FLUDROCORTISONE

First approved in 1955

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H29FO5
Molecular Weight	380.4504
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]3(F)[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=AAXVEMMRQDVLJB-BULBTXNYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.medsafe.govt.nz/profs/datasheet/f/Florineftab.pdf
Curator's Comment: description was created based on several sources, including http://www.2ndchance.info/addison's-florinef.pdf

Fludrocortisone acetate (approved as Florinef) is a synthetic adrenocortical steroid possessing very potent mineralcorticoid properties and high glucocorticoid activity. Main indications are Partial replacement therapy for primary and secondary adrenocortical insufficiency in Addison's disease and for the treatment of salt losing adrenogenital syndrome.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Mineralocorticoid receptor 53 Target ID: P22199 Gene ID: 25672.0 Gene Symbol: Nr3c2 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/611629	Agonist 2678	1.07 nM [Kd]
Mineralocorticoid receptor 53 Target ID: P08235 Gene ID: 4306.0 Gene Symbol: NR3C2 Target Organism: Homo sapiens (Human) Sources: http://www.genome.jp/kegg-bin/show_pathway?map07225+D00986	Agonist 2678
Glucocorticoid receptor 172 Target ID: P06536 Gene ID: 24413.0 Gene Symbol: Nr3c1 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/611629	Agonist 2678
Glucocorticoid receptor 172 Target ID: P04150 Gene ID: 2908.0 Gene Symbol: NR3C1 Target Organism: Homo sapiens (Human) Sources: http://www.genome.jp/kegg-bin/show_pathway?map07225+D00986	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Addison's disease 2 Sources: https://www.drugs.com/cdi/florinef.html	Primary		Approved 8429	FLORINEF Approved Use Fludrocortisone acetate tablets USP, 0.1 mg are indicated as partial replacement therapy for primary and secondary adrenocortical insufficiency in Addison's disease and for the treatment of salt-losing adrenogenital syndrome. Launch Date 1955
Salt-losing adrenogenital syndrome 2 Sources: https://www.drugs.com/cdi/florinef.html	Primary		Approved 8429	FLORINEF Approved Use Fludrocortisone acetate tablets USP, 0.1 mg are indicated as partial replacement therapy for primary and secondary adrenocortical insufficiency in Addison's disease and for the treatment of salt-losing adrenogenital syndrome. Launch Date 1955

C_max

Value	Dose	Co-administered	Analyte	Population
1241.1 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25611194	0.1 mg single, oral dose: 0.1 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUDROCORTISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.19 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27416887	50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered:		FLUDROCORTISONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
3275.8 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25611194	0.1 mg single, oral dose: 0.1 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUDROCORTISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.25 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27416887	50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered:		FLUDROCORTISONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.57 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25611194	0.1 mg single, oral dose: 0.1 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUDROCORTISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.35 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27416887	50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered:		FLUDROCORTISONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
30% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25611194	0.1 mg single, oral dose: 0.1 mg route of administration: Oral experiment type: SINGLE co-administered:		FLUDROCORTISONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
0.3 mg 1 times / day multiple, oral Highest studied dose Dose: 0.3 mg, 1 times / day Route: oral Route: multiple Dose: 0.3 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12372940	unhealthy n = 5 Health Status: unhealthy Condition: anuric patients with symptomatic hypotension Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/12372940	Other AEs: Serum potassium decreased, Rise in blood pressure... Other AEs: Serum potassium decreased (5 patients) Rise in blood pressure (5 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/12372940

AEs

AE	Significance	Dose	Population
Rise in blood pressure	5 patients	0.3 mg 1 times / day multiple, oral Highest studied dose Dose: 0.3 mg, 1 times / day Route: oral Route: multiple Dose: 0.3 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12372940	unhealthy n = 5 Health Status: unhealthy Condition: anuric patients with symptomatic hypotension Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/12372940
Serum potassium decreased	5 patients	0.3 mg 1 times / day multiple, oral Highest studied dose Dose: 0.3 mg, 1 times / day Route: oral Route: multiple Dose: 0.3 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12372940	unhealthy n = 5 Health Status: unhealthy Condition: anuric patients with symptomatic hypotension Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/12372940

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A 191

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A 191	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/Fludrocortisone#section=Metabolism-Metabolites	likely

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:50885	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50885
ChemicalBook	CB7170706	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7170706
ZINC	ZINC000004097304	http://zinc15.docking.org/substances/ZINC000004097304
eMolecules	31226069	https://www.emolecules.com/cgi-bin/more?vid=31226069

PubMed

Title	Date	PubMed
[Normokalemic periodic paralysis].	2001	11555890
Close association of urinary excretion of aquaporin-2 with appropriate and inappropriate arginine vasopressin-dependent antidiuresis in hyponatremia in elderly subjects.	2001 Apr	11297601
Endothelial cell dysfunction in mice after transgenic knockout of type 2, but not type 1, 11beta-hydroxysteroid dehydrogenase.	2001 Dec 4	11733403
[An autopsy case of pure autonomic failure with pathological features of Parkinson's disease].	2001 Jan	11433766
Cautions over idiopathic aldosteronism.	2001 Jul 28	11501537
Orthostatic hypotension and chronic fatigue syndrome.	2001 Mar 21	11255416
Orthostatic hypotension and chronic fatigue syndrome.	2001 Mar 21	11255415
Orthostatic hypotension and chronic fatigue syndrome.	2001 Mar 21	11255414
Adverse cardiac effects of salt with fludrocortisone in hypertension.	2001 Oct	11641323
Serum cortisol and 17-hydroxyprogesterone interrelation in classic 21-hydroxylase deficiency: is current replacement therapy satisfactory?	2001 Oct	11600525
Potassium-lowering effect of mineralocorticoid therapy in patients undergoing hemodialysis.	2002	12372940
Resurrection of steroids for sepsis resuscitation.	2002 Apr	12024069
[Primary adrenal insufficiency due to autoimmune adrenalitis].	2002 Aug	12360800
Outcomes for laparoscopic bilateral adrenalectomy.	2002 Aug	12269488
Longitudinal analysis of growth and puberty in 21-hydroxylase deficiency patients.	2002 Aug	12138066
Effect of treatment with low doses of hydrocortisone and fludrocortisone on mortality in patients with septic shock.	2002 Aug 21	12186604
Reducing mortality in sepsis: new directions.	2002 Dec	12720570
Chronic unexplained fatigue.	2002 Dec	12509703
[Syncope - a systematic overview of classification, pathogenesis, diagnosis and management].	2002 Feb	11823926
Corticosteroid supplementation for adrenal insufficiency.	2002 Jan 9	11779267
Salt losing nephropathy simulating congenital adrenal hyperplasia in an infant.	2002 Jul	12174243
A footnote on the origin of fluorosteroids.	2002 Jul	12077592
Screening and diagnosis of primary aldosteronism.	2002 Jul-Aug	12389057
Cortisol replacement for severe sepsis and septic shock: what should I do?	2002 Jun	12133175
Angiotensin II feedback is a regulator of renocortical renin, COX-2, and nNOS expression.	2002 Jun	12010742
Orthostatic hypotension.	2002 May	12180246
Autonomic failure mimicing dopamine agonist induced vertigo in a patient with macroprolactinoma.	2002 Oct	12397537
Hyperaldosteronism: the internist's hypertensive disease.	2002 Oct	12385496
The mineralocorticoid receptor may compensate for the loss of the glucocorticoid receptor at specific stages of mammary gland development.	2002 Sep	12198239
A pilot randomized trial of induced blood pressure elevation: effects on function and focal perfusion in acute and subacute stroke.	2003	12865611
Neurocardiogenic syncope in children : current concepts in diagnosis and management.	2003	12716219
Sepsis clinical knowledge: a role of steroid treatment.	2003 Apr	12766716
Successful treatment of severe orthostatic hypotension with erythropoietin.	2003 Jan	12685148
Neurologic complications following treatment of canine hypoadrenocorticism.	2003 Jun	12839244
Simultaneous quantification of budesonide and its two metabolites, 6beta-hydroxybudesonide and 16alpha-hydroxyprednisolone, in human plasma by liquid chromatography negative electrospray ionization tandem mass spectrometry.	2003 Mar-Apr	12717805
Corticosteroid insufficiency in acutely ill patients.	2003 May 22	12765169

Patents

Sample Use Guides

In Vivo Use Guide

0.05mg to 0.3mg FLORINEF (Fludrocortisone acetate) daily (depends on indication)

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

FLUDROCORTISONE

Official Name

English

fludrocortisone [INN]

Common Name

English

ASTONIN-H

Brand Name

English

FLUDROCORTISONE [HSDB]

Common Name

English

FLUDROCORTISONE [VANDF]

Common Name

English

9-FLUORO-11.BETA.,17,21-TRIHYDROXYPREGN-4-ENE-3,20-DIONE

Systematic Name

English

NSC-11318

Code

English

FLUDROCORTISONE [MI]

Common Name

English

Fludrocortisone [WHO-DD]

Common Name

English

ALFLORONE

Brand Name

English

Classification Tree Code System Code

WHO-ATC

S03CA05

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

WHO-ATC

S01CA06

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

WHO-ATC

H02AA02

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WHO-VATC

QS03CA05

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

WHO-ATC

S02CA07

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

WHO-VATC

QS02CA07

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

NCI_THESAURUS

C521

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

WHO-ESSENTIAL MEDICINES LIST

18.1

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

WHO-VATC

QS01CA06

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

WHO-VATC

QH02AA02

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

LIVERTOX

422

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

Code System Code Type Description

IUPHAR

2873

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

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DRUG BANK

DB00687

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SMS_ID

100000080700

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WIKIPEDIA

FLUDROCORTISONE

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

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MERCK INDEX

m5431

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Merck Index

MESH

D005438

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ECHA (EC/EINECS)

204-833-2

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

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DAILYMED

U0476M545B

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EPA CompTox

DTXSID7023061

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

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NCI_THESAURUS

C71629

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

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FDA UNII

U0476M545B

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HSDB

3332

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

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INN

460

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EVMPD

SUB07684MIG

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PUBCHEM

31378

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RXCUI

4452

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RxNorm

ChEMBL

CHEMBL1201010

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CAS

127-31-1

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CHEBI

50885

Created by admin on Fri Dec 15 16:41:37 GMT 2023 , Edited by admin on Fri Dec 15 16:41:37 GMT 2023

PRIMARY

NSC

11318

Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023

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ACTIVE MOIETY


					U0476M545B

FLUDROCORTISONE

PRODRUG (METABOLITE ACTIVE)


					V47IF0PVH4

FLUDROCORTISONE ACETATE

Details

SMILES

InChI

DescriptionSources: http://www.medsafe.govt.nz/profs/datasheet/f/Florineftab.pdfCurator's Comment: description was created based on several sources, including http://www.2ndchance.info/addison's-florinef.pdf

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.medsafe.govt.nz/profs/datasheet/f/Florineftab.pdf
Curator's Comment: description was created based on several sources, including http://www.2ndchance.info/addison's-florinef.pdf

C_max

T_1/2

F_unbound