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Fluorometholone acetate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Fluorometholone acetate
Clinical data
Trade namesFlarex, Florate, Omnitrol
Other namesOxylone acetate; 1-Dehydro-9α-fluoro-11β,17α-dihydroxy-6α-methylprogesterone 17α-acetate; 17α-Acetoxy-9α-fluoro-11β-hydroxy-6α-methylpregna-1,4-diene-3,20-dione
Drug classCorticosteroid;Glucocorticoid;Progestogen
Identifiers
  • [(6S,8S,9R,10S,11S,13S,14S,17R)-17-acetyl-9-fluoro-11-hydroxy-6,10,13-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.021.156Edit this at Wikidata
Chemical and physical data
FormulaC24H31FO5
Molar mass418.505 g·mol−1
3D model (JSmol)
  • [H][C@@]12CC[C@](OC(C)=O)(C(C)=O)[C@@]1(C)C[C@]([H])(O)[C@@]1(F)[C@@]2([H])C[C@]([H])(C)C2=CC(=O)C=C[C@]12C
  • InChI=1S/C24H31FO5/c1-13-10-19-17-7-9-23(14(2)26,30-15(3)27)22(17,5)12-20(29)24(19,25)21(4)8-6-16(28)11-18(13)21/h6,8,11,13,17,19-20,29H,7,9-10,12H2,1-5H3/t13-,17-,19-,20-,21-,22-,23-,24-/m0/s1

Fluorometholone acetate, also known asoxylone acetate and sold under the brand namesFlarex,Florate, andOmnitrol, is asyntheticglucocorticoidcorticosteroid and acorticosteroid ester, as well as aprogestogen andprogestogen ester.[1][2][3][4]: 186  It is the C17α acetate ester offluorometholone.[1][2][3]

In addition to its potent corticosteroid activity, fluorometholone acetate is a progestogen.[4] It has been studied in the treatment ofbreast cancer in women and has been found to be effective, producing remission in about 20% of women with advanced breast cancer at anoral dosage of 50 mg/day.[4] However, it also produces severeCushing's syndrome-like symptoms likeplethora,moon face,glycosuria, markedweight gain,hypertension, andosteoporosis at this dosage due to its glucocorticoid activity.[4]

See also

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References

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  1. ^abElks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 566–.ISBN 978-1-4757-2085-3.
  2. ^abIndex Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 458–459.ISBN 978-3-88763-075-1.
  3. ^abMorton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 123–.ISBN 978-94-011-4439-1.
  4. ^abcdDao TL (1975)."Pharmacology and Clinical Utility of Hormones in Hormone Related Neoplasms". In Sartorelli AC, Johns DG (eds.).Antineoplastic and Immunosuppressive Agents. pp. 170–192.doi:10.1007/978-3-642-65806-8_11.ISBN 978-3-642-65806-8.Oxylone acetate (progesterone, 1-dehydro-9-fluoro-11β,17-dihydroxy-6α-methyl-17-acetate, fluorometholone), another halogenated progesterone, has been studied in patients with breast cancer (Cooperative Breast Cancer Group, 1964). This compound, given at a dose level of 50 mg per day orally, was shown to produce remission in about 20 % of the patients with advanced breast cancer. Both of these progestational compounds possess corticoid activity, particularly oxylone acetate, which, in 50 mg doses, causes Cushingoid symptoms, hypertension, and osteoporosis. On withdrawal of the drug, vaginal bleeding occurs frequently. [...] Progesterone-like compounds with glucocorticoid activity, such as oxylone, induce severe Cushingoid symptoms such as plethora, moonface, glycosuria, marked weight gain, and hypertension, requiring discontinuation of the drug.


GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists


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