Chlorphenesin is a muscle relaxant. It blocks nerve impulses (or pain sensations) that are sent to the brain.
- Mechanism of action
The mechanism of action of chlorphenesin is not well defined, and its effects are measured mainly by subjective responses. It is known that chlorphenesin acts in the central nervous system (CNS) rather than directly on skeletal muscle.
- Absorption
Rapid and complete.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic. 85% of a dose excreted within 24 hours as the glucuronide metabolite.
- Route of elimination
Not Available
- Half-life
2.3-5 hours
- Clearance
Not Available
- 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!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Symptoms of a chlorphenesin overdose include drowsiness and nausea.
- 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 softwareBaclofen Baclofen may increase the central nervous system depressant (CNS depressant) activities of Chlorphenesin. Capmatinib The serum concentration of Capmatinib can be decreased when it is combined with Chlorphenesin. Clindamycin The metabolism of Clindamycin can be increased when combined with Chlorphenesin. Clobazam The risk or severity of sedation, somnolence, and CNS depression can be increased when Clobazam is combined with Chlorphenesin. Clozapine The serum concentration of Clozapine can be decreased when it is combined with Chlorphenesin. - Food Interactions
- No interactions found.
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.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mycil Cream Cream 10 mg / g Topical Allen & Hanburys A Glaxo Canada Ltd. Co. 1948-12-31 1996-09-10 Canada 
Mycil Powder Powder 10 mg / g Topical Allen & Hanburys A Glaxo Canada Ltd. Co. 1951-12-31 1996-09-10 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mycil Cream 1% Cream 1.0 % Topical Well Spring Pharmaceutical Corporation 1996-04-30 2004-07-19 Canada Mycil Powder 1% Powder 1 % Topical Roberts Pharmaceutical 1996-07-30 1999-08-11 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image (badiful) Antibacterial Wipes Chlorphenesin (2 mg/100mL) + Benzalkonium chloride (13 mg/100mL) + Cetylpyridinium chloride (5 mg/100mL) + Propylene glycol (2 mg/100mL) Swab Topical ZHANGZHOU KANGBEI HYGIENIC PRODUCTS CO., LTD. 2020-05-31 Not applicable US 
Alcohol Wet Tissue Chlorphenesin (0.05 g/100g) + Benzalkonium chloride (0.1 g/100g) + Cetylpyridinium chloride (0.05 g/100g) + Didecyldimethylammonium chloride (0.1 g/100g) + Ethanol (75 g/100g) Swab Topical SHANDONG PROVINCE RUNHE SANITARY MATERIALS CO.,LTD. 2020-04-13 Not applicable US Anivy Chlorphenesin (10 mg / g) + Benzocaine (10 mg / g) + Titanium dioxide (210 mg / g) + Zinc oxide (235 mg / g) Ointment Topical Allen & Hanburys A Glaxo Canada Ltd. Co. 1988-03-23 1996-09-10 Canada Disinfecting Wipes Chlorphenesin (0.05 g/100g) + Benzalkonium chloride (0.1 g/100g) + Cetylpyridinium chloride (0.05 g/100g) + Didecyldimethylammonium chloride (0.1 g/100g) + Isopropyl alcohol (75 g/100g) Swab Topical SHANDONG PROVINCE RUNHE SANITARY MATERIALS CO.,LTD. 2020-04-13 Not applicable US Hand Sanitizer Smells Clean Chlorphenesin (0.143 g/100mL) + Ethanol (70 mL/100mL) + Phenoxyethanol (0.143 g/100mL) Gel Topical IWANNA CORP SAS 2020-03-30 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image (badiful) Antibacterial Wipes Chlorphenesin (2 mg/100mL) + Benzalkonium chloride (13 mg/100mL) + Cetylpyridinium chloride (5 mg/100mL) + Propylene glycol (2 mg/100mL) Swab Topical ZHANGZHOU KANGBEI HYGIENIC PRODUCTS CO., LTD. 2020-05-31 Not applicable US Medi SM 24K Gold Hydrogel Peptide Mask Pack Chlorphenesin (0.01 g/100g) + Adenosine (0.01 g/100g) + Butylene glycol (0.01 g/100g) + Chondrus crispus (0.02 g/100g) + Glycerin (0.05 g/100g) + Glycyrrhiza glabra (0.01 g/100g) + Gold (0.01 g/100g) + Nicotinamide (0.02 g/100g) + Polysorbate 20 (0.01 g/100g) + Polysorbate 60 (0.02 g/100g) + Potassium chloride (0.02 g/100g) + Propolis wax (0.01 g/100g) + Titanium dioxide (0.01 g/100g) + Xanthan gum (0.01 g/100g) Emulsion Topical Mbg Inc (Korea Institute of Science Development) 2017-11-07 2018-11-07 US Wet Wipes Chlorphenesin (0.1 g/100g) + Benzalkonium (0.06 g/100g) + Didecyldimethylammonium chloride (0.4 g/100g) + Ethanol (10 g/100g) + Phenoxyethanol (0.3 g/100g) Cloth Topical Sourcery Ltd 2020-06-15 Not applicable US
Categories
- ATC Codes
- D01AE07 — Chlorphenesin
- Drug Categories
- Alcohols
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Dermatologicals
- Glycols
- Muscle Relaxants
- Muscle Relaxants, Centrally Acting Agents
- Peripheral Nervous System Agents
- Propylene Glycols
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Phenoxy compounds / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Secondary alcohols / 1,2-diols / Primary alcohols / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,2-diol / Alcohol / Alkyl aryl ether / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Ether / Halobenzene / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- propane-1,2-diols, monochlorobenzenes, glycol (CHEBI:3642)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- I670DAL4SZ
- CAS number
- 104-29-0
- InChI Key
- MXOAEAUPQDYUQM-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H11ClO3/c10-7-1-3-9(4-2-7)13-6-8(12)5-11/h1-4,8,11-12H,5-6H2
- IUPAC Name
- 3-(4-chlorophenoxy)propane-1,2-diol
- SMILES
- OCC(O)COC1=CC=C(Cl)C=C1
References
- Synthesis Reference
Parker, H.E.; U S . Patent 3,214,336; October 26, 1965; assigned to The Upjohn Company. Collins, R.J. and Matthews, R.J.; US. Patent 3,161,567; December 15, 1964; assigned to The Upjohn Company.
- General References
- Malley A, Baecher L: Inhibition of histamine and SRS-A from monkey lung tissue by chlorophenesin. J Immunol. 1971 Aug;107(2):586-8. [Article]
- Kurachi M, Aihara H: Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats. Jpn J Pharmacol. 1984 Sep;36(1):7-13. [Article]
- Dalessio DJ: Medical treatment of the major neuralgias. Semin Neurol. 1988 Dec;8(4):286-90. [Article]
- External Links
- Human Metabolome Database
- HMDB0014994
- KEGG Compound
- C07928
- PubChem Compound
- 7697
- PubChem Substance
- 46504714
- ChemSpider
- 7411
- 2399
- ChEBI
- 3642
- ChEMBL
- CHEMBL388751
- PharmGKB
- PA164784022
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Chlorphenesin_carbamate
- MSDS
- Download (35.8 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 data
Pharmacoeconomics
- Manufacturers
- Pharmacia and upjohn co
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Ointment Topical Swab Topical Gel Topical Emulsion Topical Cream Topical 10 mg / g Cream Topical 1.0 % Powder Topical 10 mg / g Powder Topical 1 % Cloth Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 86–92 Salim, E.F., Booth, R.E. (1967). "Qualitative and quantitative tests for chlorphenesin carbamate". Journal of Pharmaceutical Sciences 56 (5): 623–4. doi:10.1002/jps.2600560516. PMID 6032776. water solubility 1E+004 mg/L MERCK INDEX (1996); less than logP 1.2 Not Available - Predicted Properties
Property Value Source Water Solubility 10.4 mg/mL ALOGPS logP 1.46 ALOGPS logP 1.1 Chemaxon logS -1.3 ALOGPS pKa (Strongest Acidic) 13.62 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 49.69 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 49.58 m3·mol-1 Chemaxon Polarizability 20.1 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 + 0.9803 Blood Brain Barrier + 0.6433 Caco-2 permeable - 0.5562 P-glycoprotein substrate Non-substrate 0.5768 P-glycoprotein inhibitor I Non-inhibitor 0.8531 P-glycoprotein inhibitor II Non-inhibitor 0.9212 Renal organic cation transporter Non-inhibitor 0.8694 CYP450 2C9 substrate Non-substrate 0.8815 CYP450 2D6 substrate Non-substrate 0.8373 CYP450 3A4 substrate Non-substrate 0.7335 CYP450 1A2 substrate Inhibitor 0.6099 CYP450 2C9 inhibitor Non-inhibitor 0.9114 CYP450 2D6 inhibitor Non-inhibitor 0.9292 CYP450 2C19 inhibitor Non-inhibitor 0.6201 CYP450 3A4 inhibitor Non-inhibitor 0.9412 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8428 Ames test Non AMES toxic 0.7102 Carcinogenicity Non-carcinogens 0.8053 Biodegradation Not ready biodegradable 0.8233 Rat acute toxicity 2.1025 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8938 hERG inhibition (predictor II) Non-inhibitor 0.8296
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-004l-9800000000-88df1753febdfff7153d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9100000000-b2a4f9998ea4a2ab1e96 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-3900000000-d39e3d818e10f3ffb257 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9100000000-514a25e60f199f2f5867 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-002f-9400000000-d58c0eeb0fabc02ff79f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0059-9400000000-ce649188e4f159d86eb7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00dm-9400000000-b25a7178c432f800097f 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]- 140.007044 predictedDarkChem Lite v0.1.0 [M-H]- 137.71873 predictedDeepCCS 1.0 (2019) [M+H]+ 141.096944 predictedDarkChem Lite v0.1.0 [M+H]+ 141.1099 predictedDeepCCS 1.0 (2019) [M+Na]+ 139.680644 predictedDarkChem Lite v0.1.0 [M+Na]+ 150.57738 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase that catalyzes the conversion of C19 androgens, androst-4-ene-3,17-dione (androstenedione) and testosterone to the C18 estrogens, estrone and estradiol, respectively (PubMed:27702664, PubMed:2848247). Catalyzes three successive oxidations of C19 androgens: two conventional oxidations at C19 yielding 19-hydroxy and 19-oxo/19-aldehyde derivatives, followed by a third oxidative aromatization step that involves C1-beta hydrogen abstraction combined with cleavage of the C10-C19 bond to yield a phenolic A ring and formic acid (PubMed:20385561). Alternatively, the third oxidative reaction yields a 19-norsteroid and formic acid. Converts dihydrotestosterone to delta1,10-dehydro 19-nordihydrotestosterone and may play a role in homeostasis of this potent androgen (PubMed:22773874). Also displays 2-hydroxylase activity toward estrone (PubMed:22773874). 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 (CPR; NADPH-ferrihemoprotein reductase) (PubMed:20385561, PubMed:22773874)
- Specific Function
- aromatase activity
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Holloway AC, Stys KA, Foster WG: DDE-induced changes in aromatase activity in endometrial stromal cells in culture. Endocrine. 2005 Jun;27(1):45-50. [Article]
- Younglai EV, Holloway AC, Lim GE, Foster WG: Synergistic effects between FSH and 1,1-dichloro-2,2-bis(P-chlorophenyl)ethylene (P,P'-DDE) on human granulosa cell aromatase activity. Hum Reprod. 2004 May;19(5):1089-93. Epub 2004 Apr 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
- Medina-Diaz IM, Arteaga-Illan G, de Leon MB, Cisneros B, Sierra-Santoyo A, Vega L, Gonzalez FJ, Elizondo G: Pregnane X receptor-dependent induction of the CYP3A4 gene by o,p'-1,1,1,-trichloro-2,2-bis (p-chlorophenyl)ethane. Drug Metab Dispos. 2007 Jan;35(1):95-102. Epub 2006 Oct 11. [Article]
- Petersen MS, Halling J, Damkier P, Nielsen F, Grandjean P, Weihe P, Brosen K: Polychlorinated biphenyl (PCB) induction of CYP3A4 enzyme activity in healthy Faroese adults. Toxicol Appl Pharmacol. 2007 Oct 15;224(2):202-6. Epub 2007 Jul 14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro)
- Specific Function
- 2 iron, 2 sulfur cluster binding
- Gene Name
- XDH
- Uniprot ID
- P47989
- Uniprot Name
- Xanthine dehydrogenase/oxidase
- Molecular Weight
- 146422.99 Da
References
- Springer RH, Dimmitt MK, Novinson T, O'Brien DE, Robins RK, Simon LN, Miller JP: Synthesis and enzymic activity of some novel xanthine oxidase inhibitors. 3-Substituted 5,7-dihydroxypyrazolo(1,5-alpha)pyrimidines. J Med Chem. 1976 Feb;19(2):291-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Dual cyclooxygenase and peroxidase 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 (PubMed:11939906, PubMed:16373578, PubMed:19540099, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). 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 (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). 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:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). Similarly catalyzes successive cyclooxygenation and peroxidation of dihomo-gamma-linoleate (DGLA, C20:3(n-6)) and eicosapentaenoate (EPA, C20:5(n-3)) to corresponding PGH1 and PGH3, the precursors of 1- and 3-series prostaglandins (PubMed:11939906, PubMed:19540099). In an alternative pathway of prostanoid biosynthesis, converts 2-arachidonoyl lysophopholipids to prostanoid lysophopholipids, which are then hydrolyzed by intracellular phospholipases to release free prostanoids (PubMed:27642067). Metabolizes 2-arachidonoyl glycerol yielding the glyceryl ester of PGH2, a process that can contribute to pain response (PubMed:22942274). Generates lipid mediators from n-3 and n-6 polyunsaturated fatty acids (PUFAs) via a lipoxygenase-type mechanism. Oxygenates PUFAs to hydroperoxy compounds and then reduces them to corresponding alcohols (PubMed:11034610, PubMed:11192938, PubMed:9048568, PubMed:9261177). Plays a role in the generation of resolution phase interaction products (resolvins) during both sterile and infectious inflammation (PubMed:12391014). Metabolizes docosahexaenoate (DHA, C22:6(n-3)) to 17R-HDHA, a precursor of the D-series resolvins (RvDs) (PubMed:12391014). As a component of the biosynthetic pathway of E-series resolvins (RvEs), converts eicosapentaenoate (EPA, C20:5(n-3)) primarily to 18S-HEPE that is further metabolized by ALOX5 and LTA4H to generate 18S-RvE1 and 18S-RvE2 (PubMed:21206090). In vascular endothelial cells, converts docosapentaenoate (DPA, C22:5(n-3)) to 13R-HDPA, a precursor for 13-series resolvins (RvTs) shown to activate macrophage phagocytosis during bacterial infection (PubMed:26236990). In activated leukocytes, contributes to oxygenation of hydroxyeicosatetraenoates (HETE) to diHETES (5,15-diHETE and 5,11-diHETE) (PubMed:22068350, PubMed:26282205). 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). During neuroinflammation, plays a role in neuronal secretion of specialized preresolving mediators (SPMs) 15R-lipoxin A4 that regulates phagocytic microglia (By similarity)
- Specific Function
- enzyme binding
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Fernandez P, Guillen MI, Gomar F, Aller E, Molina P, Alcaraz MJ: A novel cyclo-oxygenase-2 inhibitor modulates catabolic and antiinflammatory mediators in osteoarthritis. Biochem Pharmacol. 2004 Aug 1;68(3):417-21. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters
- Specific Function
- acetylcholinesterase activity
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Westlake GE, Bunyan PJ, Stanley PI, Walker CH: The effects of 1,1-di(p-chlorophenyl)-2-chloroethylene on plasma enzymes and blood constituents in the Japanese quail. Chem Biol Interact. 1979 May;25(2-3):197-210. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 02, 2024 21:45