Medrysone

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
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 ;
PubChem CID	247839;
IUPHAR/BPS	7086;
DrugBank	DB00253 ;
ChemSpider	216968 ;
UNII	D2UFC189XF;
KEGG	D02289 ;
ChEMBL	ChEMBL1201173 ;
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 ; Key:GZENKSODFLBBHQ-ILSZZQPISA-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[edit]

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]

References[edit]

^ 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.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 640–. ISBN 978-3-88763-075-1.
^ 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.
^ "HMS - FDA prescribing information, side effects and uses".
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[Elks2014-1] 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.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 640–. ISBN 978-3-88763-075-1.

[MortonHall1999-3] 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.

[Drugs.com-4] "HMS - FDA prescribing information, side effects and uses".

[pmid5764682-5] 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.

[pmid5327794-6] 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.

[pmid5172545-7] 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.

[pmid5554878-8] 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.

[Black2021-9] 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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Medrysone

Environmental presence[edit]

See also[edit]

References[edit]