Fluorometholone acetate

Chemical 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
  • 3801-06-7
PubChem CID
  • 240767
ChemSpider
  • 210390
UNII
  • 9I50C3I3OK
KEGG
  • D04221
ChEBI
  • CHEBI:78354
ChEMBL
  • ChEMBL1201064
CompTox Dashboard (EPA)
  • DTXSID20191424 Edit this at Wikidata
ECHA InfoCard100.021.156 Edit this at Wikidata
Chemical and physical data
FormulaC24H31FO5
Molar mass418.505 g·mol−1
3D model (JSmol)
  • Interactive image
  • [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
  • 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 as oxylone acetate and sold under the brand names Flarex, Florate, and Omnitrol, is a synthetic glucocorticoid corticosteroid and a corticosteroid ester, as well as a progestogen and progestogen ester.[1][2][3][4]: 186  It is the C17α acetate ester of fluorometholone.[1][2][3]

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

See also

References

  1. ^ a b Elks 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. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 458–459. ISBN 978-3-88763-075-1.
  3. ^ a b Morton 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. ^ a b c d Dao 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.


  • v
  • t
  • e
GRTooltip Glucocorticoid receptor
Agonists
  • Nonsteroidal glucocorticoids: AZD-5423
  • GSK-9027
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others
  • Antisense oligonucleotides: IONIS-GCCRRx (ISIS-426115)
See also
Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
Mineralocorticoid receptor modulators
List of corticosteroids
  • v
  • t
  • e
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens


Stub icon

This article about a steroid is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e
Stub icon

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e