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Acemetacin

Product Name
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
Formula Weight
415.82
MOL File
53164-05-9.mol
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Acemetacin Property

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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

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

Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory.

Uses

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

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.

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View Lastest Price from Acemetacin manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Acemetacin 53164-05-9
Price
US $1.00-1.00/KG
Min. Order
1g
Purity
99%
Supply Ability
50tons
Release date
2020-04-29
Xiamen Wonderful Bio Technology Co., Ltd.
Product
acemetacin 53164-05-9
Price
US $66.00/KG
Min. Order
1250KG
Purity
99%
Supply Ability
330T
Release date
2023-07-21
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Acemetacin 53164-05-9
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98%min
Supply Ability
500kg
Release date
2021-09-30

53164-05-9, AcemetacinRelated Search:


  • (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
  • cemetacin
  • Acemetacin, 98%, COX inhibitor
  • Acemetacin:O-(1-p-Chlorobenzoyl-5-methoxy-2-methylindol-3-ylacetyl)glycolic acid
  • Acemetacin CRS
  • Acemetacin &gt
  • 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
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