ChemicalBook > CAS DataBase List > Carprofen

Carprofen

Product Name
Carprofen
CAS No.
53716-49-7
Chemical Name
Carprofen
Synonyms
c5720;imadyl;rimadyl;Ridamyl;Caroline;CARPROFEN;kanujofen;carprofeno;rac Carprofen;Carprofen CRS
CBNumber
CB0663159
Molecular Formula
C15H12ClNO2
Formula Weight
273.71
MOL File
53716-49-7.mol
More
Less

Carprofen Property

Melting point:
186-1880C
Boiling point:
509.1±35.0 °C(Predicted)
Density 
1.2011 (rough estimate)
refractive index 
1.5200 (estimate)
storage temp. 
Sealed in dry,2-8°C
solubility 
DMSO: soluble20mg/mL, clear
form 
powder
pka
4.84±0.30(Predicted)
color 
white to beige
Merck 
14,1862
InChI
InChI=1S/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)
InChIKey
PUXBGTOOZJQSKH-UHFFFAOYSA-N
SMILES
N1C2=C(C=C(Cl)C=C2)C2=C1C=C(C(C)C(O)=O)C=C2
CAS DataBase Reference
53716-49-7(CAS DataBase Reference)
EPA Substance Registry System
9H-Carbazole-2-acetic acid, 6-chloro-.alpha.-methyl- (53716-49-7)
More
Less

Safety

Hazard Codes 
T,Xn
Risk Statements 
25-36/37/38-20/21/22
Safety Statements 
45-36-26
RIDADR 
UN 2811
WGK Germany 
3
RTECS 
FE3180000
HazardClass 
6.1
PackingGroup 
III
HS Code 
29339900
Toxicity
LD50 orally in mice: 400 mg/kg (Berger, Corraz)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
33975
Product name
Carprofen
Purity
VETRANAL?, analytical standard
Packaging
100mg
Price
$119
Updated
2024/03/01
Sigma-Aldrich
Product number
1096699
Product name
Carprofen
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
C2701
Product name
Carprofen
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$82
Updated
2024/03/01
TCI Chemical
Product number
C2701
Product name
Carprofen
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$246
Updated
2024/03/01
Cayman Chemical
Product number
16409
Product name
Carprofen
Purity
≥98%
Packaging
1g
Price
$70
Updated
2024/03/01
More
Less

Carprofen Chemical Properties,Usage,Production

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

History

Carprofen has strong anti-inflammatory and analgesic activity. It has been used in human medicine for more than 10 years at doses of 150 to 600 mg per day. In human clinical trials, Carprofen was generally well tolerated. Most adverse reactions were transient and mild, such as gastrointestinal discomfort or pain and nausea. The incidence of side effects in humans is similar to that of aspirin and other NSAIDs. However, for commercial reasons, carprofen has been withdrawn from the market and is no longer available for human use.

Uses

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 .

Uses

antiinflammatory, analgesic

Uses

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

Mechanism of action

Carprofeng is a non-narcotic NSAID with analgesic and antipyretic properties. It acts in the same way as most NSAIDs in that Carprofeng acts by inhibiting cyclooxygenase (COX), which selectively inhibits COX-2, thereby inhibiting the release of several prostaglandins involved in the chronic inflammatory response that is thought to be present in canine OA.

Side effects

Common side effects of Carprofeng in dogs include vomiting, diarrhoea, loss of appetite, constipation, behavioural changes; and in severe cases, black stools, gastrointestinal ulcers and gastrointestinal haemorrhage, jaundice, skin changes, involuntary muscle movements, and kidney damage (increased thirst, increased urination, and refusal to eat).

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.

Carprofen Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Carprofen Suppliers

Americas 1 Belgium 1 Brazil 2 Canada 6 China 278 China Hong Kong 1 Czech Republic 2 Europe 4 France 3 Germany 8 India 44 Italy 4 Japan 2 Singapore 1 Switzerland 2 United Kingdom 17 United States 44 Uruguay 1 Global 421
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
HBCChem, Inc.
Tel
+1-510-219-6317
Fax
+1-650-486-1361
Email
sales@hbcchem.com
Country
United States
ProdList
10648
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
BOC Sciences
Tel
+1-631-485-4226
Fax
1-631-614-7828
Email
inquiry@bocsci.com
Country
United States
ProdList
19553
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
Olinax Inc.
Tel
--
Fax
--
Email
info@olinax.com
Country
United States
ProdList
404
Advantage
50
Cambrex Pharma & Biopharmaceuticals
Tel
--
Fax
--
Email
pharma@cambrex.com
Country
United States
ProdList
261
Advantage
75
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
API's, Inc. (d/b/a GDL International)
Tel
--
Fax
--
Email
marcy@gdlinternational.com
Country
United States
ProdList
11
Advantage
58
International Specialty Chemicals & Pharmaceuticals, Inc. (ISC&P)
Tel
--
Fax
--
Email
info@ischem.com
Country
United States
ProdList
77
Advantage
58
CHEMWERTH INC
Tel
--
Fax
--
Email
sales@chemwerth.com
Country
United States
ProdList
56
Advantage
58
Selleck Chemicals LLC
Tel
--
Fax
--
Email
sales@selleckchem.com
Country
United States
ProdList
1848
Advantage
58
American International Chemical LLC.
Tel
--
Fax
--
Email
info@aicma.com
Country
United States
ProdList
90
Advantage
58
SST Corporation
Tel
--
Fax
--
Email
info@sst-corp.com
Country
United States
ProdList
237
Advantage
38
Genegobio Inc.
Tel
--
Fax
--
Email
mark@genegobio.com
Country
United States
ProdList
195
Advantage
0
OChem Incorporation
Tel
--
Fax
--
Email
sales@ocheminc.com
Country
United States
ProdList
6501
Advantage
60
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Combi-Blocks Inc.
Tel
--
Fax
--
Email
sales@combi-blocks.com
Country
United States
ProdList
6618
Advantage
69
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
TCI America
Tel
--
Fax
--
Email
sales@tciamerica.com
Country
United States
ProdList
6909
Advantage
75
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
Ivy Fine Chemicals
Tel
--
Fax
--
Email
sales@ivychem.com
Country
United States
ProdList
6493
Advantage
58
Santa Cruz Biotechnology, Inc.
Tel
--
Fax
--
Email
scbt@scbt.com
Country
United States
ProdList
3597
Advantage
60
Selleck Chemicals LLC
Tel
--
Fax
--
Email
info@selleckchem.com
Country
United States
ProdList
824
Advantage
60
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
HBCChem Inc.
Tel
--
Fax
--
Email
sales@hbcchem-inc.com
Country
United States
ProdList
4569
Advantage
30
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
Medical Isotopes
Tel
--
Fax
--
Email
stohler@medicalisotopes.com
Country
United States
ProdList
6181
Advantage
68
ACIC Fine Chemicals Inc.
Tel
--
Fax
--
Email
sales@acic.com
Country
United States
ProdList
492
Advantage
48
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
APAC Pharmaceutical, LLC
Tel
--
Fax
--
Email
sales@apacpharma.com
Country
United States
ProdList
6322
Advantage
38
ChemPacific Corporation
Tel
--
Fax
--
Email
sales@chempacific.com
Country
United States
ProdList
6891
Advantage
51
American Custom Chemicals Corporation
Tel
--
Fax
--
Email
sales@acccorporation.com
Country
United States
ProdList
6820
Advantage
51
BOSCHE SCIENTIFIC, LLC
Tel
--
Fax
--
Email
Sales@BoscheSci.com
Country
United States
ProdList
6477
Advantage
55
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
More
Less

View Lastest Price from Carprofen manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Carprofen 53716-49-7
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98.5% ~101.5%; EP8.0
Supply Ability
800kg/month
Release date
2021-06-03
Hebei Weibang Biotechnology Co., Ltd
Product
Carprofen 53716-49-7
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-19
Hebei Yanxi Chemical Co., Ltd.
Product
Carprofen 53716-49-7
Price
US $100.00/Kg/Drum
Min. Order
1KG
Purity
99%
Supply Ability
10tons/month
Release date
2020-08-27

53716-49-7, CarprofenRelated Search:

α-Lipoic Acid Ethyl chloroacetate Methyl chloroacetate Fluroxypyr Ethyl 2-(Chlorosulfonyl)acetate Chloroacetic acid Acetic anhydride Difluorochloromethane 5-Chloroindole 6-Methylindole Carprofen, Vetranal Phenylacetic acid Carprofen Related Compound A Ibuprofen Carbazole 6-ISOPROPYLINDOLE 97 1-(6-Chloro-9H-carbazol-2-yl)ethanone (Carprofen Impurity) 1H-Indole-6-aceticacid(9CI)

  • 6-CHLORO-ALPHA-METHYL-9H-CARBAZOLE-2-ACETIC ACID
  • (+/-)-6-chloro-alpha-methylcarbazole-2-acetic acid
  • CARPROFEN
  • 2-(6-chloro-9H-carbazol-2-yl)propanoic acid
  • methylcarbazole-2-acetic acid
  • Carprofen,6-Chloro-α-methyl-9H-carbazole-2-acetic acid
  • Carprofen (200 mg)
  • Carprofen (200 mg) (AS)
  • rac Carprofen
  • (dl)-6-Chloro-α-Methylcarbazole- 2-acetic Acid
  • 9H-Carbazole-2-acetic acid, 6-chloro-α-methyl-
  • Carprofen Solution, 100ppm
  • Carprofen, >=98%
  • 33975 - VETRANAL, analytical standard
  • Carprofen, 98%, a COX2 inhibitor
  • kanujofen
  • Ro-20-5720/000
  • 6-Chloro-a-methyl-9H-carbazole-2-acetic Acid
  • 6-Chloro-α-methylcarbazole-2-acetic acid
  • 9H-Carbazole-2-acetic acid, 6-chloro-.alpha.-methyl-
  • 6-chloro-α-methyl-9h-carbazole-2-acetic acid
  • (+-)-9h-carbazole-2-aceticaci
  • c5720
  • carprofeno
  • dl-6-chloro-alpha-methylcarbazole-2-aceticacid
  • imadyl
  • rimadyl
  • D-(+)-GLUCOSE SOLUTION (45%) CELL*CULTUR E TESTED
  • Caroline
  • Carprofen Standard
  • Carprofen CRS
  • Carprofen for system suitability CRS
  • Carprofen &gt
  • Ridamyl
  • (2RS)-2-(6-Chloro-9H-carbazol-2-yl)propanoic acid
  • 2-(6-chloro-9H-carbazol-2-yl)-3,3,3-trideuteriopropanoic acid
  • Carprofen USP/EP/BP
  • Carprofen-13C,d3
  • Carprofen (Y0000846)
  • CarprofenQ: What is Carprofen Q: What is the CAS Number of Carprofen
  • (+/-)-6-chloro-alpha-methylcarbazole-2-acetic acid
  • Carprofen (1096699)
  • chloro-alpha-methylcarbazole
  • 2-(6-Chloro-carbazol-2-yl)-propionic acid
  • Pregabalin Impurity 87
  • Carprofen EP/USP
  • Ridamyl|||Imadyl|||Rimadyl
  • Carprofen in methanol
  • C11045850 Carprofen
  • 53716-49-7
  • 3716-49-7
  • C15H12ClNO2
  • API
  • RIMADYL
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Active Pharmaceutical Ingredients
  • Heterocycles