NAV

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 It was withdrawn from the market in the United Kingdom in 1979.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Approved, Withdrawn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
3D
Similar Structures
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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Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
AProstaglandin G/H synthase 2
antagonist
Humans
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
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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAlclofenac may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Alclofenac is combined with Abciximab.
AcebutololAlclofenac may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Alclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Alclofenac is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Alclofenac is combined with Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Alclofenac.
AcetazolamideAcetazolamide may increase the excretion rate of Alclofenac which could result in a lower serum level and potentially a reduction in efficacy.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Alclofenac.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Alclofenac.
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Food Interactions
Not Available

Products

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International/Other Brands
Allopydin / Medifenac / Mervan / Neosten / Neoston / Prinalgin / Reufenac / Zumaril

Categories

ATC Codes
M01AB06 — Alclofenac
Drug Categories
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
  1. Wiggins LF: The chemical and biological background to alclofenac. Curr Med Res Opin. 1975;3(5):241-8. [Article]
  2. Lambotte F: Therapeutic activity of 4-allyloxy-3-chlorophenylacetic acid. Arzneimittelforschung. 1970 Apr;20(4):569-71. [Article]
  3. 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]
  4. 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]
  5. 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]
KEGG Drug
D01252
PubChem Compound
30951
PubChem Substance
347829274
ChemSpider
28714
ChEBI
31183
ChEMBL
CHEMBL94081
ZINC
ZINC000002014875
Wikipedia
Alclofenac

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.288 mg/mLALOGPS
logP3.01ALOGPS
logP2.79Chemaxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.71Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area46.53 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity57.8 m3·mol-1Chemaxon
Polarizability22.28 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Prostaglandin G/H synthase 2
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
  1. 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