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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H29FO5
Molecular Weight 380.4512
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUDROCORTISONE

SMILES

C[C@@]12CCC(=O)C=C2CC[C@@]3([H])[C@]4([H])CC[C@](C(=O)CO)([C@@]4(C)C[C@@]([H])([C@@]31F)O)O

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
Curator's Comment:: 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

Fried, J.|Sabo, E.F.
2
Curator's Comment:: refernce was retrived from https://www.researchgate.net/publication/284208027_Fludrocortisone_Acetate

Approval Year

1955
94
Targets

Targets

Primary TargetPharmacologyConditionPotency
Mineralocorticoid receptor
49
Target ID: P22199
Gene ID: 25672
Gene Symbol: Nr3c2
Target Organism: Rattus norvegicus (Rat)
Agonist
2456
 1.07000000000000006 nM [Kd]
Mineralocorticoid receptor
49
Target ID: P08235
Gene ID: 4306
Gene Symbol: NR3C2
Target Organism: Homo sapiens (Human)
Agonist
2456
Salt-losing adrenogenital syndrome
Addison's disease
Glucocorticoid receptor
167
Target ID: P06536
Gene ID: 24413
Gene Symbol: Nr3c1
Target Organism: Rattus norvegicus (Rat)
Agonist
2456
Glucocorticoid receptor
167
Target ID: P04150
Gene ID: 2908
Gene Symbol: NR3C1
Target Organism: Homo sapiens (Human)
Agonist
2456
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Mineralocorticoid receptor
Approved
7997
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

-453600000000
Primary
Mineralocorticoid receptor
Approved
7997
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

-453600000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
0.3 mg 1 times / day multiple, oral
Highest studied dose
dose: 0.3 mg 1 times / day
route: oral
experiment_type: multiple
dose_type: Highest studied dose
co-adm with
    data_source:
    https://pubmed.ncbi.nlm.nih.gov/12372940
    unhealthy
    population: unhealthy
    age:
    sex:
    food_status:
    n:
    data_source:
    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)

    data_source:
    https://pubmed.ncbi.nlm.nih.gov/12372940
    AEs

    AEs

    AESignificanceDosePopulation
    Rise in blood pressure 5 pts%
    0.3 mg 1 times / day multiple, oral
    Highest studied dose
    dose: 0.3 mg 1 times / day
    route: oral
    experiment_type: multiple
    dose_type: Highest studied dose
    co-adm with
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/12372940
      unhealthy
      population:
      age:
      sex:
      food_status:
      n:
      data_source:
      https://pubmed.ncbi.nlm.nih.gov/12372940
      Serum potassium decreased 5 pts%
      0.3 mg 1 times / day multiple, oral
      Highest studied dose
      dose: 0.3 mg 1 times / day
      route: oral
      experiment_type: multiple
      dose_type: Highest studied dose
      co-adm with
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/12372940
        unhealthy
        population:
        age:
        sex:
        food_status:
        n:
        data_source:
        https://pubmed.ncbi.nlm.nih.gov/12372940
        Overview

        Overview

        CYP3A4CYP2C9CYP2D6hERG

        OverviewOther

        Other InhibitorOther SubstrateOther Inducer
        CYP3A
        154
        Drug as victim

        Drug as victim

        TargetModalityActivityMetaboliteClinical evidence
        CYP3A
        154
        		 likely
        Sourcing

        Sourcing

        Vendor/AggregatorIDURL
        ChEBI
        CHEBI:50885
        https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50885
        ZINC
        ZINC000004097304
        http://zinc15.docking.org/substances/ZINC000004097304
        PubMed

        PubMed

        TitleDatePubMed
        Potassium-lowering effect of mineralocorticoid therapy in patients undergoing hemodialysis.
        2002
        [Primary adrenal insufficiency due to autoimmune adrenalitis].
        2002 Aug
        Outcomes for laparoscopic bilateral adrenalectomy.
        2002 Aug
        Longitudinal analysis of growth and puberty in 21-hydroxylase deficiency patients.
        2002 Aug
        Effect of treatment with low doses of hydrocortisone and fludrocortisone on mortality in patients with septic shock.
        2002 Aug 21
        Reducing mortality in sepsis: new directions.
        2002 Dec
        Chronic unexplained fatigue.
        2002 Dec
        Treatment of orthostatic hypotension.
        2002 Dec
        Salt losing nephropathy simulating congenital adrenal hyperplasia in an infant.
        2002 Jul
        A footnote on the origin of fluorosteroids.
        2002 Jul
        Screening and diagnosis of primary aldosteronism.
        2002 Jul-Aug
        Yoghurt biotherapy: contraindicated in immunosuppressed patients?
        2002 Jun
        Cortisol replacement for severe sepsis and septic shock: what should I do?
        2002 Jun
        Orthostatic hypotension.
        2002 May
        [Generic carbamazepine-induced subacute adrenal insufficiency?].
        2002 Nov
        Dysautonomias: clinical disorders of the autonomic nervous system.
        2002 Nov 5
        [Diabetic neuropathy--concept, staging, diagnosis, treatment].
        2002 Oct
        Recently published papers: new evidence for old debates, new drugs and some timely reminders.
        2002 Oct
        Autonomic failure mimicing dopamine agonist induced vertigo in a patient with macroprolactinoma.
        2002 Oct
        Hyperaldosteronism: the internist's hypertensive disease.
        2002 Oct
        The mineralocorticoid receptor may compensate for the loss of the glucocorticoid receptor at specific stages of mammary gland development.
        2002 Sep
        A pilot randomized trial of induced blood pressure elevation: effects on function and focal perfusion in acute and subacute stroke.
        2003
        Neurocardiogenic syncope in children : current concepts in diagnosis and management.
        2003
        Sepsis clinical knowledge: a role of steroid treatment.
        2003 Apr
        Bench-to-bedside review: endothelial cell dysfunction in severe sepsis: a role in organ dysfunction?
        2003 Apr
        Diminished renal kallikrein responses to mineralocorticoid stimulation in African Americans: determinants of an intermediate phenotype for hypertension.
        2003 Apr
        Monozygotic twins with congenital adrenal hyperplasia: long-term endocrine evaluation and gene analysis.
        2003 Apr-May
        Association between supine hypertension and orthostatic hypotension in autonomic failure.
        2003 Aug
        Primary aldosteronism and hypertensive disease.
        2003 Aug
        Recently published papers: a number of treatment controversies.
        2003 Feb
        Chronic fatigue syndrome and Addison's disease.
        2003 Feb
        Successful treatment of severe orthostatic hypotension with erythropoietin.
        2003 Jan
        [Investigation of hyperaldosteronism in the hypertensive patient. Why? When? How?].
        2003 Jan
        Drug treatment of orthostatic hypotension and vasovagal syncope.
        2003 Jan-Feb
        Treating interdialytic hyperkalemia with fludrocortisone.
        2003 Jan-Feb
        Serum leptin levels in patients with 21-hydroxylase deficiency before and after treatment.
        2003 Jan-Mar
        Automated coupling of capillary-HPLC to matrix-assisted laser desorption/ionization mass spectrometry for the analysis of small molecules utilizing a reactive matrix.
        2003 Jul
        Neurologic complications following treatment of canine hypoadrenocorticism.
        2003 Jun
        Impact of smoking on the response to treatment of thyroid associated ophthalmopathy.
        2003 Jun
        [A 47-year-old man with "pure autonomic failure" and pernicious anemia].
        2003 Jun 13
        Combination therapy with hydrocortisone and fludrocortisone does not improve symptoms in chronic fatigue syndrome: a randomized, placebo-controlled, double-blind, crossover study.
        2003 Jun 15
        Stability of fludrocortisone acetate solutions prepared from tablets and powder.
        2003 Mar
        Parkinsonism associated with Addison's disease.
        2003 Mar
        Granulomatous interstitial nephritis.
        2003 Mar
        Congenital adrenal hypoplasia presenting as a chronic respiratory condition.
        2003 Mar
        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
        Hydrocortisone and fludrocortisone improved 28-day survival in septic shock and adrenal insufficiency.
        2003 Mar-Apr
        Hyperpigmentation mimicking Laugier syndrome, levodopa therapy and Addison's disease.
        2003 May
        Blood pressure in children and adolescents with congenital adrenal hyperplasia (21-hydroxylase deficiency): a preliminary report.
        2003 May
        Corticosteroid insufficiency in acutely ill patients.
        2003 May 22
        Patents

        Patents

        DE19911555A1
        2
        US20060013858
        2

        Sample Use Guides

        In Vivo Use Guide
        0.05mg to 0.3mg FLORINEF (Fludrocortisone acetate) daily (depends on indication)
        Route of Administration: Oral
        Name Type Language
        FLUDROCORTISONE
        HSDB   INN   MI   VANDF   WHO-DD  
        INN  
        		Official Name English
        FLUDROCORTISONE [INN]
        		Common Name English
        ASTONIN-H
        		Brand Name English
        FLUDROCORTISONE [HSDB]
        		Common Name English
        FLUDROCORTISONE [VANDF]
        		Common Name English
        FLUDROCORTISONE [WHO-DD]
        		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
        Classification Tree Code System Code
        		WHO-ATC S03CA05
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		WHO-ATC S01CA06
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		WHO-ATC H02AA02
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		WHO-VATC QS03CA05
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		WHO-ATC S02CA07
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		WHO-VATC QS02CA07
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		NCI_THESAURUS C521
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		WHO-ESSENTIAL MEDICINES LIST 18.1
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		WHO-VATC QS01CA06
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		WHO-VATC QH02AA02
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		LIVERTOX 422
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        Code System Code Type Description
        IUPHAR
        		2873
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		PRIMARY
        DRUG BANK
        		DB00687
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        WIKIPEDIA
        		FLUDROCORTISONE
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		PRIMARY
        MERCK INDEX
        		M5431
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		PRIMARY Merck Index
        MESH
        		D005438
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		PRIMARY
        ECHA (EC/EINECS)
        		204-833-2
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        EPA CompTox
        		127-31-1
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        NCI_THESAURUS
        		C71629
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		PRIMARY
        FDA UNII
        		U0476M545B
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        HSDB
        		3332
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        INN
        		460
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        EVMPD
        		SUB07684MIG
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        PUBCHEM
        		31378
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		PRIMARY
        RXCUI
        		4452
        Created by admin on Sat Jun 26 16:40:36 UTC 2021 , Edited by admin on Sat Jun 26 16:40:36 UTC 2021
        		PRIMARY RxNorm
        ChEMBL
        		CHEMBL1201010
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        CAS
        		127-31-1
        Created by admin on Sat Jun 26 16:40:35 UTC 2021 , Edited by admin on Sat Jun 26 16:40:35 UTC 2021
        		PRIMARY
        ACTIVE MOIETY
        Structure of FLUDROCORTISONE
        NIH
        NCATS
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        DISCLAIMER
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