Synonym
Medrysone; U 8471; U-8471; U8471; NSC 63278; Visudrisone
IUPAC/Chemical Name
(6S,8S,9S,10R,11S,13S,14S,17S)-17-acetyl-11-hydroxy-6,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
InChi Key
GZENKSODFLBBHQ-ILSZZQPISA-N
InChi Code
InChI=1S/C22H32O3/c1-12-9-15-17-6-5-16(13(2)23)22(17,4)11-19(25)20(15)21(3)8-7-14(24)10-18(12)21/h10,12,15-17,19-20,25H,5-9,11H2,1-4H3/t12-,15-,16+,17-,19-,20+,21-,22+/m0/s1
SMILES Code
O=C1CC[C@]2(C)[C@@]3([H])[C@@H](O)C[C@]4(C)[C@@H](C(C)=O)CC[C@@]4([H])[C@]3([H])C[C@H](C)C2=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
>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
Biological target:
Medrysone is a corticosteroid, in ophthalmology for the treatment of eye inflammations.
In vitro activity:
Microbial transformation of the anti-inflammatory steroid medrysone (1) was carried out for the first time with the filamentous fungi Cunninghamella blakesleeana (ATCC 8688a), Neurospora crassa (ATCC 18419), and Rhizopus stolonifer (TSY 0471). Compounds 1, 4, 5, 7, and 8 strongly inhibited the proliferation of T-cells with IC50 values between <0.2-10.4 μg/mL. Compounds 1, and 7 also inhibited the production of pro-inflammatory cytokine TNF-α.
Reference: PLoS One. 2016 Apr 22;11(4):e0153951. https://pubmed.ncbi.nlm.nih.gov/27104348/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Acetonitrile |
1.0 |
2.90 |
| DMSO |
50.0 |
145.14 |
| Ethanol |
13.0 |
37.74 |
| Methanol |
1.0 |
2.90 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
344.50
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 |
Formulation protocol:
1. Silva Oliveira Junior M, Schira-Heinen J, Reiche L, Han S, de Amorim VCM, Lewen I, Gruchot J, Göttle P, Akkermann R, Azim K, Küry P. Myelin repair is fostered by the corticosteroid medrysone specifically acting on astroglial subpopulations. EBioMedicine. 2022 Sep;83:104204. doi: 10.1016/j.ebiom.2022.104204. Epub 2022 Aug 8. PMID: 35952494; PMCID: PMC9385547.
2. Bano S, Wahab AT, Yousuf S, Jabeen A, Mesaik MA, Rahman AU, Choudhary MI. New Anti-Inflammatory Metabolites by Microbial Transformation of Medrysone. PLoS One. 2016 Apr 22;11(4):e0153951. doi: 10.1371/journal.pone.0153951. PMID: 27104348; PMCID: PMC4841542.
In vitro protocol:
1. Silva Oliveira Junior M, Schira-Heinen J, Reiche L, Han S, de Amorim VCM, Lewen I, Gruchot J, Göttle P, Akkermann R, Azim K, Küry P. Myelin repair is fostered by the corticosteroid medrysone specifically acting on astroglial subpopulations. EBioMedicine. 2022 Sep;83:104204. doi: 10.1016/j.ebiom.2022.104204. Epub 2022 Aug 8. PMID: 35952494; PMCID: PMC9385547.
2. Bano S, Wahab AT, Yousuf S, Jabeen A, Mesaik MA, Rahman AU, Choudhary MI. New Anti-Inflammatory Metabolites by Microbial Transformation of Medrysone. PLoS One. 2016 Apr 22;11(4):e0153951. doi: 10.1371/journal.pone.0153951. PMID: 27104348; PMCID: PMC4841542.
1: Mindel JS, Tavitian HO, Smith H Jr, Walker EC. Comparative ocular pressure elevation by medrysone, fluorometholone, and dexamethasone phosphate. Arch Ophthalmol. 1980 Sep;98(9):1577-8. PubMed PMID: 6893544.
2: Medrysone: a review. Drugs. 1971;2(1):5-19. Review. PubMed PMID: 4948856.
3: Rastogi RK, Mathur A, Raizada IN. Efficacy of medrysone as anti-inflammatory agent. Indian J Ophthalmol. 1985 Sep-Oct;33(5):295-7. PubMed PMID: 3843339.
4: Bano S, Wahab AT, Yousuf S, Jabeen A, Mesaik MA, Rahman AU, Choudhary MI. New Anti-Inflammatory Metabolites by Microbial Transformation of Medrysone. PLoS One. 2016 Apr 22;11(4):e0153951. doi: 10.1371/journal.pone.0153951. eCollection 2016. PubMed PMID: 27104348; PubMed Central PMCID: PMC4841542.
5: Vajpayee RB, Gupta SK, Uppal RK. Evaluation of sodium cromoglycate and medrysone in the management of atopic keratoconjunctivitis: a double masked clinical study. Aust N Z J Ophthalmol. 1986 Aug;14(3):251-3. PubMed PMID: 3094562.
6: Smolin G. Medrysone hypersensitivity. Report of a case. Arch Ophthalmol. 1971 Apr;85(4):478-9. PubMed PMID: 5554878.
7: Li F, Zou XJ, Zheng H, Xiang Y. LC-MS/MS method for determination of megestrol in human plasma and its application in bioequivalence study. J Huazhong Univ Sci Technolog Med Sci. 2013 Dec;33(6):912-916. doi: 10.1007/s11596-013-1221-9. Epub 2013 Dec 13. PubMed PMID: 24337858.
8: Green K, Cheeks L, Slagle T, Phillips CI. Interaction between progesterone and mifepristone on intraocular pressure in rabbits. Curr Eye Res. 1989 Mar;8(3):317-20. PubMed PMID: 2707047.
9: Mohan R, Muralidharan AR. Steroid induced glaucoma and cataract. Indian J Ophthalmol. 1989 Jan-Mar;37(1):13-6. PubMed PMID: 2807493.
10: Kitazawa Y, Nose H, Chatranonta T. [Effects of a new corticosteroid "Medrysone" on intraocular pressure]. Nihon Ganka Kiyo. 1971 Dec;22(12):1073-7. Japanese. PubMed PMID: 5169300.
11: Offret G, Renard G. [Study of intraocular pressure following intervention on cataract in 50 patients treated either with medrysone or with dexamethasone]. Bull Soc Ophtalmol Fr. 1978 Feb;78(2):135-7. French. PubMed PMID: 371843.
12: Kitazawa Y. Increased intraocular pressure induced by corticosteroids. Am J Ophthalmol. 1976 Sep;82(3):492-5. PubMed PMID: 961801.
13: Sabiston DW. "Medrysone": a new topical steroid. Trans Aust Coll Ophthalmol. 1970;2:49-53. PubMed PMID: 5538167.
14: Drance SM, Scott S. A comparison of action of dexamethasone and medrysone on human intraocular pressure. Can J Ophthalmol. 1968 Apr;3(2):159-61. PubMed PMID: 5660429.
15: Bedrossian RH, Eriksen SP. The treatment of ocular inflammation with medrysone. Arch Ophthalmol. 1969 Feb;81(2):184-91. PubMed PMID: 5764682.
16: Demailly P, Ecoffet-Jeaneau M. [Value of medrysone in the treatment of allergic blepharoconjunctivitis in patients with glaucoma treated with epinephrine]. Bull Soc Ophtalmol Fr. 1977 Mar;77(3):225-8. French. PubMed PMID: 342135.
17: Scullica L, Bisantis C, Cantarella S. [Comparative effects of hydroxymethylprogesterone (medrysone) and of fluoro-methyl-prednisolone (dexamethasone) on crystalline lens epithelium]. Boll Ocul. 1970 Aug;49(8):430-7. Italian. PubMed PMID: 5521490.
18: Dorsch W, Thygeson P. The clinical efficacy of medrysone, a new ophthalmic steroid. Am J Ophthalmol. 1968 Jan;65(1):74-5. PubMed PMID: 5638193.
19: Thorson JC, Eriksen SP. Anti-inflammatory properties of medrysone in external ocular inflammations. Am J Ophthalmol. 1971 Apr;71(4):844-6. PubMed PMID: 4928531.
20: Schwartz A, Leopold IH. Topical anti-inflammatory steroids and intraocular pressure: the place of medrysone. Drugs. 1971;2(1):1-4. PubMed PMID: 5172545.
