FLUDROCORTISONE ACETATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H31FO6
Molecular Weight	422.487
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C

InChI

InChIKey=SYWHXTATXSMDSB-GSLJADNHSA-N

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

HIDE SMILES / InChI

Molecular Formula	C23H31FO6
Molecular Weight	422.487
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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	Agonist 2,752	1.07 nM [Kd]
Mineralocorticoid receptor 53	Agonist 2,752
Glucocorticoid receptor 173	Agonist 2,752
Glucocorticoid receptor 173	Agonist 2,752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Addison's disease 2	Primary		Approved 8,583	FLORINEF
Salt-losing adrenogenital syndrome 2	Primary		Approved 8,583	FLORINEF

C_max

Value	Dose	Co-administered	Analyte	Population
1241.1 pg/mL	0.1 mg single, oral		FLUDROCORTISONE plasma	Homo sapiens
0.19 μg/L	50 μg single, oral		FLUDROCORTISONE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
3275.8 pg × h/mL	0.1 mg single, oral		FLUDROCORTISONE plasma	Homo sapiens
1.25 μg × h/L	50 μg single, oral		FLUDROCORTISONE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.57 h	0.1 mg single, oral		FLUDROCORTISONE plasma	Homo sapiens
1.35 h	50 μg single, oral		FLUDROCORTISONE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
30%	0.1 mg single, oral		FLUDROCORTISONE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
0.3 mg 1 times / day multiple, oral Highest studied dose	unhealthy	Other AEs: Serum potassium decreased, Rise in blood pressure...

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AEs

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AE	Significance	Dose	Population
Rise in blood pressure	5 patients	0.3 mg 1 times / day multiple, oral Highest studied dose	unhealthy
Serum potassium decreased	5 patients	0.3 mg 1 times / day multiple, oral Highest studied dose	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A 220

Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A 220	substrate 4,014	likely

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Sourcing

Sourcing

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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
eMolecules	31226069	https://www.emolecules.com/cgi-bin/more?vid=31226069
ZINC	ZINC000004097304	http://zinc15.docking.org/substances/ZINC000004097304

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PubMed

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Title	Date	PubMed
The use of oral vasopressors in the management of autonomic dysfunction and orthostatic hypotension.	1999 May	10369619
[Addisonian myopathy].	2001	11596401
Steroids in sepsis--more effective than activated protein C?	2001 Aug	11868733
Mechanisms underlying the impairment in orthostatic tolerance after nocturnal recumbency in patients with autonomic failure.	2001 Dec	11724647
Fertility and body composition after laparoscopic bilateral adrenalectomy in a 30-year-old female with congenital adrenal hyperplasia.	2001 Feb	11157995

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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

Substance Class	Chemical
Record UNII	V47IF0PVH4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUDROCORTISONE ACETATE

Common Name

English

FLUDROCORTISONE 21-ACETATE

Preferred Name

English

FLORINEF

Brand Name

English

FLUDROCORTISONE ACETATE [JAN]

Common Name

English

FLUDROCORTISONI ACETAS [WHO-IP LATIN]

Common Name

English

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Classification Tree

Code System

Code

Therapeutic Corticosteroid

NCI_THESAURUS

C521

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Code System

Code

Type

Description

NCI_THESAURUS

C1103

PRIMARY

DAILYMED

V47IF0PVH4

PRIMARY

WHO INTERNATIONAL PHARMACOPEIA

FLUDROCORTISONE ACETATE

PRIMARY

Description: A white or almost white, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water; sparingly soluble in ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Adrenal hormone. Storage: Fludrocortisone acetate should be kept in a well-closed container, protected from light. Additional information: Fludrocortisone acetate is hygroscopic. Definition: Fludrocortisone acetate contains not less than 96.0% and not more than 104.0% of C23H31FO6, calculated with reference to the dried substance.

FDA UNII

V47IF0PVH4

PRIMARY

NSC

15186

PRIMARY

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Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound