53716-49-7 Usage
Description
Carprofen is a non-steroidal anti-inflammatory drug (NSAID) commonly used in animals to combat pain and inflammation, particularly as associated with osteoarthritis. Like many NSAIDs, carprofen inhibits both cyclooxygenases COX-1 and COX-2 (IC50s = 22.3 and 3.9 μM, respectively). It also inhibits fatty acid amide hydrolase (IC50 = 74 μM), blocking the metabolism of the cannabinoid receptor ligand, arachidonoyl ethanolamide .
Chemical Properties
Off-White Crystalline Solid
Originator
Imadyl,Roche,Switz.,1981
Uses
Different sources of media describe the Uses of 53716-49-7 differently. You can refer to the following data:
1. Carprofen is a non-steroidal anti-inflammatory drug (NSAID) commonly used in animals to combat pain and inflammation, particularly as associated with osteoarthritis. Like many NSAIDs, carprofen inhibits both cyclooxygenases COX-1 and COX-2 (IC50s = 22.3 and 3.9 μM, respectively). It also inhibits fatty acid amide hydrolase (IC50 = 74 μM), blocking the metabolism of the cannabinoid receptor ligand, arachidonoyl ethanolamide .
2. antiinflammatory, analgesic
3. Carprofen is a non steroidal anti-inflammatory that is used by veterinarians for the relief of arthritic systems in dogs. It can be used for joint pain or post operative inflammation. Carprofen, is al
so used for the relief from pain and inflammation associated with osteoarthritis, hip dysplasia and other joint issues.
Definition
ChEBI: Propanoic acid in which one of the methylene hydrogens is substituted by a 6-chloro-9H-carbazol-2-yl group. A non-steroidal anti-inflammatory drug, it is no longer used in human medicine but is still used for treatment of arthritis in elderly dogs.
Manufacturing Process
A mixture of 34.9 g of 6-chloro-α-methyl-1,2,3,4-tetrahydrocarbazole-2-acetic
acid ethyl ester (mixture of diastereomers), 350 ml CP xylene and 56.0 g of
p-chloranil was stirred and heated under an atmosphere of dry nitrogen. The
reaction flask was wrapped in aluminum foil in order to keep out any
extraneous light. After the reaction mixture had stirred at reflux temperature
for 6 hours, heating and stirring were stopped and the reaction mixture was
left overnight at room temperature. The supernatant liquid was decanted through a filter. The residue was triturated with 100 ml of warm benzene and
the supernatant liquid was decanted through a filter. This process was
repeated three more times. Ether (300 ml) was added to the combined
filtrates. The solution was extracted with cold 2 N sodium hydroxide (3 x 100
ml), washed by extraction with water until neutral and dried over anhydrous
magnesium sulfate. Following filtration of the desiccant and evaporation of the
solvent, a residue of 35.5 g remained. Crystallization from 50 ml of methanol
gave 14.8 g of 6-chloro-α-methylcarbazole-2-acetic acid ethyl ester, MP 106°-
107.5°C (43.2%).A stirred mixture of 11 g of 6-chloro-α-methylcarbazole-2-acetic acid ethyl
ester, 100 ml ethanol and 100 ml of 3 N sodium hydroxide was heated (N2
atmosphere). After 2 hours at reflux, the reaction mixture was concentrated
to dryness under reduced pressure. Water (300 ml) and ice (200 g) were
added to the residue and concentrated hydrochloric acid was added until the
mixture was strongly acid. The acidic mixture was extracted with ether (3 x
200 ml). The ether extracts were combined, washed by extraction with water
(3 x 100 ml) and dried over anhydrous magnesium sulfate. Following filtration
of the desiccant and evaporation of the solvent, a yield of 9.89 (98.2%) was
obtained. Crystallization from CHCl3 yielded 6.2 g (62.0%) of 6-chloro-α-
methylcarbazole-2-acetic acid, MP 197°-198°C. A second crop of 1.6 g, MP
195°-199°C was obtained from the mother liquors.
Therapeutic Function
Antiinflammatory
Veterinary Drugs and Treatments
Carprofen is labeled (in the USA) for the relief of pain and inflammation
in dogs. It may also prove to be of benefit in other species as
well, but data is scant to support its safety beyond very short-term
use at this time. In Europe, carprofen is reportedly registered for
single dose use in cats, but there have been reported problems (e.g.,
vomiting) with cats receiving more than a single dose.
Carprofen is being investigated for antineoplastic effects in dogs
and may be a useful adjunctive treatment for some types of tumors
with COX-2 overexpression.
Check Digit Verification of cas no
The CAS Registry Mumber 53716-49-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,7,1 and 6 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 53716-49:
(7*5)+(6*3)+(5*7)+(4*1)+(3*6)+(2*4)+(1*9)=127
127 % 10 = 7
So 53716-49-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H12ClNO2/c1-8(15(18)19)9-2-4-11-12-7-10(16)3-5-13(12)17-14(11)6-9/h2-8,17H,1H3,(H,18,19)
53716-49-7Relevant articles and documents
Electrochemical Synthesis of Carbazoles by Dehydrogenative Coupling Reaction
Kehl, Anton,Schupp, Niclas,Breising, Valentina M.,Schollmeyer, Dieter,Waldvogel, Siegfried R.
, p. 15847 - 15851 (2020/11/02)
A constant current protocol, employing undivided cells, a remarkably low supporting electrolyte concentration, inexpensive electrode materials, and a straightforward precursor synthesis enabling a novel access to N-protected carbazoles by anodic N,C bond formation using directly generated amidyl radicals is reported. Scalability of the reaction is demonstrated and an easy deblocking of the benzoyl protecting group is presented.
Carprofen and its intermediate synthesis method
-
, (2019/06/05)
A synthesis of carprofen, (1) 2 - (3 - bromo - 4 - chlorophenyl) propionic acid and P-nitro aniline reaction, formula C - 1 as shown in the; (2) Type C - 1 as shown in the compound is subjected to reduction reaction, formula C - 2 as shown in the; (3) Type C - 2 shown compound is subjected to diazotization reaction, preparation formula B - 3 as shown in the and by-product B - 31 shown compound mixture; (4) Type B - 3 and the product of a compound represented by B - 31 shown compound mixture through processing formula B - 3 illustrated compound; (5) Type B - 3 as shown in the reaction shown in formula A carprofen;
Carprofen and its intermediate synthesis method
-
, (2019/06/05)
A synthesis of carprofen, comprising the following steps: (1) 2 - (3 - chloro - 4 - nitrophenyl) propionic acid and to P-chloroaniline reaction, formula A - 1 as shown in the; (2) Type A - 1 shown compound is subjected to reduction reaction, formula A - 2 illustrated compound; (3) Type A - 2 shown through the diazo coupling reaction compound, a compound represented by formula A preparation, and by-product A - 3 illustrated compound; (4) Steps (3) to obtain the compound of formula A shown and by-product A - 3 shown compound mixture through purification treatment, to obtain not comprising by-product A - 3 of formula A shown carprofen.
