Alclofenac
Identification
- Generic Name
- Alclofenac
- DrugBank Accession Number
- DB13167
- Background
Alclofenac is a non-steroidal anti-inflammatory drug. It was withdrawn from the market in the United Kingdom in 1979.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
- Weight
- Average: 226.66
Monoisotopic: 226.0396719 - Chemical Formula
- C11H11ClO3
- Synonyms
- (4-Allyloxy-3-chlorphenyl)essigsäure
- [4-(allyloxy)-3-chlorophenyl]acetic acid
- 3-Chloro-4-(2-propenyloxy)benzeneacetic acid
- Alclofénac
- Alclofenac
- Alclofenaco
- Alclofenacum
- Alclophenac
- External IDs
- MY-101
- W 7320
- W-7320
Pharmacology
- Indication
Alclofenac is indicated in rheumatology, in particular for the treatment of rheumatoid arthritis, ankylosing spondylitis and, as an analgesic, in painful arthritic pathologies.
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- Pharmacodynamics
Not Available
- Mechanism of action
Alclofenac is an inhibitor of prostaglandin H2 synthase. The inhibition of the enzyme occurs through the reversible block of cyclooxygenase enzyme. Therefore, it prevents the production of inflammatory mediators (and pain) as prostacyclins and prostaglandins. Aclofenac has the ability to inhibit the biosynthesis of prostaglandins which may be an important factor in the action of these drugs, but in addition, the effect of these agents in displacing endogenous anti-inflammatory substances from plasma protein binding sites is thought to be an equally important effect in their mechanism of action
Target Actions Organism AProstaglandin G/H synthase 2 antagonistHumans - Absorption
The absorption of alclofenac from the gastrointestinal tract is irregular. After oral or rectal administration maximum plasma concentrations are reached within 1-4 hours.
- Volume of distribution
The volume of distribution is 0.1 L / kg
- Protein binding
The binding to plasma proteins is 90-99%.
- Metabolism
the main metabolic product is alclofenac itself and alclofenac glucuronide
- Route of elimination
Alclofenac is excreted in the urine mainly as glucuronide and as unchanged active substance.
- Half-life
The plasma half-life varies between 1.5 and 5.5 hours.
- Clearance
For oral dose of 500mg: Renal clearance constant (av) 35ml/min Overall clearance constant (av) 37-69ml/min
- Adverse Effects
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- Toxicity
The lethal dose orally: 1100 (mice), 1050 (rats) mg / kg ;
under the skin: 600 (mice), 630 (rats) mg / kg intraperitoneally: 550 (mice), 530 (rats) mg / kg- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Alclofenac may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Alclofenac is combined with Abciximab. Acebutolol Alclofenac may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Alclofenac. Acemetacin The risk or severity of adverse effects can be increased when Alclofenac is combined with Acemetacin. - 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 drug product information from over 10 global regions.
- International/Other Brands
- Allopydin / Medifenac / Mervan / Neosten / Neoston / Prinalgin / Reufenac / Zumaril
Categories
- ATC Codes
- M01AB06 — Alclofenac
- Drug Categories
- Acetic Acid Derivatives and Related Substances
- Acids, Carbocyclic
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antirheumatic Agents
- Drugs that are Mainly Renally Excreted
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Sensory System Agents
- 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 / Monocarboxylic acids and derivatives / Carboxylic acids / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alkyl aryl ether / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Chlorobenzene / Ether / Halobenzene
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aromatic ether, monocarboxylic acid, monochlorobenzenes (CHEBI:31183)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- M9CP5H21N8
- CAS number
- 22131-79-9
- InChI Key
- ARHWPKZXBHOEEE-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H11ClO3/c1-2-5-15-10-4-3-8(6-9(10)12)7-11(13)14/h2-4,6H,1,5,7H2,(H,13,14)
- IUPAC Name
- 2-[3-chloro-4-(prop-2-en-1-yloxy)phenyl]acetic acid
- SMILES
- OC(=O)CC1=CC(Cl)=C(OCC=C)C=C1
References
- General References
- Wiggins LF: The chemical and biological background to alclofenac. Curr Med Res Opin. 1975;3(5):241-8. [Article]
- Lambotte F: Therapeutic activity of 4-allyloxy-3-chlorophenylacetic acid. Arzneimittelforschung. 1970 Apr;20(4):569-71. [Article]
- Thomas GM, Rees P, Dippy JE, Maddock J: Simultaneous pharmacokinetics of alclofenace in plasma and synovial fluid in patients with rheumatoid arthritis. Curr Med Res Opin. 1975;3(5):264-7. [Article]
- Selinsky BS, Gupta K, Sharkey CT, Loll PJ: Structural analysis of NSAID binding by prostaglandin H2 synthase: time-dependent and time-independent inhibitors elicit identical enzyme conformations. Biochemistry. 2001 May 1;40(17):5172-80. [Article]
- Brogden RN, Heel RC, Speight TM, Avery GS: Alclofenac: a review of its pharmacological properties and therapeutic efficacy in rheumatoid arthritis and allied rheumatic disorders. Drugs. 1977 Oct;14(4):241-59. [Article]
- External Links
- KEGG Drug
- D01252
- PubChem Compound
- 30951
- PubChem Substance
- 347829274
- ChemSpider
- 28714
- ChEBI
- 31183
- ChEMBL
- CHEMBL94081
- ZINC
- ZINC000002014875
- Wikipedia
- Alclofenac
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.288 mg/mL ALOGPS logP 3.01 ALOGPS logP 2.79 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 3.71 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 57.8 m3·mol-1 Chemaxon Polarizability 22.28 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0930000000-9ceb671908b7c6179d18 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-056r-0290000000-7c50877b85d748c546a2 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000f-0900000000-bcd7ef1cf88debd11192 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-052f-0940000000-893cf257f96fdfcc46b0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004l-0900000000-8481a5ff8076038bac23 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0900000000-c9cc03aace39bca0d6ef 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]- 146.59303 predictedDeepCCS 1.0 (2019) [M+H]+ 148.98859 predictedDeepCCS 1.0 (2019) [M+Na]+ 155.27284 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Thomas GM, Rees P, Dippy JE, Maddock J: Simultaneous pharmacokinetics of alclofenace in plasma and synovial fluid in patients with rheumatoid arthritis. Curr Med Res Opin. 1975;3(5):264-7. [Article]
Drug created at February 11, 2017 18:07 / Updated at February 21, 2021 18:54