WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H558284
CAS#: 181695-72-7
Description: Valdecoxib, also known as SC-65872, is a non-steroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, and painful menstruation and menstrual symptoms. It is a selective cyclooxygenase-2 inhibitor. It was approved in 2001 to treat arthritis and menstrual cramps. It was withdraw in 2005.
Hodoodo Cat#: H558284
Name: Valdecoxib
CAS#: 181695-72-7
Chemical Formula: C16H14N2O3S
Exact Mass: 314.07
Molecular Weight: 314.359
Elemental Analysis: C, 61.13; H, 4.49; N, 8.91; O, 15.27; S, 10.20
Synonym: SC-65872; SC65872; SC 65872; Valdecoxib; Bextra
IUPAC/Chemical Name: 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide
InChi Key: LNPDTQAFDNKSHK-UHFFFAOYSA-N
InChi Code: InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
SMILES Code: CC1=C(C2=CC=C(S(N)(=O)=O)C=C2)C(C3=CC=CC=C3)=NO1
Appearance: White to off-white 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
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:
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The following data is based on the product molecular weight 314.36 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: | |
| In vivo protocol: |
1: Inan Genç A, Gok S, Banerjee S, Severcan F. Valdecoxib Recovers the Lipid Composition, Order and Dynamics in Colon Cancer Cell Lines Independent of COX-2 Expression: An ATR-FTIR Spectroscopy Study. Appl Spectrosc. 2016 Jun 27. pii: 0003702816654164. [Epub ahead of print] PubMed PMID: 27354402.
2: Liu M, Yu Q, Li P, Zhu M, Fang M, Sun B, Sun M, Sun Y, Zhang P, He Z, Sun J, Wang Y, Liu X. Simultaneous determination of parecoxib sodium and its active metabolite valdecoxib in rat plasma by UPLC-MS/MS and its application to a pharmacokinetic study after intravenous and intramuscular administration. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Jun 1;1022:220-9. doi: 10.1016/j.jchromb.2016.04.009. Epub 2016 Apr 6. PubMed PMID: 27107851.
3: Dong KY, Qin HT, Bao XX, Liu F, Zhu C. Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin. Org Lett. 2014 Oct 17;16(20):5266-8. doi: 10.1021/ol502246t. Epub 2014 Sep 25. PubMed PMID: 25255195.
4: Kim TW, Vercelli C, Briganti A, Re G, Giorgi M. The pharmacokinetics and in vitro/ex vivo cyclooxygenase selectivity of parecoxib and its active metabolite valdecoxib in cats. Vet J. 2014 Oct;202(1):37-42. doi: 10.1016/j.tvjl.2014.07.025. Epub 2014 Jul 30. PubMed PMID: 25135338.
5: Hu H, Jing X, Zou X, Wu J. [Role of cyclooxygenase 2 and its inhibitor valdecoxib in liver fibrosis]. Zhonghua Yi Xue Za Zhi. 2014 Mar 18;94(10):784-7. Chinese. PubMed PMID: 24844967.
6: Wiktorowska-Owczarek A. The effect of valdecoxib on the production of growth factors evoked by hypoxia and bacterial lipopolysaccharide in HMEC-1 cells. Adv Clin Exp Med. 2013 Nov-Dec;22(6):795-800. PubMed PMID: 24431307.
7: Millington E. Death related to Ibuprofen, valdecoxib, and medical errors: case report and medicolegal issues. J Occup Environ Med. 2013 Dec;55(12):1383. doi: 10.1097/JOM.0000000000000022. PubMed PMID: 24316721.
8: Bartzatt R. Drug analogs of COX-2 selective inhibitors lumiracoxib and valdecoxib derived from in silico search and optimization. Antiinflamm Antiallergy Agents Med Chem. 2014 Mar;13(1):17-28. PubMed PMID: 23984829.
9: Encinas MV, Lissi E, Vergara C. Association of valdecoxib, a nonsteroidal anti-inflammatory drug, with human serum albumin. Photochem Photobiol. 2013 Nov-Dec;89(6):1399-405. doi: 10.1111/php.12158. Epub 2013 Sep 16. PubMed PMID: 23952101.
10: Lohiya GS, Lohiya P, Krishna V, Lohiya S. Death related to Ibuprofen, valdecoxib, and medical errors: case report and medicolegal issues. J Occup Environ Med. 2013 Jun;55(6):601-3. doi: 10.1097/JOM.0b013e3182972ecf. PubMed PMID: 23743867.
11: Atukorala I, Hunter DJ. Valdecoxib : the rise and fall of a COX-2 inhibitor. Expert Opin Pharmacother. 2013 Jun;14(8):1077-86. doi: 10.1517/14656566.2013.783568. Epub 2013 Mar 22. Review. PubMed PMID: 23517091.
12: Hullett B, Salman S, O'Halloran SJ, Peirce D, Davies K, Ilett KF. Development of a population pharmacokinetic model for parecoxib and its active metabolite valdecoxib after parenteral parecoxib administration in children. Anesthesiology. 2012 May;116(5):1124-33. doi: 10.1097/ALN.0b013e31825154ef. PubMed PMID: 22450476.
13: Paech MJ, Salman S, Ilett KF, O'Halloran SJ, Muchatuta NA. Transfer of parecoxib and its primary active metabolite valdecoxib via transitional breastmilk following intravenous parecoxib use after cesarean delivery: a comparison of naive pooled data analysis and nonlinear mixed-effects modeling. Anesth Analg. 2012 Apr;114(4):837-44. doi: 10.1213/ANE.0b013e3182468fa7. Epub 2012 Feb 17. PubMed PMID: 22344242.
14: Saccomanni G, Giorgi M, Del Carlo S, Manera C, Saba A, Macchia M. Simultaneous detection and quantification of parecoxib and valdecoxib in canine plasma by HPLC with spectrofluorimetric detection: development and validation of a new methodology. Anal Bioanal Chem. 2011 Sep;401(5):1677-84. doi: 10.1007/s00216-011-5244-4. Epub 2011 Jul 19. PubMed PMID: 21769548.
15: Thakral NK, Ray AR, Bar-Shalom D, Eriksson AH, Majumdar DK. The quest for targeted delivery in colon cancer: mucoadhesive valdecoxib microspheres. Int J Nanomedicine. 2011;6:1057-68. doi: 10.2147/IJN.S19561. Epub 2011 May 19. PubMed PMID: 21720517; PubMed Central PMCID: PMC3124854.
16: Schröder H, Höllt V, Becker A. Parecoxib and its metabolite valdecoxib directly interact with cannabinoid binding sites in CB1-expressing HEK 293 cells and rat brain tissue. Neurochem Int. 2011 Jan;58(1):9-13. doi: 10.1016/j.neuint.2010.10.018. Epub 2010 Nov 10. PubMed PMID: 21073910.
17: Dadiboyena S, Nefzi A. Recent methodologies toward the synthesis of valdecoxib: a potential 3,4-diarylisoxazolyl COX-II inhibitor. Eur J Med Chem. 2010 Nov;45(11):4697-707. doi: 10.1016/j.ejmech.2010.07.045. Epub 2010 Aug 6. Review. PubMed PMID: 20724040; PubMed Central PMCID: PMC3263766.
18: Bhatia V, Ahuja V, Acharya SK, Garg PK. A randomized controlled trial of valdecoxib and glyceryl trinitrate for the prevention of post-ERCP pancreatitis. J Clin Gastroenterol. 2011 Feb;45(2):170-6. doi: 10.1097/MCG.0b013e3181eb600e. PubMed PMID: 20717044.
19: Havemeyer A, Grünewald S, Wahl B, Bittner F, Mendel R, Erdélyi P, Fischer J, Clement B. Reduction of N-hydroxy-sulfonamides, including N-hydroxy-valdecoxib, by the molybdenum-containing enzyme mARC. Drug Metab Dispos. 2010 Nov;38(11):1917-21. doi: 10.1124/dmd.110.032813. Epub 2010 Aug 10. PubMed PMID: 20699408.
20: Thakral NK, Ray AR, Majumdar DK. Eudragit S-100 entrapped chitosan microspheres of valdecoxib for colon cancer. J Mater Sci Mater Med. 2010 Sep;21(9):2691-9. doi: 10.1007/s10856-010-4109-2. Epub 2010 Jun 10. PubMed PMID: 20535630.
