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Aceclofenac, ацеклофенак , أسيكلوفيناك , 醋氯芬酸 , アセクロフェナク

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Aceclofenac

アセクロフェナク

  • Molecular FormulaC16H13Cl2NO4
  • Average mass354.185 Da
(2-{2-[(2,6-Dichlorophenyl)amino]phenyl}acetoxy)acetic acid [ACD/IUPAC Name]
(2-{2-[(2,6-Dichlorphenyl)amino]phenyl}acetoxy)essigsäure [German] [ACD/IUPAC Name]
5608
89796-99-6 [RN]
Aceclofenac [BAN] [INN] [JAN] [Wiki]
acéclofénac [French] [INN]
Aceclofenaco [Spanish] [INN]
Aceclofenacum [Latin] [INN]
Acide (2-{2-[(2,6-dichlorophényl)amino]phényl}acétoxy)acétique [French] [ACD/IUPAC Name]
Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-, carboxymethyl ester [ACD/Index Name]
RPK779R03H
ацеклофенак[Russian][INN]
أسيكلوفيناك[Arabic][INN]
醋氯芬酸[Chinese][INN]
[({2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)oxy]acetic acid
[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid carboxymethyl ester
Aceclofenac
CAS Registry Number: 89796-99-6
CAS Name: 2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid carboxymethyl ester
Additional Names: 2-[(2,6-dichlorophenyl)amino]phenylacetoxyacetic acid; glycolic acid [o-(2,6-dichloroanilino)phenyl]acetate ester
Manufacturers’ Codes: PR-82/3
Trademarks: Airtal (Prodes); Falcol (Bayer); Gerbin (Sanofi Winthrop); Preservex (BMS)
Molecular Formula: C16H13Cl2NO4
Molecular Weight: 354.18
Percent Composition: C 54.26%, H 3.70%, Cl 20.02%, N 3.95%, O 18.07%
Literature References: Prepn: A. V. Casas, ES8404783idem,US4548952 (1984, 1985 both to Prodes). Gastrointestinal tolerance in rats in comparison with diclofenac, q.v.: V. Rimbau et al.,Farmaco Ed. Prat.43, 19 (1988). Clinical trial in comparison with acetaminophen, q.v., in episiotomal pain: A. Yscla, Drugs Exp. Clin. Res.14, 491 (1988). Clinical evaluation in rheumatoid arthritis: R. Ballesteros et al.,Clin. Trials J.27, 12 (1990).
Properties: White crystals from cyclohexane, mp 149-150°. uv max (ethanol): 275 nm (log e 4.14).
Melting point: mp 149-150°
Absorption maximum: uv max (ethanol): 275 nm (log e 4.14)
Therap-Cat: Anti-inflammatory; analgesic.
Keywords: Analgesic (Non-Narcotic); Anti-inflammatory (Nonsteroidal); Arylacetic Acid Derivatives.
UV-Vis spectra of Aceclofenac.
Fig. 9

 Characterization of Aceclofenac by 1H NMR spectroscopy

1H NMR (400 MHz, DMSO-d6δ (ppm) 3.896 (s, 2H, Aliphatic –CH2), 4.634 (s, 2H, Aliphatic –CH2), 6.279 (d J= 8.00HZ, 1H, Aromatic), 6.887 (t, J = 7.2 Hz, 1H), 6.936 (s, 1H, NH), 7.039(t, J = 7.6 Hz, 1H, Aromatic), 7.225 (t J= 8.00 HZ, 1H, Aromatic), 7.260 (d J= 8.00 HZ, 1H, Aromatic), 7.537 (d J= 8.4HZ, 2H, Aromatic), 13.076 (s, 1H, Carboxylic acid) …https://www.sciencedirect.com/science/article/pii/S2214180417301290

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https://www.dea.gov/sites/default/files/pr/microgram-journals/2014/mj11-1_29-41.pdf

Aceclofenac is a nonsteroidal anti-inflammatory drug (NSAID) analog of diclofenac. It is used for the relief of pain and inflammation in rheumatoid arthritisosteoarthritis and ankylosing spondylitis.

Aceclofenac (C16H13Cl2NO4), chemically [(2-{2, 6-dichlorophenyl) amino} phenylacetooxyacetic acid], is a crystalline powder with a molecular weight of 354.19. It is practically insoluble in water with good permeability. It is metabolized in human hepatocytes and human microsomes to form [2-(2′,6′-dichloro-4′-hydroxy- phenylamino) phenyl] acetoxyacetic acid as the major metabolite, which is then further conjugated. According to the Biopharmaceutical Classification System (BCS) drug substances are classified to four classes upon their solubility and permeability. Aceclofenac falls under the BCS Class II, poorly soluble and highly permeable drug.[1]

Aceclofenac works by inhibiting the action of cyclooxygenase (COX) that is involved in the production of prostaglandins (PG) which is accountable for pain, swelling, inflammation and fever. The incidence of gastric ulcerogenicity of aceclofenac has been reported to be significantly lower than that of the other frequently prescribed NSAIDs, for instance, 2-folds lesser than naproxen, 4-folds lesser than diclofenac, and 7-folds lesser than indomethacin.

Aceclofenac should not be given to people with porphyria or breast-feeding mothers, and is not recommended for children. It should be avoided near term in a pregnant woman because of the risk of having a patent ductus arteriosus in the neonate.

Image result for aceclofenac

SYN

Manufacturing Process for Aceclofenac
Stage-1
T Butanol and Chloro Acetyl Chloride react in presence of NN Dimethyl Aniline at low temperature. After reaction
organics mass wash with water and sodium bicarbonate solution to get stage-1

Stage-2
Stage-I react with Diclofenac Sodium in presence of TBAB in Toluene media, further react with formic acid and
reaction mass quenching in water and product is isolated by filtration. Finally Crude Aceclofenac purified in ethyl
acetate and charcoal. Pure product isolated by filtration.

str1 str2 str3

SYN’

EP 0119932; US 4548952

Alkylation of the sodium salt of diclofenac (I) with benzyl bromoacetate (II) in hot DMF yielded the (arylacetoxy)acetate (III). Subsequent hydrogenolysis of the benzyl ester of (III) in the presence of Pd/C gave the title carboxylic acid. Alternatively, the benzyl ester group of (III) was cleaved by means of the combination of chlorotrimethylsilane and sodium iodide. This method of selective ester hydrolysis with in situ generated iodotrimethylsilane was also applied to the corresponding methyl (IV) and tert-butyl (V) esters. In a related procedure, tert-butyl ester (V) was prepared by alkylation of diclofenac (VI) with tert-butyl bromoacetate (VII) in the presence of tertiary amines. Selective cleavage of the tert-butyl ester group of (V) was then performed by treatment with either trifluoroacetic or formic acid.

SYN

ES 2046141

Aceclofenac was prepared by selective hydrolysis of other labile ester precursors. Alkylation of diclofenac sodium (I) with tetrahydropyranyl chloroacetate (IX), prepared by protection of chloroacetic acid (VIII) with dihydropyran, furnished the tetrahydropyranyl ester of aceclofenac (X), which was then deprotected by treatment with HCl. Similarly, the preparation of aceclofenac was reported by acidic hydrolysis of the analogous tetrahydrofuranyl ester (XI).

References

  1. ^ Karmoker, J.R.; Sarkar, S.; Joydhar, P.; Chowdhury, S.F. (2016). “Comparative in vitro equivalence evaluation of some Aceclofenac generic tablets marketed in Bangladesh” (PDF)The Pharma Innovation Journal5: 3–7. Retrieved 2016-09-01.
Sources

References

    • EP 119 932 (Prodes; appl. 19.3.1984; E-prior. 21.3.1983).
    • US 4 548 952 (Prodes; 22.10.1985; appl. 15.3.1984; E-prior. 21.3.1983).
  • Alternative synthesis:

    • ES 2 020 146 (Prodesfarma; appl. 29.5.1990).
    • ATC:M01AB16
  • Use:non-steroidal anti-inflammatory, analgesic, non-selective cyclooxigenase inhibitor
  • Chemical name:2-[(2,6-dichlorophenyl)amino]benzeneacetic acid carboxymethyl ester
  • Formula:C16H13Cl2NO4
  • MW:354.19 g/mol
  • CAS-RN:89796-99-6
  • InChI Key:MNIPYSSQXLZQLJ-UHFFFAOYSA-N
  • InChI:InChI=1S/C16H13Cl2NO4/c17-11-5-3-6-12(18)16(11)19-13-7-2-1-4-10(13)8-15(22)23-9-14(20)21/h1-7,19H,8-9H2,(H,20,21)
  • LD50:121 mg/kg (M, p.o.)
Aceclofenac
Aceclofenac.png
Clinical data
Trade names Hifenac, Cincofen, Zerodol, Nacsiv, Acenac, others
AHFS/Drugs.com International Drug Names
Routes of
administration
oral, topical
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.169.686 Edit this at Wikidata
Chemical and physical data
Formula C16H13Cl2NO4
Molar mass 353.02161 g/mol
3D model (JSmol)

//////////Aceclofenac, ацеклофенак أسيكلوفيناك 醋氯芬酸 , アセクロフェナク


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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with AFRICURE PHARMA as ADVISOR, earlier assignment was with GLENMARK LIFE SCIENCES LTD, as CONSUlTANT, Retired from GLENMARK in Jan2022 Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 32 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 32 PLUS year tenure till date Feb 2023, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 100 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 100 Lakh plus views on dozen plus blogs, 227 countries, 7 continents, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 38 lakh plus views on New Drug Approvals Blog in 227 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc He has total of 32 International and Indian awards

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