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 ;
	(what is this?) (verify)

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]

References

^ 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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Environmental presence

See also

References