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Medrysone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
Identifiers
  • (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
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.018.371Edit this at Wikidata
Chemical and physical data
FormulaC22H32O3
Molar mass344.495 g·mol−1
3D model (JSmol)
  • 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=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
 ☒NcheckY (what is this?)  (verify)

Medrysone (INN,USAN; brand namesHMS,Medrocort, others; former developmental codeNSC-63278; also known ashydroxymethylprogesterone,methylhydroxyprogesterone,hydroxymesterone,6α-methyl-11β-hydroxyprogesterone, or6α-methyl-11β-hydroxypregn-4-ene-3,20-dione) is asyntheticglucocorticoid that is or has been used in the treatment ofinflammatoryeye diseases.[1][2][3] It has been discontinued in theUnited States.[4] Although it is very similar instructure toprogesterone,[5] neitherprogestogenic norandrogenic activity has been demonstrated for or attributed to medrysone.[6][7][8]

Environmental presence

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

See also

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References

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  1. ^Elks J (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. ^Morton IK, Hall JM (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 (February 1969). "The treatment of ocular inflammation with medrysone".Archives of Ophthalmology.81 (2):184–191.doi:10.1001/archopht.1969.00990010186008.PMID 5764682.
  6. ^Spaeth GL (June 1966). "Hydroxymethylprogesterone. An anti-inflammatory steroid without apparent effect on intraocular pressure".Archives of Ophthalmology.75 (6):783–787.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 (April 1971). "Medrysone hypersensitivity. Report of a case".Archives of Ophthalmology.85 (4):478–479.doi:10.1001/archopht.1971.00990050480015.PMID 5554878.
  9. ^Black GP, He G, Denison MS, Young TM (May 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.PMC 8378343.PMID 33909413.
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