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MedKoo Cat#: 565263 | Name: Flumethasone 21-acetate

Description:

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

Flumethasone 21-acetate is an anti-inflammatory corticosteroid.

Chemical Structure

Flumethasone 21-acetate
Flumethasone 21-acetate
CAS#2823-42-9 (acetate)

Theoretical Analysis

MedKoo Cat#: 565263

Name: Flumethasone 21-acetate

CAS#: 2823-42-9 (acetate)

Chemical Formula: C24H30F2O6

Exact Mass: 452.2010

Molecular Weight: 452.49

Elemental Analysis: C, 63.71; H, 6.68; F, 8.40; O, 21.21

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Related CAS #
2135-17-3 (free acid) 2823-42-9 (acetate) 2002-29-1 (pivalate)
Synonym
Flumethasone 21-acetate; Flumethasone acetate; Flumethasone-17-acetate; Flumetasone acetate
IUPAC/Chemical Name
2-((6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
InChi Key
ISSQQUKLQJHHOR-OSNGSNEUSA-N
InChi Code
InChI=1S/C24H30F2O6/c1-12-7-15-16-9-18(25)17-8-14(28)5-6-21(17,3)23(16,26)19(29)10-22(15,4)24(12,31)20(30)11-32-13(2)27/h5-6,8,12,15-16,18-19,29,31H,7,9-11H2,1-4H3/t12-,15+,16+,18+,19+,21+,22+,23+,24+/m1/s1
SMILES Code
CC(OCC([C@@]1(O)[C@H](C)C[C@@]2([H])[C@]3([H])C[C@H](F)C4=CC(C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C)=O)=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
Shelf Life
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 452.49 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.

Recalculate based on batch purity %
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
1: Zhou Y, Zhou Y, Wang K, Li T, Yang M, Wang R, Chen Y, Cao M, Hu R. Flumethasone enhances the efficacy of chemotherapeutic drugs in lung cancer by inhibiting Nrf2 signaling pathway. Cancer Lett. 2020 Apr 1;474:94-105. doi: 10.1016/j.canlet.2020.01.010. Epub 2020 Jan 16. PMID: 31954771. 2: Sternbauer K, Luthman J, Jacobsson SO. Flumethasone-induced insulin resistance in calves. Zentralbl Veterinarmed A. 1998 Sep;45(6-7):441-3. doi: 10.1111/j.1439-0442.1998.tb00846.x. PMID: 9793474. 3: Flumethasone pivalate (Locorten). Anti-inflammatory, antipruritic. Clin Pharmacol Ther. 1970 Nov-Dec;11(6):927-9. doi: 10.1002/cpt1970116927. PMID: 5481576. 4: Finley AG, Gunther WW. Flumethasone pivalate ("locacorten"), a new topical corticosteroid. Med J Aust. 1965 Nov 6;2(19):787-90. doi: 10.5694/j.1326-5377.1965.tb19272.x. PMID: 5852207. 5: Panaretto BA, Wallace AL. The administration of flumethasone, by three different routes, its measurement in the plasma and some effects on wool growth in Merino wethers. Aust J Biol Sci. 1978 Dec;31(6):601-19. doi: 10.1071/bi9780601. PMID: 754682. 6: Blake RL. Flumethasone induction of liver tyrosine aminotransferase activity in inbred strains and obese mutant mice. Biochem Pharmacol. 1970 May;19(5):1803-15. doi: 10.1016/0006-2952(70)90174-7. PMID: 4398019. 7: Carr RD, Wieland RG. Adrenocortical suppression with topical flumethasone. Arch Dermatol. 1967 Sep;96(3):269-72. PMID: 6038752. 8: Hojyo T. Combination dermatological products: a comparison of betamethasone dipropionate/clotrimazole/gentamicin sulphate and flumethasone pivalate/clioquinol creams. J Int Med Res. 1987 Sep-Oct;15(5):255-63. doi: 10.1177/030006058701500501. PMID: 2960577. 9: Willi RA, Salgueiro-González N, Faltermann S, Hettich T, Fent K. Environmental glucocorticoids corticosterone, betamethasone and flumethasone induce more potent physiological than transcriptional effects in zebrafish embryos. Sci Total Environ. 2019 Jul 1;672:183-191. doi: 10.1016/j.scitotenv.2019.03.426. Epub 2019 Mar 28. PMID: 30954817. 10: Brambilla G, Buiarelli F, Cartoni GP, Coccioli F, Colamonici C, Fagiolo A, Giannini C, Neri B. Determination of flumethasone in calf urine and serum by liquid chromatography-tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 May 5;755(1-2):265-78. doi: 10.1016/s0378-4347(01)00122-0. PMID: 11393713. 11: Reding J, Sahin A, Schlatter J, Naegeli H. Dexamethasone and flumethasone residues in milk of intramuscularly dosed cows. J Vet Pharmacol Ther. 1997 Jun;20(3):198-203. doi: 10.1111/j.1365-2885.1997.tb00095.x. PMID: 9185085. 12: A Sayed R, Mohamed AR, Hassan WS, Elmasry MS. Comparative study of novel green UV-spectrophotometric platforms for simultaneous rapid analysis of flumethasone pivalate and clioquinol in their combined formulation. Drug Dev Ind Pharm. 2021 Jun;47(6):867-877. doi: 10.1080/03639045.2021.1908341. Epub 2021 Jul 5. PMID: 34224277. 13: Lodge BA, Vincent A. Analysis of flumethasone pivalate formulations by high- performance liquid chromatography. J Chromatogr. 1984 Oct 5;301(2):477-80. doi: 10.1016/s0021-9673(01)89223-2. PMID: 6501501. 14: Abdel-Aleem EA, Hegazy MA, Sayed NW, Abdelkawy M, Abdelfatah RM. Novel spectrophotometric determination of flumethasone pivalate and clioquinol in their binary mixture and pharmaceutical formulation. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Feb 5;136 Pt B:707-13. doi: 10.1016/j.saa.2014.09.085. Epub 2014 Sep 30. PMID: 25448970. 15: Zhang D, Park JA, Kim SK, Cho SH, Jeong D, Cho SM, Yi H, Shim JH, Kim JS, Abd El-Aty AM, Shin HC. Simultaneous detection of flumethasone, dl- methylephedrine, and 2-hydroxy-4,6-dimethylpyrimidine in porcine muscle and pasteurized cow milk using liquid chromatography coupled with triple-quadrupole mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Feb 15;1012-1013:8-16. doi: 10.1016/j.jchromb.2016.01.011. Epub 2016 Jan 12. PMID: 26797492. 16: List RJ, Flook EP, Tay HL. Tympanoplasty graft preparation using ear drops containing polyethylene glycol, flumethasone and clioquinol. J Laryngol Otol. 2011 Aug;125(8):853-5. doi: 10.1017/S0022215111001083. Epub 2011 May 31. PMID: 21729449. 17: Grater WC, Grover FW. Evolution of a topical corticosteroid (flumethasone pivalate) in allergic dermatoses. South Med J. 1967 Nov;60(11):1153-8. doi: 10.1097/00007611-196711000-00001. PMID: 4228807. 18: Herasym K, Bonaparte JP, Kilty S. A comparison of Locacorten-Vioform and clotrimazole in otomycosis: A systematic review and one-way meta-analysis. Laryngoscope. 2016 Jun;126(6):1411-9. doi: 10.1002/lary.25761. Epub 2015 Nov 24. PMID: 26600419. 19: Swanson LV, Lind RE. Lactational response of dairy cows to oral administration of a synthetic glucocorticoid. J Dairy Sci. 1976 Apr;59(4):614-9. doi: 10.3168/jds.S0022-0302(76)84249-X. PMID: 1262575. 20: Park KH, Choi JH, Abd El-Aty AM, Cho SK, Park JH, Kwon KS, Park HR, Kim HS, Shin HC, Kim MR, Shim JH. Development of QuEChERS-based extraction and liquid chromatography-tandem mass spectrometry method for quantifying flumethasone residues in beef muscle. Meat Sci. 2012 Dec;92(4):749-53. doi: 10.1016/j.meatsci.2012.06.033. Epub 2012 Jun 29. PMID: 22819726.