Synonym
Methylprednisolone Aceponate; MPA; Advantan; SH-440; SH 440; SH440;
IUPAC/Chemical Name
(6S,8S,9R,11S,13S,14S,17R)-17-(2-acetoxyacetyl)-11-hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl propionate
InChi Key
DALKLAYLIPSCQL-NSXGOKPNSA-N
InChi Code
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
SMILES Code
O=C1C=CC2(C)C([C@@H](C)C[C@@H]3[C@H]2[C@@H](O)C[C@@]4(C)[C@H]3CC[C@]4(OC(CC)=O)C(COC(C)=O)=O)=C1
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
472.57
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 |
1: Fölster-Holst R, Abeck D, Torrelo A. Topical hydrocortisone 17-butyrate 21-propionate in the treatment of inflammatory skin diseases: pharmacological data, clinical efficacy, safety and calculation of the therapeutic index. Pharmazie. 2016 Mar;71(3):115-21. Review. PubMed PMID: 27183704.
2: Metz M, Wahn U, Gieler U, Stock P, Schmitt J, Blume-Peytavi U. Chronic pruritus associated with dermatologic disease in infancy and childhood: update from an interdisciplinary group of dermatologists and pediatricians. Pediatr Allergy Immunol. 2013 Sep;24(6):527-39. doi: 10.1111/pai.12115. Review. PubMed PMID: 23980845.
3: García Ponte L, Ebert U. Frontiers of rapid itch relief: a review of methylprednisolone aceponate. J Eur Acad Dermatol Venereol. 2012 Nov;26 Suppl 6:9-13. doi: 10.1111/j.1468-3083.2012.04711.x. Review. PubMed PMID: 23067432.
4: Blume-Peytavi U, Metz M. Atopic dermatitis in children: management of pruritus. J Eur Acad Dermatol Venereol. 2012 Nov;26 Suppl 6:2-8. doi: 10.1111/j.1468-3083.2012.04710.x. Review. PubMed PMID: 23067431.
5: Korting HC, Schöllmann C. Topical fluticasone propionate: intervention and maintenance treatment options of atopic dermatitis based on a high therapeutic index. J Eur Acad Dermatol Venereol. 2012 Feb;26(2):133-40. doi: 10.1111/j.1468-3083.2011.04195.x. Epub 2011 Oct 7. Review. PubMed PMID: 21977914.
6: Blume-Peytavi U, Wahn U. Optimizing the treatment of atopic dermatitis in children: a review of the benefit/risk ratio of methylprednisolone aceponate. J Eur Acad Dermatol Venereol. 2011 May;25(5):508-15. doi: 10.1111/j.1468-3083.2010.03942.x. Review. PubMed PMID: 21492244.
7: Luger TA. Balancing efficacy and safety in the management of atopic dermatitis: the role of methylprednisolone aceponate. J Eur Acad Dermatol Venereol. 2011 Mar;25(3):251-8. doi: 10.1111/j.1468-3083.2010.03789.x. Review. PubMed PMID: 21294777.
8: Schmitt J, von Kobyletzki L, Svensson A, Apfelbacher C. Efficacy and tolerability of proactive treatment with topical corticosteroids and calcineurin inhibitors for atopic eczema: systematic review and meta-analysis of randomized controlled trials. Br J Dermatol. 2011 Feb;164(2):415-28. doi: 10.1111/j.1365-2133.2010.10030.x. Epub 2010 Nov 23. Review. PubMed PMID: 20819086.
9: Gómez-de la Fuente E, Rosado A, Gutiérrez-Pascual M, Vicente FJ, López-Estebaranz JL. [Allergic contact dermatitis and systemic contact dermatitis in a patient with polysensitization to topical corticosteroids]. Actas Dermosifiliogr. 2009 Nov;100(9):817-20. Review. Spanish. PubMed PMID: 19889306.
10: Ruzicka T. Methylprednisolone aceponate in eczema and other inflammatory skin disorders -- a clinical update. Int J Clin Pract. 2006 Jan;60(1):85-92. Review. PubMed PMID: 16409433.
11: Bayés M, Rabasseda X, Prous JR. Gateways to Clinical Trials. Methods Find Exp Clin Pharmacol. 2002 Sep;24(7):431-55. Review. PubMed PMID: 12428432.
12: Brazzini B, Pimpinelli N. New and established topical corticosteroids in dermatology: clinical pharmacology and therapeutic use. Am J Clin Dermatol. 2002;3(1):47-58. Review. PubMed PMID: 11817968.
13: Prakash A, Benfield P. Topical mometasone. A review of its pharmacological properties and therapeutic use in the treatment of dermatological disorders. Drugs. 1998 Jan;55(1):145-63. Review. PubMed PMID: 9463794.
