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. In adrenal insufficiency, it is generally taken together with hydrocortisone. Fludrocortisone is taken by mouth and is most commonly used in its acetate form.

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

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

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