Fludrocortisone acetateProduct ingredient for Fludrocortisone

Name
Fludrocortisone acetate
Drug Entry
Fludrocortisone

Fludrocortisone is a synthetic mineralocorticoid used in conjunction with hydrocortisone to replace missing endogenous corticosteroids in patients with adrenal insufficiency.9,11 It is functionally similar to aldosterone, the body's primary endogenous mineralocorticoid, and is structurally analogous to cortisol, differing only by a fluorine atom at the 9-position of the steroid structure - this fluorination is thought to be crucial to fludrocortisone's significant mineralocorticoid potency.7

Accession Number
DBSALT000659
Structure
Synonyms
fludrocortisone 21-acetate
UNII
V47IF0PVH4
CAS Number
514-36-3
Weight
Average: 422.487
Monoisotopic: 422.210466929
Chemical Formula
C23H31FO6
InChI Key
SYWHXTATXSMDSB-GSLJADNHSA-N
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
IUPAC Name
2-[(1R,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]-2-oxoethyl acetate
SMILES
[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C
KEGG Compound
C08186
PubChem Compound
225609
ChemSpider
196144
ChEBI
5102
ChEMBL
CHEMBL1201010
ZINC
ZINC000003977990
Wikipedia
Fludrocortisone
Predicted Properties
PropertyValueSource
Water Solubility0.0483 mg/mLALOGPS
logP2.16ALOGPS
logP1.76Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.58Chemaxon
pKa (Strongest Basic)-3.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area100.9 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity106.08 m3·mol-1Chemaxon
Polarizability44.42 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon