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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 of FLUDROCORTISONE

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
Molecular Formula C21H29FO5
Molecular Weight 380.4504
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

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

Approval Year

1955
116
Targets

Targets

Primary TargetPharmacologyConditionPotency
Mineralocorticoid receptor
53
Target ID: P22199
Gene ID: 25672.0
Gene Symbol: Nr3c2
Target Organism: Rattus norvegicus (Rat)
Agonist
2678
 1.07 nM [Kd]
Mineralocorticoid receptor
53
Target ID: P08235
Gene ID: 4306.0
Gene Symbol: NR3C2
Target Organism: Homo sapiens (Human)
Agonist
2678
Glucocorticoid receptor
172
Target ID: P06536
Gene ID: 24413.0
Gene Symbol: Nr3c1
Target Organism: Rattus norvegicus (Rat)
Agonist
2678
Glucocorticoid receptor
172
Target ID: P04150
Gene ID: 2908.0
Gene Symbol: NR3C1
Target Organism: Homo sapiens (Human)
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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
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
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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP3A
191
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A
191
 likely
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Clinical improvement in patients with orthostatic intolerance after treatment with bisoprolol and fludrocortisone.
2000 Oct
[Addisonian myopathy].
2001
Close association of urinary excretion of aquaporin-2 with appropriate and inappropriate arginine vasopressin-dependent antidiuresis in hyponatremia in elderly subjects.
2001 Apr
Endocrine evaluation for muscle pain.
2001 Aug
Mechanisms underlying the impairment in orthostatic tolerance after nocturnal recumbency in patients with autonomic failure.
2001 Dec
Fertility and body composition after laparoscopic bilateral adrenalectomy in a 30-year-old female with congenital adrenal hyperplasia.
2001 Feb
[An autopsy case of pure autonomic failure with pathological features of Parkinson's disease].
2001 Jan
Hydrocortisone suspension and hydrocortisone tablets are not bioequivalent in the treatment of children with congenital adrenal hyperplasia.
2001 Jan
Aldosterone synthase deficiency type I with no documented homozygous mutations in the CYP11B2 gene.
2001 Jan
Dehydroepiandrosterone replacement in addison's disease.
2001 Jul
Congenital hyperreninemic hypoaldosteronism unlinked to the aldosterone synthase (CYP11B2) gene.
2001 Nov
[Adrenal insufficiency caused by treatment with levothyroxine].
2001 Nov 29
Fludrocortisone treatment in a child with severe cerebral salt wasting.
2001 Oct
Serum cortisol and 17-hydroxyprogesterone interrelation in classic 21-hydroxylase deficiency: is current replacement therapy satisfactory?
2001 Oct
Outcomes for laparoscopic bilateral adrenalectomy.
2002 Aug
Effect of treatment with low doses of hydrocortisone and fludrocortisone on mortality in patients with septic shock.
2002 Aug 21
Salt losing nephropathy simulating congenital adrenal hyperplasia in an infant.
2002 Jul
A footnote on the origin of fluorosteroids.
2002 Jul
Yoghurt biotherapy: contraindicated in immunosuppressed patients?
2002 Jun
Cortisol replacement for severe sepsis and septic shock: what should I do?
2002 Jun
Angiotensin II feedback is a regulator of renocortical renin, COX-2, and nNOS expression.
2002 Jun
Orthostatic hypotension.
2002 May
[Fatigue, weight loss and decline in general health in a young patient. Addison disease].
2002 May 8
[Generic carbamazepine-induced subacute adrenal insufficiency?].
2002 Nov
Recently published papers: new evidence for old debates, new drugs and some timely reminders.
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
Bench-to-bedside review: endothelial cell dysfunction in severe sepsis: a role in organ dysfunction?
2003 Apr
Recently published papers: a number of treatment controversies.
2003 Feb
Successful treatment of severe orthostatic hypotension with erythropoietin.
2003 Jan
Drug treatment of orthostatic hypotension and vasovagal syncope.
2003 Jan-Feb
Neurologic complications following treatment of canine hypoadrenocorticism.
2003 Jun
Stability of fludrocortisone acetate solutions prepared from tablets and powder.
2003 Mar
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:41:37 GMT 2023
Edited
by admin
on Fri Dec 15 16:41:37 GMT 2023
Record UNII
U0476M545B
Record Status Validated (UNII)
Record Version
  • Download
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
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
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 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
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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
PRIMARY
DRUG BANK
DB00687
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
SMS_ID
100000080700
Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023
PRIMARY
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
PRIMARY
MERCK INDEX
m5431
Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023
PRIMARY Merck Index
MESH
D005438
Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-833-2
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PRIMARY
DAILYMED
U0476M545B
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
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
PRIMARY
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
PRIMARY
FDA UNII
U0476M545B
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
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
PRIMARY
INN
460
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PRIMARY
EVMPD
SUB07684MIG
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
PUBCHEM
31378
Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023
PRIMARY
RXCUI
4452
Created by admin on Fri Dec 15 16:41:38 GMT 2023 , Edited by admin on Fri Dec 15 16:41:38 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1201010
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
CAS
127-31-1
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
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
PRIMARY
Related Record Type Details
Structure of FLUDROCORTISONE ACETATE
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of FLUDROCORTISONE
ACTIVE MOIETY
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