Methylprednisolone aceponate: Difference between revisions

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 387713856

| width = 250px

<!--Clinical data-->

| tradename = Advantan, Avancort

| Drugs.com = {{drugs.com|CDI|methylprednisolone_aceponate}}

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_US = <!-- A / B / C / D / X -->

| pregnancy_category =

| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->

| legal_UK = <!-- GSL / P / POM / CD -->

| legal_US = <!-- OTC / Rx-only -->

| legal_status =

| routes_of_administration =

<!--Pharmacokinetic data-->

<!--Identifiers-->

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 86401-95-8

| ATC_prefix = D07

| ATC_suffix = AC14

| PubChem = 63019

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB14643

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = ET54W9J4U2

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 56717

| ChEBI = 135762

| ChEMBL = 1697782

| synonyms = Methylprednisolone 17α-propionate 21-acetate; ZK-91588

<!--Chemical data-->

| C=27 | H=36 | O=7

| 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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = DALKLAYLIPSCQL-YPYQNWSCSA-N

'''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]] [[ester|diester]] of [[methylprednisolone]].<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA811|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=811–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA675|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=675–}}</ref><ref name="pmid17298428">{{cite journal |vauthors=Bieber T, Vick K, Fölster-Holst R, etal |title=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 |journal=Allergy |volume=62 |issue=2 |pages=184–9 |date=February 2007 |pmid=17298428 |doi=10.1111/j.1398-9995.2006.01269.x |s2cid=41761398 }}</ref>

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.<ref>{{cite web |title=Advantan (methylprednisolone aceponate) Full Prescribing Information Lists |url=https://grls.rosminzdrav.ru/GRLS.aspx?RegNumber=&MnnR=&lf=&TradeNmR=адвантан&OwnerName=&MnfOrg=&MnfOrgCountry=&isfs=0&regtype=1%2c6&pageSize=10&order=Registered&orderType=desc&pageNum=1 |website=State Register of Medicines |access-date=31 March 2023 |language=Russian}}</ref>

==Synthesis==

[[File:Methylprednisolone Aceponate synthesis.svg|thumb|center|500px|[https://www.chemdrug.com/article/8/3284/16419980.html ChemDrug] Synthesis:<ref>Prous, J.; Castaer, J.; Methylprednisolone Aceponate. Drugs Fut 1993, 18, 2, 130.</ref><ref>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.</ref> Patent:<ref>Klaus Annen, et al. {{US patent|4587236}} (1986 to Bayer Pharma AG).</ref>]]

*methylprednisolone [83-43-2] (1)

*Triethyl orthopropionate [115-80-0] (2)

*[https://pubchem.ncbi.nlm.nih.gov/compound/13131717 PC13131717] (3)

*[79512-61-1] (4)

* [[List of corticosteroid esters#Methylprednisolone esters|List of corticosteroid esters § Methylprednisolone esters]]

{{Glucocorticoids and antiglucocorticoids}}

{{Glucocorticoid receptor modulators}}

[[Category:Corticosteroid esters]]

[[Category:Corticosteroids]]

[[Category:Propionate esters]]

[[Category:Acetate esters]]

{{steroid-stub}}