Carprofen | CAS#53716-49-7 | Anti-inflammatory Drug

MedKoo Cat#: 317375 | Name: Carprofen

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Carprofen is a non-steroidal anti-inflammatory drug that veterinarians prescribe as a supportive treatment for various conditions. It provides day-to-day treatment for pain and inflammation from arthritis in geriatric dogs, joint pain, osteoarthritis, hip dysplasia, and other forms of joint deterioration. It is also used to relieve short-term post-operative pain, inflammation, and swelling after spaying, neutering, and other procedures. Carprofen reduces inflammation by inhibition of COX-2 and other sources of inflammatory prostaglandins. This is targeted protection, in that it does not interfere with COX-1 activity.

Chemical Structure

Carprofen

CAS#53716-49-7

Theoretical Analysis

MedKoo Cat#: 317375

Name: Carprofen

CAS#: 53716-49-7

Chemical Formula: C15H12ClNO2

Exact Mass: 273.0557

Molecular Weight: 273.71

Elemental Analysis: C, 65.82; H, 4.42; Cl, 12.95; N, 5.12; O, 11.69

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 650.00	2 Weeks
10g	USD 950.00	2 Weeks

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Synonym

Carprofen; Imadyl; Rimadyl; Ridamyl; Ro 20-5720; Ro 205720; C 5720; Imadyl; quellin; Novox; Imafen; Rovera;

IUPAC/Chemical Name

2-(6-chloro-9H-carbazol-2-yl)propanoic acid

InChi Key

PUXBGTOOZJQSKH-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

CC(C1=CC2=C(C=C1)C3=C(N2)C=CC(=C3)Cl)C(=O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Carprofen is a nonsteroid anti-inflammatory agent, acts as a multi-target FAAH/COX inhibitor, with IC50s of 3.9 μM, 22.3 μM and 78.6 μM for COX-2, COX-1 and FAAH, respectively.

In vitro activity:

Cytoprotective effects of NSAIDs were dependent on the extent of SNP-induced apoptosis and were greatest in CCL and CaCL cell cultures with moderate SNP-induced cytotoxic effects. Preincubation with an NSAID improved cell viability by 15% to 45% when CCL and CaCL cells were subsequently incubated with SNP. Carprofen (10 μg/mL) had the greatest cytoprotective effects for CCL and CaCL cells. Incubation with NSAIDs resulted in a nonsignificant decrease in PGE(2) production from SNP-damaged cells. Reference: Am J Vet Res. 2012 Nov;73(11):1752-8. https://avmajournals.avma.org/doi/10.2460/ajvr.73.11.1752?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed

In vivo activity:

Traumatic brain injury (TBI) initiates acute and chronic inflammatory processes involving cyclooxygenase-2 (COX-2), which may have detrimental effects on outcome and especially on brain regeneration. Therefore carprofen, a COX-2 inhibitor, was studied for whether it would improve outcome and increase neurogenesis after TBI. TBI was induced in Sabra mice that were then treated with vehicle or carprofen for 7 days. Functional outcome was evaluated with the Neurological Severity Score (NSS).Cytokine levels were assessed 4 h post-TBI and water content was measured 24 h post TBI. Mice were given BrdU to label newborn cells for 10 days. The animals were killed 90 days post-TBI and the lesion size as well as newborn cell fate were assessed. Carprofen significantly reduced lesion size (p=0.002), decreased water content in the lesioned cortex (p=0.03), reduced the number of microglia in the lesioned cortex (p<0.0001), and lowered the levels of proinflammatory cytokines (IL-1β, p=0.03; IL-6, p=0.02). Carprofen led to significantly larger improvements in functional outcome (p≤0.008) which were durable over 90 days. Carprofen also induced a threefold increase in the proliferation of new cells in the peri-lesion area (p≤0.002), but newborn cells differentiated mainly into glia in both groups. Carprofen is neuroprotective and induces cell proliferation and gliogenesis after TBI. Treatment with carprofen is consistently associated with better functional outcome. Our results imply that anti-inflammatory drugs may represent novel therapeutic options for TBI. Reference: J Neurotrauma. 2012 Jan 20;29(2):375-84. https://www.liebertpub.com/doi/10.1089/neu.2010.1673?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%20%200pubmed

	Solvent	mg/mL	mM
Solubility
	DMSO	55.0	200.94
	Ethanol	55.0	200.94

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 273.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

In vitro protocol:

1. Waldherr K, Zurbriggen A, Spreng DE, Forterre S. In vitro cytoprotective effects of acetylsalicylic acid, carprofen, meloxicam, or robenacoxib against apoptosis induced by sodium nitroprusside in canine cruciate ligament cells. Am J Vet Res. 2012 Nov;73(11):1752-8. doi: 10.2460/ajvr.73.11.1752. PMID: 23106460.

In vivo protocol:

1. Thau-Zuchman O, Shohami E, Alexandrovich AG, Trembovler V, Leker RR. The anti-inflammatory drug carprofen improves long-term outcome and induces gliogenesis after traumatic brain injury. J Neurotrauma. 2012 Jan 20;29(2):375-84. doi: 10.1089/neu.2010.1673. Epub 2011 Aug 29. PMID: 21561314.

1: Tang M, Guo Y, Gao Y, Tang C, Dang X, Zhou Z, Sun Y, Wang K. Albumin's Influence on Carprofen Enantiomers-Hymecromone Interaction. Chirality. 2015 Dec 28. doi: 10.1002/chir.22562. [Epub ahead of print] PubMed PMID: 26708612. 2: Messenger KM, Wofford JA, Papich MG. Carprofen pharmacokinetics in plasma and in control and inflamed canine tissue fluid using in vivo ultrafiltration. J Vet Pharmacol Ther. 2016 Feb;39(1):32-9. doi: 10.1111/jvp.12233. Epub 2015 May 10. PubMed PMID: 25958925. 3: Fang ZZ, Wang H, Cao YF, Sun DX, Wang LX, Hong M, Huang T, Chen JX, Zeng J. Enantioselective inhibition of carprofen towards UDP-glucuronosyltransferase (UGT) 2B7. Chirality. 2015 Mar;27(3):189-93. doi: 10.1002/chir.22412. Epub 2014 Dec 12. PubMed PMID: 25502512. 4: Euppayo T, Siengdee P, Buddhachat K, Pradit W, Viriyakhasem N, Chomdej S, Ongchai S, Harada Y, Nganvongpanit K. Effects of low molecular weight hyaluronan combined with carprofen on canine osteoarthritis articular chondrocytes and cartilage explants in vitro. In Vitro Cell Dev Biol Anim. 2015 Sep;51(8):857-65. doi: 10.1007/s11626-015-9908-9. Epub 2015 May 16. PubMed PMID: 25982358. 5: Koenigshof AM, Beal MW, Poppenga RH, Jutkowitz LA. Effect of sorbitol, single, and multidose activated charcoal administration on carprofen absorption following experimental overdose in dogs. J Vet Emerg Crit Care (San Antonio). 2015 Sep-Oct;25(5):606-10. doi: 10.1111/vec.12305. Epub 2015 Apr 16. PubMed PMID: 25891141. 6: Snow LA, McConnico RS, Morgan TW, Hartmann E, Davidson JR, Hosgood G. Carprofen-induced oxidative stress in mitochondria of the colonic mucosa of the dog. Can J Vet Res. 2014 Jul;78(3):183-92. PubMed PMID: 24982549; PubMed Central PMCID: PMC4068409. 7: Kalchofner Guerrero KS, Schwarz A, Wuhrmann R, Feldmann S, Hartnack S, Bettschart-Wolfensberger R. Comparison of a new metamizole formulation and carprofen for extended post-operative analgesia in dogs undergoing ovariohysterectomy. Vet J. 2015 Apr;204(1):99-104. doi: 10.1016/j.tvjl.2015.01.028. Epub 2015 Feb 7. PubMed PMID: 25744803. 8: Delgado C, Bentley E, Hetzel S, Smith LJ. Comparison of carprofen and tramadol for postoperative analgesia in dogs undergoing enucleation. J Am Vet Med Assoc. 2014 Dec 15;245(12):1375-81. doi: 10.2460/javma.245.12.1375. PubMed PMID: 25459482; PubMed Central PMCID: PMC4378264. 9: Luna SP, Martino ID, Lorena SE, Capua ML, Lima AF, Santos BP, Brondani JT, Vesce G. Acupuncture and pharmacopuncture are as effective as morphine or carprofen for postoperative analgesia in bitches undergoing ovariohysterectomy. Acta Cir Bras. 2015 Dec;30(12):831-7. doi: 10.1590/S0102-865020150120000007. PubMed PMID: 26735055. 10: Szweda M, Szarek J, Dublan K, Męcik-Kronenberg T, Kiełbowicz Z, Bigoszewski M. Effect of mucoprotective plant-derived therapies on damage to colonic mucosa caused by carprofen and robenacoxib administered to healthy dogs for 21 days. Vet Q. 2014;34(4):185-93. doi: 10.1080/01652176.2014.968939. Epub 2014 Oct 20. PubMed PMID: 25330194. 11: Payne-Johnson M, Becskei C, Chaudhry Y, Stegemann MR. Comparative efficacy and safety of mavacoxib and carprofen in the treatment of canine osteoarthritis. Vet Rec. 2015 Mar 14;176(11):284. doi: 10.1136/vr.102397. Epub 2014 Nov 27. PubMed PMID: 25433056; PubMed Central PMCID: PMC4392193. 12: Fishback JE, Stronsky SM, Green CA, Bean KD, Froude JW. Antibody production in rabbits administered Freund's complete adjuvant and carprofen concurrently. Lab Anim (NY). 2016 Jan 27;45(2):63-6. doi: 10.1038/laban.937. PubMed PMID: 26814352. 13: Sidler M, Fouché N, Meth I, von Hahn F, von Rechenberg B, Kronen PW. Preliminary study on carprofen concentration measurements after transcutaneous treatment with Vetdrop® in a microfracture joint defect model in sheep. BMC Vet Res. 2014 Dec 9;10:268. doi: 10.1186/s12917-014-0268-6. PubMed PMID: 25488522; PubMed Central PMCID: PMC4263071. 14: Parra A, Clares B, Rosselló A, Garduño-Ramírez ML, Abrego G, García ML, Calpena AC. Ex vivo permeation of carprofen from nanoparticles: A compressive study through human, porcine and bovine skin as anti-inflammatory agent. Int J Pharm. 2016 Jan 27. pii: S0378-5173(16)30056-4. doi: 10.1016/j.ijpharm.2016.01.056. [Epub ahead of print] PubMed PMID: 26826569. 15: Marini D, Pippia J, Colditz IG, Hinch G, Petherick JC, Lee C. Randomised trial of the bioavailability and efficacy of orally administered flunixin, carprofen and ketoprofen in a pain model in sheep. Aust Vet J. 2015 Aug;93(8):265-70. doi: 10.1111/avj.12351. PubMed PMID: 26220318. 16: Ingrao JC, Johnson R, Tor E, Gu Y, Litman M, Turner PV. Aqueous stability and oral pharmacokinetics of meloxicam and carprofen in male C57BL/6 mice. J Am Assoc Lab Anim Sci. 2013 Sep;52(5):553-9. PubMed PMID: 24041210; PubMed Central PMCID: PMC3784660. 17: Brentnall C, Cheng Z, McKellar QA, Lees P. Influence of oxytetracycline on carprofen pharmacodynamics and pharmacokinetics in calves. J Vet Pharmacol Ther. 2013 Aug;36(4):320-8. doi: 10.1111/jvp.12000. Epub 2012 Aug 23. PubMed PMID: 22913421. 18: Zhou X, Zhao X, Wang Y, Wu B, Shen J, Li L, Li Q. Eu(III) and Tb(III) complexes with the nonsteroidal anti-inflammatory drug carprofen: synthesis, crystal structure, and photophysical properties. Inorg Chem. 2014 Dec 1;53(23):12275-82. doi: 10.1021/ic501252x. Epub 2014 Nov 17. PubMed PMID: 25402730. 19: Torres A, Chagas E Silva J, Diniz P, Lopes-da-Costa L. Evaluation of treatments with hCG and carprofen at embryo transfer in a demi-embryo and recipient virgin heifer model. Animal. 2013 Aug;7(8):1317-22. doi: 10.1017/S1751731113000426. Epub 2013 Mar 14. PubMed PMID: 23506998. 20: Parra A, Mallandrich M, Clares B, Egea MA, Espina M, García ML, Calpena AC. Design and elaboration of freeze-dried PLGA nanoparticles for the transcorneal permeation of carprofen: Ocular anti-inflammatory applications. Colloids Surf B Biointerfaces. 2015 Dec 1;136:935-43. doi: 10.1016/j.colsurfb.2015.10.026. Epub 2015 Oct 26. PubMed PMID: 26551871.