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Alclofenac

Alclofenac structure

Alclofenac 

structure
  • CAS No:

    22131-79-9

  • Formula:

    C11H11ClO3

  • Chemical Name:

    Alclofenac

  • 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

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links an allyl group to the 4-position of (3-chlorophenyl)acetic acid.A non-steroidal anti-inflammatory drug, it was withdrawn from the UK market in 1979 due to concerns with its association with vasculitis and rash.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 It was withdrawn from the market in the United Kingdom in 1979.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

Methods of 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%.

Uses

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

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