medrysone

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 408087713

| 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

| image = Medrysone.svg

| width = 250

| tradename = HMS, Medrocort, others

| Drugs.com = {{drugs.com|CONS|medrysone}}

| MedlinePlus = a606003

| pregnancy_AU =

| pregnancy_US = C

| pregnancy_category =

| legal_AU =

| legal_UK =

| legal_US_comment = Discontinued

| legal_status =

| routes_of_administration = Eye drops

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 7086

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 2668-66-8

| ATC_prefix = S01

| ATC_suffix = BA08

| ATC_supplemental =

| PubChem = 247839

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB00253

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 216968

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = D2UFC189XF

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D02289

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201173

| C=22 | H=32 | O=3

| 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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI=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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GZENKSODFLBBHQ-ILSZZQPISA-N

| synonyms = NSC-63278; Hydroxymethylprogesterone; Methylhydroxyprogesterone; Hydroxymesterone; 6α-Methyl-11β-hydroxyprogesterone; 6α-Methyl-11β-hydroxypregn-4-ene-3,20-dione

}}

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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA760|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=760–}}{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA640|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=640–}}{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=mqaOMOtk61IC&pg=PA173|date=31 October 1999|publisher=Springer Science & Business Media|isbn=978-0-7514-0499-9|pages=173–}} It has been discontinued in the United States.{{Cite web|url=https://www.drugs.com/pro/hms.html|title = HMS - FDA prescribing information, side effects and uses}} Although it is very similar in structure to progesterone,{{cite journal | vauthors = Bedrossian RH, Eriksen SP | title = The treatment of ocular inflammation with medrysone | journal = Archives of Ophthalmology | volume = 81 | issue = 2 | pages = 184–191 | date = February 1969 | pmid = 5764682 | doi = 10.1001/archopht.1969.00990010186008 }} neither progestogenic nor androgenic activity has been demonstrated for or attributed to medrysone.{{cite journal | vauthors = Spaeth GL | title = Hydroxymethylprogesterone. An anti-inflammatory steroid without apparent effect on intraocular pressure | journal = Archives of Ophthalmology | volume = 75 | issue = 6 | pages = 783–787 | date = June 1966 | pmid = 5327794 | doi = 10.1001/archopht.1966.00970050785014 }}{{cite journal | vauthors = Schwartz A, Leopold IH | title = Topical anti-inflammatory steroids and intraocular pressure: the place of medrysone | journal = Drugs | volume = 2 | issue = 1 | pages = 1–4 | year = 1971 | pmid = 5172545 | doi = 10.2165/00003495-197102010-00001 | s2cid = 37303359 }}{{cite journal | vauthors = Smolin G | title = Medrysone hypersensitivity. Report of a case | journal = Archives of Ophthalmology | volume = 85 | issue = 4 | pages = 478–479 | date = April 1971 | pmid = 5554878 | doi = 10.1001/archopht.1971.00990050480015 }}