Medrysone

Medrysone
Clinical data
Trade namesHMS, Medrocort, others
Other namesNSC-63278; Hydroxymethylprogesterone; Methylhydroxyprogesterone; Hydroxymesterone; 6α-Methyl-11β-hydroxyprogesterone; 6α-Methyl-11β-hydroxypregn-4-ene-3,20-dione
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa606003
Routes of
administration		Eye drops
ATC code
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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.018.371
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Chemical and physical data
FormulaC22H32O3
Molar mass344.495 g·mol−1
3D model (JSmol)
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
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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]


Environmental presence

In 2021, medrysone was one of the 12 compounds identified in sludge samples taken from 12 wastewater treatment plants in California that were associated with estrogenic activity in in vitro. [9]

See also

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. ↑ "HMS - FDA prescribing information, side effects and uses".
  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. S2CID 37303359.
  8. ↑ Smolin G (1971). "Medrysone hypersensitivity. Report of a case". Arch. Ophthalmol. 85 (4): 478–9. doi:10.1001/archopht.1971.00990050480015. PMID 5554878.
  9. ↑ Gabrielle P. Black (2021). "Using Estrogenic Activity and Nontargeted Chemical Analysis to Identify Contaminants in Sewage Sludge". Environmental Science & Technology. 55 (10): 6729–6739. Bibcode:2021EnST...55.6729B. doi:10.1021/acs.est.0c07846. ISSN 0013-936X. PMC 8378343. PMID 33909413.



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