Fludrocortisone

Fludrocortisone acetate
Clinical data
Trade names	Cortineff, Florinef, Florinefe, Fludrocortison, others
Other names	Fluorohydrocortisone 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 class	Corticosteroid; glucocorticoid; mineralocorticoid
Pharmacokinetic data
Metabolism	Liver
Identifiers
	IUPAC name [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	514-36-3;
PubChem CID	225609;
ChemSpider	196144;
UNII	V47IF0PVH4;
KEGG	D00986;
ChEBI	CHEBI:5102;
ChEMBL	ChEMBL1201010;
CompTox Dashboard (EPA)	DTXSID7023061 ;
ECHA InfoCard	100.004.395
Chemical and physical data
Formula	C23H31FO6
Molar mass	422.493 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	260 to 262 °C (500 to 504 °F) (dec.)
	SMILES 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 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
Clinical data
Trade names	Astonin, Astonin-H, others
Other names	StC-1400; 9α-Fluorohydrocortisone; 9α-Fluorocortisol; 9α-Fluoro-17α-hydroxycorticosterone; 9α-Fluoro-11β,17α,21-trihydroxypregn-4-ene-3,20-dione
AHFS/Drugs.com	Monograph
Pregnancy; category	C;
Routes of; administration	By mouth
Drug class	Corticosteroid; glucocorticoid; mineralocorticoid
ATC code	H02AA02 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Protein binding	High
Metabolism	Liver
Elimination half-life	3.5 hours
Identifiers
	IUPAC name (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	127-31-1 ; Acetate: U0476M545B ;
PubChem CID	31378;
PubChem SID	46508616;
IUPHAR/BPS	2873;
DrugBank	DB00687 ;
ChemSpider	29111 ;
UNII	U0476M545B;
KEGG	D07967 ;
ChEBI	CHEBI:50885 ;
ChEMBL	ChEMBL1201388 ;
PDB ligand	ZK5 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID7023061 ;
ECHA InfoCard	100.004.395
Chemical and physical data
Formula	C21H29FO5
Molar mass	380.456 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:AAXVEMMRQDVLJB-BULBTXNYSA-N ;
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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]

^ 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.
^ 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.
^ ^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.
^ 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.
^ "Fludrocortisone Use During Pregnancy | Drugs.com". www.drugs.com. Archived from the original on 24 December 2016. Retrieved 24 December 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 484. ISBN 9783527607495. Archived from the original on 2017-11-05.
^ 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.