Fludrocortisone

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Fludrocortisone
Fludrocortisone structure.png
Fludrocortisone-from-xtal-1972-3D-balls.png
Systematic (IUPAC) name
9-fluoro-11,17-dihydroxy-17- (2-hydroxyacetyl)- 10,13-dimethyl- 1,2,6,7,8,9,10,11,12, 13,14,15,16,17- tetradecahydrocyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.commonograph
Pregnancy cat.C
Legal status?
RoutesOral
Pharmacokinetic data
Protein bindingHigh
MetabolismHepatic
Half-life3.5 hours
Identifiers
CAS number127-31-1 YesY
ATC codeH02AA02
PubChemCID 31378
IUPHAR ligand2873
DrugBankDB00687
ChemSpider29111 YesY
UNIIU0476M545B YesY
KEGGD07967 YesY
ChEBICHEBI:50885 YesY
ChEMBLCHEMBL1201388 N
Chemical data
FormulaC21H29FO5 
Mol. mass380.45 g/mol
 N (what is this?)  (verify)
 
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Fludrocortisone
Fludrocortisone structure.png
Fludrocortisone-from-xtal-1972-3D-balls.png
Systematic (IUPAC) name
9-fluoro-11,17-dihydroxy-17- (2-hydroxyacetyl)- 10,13-dimethyl- 1,2,6,7,8,9,10,11,12, 13,14,15,16,17- tetradecahydrocyclopenta[a]phenanthren-3-one
Clinical data
AHFS/Drugs.commonograph
Pregnancy cat.C
Legal status?
RoutesOral
Pharmacokinetic data
Protein bindingHigh
MetabolismHepatic
Half-life3.5 hours
Identifiers
CAS number127-31-1 YesY
ATC codeH02AA02
PubChemCID 31378
IUPHAR ligand2873
DrugBankDB00687
ChemSpider29111 YesY
UNIIU0476M545B YesY
KEGGD07967 YesY
ChEBICHEBI:50885 YesY
ChEMBLCHEMBL1201388 N
Chemical data
FormulaC21H29FO5 
Mol. mass380.45 g/mol
 N (what is this?)  (verify)

Fludrocortisone (also called 9α-fluorocortisol or 9α-fluorohydrocortisone) is a synthetic corticosteroid with moderate glucocorticoid potency and much greater mineralocorticoid potency.

The brand name in the U.S. and Canada is Florinef. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[1]

Medical uses[edit]

Fludrocortisone has been used in the treatment of cerebral salt wasting.[2] It is used primarily to replace the missing hormone aldosterone in various forms of adrenal insufficiency such as Addison's disease and the classic salt wasting (21-hydroxylase deficiency) form of congenital adrenal hyperplasia. Due to its effects on increasing Na+ levels, and therefore blood volume, fludrocortisone is the first line of treatment for orthostatic intolerance and Postural Orthostatic Tachycardia Syndrome (POTS).[3] It can be used to treat low blood pressure.

Fludrocortisone is also a confirmation test for diagnosing Conns syndrome (aldosterone producing-adrenal adenoma), the fludrocortisone suppression test. Loading the patient with fludrocortisone would suppress serum aldosterone level in a normal patient, whereas the level will not be altered in a Conns patient.

Side effects[edit]

Dosing[edit]

Renin plasma, sodium, and potassium is checked through blood tests in order to verify that the correct dosage is reached.

Chemical properties[edit]

Chemically, fludrocortisone is identical to cortisol except for the substitution of fluorine in place of one hydrogen. Fluorine is a good bioisostere for hydrogen because it is similar in size. The major difference is in its electronegativity.

References[edit]

  1. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  2. ^ Taplin CE, Cowell CT, Silink M, Ambler GR (December 2006). "Fludrocortisone therapy in cerebral salt wasting". Pediatrics 118 (6): e1904–8. doi:10.1542/peds.2006-0702. PMID 17101713. 
  3. ^ Freitas J, Santos R, Azevedo E, Costa O, Carvalho M and Falcão de Freitas A (2000). "Clinical improvement in patients with orthostatic intolerance after treatment with bisoprolol and fludrocortisone". Clinical Autonomic Research 10 (5): 293–299. doi:10.1007/BF02281112.