Methylprednisolone aceponate

Methylprednisolone aceponate
Clinical data
Trade names	Advantan, Avancort
Other names	Methylprednisolone 17α-propionate 21-acetate; ZK-91588
AHFS/Drugs.com	Consumer Drug Information
ATC code	D07AC14 (WHO) ;
Identifiers
CAS Number	86401-95-8 ;
PubChem CID	63019;
DrugBank	DB14643 ;
ChemSpider	56717 ;
UNII	ET54W9J4U2;
ChEBI	CHEBI:135762;
ChEMBL	ChEMBL1697782;
CompTox Dashboard (EPA)	DTXSID2023301 ;
ECHA InfoCard	100.184.880
Chemical and physical data
Formula	C27H36O7
Molar mass	472.578 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:DALKLAYLIPSCQL-YPYQNWSCSA-N ;
	(what is this?) (verify)

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

methylprednisolone [83-43-2] (1)
Triethyl orthopropionate [115-80-0] (2)
PC13131717 (3)
[79512-61-1] (4)

References

^ 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.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 675–. ISBN 978-3-88763-075-1.
^ 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.
^ "Advantan (methylprednisolone aceponate) Full Prescribing Information Lists". State Register of Medicines (in Russian). Retrieved 31 March 2023.
^ Prous, J.; Castaer, J.; Methylprednisolone Aceponate. Drugs Fut 1993, 18, 2, 130.
^ 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.
^ Klaus Annen, et al. U.S. patent 4,587,236 (1986 to Bayer Pharma AG).

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[Elks2014-1] 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.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 675–. ISBN 978-3-88763-075-1.

[pmid17298428-3] 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).

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Synthesis

See also

References