Fludrocortisone

Fludrocortisone
Clinical data
Trade namesAstonin, Astonin-H, others
Other namesStC-1400; 9α-Fluorohydrocortisone; 9α-Fluorocortisol; 9α-Fluoro-17α-hydroxycorticosterone; 9α-Fluoro-11β,17α,21-trihydroxypregn-4-ene-3,20-dione
AHFS/Drugs.comMonograph
Pregnancy
category
  • C
Routes of
administration		By mouth
Drug classCorticosteroid; glucocorticoid; mineralocorticoid
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein bindingHigh
MetabolismLiver
Elimination half-life3.5 hours
Identifiers
  • (8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
PubChem SID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.004.395 Edit this at Wikidata
Chemical and physical data
FormulaC21H29FO5
Molar mass380.456 g·mol−1
3D model (JSmol)
  • O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]1(/C(=C\C(=O)CC1)CC[C@H]4[C@@H]2CC3)C)C
  • InChI=1S/C21H29FO5/c1-18-7-5-13(24)9-12(18)3-4-15-14-6-8-20(27,17(26)11-23)19(14,2)10-16(25)21(15,18)22/h9,14-16,23,25,27H,3-8,10-11H2,1-2H3/t14-,15-,16-,18-,19-,20-,21-/m0/s1 checkY
  • Key:AAXVEMMRQDVLJB-BULBTXNYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
Fludrocortisone acetate
Clinical data
Trade namesCortineff, Florinef, Florinefe, Fludrocortison, others
Other namesFluorohydrocortisone acetate; 9α-Fluorohydrocortisone 21-acetate; 9α-Fluoro-17α-hydroxycorticosterone 21-acetate; 9α-Fluoro-11β,17α,21-trihydroxypregn-4-ene-3,20-dione 21-acetate
Routes of
administration		By mouth
Drug classCorticosteroid; glucocorticoid; mineralocorticoid
Pharmacokinetic data
MetabolismLiver
Identifiers
  • [2-[(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.395 Edit this at Wikidata
Chemical and physical data
FormulaC23H31FO6
Molar mass422.493 g·mol−1
3D model (JSmol)
Melting point260 to 262 °C (500 to 504 °F) (dec.)
  • CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)CC[C@@]43C)F)O)C)O
  • InChI=1S/C23H31FO6/c1-13(25)30-12-19(28)22(29)9-7-16-17-5-4-14-10-15(26)6-8-20(14,2)23(17,24)18(27)11-21(16,22)3/h10,16-18,27,29H,4-9,11-12H2,1-3H3/t16-,17-,18-,20-,21-,22-,23-/m0/s1
  • Key:SYWHXTATXSMDSB-GSLJADNHSA-N

Fludrocortisone, sold under the brand name Florinef, among others, is a corticosteroid used to treat adrenogenital syndrome, postural hypotension, and adrenal insufficiency.[1][2][3] In adrenal insufficiency, it is generally taken together with hydrocortisone.[3] Fludrocortisone is taken by mouth[3] and is most commonly used in its acetate form.[4]

Common side effects of fludrocortisone include high blood pressure, swelling, heart failure, and low blood potassium.[3] Other serious side effects can include low immune-system function, cataracts, muscle weakness, and mood changes.[3] Whether use of fludrocortisone during pregnancy is safe for the fetus is unknown.[5] Fludrocortisone is mostly a mineralocorticoid, but it also has glucocorticoid effects.[3]

Fludrocortisone was patented in 1953.[6] It is on the World Health Organization's List of Essential Medicines.[7]

  1. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 558–. ISBN 978-1-4757-2085-3. Archived from the original on 5 November 2017.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 450–. ISBN 978-3-88763-075-1. Archived from the original on 2017-11-05.
  3. ^ a b c d e f "Fludrocortisone Acetate". The American Society of Health-System Pharmacists. Archived from the original on 5 July 2017. Retrieved 8 December 2016.
  4. ^ Day RO, Furst DE, van Riel PL, Bresnihan B, eds. (30 May 2010). "Medicinal Chemistry of the Disease Modifying Antirheumatic Drugs". Antirheumatic Therapy: Actions and Outcomes. Springer Science & Business Media. pp. 21–. ISBN 978-3-7643-7726-7. Archived from the original on 5 November 2017.
  5. ^ "Fludrocortisone Use During Pregnancy". Drugs.com. Archived from the original on 24 December 2016. Retrieved 24 December 2016.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 484. ISBN 9783527607495. Archived from the original on 2017-11-05.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.