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Acemetacin

CAS No.
53164-05-9
Chemical Name:
Acemetacin
Synonyms
k-708;Solart;Emflex;acemix;tv1322;rantudil;TVX-1322;aximeixin;rheumibis;BAY f4975
CBNumber:
CB1492822
Molecular Formula:
C21H18ClNO6
Molecular Weight:
415.82
MDL Number:
MFCD00151473
MOL File:
53164-05-9.mol
Last updated:2024-03-19 15:37:50

Acemetacin Properties

Melting point 151.5°C
Boiling point 565.5±50.0 °C(Predicted)
Density 1.2387 (rough estimate)
refractive index 1.6000 (estimate)
RTECS NL3521400
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility Practically insoluble in water, soluble in acetone, slightly soluble in anhydrous ethanol.
pka 2.60±0.10(Predicted)
color Very fine, pale-yellow crystals from pet eth
Merck 14,27
CAS DataBase Reference 53164-05-9(CAS DataBase Reference)
FDA UNII 5V141XK28X
ATC code M01AB11

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300+H310+H330
Precautionary statements  P260-P262-P264-P280-P302+P352+P310-P304+P340+P310
Hazard Codes  T+
Risk Statements  26/27/28
Safety Statements  22-25-36/37/39-45-24/25
RIDADR  UN 2811
WGK Germany  3
HazardClass  6.1(a)
PackingGroup  II
HS Code  29339900
Toxicity LD50 in male, female mice, male, female rats (mg/kg): 55.5, 18.42, 24.2, 30.1 orally; 34.1, 51.1, 38.1, 28.3 i.v. (Jacobi, Dell)
NFPA 704
0
4 0

Acemetacin price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Y0000810 Acemetacin European Pharmacopoeia (EP) Reference Standard 53164-05-9 y0000810 $150 2024-03-01 Buy
Sigma-Aldrich A1674 Acemetacin analytical standard 53164-05-9 1g $42.4 2022-05-15 Buy
TCI Chemical A2452 Acemetacin >98.0%(GC)(T) 53164-05-9 5g $66 2024-03-01 Buy
TCI Chemical A2452 Acemetacin >98.0%(GC)(T) 53164-05-9 25g $197 2024-03-01 Buy
Alfa Aesar J63583 Acemetacin 53164-05-9 2g $59.65 2024-03-01 Buy
Product number Packaging Price Buy
Y0000810 y0000810 $150 Buy
A1674 1g $42.4 Buy
A2452 5g $66 Buy
A2452 25g $197 Buy
J63583 2g $59.65 Buy

Acemetacin Chemical Properties,Uses,Production

Description

Acemetacin is used in the treatment of pain and restricted mobility resulting from chronic articular rheumatism, degenerative articular disease, gout, and inflammation of muscle, joints, and tendons. Acemetacin causes less gastrointestinal blood loss than indomethacin. Its anti-inflammatory activity results from liberation of the parent compound, indomethacin.

Chemical Properties

Light Yellow Solid

Originator

Rantudil ,Bayer ,W. Germany ,1980

Uses

A potent inhibitor of COX-2 found to have anti-tumor activity in the colon

Uses

Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory.

Definition

ChEBI: A carboxylic ester that is the carboxymethyl ester of indometacin. A non-steroidal anti-inflammatory drug, it is used in the treatment of rheumatoid arthritis, osteoarthritis, and low back pain, as well as for postoperative pain and inflammation. Its activ ty is due to both acemetacin and its major metabolite, indometacin.

Manufacturing Process

25.4 g (0.050 mol) of [1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3- indoleacetoxy]-benzyl acetate were dissolved in 400 ml of glacial acetic acid and hydrogenated on 2.0 g of palladium carbon at room temperature. After the absorption of hydrogen had finished (1 hour), the catalyst was filtered off, the filtrate was concentrated by evaporation under vacuum and the compound was caused to crystallize by adding petroleum ether. The compound melted at 149.5-150.5°C (determined on the micro-Kofler bench); the yield was 19.4 g which corresponds to 93% of the theoretical yield.
The starting material for the above step may be prepared as follows: 5 g (0.016 mol) of N1-(p-methoxyphenyl)-p-chlorobenzhydrazide hydrochloride and 4.75 g (0.018 mol) of benzyl levulinoyloxyacetate were heated in 25 ml of glacial acetic acid for 3 hours at 80°C. The solvent was then evaporated off under vacuum. The residue was taken up in chloroform and the solution was washed neutral by shaking with sodium bicarbonate solution and thereafter with water. After drying the chloroform solution, this was subjected to chromatography on aluminium oxide, the eluate was concentrated by evaporation and the viscous oil remaining as residue was crystallized by adding ether. The compound melted at 94-95°C. The yield was 4.1 g which corresponds to 50.7% of the theoretical yield.

Therapeutic Function

Antiinflammatory

Trade name

Acemetacin (Heumann, Stada, Germany), Acemix (Bioprogress, Italy), Altren (Rh?one-Poulenc Rorer, Belgium), Emflex (Merck, UK), Rantudil (Bayer Pharma Deutschland, Germany)

Clinical Use

Acemetacin is a nonsteroidal anti-inflammatory drug acting directly and via its major metabolite indomethacin. Acemetacin is used in chronic joint pain as well as in postoperative pain.

Safety Profile

Poison by ingestion, subcutaneous,intraperitoneal, intravenous, and intramuscular routes. Anexperimental teratogen. Other experimental reproductiveeffects. When heated to decomposition it emits toxic fumesof Cl?? and NOx. An anti-inflammatory agent.

Synthesis

alkylation of indomethacin with benzyl bromoacetate in K2CO3/N,N-dimethylformamide gives the corresponding benzyl glycolate ester, which is hydrogenated over 10 % palladium on charcoal in acetic acid to yield acemetacin.

75302-98-6
53164-05-9
Synthesis of Acemetacin from ACEMETACINTERT-BUTYLESTER
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View Lastest Price from Acemetacin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
acemetacin pictures 2024-01-18 acemetacin
53164-05-9
US $66.00 / KG 1250KG 99% 330T Xiamen Wonderful Bio Technology Co., Ltd.
Acemetacin pictures 2023-08-18 Acemetacin
53164-05-9
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Acemetacin pictures 2023-04-04 Acemetacin
53164-05-9
US $0.00 / kg 1kg 99% 1000kg Zhejiang Hengkang Pharmaceutical Co., Ltd.
  • acemetacin pictures
  • acemetacin
    53164-05-9
  • US $66.00 / KG
  • 99%
  • Xiamen Wonderful Bio Technology Co., Ltd.
  • Acemetacin pictures
  • Acemetacin
    53164-05-9
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd
  • Acemetacin pictures
  • Acemetacin
    53164-05-9
  • US $0.00 / kg
  • 99%
  • Zhejiang Hengkang Pharmaceutical Co., Ltd.

Acemetacin Spectrum

(1-(p-chlorbenzoyl)-5-methoxy-2-methylindol-3-acetoxy)essigsaeure AURORA KA-6229 ACEMETACIN [1-(4-CHLORO-BENZOYL)-5-METHOXY-2-METHYL-1H-INDOL-3-YL]-ACETIC ACID CARBOXYMETHYL ESTER 1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic Acid Carboxymethyl Ester Emflex Solart 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole-3-acetic aci carboxymethyl ((1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl)acetoxy)acetic acid (1-(p-chlorbenzoyl)-5-methoxy-2-methylindol-3-acetoxy)essigsaeure 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole-3-acetic acid carboxymethyl 2-(2-(1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl)acetoxy)acetic acid acemetacin acemetacinum acemix 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole-3-aceticacicarboxymethyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole-3-aceticacidcarboxymethyl 2-(2-(1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl)acetoxy)aceticacid acemetacinum acemix aximeixin k-708 rantudil rheumibis tv1322 1-[P-CHLOROBENZOYL]-5-METHOXY-2-METHYLINDOLE-3-ACETIC ACID CARBOXYMETHYL ESTER Acemix:Emflex:Rheumibis:Solart BAY f4975 TVX-1322 2-[2-[1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methylindol-3-yl]acetyloxy]acetic acid 1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid carboxymethyl 2-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-indol-3-yl]acetyl]oxyacetic acid 2-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyacetic acid 2-[2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]ethanoyloxy]ethanoic acid ((1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl)acetoxy)aceticacid AceMetacin (EMflex) [1-(4-Chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetoxyacetic Acid 1-(4-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic Acid Carboxymethyl Ester 2-(2-(1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-1H-indol-3-yl)acetoxy)acetic acid 1H-Indole-3-aceticacid, 1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-, carboxyMethyl ester Acemetacin:O-(1-p-Chlorobenzoyl-5-methoxy-2-methylindol-3-ylacetyl)glycolic acid cemetacin Acemetacin, 98%, COX inhibitor Acemetacin CRS Acemetacin > Acemetacin impurity mixture CRS [[[1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl]oxy]acetic acid 1-(4-Chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic Acid Carboxymethyl Ester Acemetacin USP/EP/BP Acemetacin (K-708 Acemetacin/TVX1322 I.?1-(2,6-dichlorophenyl)-1,3-dihydro-2H-indol-2-one. 53164-05-9 C21H18ClNO6 Analytical Standards Analytical Chromatography Product Catalog Alphabetic AA to AL Intermediates & Fine Chemicals Pharmaceuticals EMFLEX API