Alclofenac
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Alclofenac
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CAS No:
22131-79-9
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Formula:
C11H11ClO3
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Chemical Name:
Alclofenac
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Synonyms:
Benzeneacetic acid,3-chloro-4-(2-propen-1-yloxy)-;Acetic acid,[4-(allyloxy)-3-chlorophenyl]-;Benzeneacetic acid,3-chloro-4-(2-propenyloxy)-;3-Chloro-4-(2-propen-1-yloxy)benzeneacetic acid;[4-(Allyloxy)-3-chlorophenyl]acetic acid;Mervan;Alclofenac;W 7320;Alclophenac;Neosten;Prinalgin;[3-Chloro-4-(allyloxy)phenyl]acetic acid;Neoston;MY 101;Allopydin;Medifenac;Zumaril;Epinal;Reufenac;Aclofenac;2-[3-Chloro-4-(prop-2-en-1-yloxy)phenyl]acetic acid;2-(4-(Allyloxy)-3-chlorophenyl)acetic acid;2-(4-(Allyloxy)-3-chlorophenyl)aceticacid
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CAS No:
Description
Off-White to Pale Yellow Solid
Alclofenac is an aromatic ether in which the ether oxygen links an allyl group to the 4-position of (3-chlorophenyl)acetic acid.A non-steroidal anti-inflammatory drug, it was withdrawn from the UK market in 1979 due to concerns with its association with vasculitis and rash. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic and a drug allergen. It is an aromatic ether, a monocarboxylic acid and a member of monochlorobenzenes.|Alclofenac is a non-steroidal anti-inflammatory drug. It was withdrawn from the market in the United Kingdom in 1979.
Alclofenac Basic Attributes
226.66
226.66
244-795-4
M9CP5H21N8
DTXSID4020038
M - Musculo-skeletal system
2918990090
Characteristics
46.5
2.53190
1.252g/cm3
92.5 °C
368.3ºC at 760mmHg
176.6ºC
1.553
13.1mg/L(25 ºC)
Refrigerator
4.49E-06mmHg at 25°C
Oral-rat LD50: 1050 mg/kg; Oral-Mouse LD50: 1100 mg/kg
Flammable; burning produces toxic chloride fumes
Safety Information
Treasury is ventilated, low temperature and dry; stored separately from food materials
P264, P270, P301+P312, P330, P501
H302
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.
Toxicity
moderately toxic
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
The binding to plasma proteins is 90-99%.
Drug Information
Alclofenac is indicated in rheumatology, in particular for the treatment of rheumatoid arthritis, ankylosing spondylitis and, as an analgesic, in painful arthritic pathologies.
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)
The absorption of alclofenac from the gastrointestinal tract is irregular. After oral or rectal administration maximum plasma concentrations are reached within 1-4 hours.|Alclofenac is excreted in the urine mainly as glucuronide and as unchanged active substance.|The volume of distribution is 0.1 L / kg|For oral dose of 500mg: Renal clearance constant (av) 35ml/min Overall clearance constant (av) 37-69ml/min
the main metabolic product is alclofenac itself and alclofenac glucuronide
The plasma half-life varies between 1.5 and 5.5 hours.
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
4-allyloxy-3-chlorophenylacetic acid
Alclofenac Use and Manufacturing
The mixture of 3-chloro-4-allyloxybenzene acetonitrile, ethanol, potassium hydroxide and water was refluxed for 4h, ie, enchlorobenzene acetic acid was generated with a yield of 81%.
Analgesic; antipyretic; anti-inflammatory.
Pharmaceuticals
Computed Properties
Molecular Weight:226.65
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:226.0396719
Monoisotopic Mass:226.0396719
Topological Polar Surface Area:46.5
Heavy Atom Count:15
Complexity:230
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes