Medrysone

Medrysone (INN, USAN) (brand names HMS, Medrocort, others; former developmental code name NSC-63278), also known as hydroxymethylprogesterone, methylhydroxyprogesterone, or hydroxymesterone, as well as 6α-methyl-11β-hydroxyprogesterone or 6α-methyl-11β-hydroxypregn-4-ene-3,20-dione, is a synthetic glucocorticoid that is or has been used in the treatment of inflammatory eye diseases.[1][2][3] It has been discontinued in the United States.[4] Although it is very similar in structure to progesterone,[5] neither progestogenic nor androgenic activity has been demonstrated for or attributed to medrysone.[6][7][8]

Medrysone

Clinical data
Trade names	HMS, Medrocort, others
Other names	NSC-63278; Hydroxymethylprogesterone; Methylhydroxyprogesterone; Hydroxymesterone; 6α-Methyl-11β-hydroxyprogesterone; 6α-Methyl-11β-hydroxypregn-4-ene-3,20-dione
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a606003
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Eye drops
ATC code	S01BA08 (WHO)
Legal status
Legal status	US: Discontinued
Identifiers
IUPAC name (6S,8S,9S,10R,11S,13R,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
CAS Number	2668-66-8^Y
PubChem CID	247839
IUPHAR/BPS	7086
DrugBank	DB00253^N
ChemSpider	216968^N
UNII	D2UFC189XF
KEGG	D02289^Y
ChEMBL	ChEMBL1201173^N
CompTox Dashboard (EPA)	DTXSID6045371
ECHA InfoCard	100.018.371
Chemical and physical data
Formula	C22H32O3
Molar mass	344.495 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@H]1C[C@H]2[C@@H]3CC[C@@H]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)CC4)C)O)C)C(=O)C
InChI 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^N Key:GZENKSODFLBBHQ-ILSZZQPISA-N^N
^NY (what is this?)  (verify)

See also

• 9α-Bromo-11-ketoprogesterone
• 11β-Hydroxyprogesterone
• Endrisone
• Flugestone
• Fluorometholone

References

1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 760–. ISBN 978-1-4757-2085-3.
2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 640–. ISBN 978-3-88763-075-1.
3. I.K. Morton; Judith M. Hall (31 October 1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 173–. ISBN 978-0-7514-0499-9.
4. https://www.drugs.com/pro/hms.html
5. Bedrossian RH, Eriksen SP (1969). "The treatment of ocular inflammation with medrysone". Arch. Ophthalmol. 81 (2): 184–91. doi:10.1001/archopht.1969.00990010186008. PMID 5764682.
6. Spaeth GL (1966). "Hydroxymethylprogesterone. An anti-inflammatory steroid without apparent effect on intraocular pressure". Arch. Ophthalmol. 75 (6): 783–7. doi:10.1001/archopht.1966.00970050785014. PMID 5327794.
7. Schwartz A, Leopold IH (1971). "Topical anti-inflammatory steroids and intraocular pressure: the place of medrysone". Drugs. 2 (1): 1–4. doi:10.2165/00003495-197102010-00001. PMID 5172545.
8. Smolin G (1971). "Medrysone hypersensitivity. Report of a case". Arch. Ophthalmol. 85 (4): 478–9. doi:10.1001/archopht.1971.00990050480015. PMID 5554878.