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Methylprednisolone aceponate

From Wikipedia, the free encyclopedia
Methylprednisolone aceponate
Clinical data
Trade namesAdvantan, Avancort
Other namesMethylprednisolone 17α-propionate 21-acetate; ZK-91588
AHFS/Drugs.comConsumer Drug Information
ATC code
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.184.880 Edit this at Wikidata
Chemical and physical data
FormulaC27H36O7
Molar mass472.578 g·mol−1
3D model (JSmol)
  • CCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2C[C@@H](C4=CC(=O)C=C[C@]34C)C)O)C)C(=O)COC(=O)C
  • InChI=1S/C27H36O7/c1-6-23(32)34-27(22(31)14-33-16(3)28)10-8-19-18-11-15(2)20-12-17(29)7-9-25(20,4)24(18)21(30)13-26(19,27)5/h7,9,12,15,18-19,21,24,30H,6,8,10-11,13-14H2,1-5H3/t15-,18-,19-,21-,24+,25-,26-,27-/m0/s1 ☒N
  • Key:DALKLAYLIPSCQL-YPYQNWSCSA-N ☒N
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Methylprednisolone aceponate, or methylprednisolone acetate propionate, sold under the brand names Advantan and Avancort, is a glucocorticoid and a corticosteroid ester—specifically the C17α propionate and C21 acetate diester of methylprednisolone.[1][2][3]

In Russia and some other countries the drug is available in 4 dosage forms differing in consistency and water content: emulsion (or lotion), cream, ointment and fatty ointment.[4]

Synthesis

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ChemDrug Synthesis:[5][6] Patent:[7]
  • methylprednisolone [83-43-2] (1)
  • Triethyl orthopropionate [115-80-0] (2)
  • PC13131717 (3)
  • [79512-61-1] (4)

See also

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References

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  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 811–. ISBN 978-1-4757-2085-3.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 675–. ISBN 978-3-88763-075-1.
  3. ^ Bieber T, Vick K, Fölster-Holst R, et al. (February 2007). "Efficacy and safety of methylprednisolone aceponate ointment 0.1% compared to tacrolimus 0.03% in children and adolescents with an acute flare of severe atopic dermatitis". Allergy. 62 (2): 184–9. doi:10.1111/j.1398-9995.2006.01269.x. PMID 17298428. S2CID 41761398.
  4. ^ "Advantan (methylprednisolone aceponate) Full Prescribing Information Lists". State Register of Medicines (in Russian). Retrieved 31 March 2023.
  5. ^ Prous, J.; Castaer, J.; Methylprednisolone Aceponate. Drugs Fut 1993, 18, 2, 130.
  6. ^ Sugai, S., Okazaki, T., Kajiwara, Y., Kanbara, T., Naito, Y., Yoshida, S., Akaboshi, S., Ikegami, S., Kamano, Y. (1985). "Studies on topical antiinflammatory corticosteroids. I. Syntheses and vasoconstrictive activities of 11.BETA.,17.ALPHA.,21-trihydroxy-6.ALPHA.-methyl-1,4-pregnadiene-3,20-dione 17-ester and 17,21-diester derivatives". Chemical and Pharmaceutical Bulletin. 33 (5): 1889–1898. doi:10.1248/cpb.33.1889.
  7. ^ Klaus Annen, et al. U.S. patent 4,587,236 (1986 to Bayer Pharma AG).