IUPAC Name	(8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	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	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	AAXVEMMRQDVLJB-BULBTXNYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CC12CCC(=O)C=C1CCC3C2(C(CC4(C3CCC4(C(=O)CO)O)C)O)F	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Isomeric SMILES	C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@]2([C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O)F	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C21H29FO5	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

DSSTOX Substance ID	DTXSID7023061	Source
Record name	Fludrocortisone
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID7023061
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	380.4 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Solid	Source
Record name	Fludrocortisone
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014825
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
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Solubility	In water, 140 mg/L at 25 °C, 2.24e-01 g/L	Source
Record name	FLUDROCORTISONE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3332
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Fludrocortisone
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014825
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Mechanism of Action	The main endogenous mineralocorticoid, aldosterone, is produced in the zona glomerulosa of the adrenal cortex - it acts on mineralocorticoid receptors in the kidneys to increase sodium reabsorption and potassium excretion, which in turn helps to regulate plasma electrolyte composition and blood pressure. In conditions of adrenal insufficiency, such as Addison’s disease, aldosterone is not produced (or is produced in insufficient quantities) and must be replaced by exogenous mineralocorticoids such as fludrocortisone. Fludrocortisone binding to mineralocorticoid receptors causes alterations to DNA transcription and translation of proteins that result in an increased density of sodium channels on the apical side of renal tubule cells and an increased density of Na⁺-K⁺-ATPase on the basolateral side. These increases in receptor density result in increased plasma sodium concentrations, and thus increased blood pressure, as well as a decreased plasma potassium concentration. Fludrocortisone may also exert a direct effect on plasma sodium levels via action at the Na⁺-H⁺ exchanger found in the apical membrane of renal tubule cells. Fludrocortisone also acts on glucocorticoid receptors, albeit with a much lower affinity - the glucocorticoid potency of fludrocortisone is approximately 5-10 times that of endogenous cortisol, whereas its mineralocorticoid potency is 200-400 times greater., At the cellular level, corticosteroids diffuse across cell membranes and complex with specific cytoplasmic receptors. These complexes then enter the cell nucleus, bind to DNA (chromatin), and stimulate transcription of mRNA (messenger RNA) and subsequent protein synthesis of various enzymes thought to be ultimately responsible for the physiological effects of these hormones., Mineralocorticoids act on the distal tubules to increase potassium excretion, hydrogen ion excretion, and sodium reabsorption and subsequent water retention. Cation transport in other secretory cells is similarly affected; excretion of water and electrolytes by the large intestine and by salivary and sweat glands is also altered, but to a lesser extent.	Source
Record name	Fludrocortisone
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00687
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Record name	FLUDROCORTISONE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3332
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Color/Form	Crystals
CAS No.	127-31-1	Source
Record name	Fludrocortisone
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=127-31-1
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Record name	Fludrocortisone [INN:BAN]
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Record name	Fludrocortisone
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Record name	fludrocortisone
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Record name	Fludrocortisone
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Record name	Fludrocortisone
Source	European Chemicals Agency (ECHA)
URL	https://echa.europa.eu/substance-information/-/substanceinfo/100.004.395
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Record name	FLUDROCORTISONE
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Record name	FLUDROCORTISONE
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Record name	Fludrocortisone
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014825
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Fludrocortisone

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Q & A

Q1: How does fludrocortisone exert its effects in the body?

A1: Fludrocortisone is a synthetic mineralocorticoid, primarily acting as an analog of aldosterone. It binds to the mineralocorticoid receptor (MR) in the distal tubules of the kidney, promoting sodium reabsorption and increasing the excretion of potassium and hydrogen ions. [, , , ] This action leads to increased plasma volume, contributing to increased blood pressure, making it clinically relevant for managing conditions like postural hypotension and adrenal insufficiency. [, , , ]

Q2: Can fludrocortisone's glucocorticoid activity contribute to its clinical effects?

A2: While fludrocortisone primarily acts as a mineralocorticoid, it also possesses glucocorticoid activity, though significantly less potent than its mineralocorticoid effects. [, ] This glucocorticoid activity becomes particularly relevant at higher doses, as seen in the treatment of postural hypotension, where it may contribute to side effects like posterior subcapsular cataract formation. []

Q3: How does fludrocortisone impact potassium levels?

A3: Fludrocortisone's interaction with MR in the distal tubules promotes potassium excretion. This effect can lead to hypokalemia, especially with prolonged use or high doses. [, , , , , , ] Monitoring potassium levels is crucial during fludrocortisone therapy. [, ]

Q4: What is the chemical structure of fludrocortisone?

A4: Fludrocortisone is a synthetic halogenated derivative of hydrocortisone, specifically 9α-Fluorohydrocortisone. Its chemical formula is C21H29FO5.

Q5: What are the common clinical uses of fludrocortisone?

A5: Fludrocortisone is used in the management of:

Primary adrenocortical insufficiency (Addison's disease): Supplementing mineralocorticoid deficiency. [, ]
Postural hypotension (orthostatic hypotension): Increasing blood volume to alleviate symptoms. [, , , , ]
Cerebral salt wasting syndrome (CSWS): Correcting hyponatremia by promoting sodium reabsorption. [, ]

Q6: Are there differences in the effectiveness of fludrocortisone compared to other treatments for orthostatic hypotension?

A7: Evidence comparing fludrocortisone to other treatments for orthostatic hypotension, such as midodrine or droxidopa, remains limited. Some studies suggest that while fludrocortisone may be effective, it might be associated with a higher risk of side effects, particularly in elderly patients or those with pre-existing conditions like congestive heart failure. [, , , , ]

Q7: Is fludrocortisone effective in managing hyperkalemia in hemodialysis patients?

A8: A randomized controlled trial investigated the use of fludrocortisone for hyperkalemia in hemodialysis patients. [] While the treatment was safe and well-tolerated, it did not demonstrate clinically significant reductions in serum potassium levels. []

Q8: What is the role of fludrocortisone in managing subarachnoid hemorrhage (SAH)?

A9: Fludrocortisone has been investigated for its potential to prevent hyponatremia and subsequent complications in patients with SAH. [, , ] Some studies suggest that early administration of fludrocortisone, particularly in patients with increased urinary sodium excretion, may reduce the incidence of symptomatic cerebral vasospasm. []

Q9: What are the potential adverse effects associated with fludrocortisone?

A9: Potential adverse effects of fludrocortisone, particularly with prolonged use or high doses, include:

Hypokalemia: Due to increased potassium excretion. [, , , , , , ]
Hypertension: Due to increased sodium and water retention. [, , , , ]
Fluid retention and edema: [, , ]
Posterior subcapsular cataract formation: Primarily associated with the glucocorticoid activity. []

Q10: Are there any significant drug interactions with fludrocortisone?

A10: Fludrocortisone may interact with various medications, including:

Potassium-lowering drugs (e.g., diuretics): May increase the risk of hypokalemia. []
Corticosteroids: May increase the risk of side effects. []

Q11: What factors should clinicians consider when prescribing fludrocortisone?

A11: Clinicians should consider the following:

Patient age: Elderly patients may be more susceptible to adverse effects. []
Co-existing medical conditions: Conditions like congestive heart failure, hypertension, and renal insufficiency may influence treatment decisions. [, ]
Concomitant medications: Assess for potential drug interactions. []
Monitoring: Regular monitoring of blood pressure, electrolytes (particularly potassium), and signs of fluid retention is essential. [, , ]

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