Fludrocortisone

Identification

Summary

Fludrocortisone is a mineralocorticoid used to treat adrenocortical insufficiency and salt-losing adrenogenital syndrome.

Brand Names
Florinef
Generic Name
Fludrocortisone
DrugBank Accession Number
DB00687
Background

Fludrocortisone is a synthetic mineralocorticoid used in conjunction with hydrocortisone to replace missing endogenous corticosteroids in patients with adrenal insufficiency.9,11 It is functionally similar to aldosterone, the body's primary endogenous mineralocorticoid, and is structurally analogous to cortisol, differing only by a fluorine atom at the 9-position of the steroid structure - this fluorination is thought to be crucial to fludrocortisone's significant mineralocorticoid potency.7

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 380.4504
Monoisotopic: 380.199902243
Chemical Formula
C21H29FO5
Synonyms
  • 9alpha-Fluorocortisol
  • Fludrocortison
  • Fludrocortisona
  • Fludrocortisone
  • Fludrocortisonum
  • Fluohydrocortisone
External IDs
  • StC 1400
  • U 5963

Pharmacology

Indication

Fludrocortisone is indicated as partial replacement therapy for primary or secondary adrenocortical insufficiency in Addison's disease. It is also indicated for the treatment of salt-losing androgenital syndrome.14

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatOtitis externaCombination Product in combination with: Polymyxin B (DB00781), Lidocaine (DB00281), Neomycin (DB00994), Furaltadone (DB16567)••••••••••••••••••
Used in combination to treatOtitis media (om)Combination Product in combination with: Polymyxin B (DB00781), Lidocaine (DB00281), Furaltadone (DB16567), Neomycin (DB00994)••••••••••••••••••
Management ofPrimary adrenocortical insufficiency••••••••••••
Management ofSecondary adrenocortical insufficiency••••••••••••
Treatment ofSalt-losing androgenital syndrome••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Fludrocortisone is a synthetic mineralocorticoid used to replace endogenous aldosterone in conditions resulting in missing or inadequate endogenous synthesis.14,15 It acts on the kidneys to increase both sodium reabsorption and potassium excretion.13,11 As its effects are exerted at the transcriptional level, a single dose of fludrocortisone may work over the course of 1-2 days15 despite a relatively short plasma half-life.6,9,10 Like other systemic corticosteroids, fludrocortisone may mask signs of infection by depressing the normal immune response - infections occurring during fludrocortisone therapy should be promptly treated with appropriate antimicrobial therapy.14

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.13 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.11

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.13 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.13

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.7

TargetActionsOrganism
AMineralocorticoid receptor
agonist
Humans
UGlucocorticoid receptor
agonist
Humans
Absorption

Absorption of fludrocortisone following oral administration is rapid and complete.16,9,10,6 Pharmacokinetic studies have estimated the Cmax to be 0.0012 to 0.20 μg/L with a Tmax between 0.5 and 2 hours.9,10 The AUC0-∞ of fludrocortisone after oral administration has been variably estimated to be between 1.22 to 3.07 μg.h/L.9,10

Volume of distribution

The apparent volume of distribution of fludrocortisone is 80-85 L.9,6 Distribution into CSF appears minimal - the observed ratio of CSF drug concentration versus plasma drug concentration is 1:6.16

Protein binding

Fludrocortisone is 70-80% protein bound in plasma, mostly to albumin and corticosteroid-binding globulin.16,10

Metabolism

There exists is a paucity of information regarding the specific metabolic pathway in vivo of fludrocortisone. The 9α-fluorination of fludrocortisone appears to greatly simplify its metabolism as compared to other corticosteroids8 - while oxidation via 11-hydroxysteroid dehydrogenases has been observed,3 this reaction is greatly impaired as the fluorine moiety appears to confer "protection" from 11β-oxidation by these enzymes. The reduction in 11β-oxidation is thought to be one of the reasons behind fludrocortisone's profound mineralocorticoid potency.7 An in vitro study generated only two metabolites following incubation in human liver microsomes and cytosol, namely 20β-dihydrofluorocortisol and 6β-hydroxyfluorocortisol, and did not explore in detail the potential enzymes responsible for this reaction.8

Given that fludrocortisone is a corticosteroid, a class of medications known to be metabolized by the CYP3A family,12 and is not recommended to be given with strong inhibitors/inducers of CYP3A,15 it is likely that the CYP3A family of enzymes contributes in some way to its metabolism (though this information does not appear to have been specifically elucidated for fludrocortisone).

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Route of elimination

Approximately 80% of an administered dose of fludrocortisone shows up in the urine, with the other 20% likely eliminated via fecal or biliary route.16,10

Half-life

The plasma half-life of fludrocortisone has been variably reported to be between 1-3.5 hours,6,9,10 though prescribing information gives an approximate half-life of 18-36 hours.15

Clearance

Population pharmacokinetics have estimated the plasma clearance of fludrocortisone to be 40.8 L/h.9

Adverse Effects
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Toxicity

The oral LD50 of fludrocortisone in rats is >1g/kg.17 Acute overdosage of fludrocortisone is likely to result in symptoms consistent with its adverse effect profile. Patients receiving a single large dose should be treated with plenty of water by mouth and should undergo monitoring of serum electrolytes, particularly potassium and sodium, and be treated appropriately for any developing imbalances.15,16

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Fludrocortisone can be increased when it is combined with Abametapir.
AbataceptThe risk or severity of adverse effects can be increased when Fludrocortisone is combined with Abatacept.
AcarboseThe risk or severity of hyperglycemia can be increased when Fludrocortisone is combined with Acarbose.
AceclofenacThe risk or severity of gastrointestinal irritation can be increased when Fludrocortisone is combined with Aceclofenac.
AcemetacinThe risk or severity of gastrointestinal irritation can be increased when Fludrocortisone is combined with Acemetacin.
Food Interactions
  • Limit salt intake. Excessive intake of salt can result in hypertension and edema.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Fludrocortisone acetateV47IF0PVH4514-36-3SYWHXTATXSMDSB-GSLJADNHSA-N
Product Images
International/Other Brands
Adixone (Genopharm) / Astonin (Merck) / Cortineff (Polfa Pabianice) / Florinef Acetaat (Bristol-Myers Squibb) / Florinefe (Bristol-Myers Squibb) / Fludrocortison (Bristol-Myers Squibb) / Lonikan (Merck)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FlorinefTablet0.1 mgOralPaladin Labs Inc1995-12-31Not applicableCanada flag
Florinef AcetateTablet.1 mg/1OralMonarch Pharmaceuticals, Inc.1955-08-182007-09-20US flag
Florinef AcetateTablet0.1 mg/1OralPhysicians Total Care, Inc.1993-11-022011-05-31US flag
Florinef Acetate 0.1mgTablet.1 mg / tabOralSquibb Canada Inc., Division Of Bristol Myers Squibb Canada Inc.1958-12-311997-08-14Canada flag
Truemed Group LLCTablet0.1 mg/0.1mgOralTruemed Group LLC2022-09-17Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Fludrocortisone AcetateTablet0.1 mg/1Oralbryant ranch prepack2003-02-14Not applicableUS flag
Fludrocortisone AcetateTablet0.1 mg/1OralAmneal Pharmaceuticals NY LLC2002-03-18Not applicableUS flag
Fludrocortisone AcetateTablet0.1 mg/1OralAvPAK2011-08-01Not applicableUS flag
Fludrocortisone AcetateTablet0.1 mg/1OralAmerican Health Packaging2008-09-09Not applicableUS flag
Fludrocortisone AcetateTablet0.1 mg/1OralNorthStar Rx LLC2023-09-07Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
OTOPAINFludrocortisone acetate (1 mg/ml) + Lidocaine hydrochloride (40 mg/ml) + Neomycin sulfate (5 mg/ml) + Polymyxin B sulfate (10000 iU/ml)Solution / dropsAuricular (otic)Interbat2018-03-092027-04-05Indonesia flag
OTOZAMBONFludrocortisone (0.1 G/100ML) + Furaltadone (0.45 G/100ML) + Lidocaine (4 G/100ML) + Neomycin (0.375 G/100ML) + Polymyxin B (1 MU/100ML)LiquidAuricular (otic)บริษัท เสริมมิตรพาณิชย์ จำกัด จำกัด1980-01-012020-09-29Thailand flag
ออโตสามธงFludrocortisone (0.1 G/100ML) + Furaltadone (0.45 G/100ML) + Lidocaine (4 G/100ML) + Neomycin (0.375 G/100ML) + Polymyxin B (1 MU/100ML)LiquidAuricular (otic)บริษัท เอส.เอ็ม.ฟาร์มาซูติคอล จำกัด จำกัด1990-09-17Not applicableThailand flag
เอส.เอ็ม. ออโตFludrocortisone (0.1 G/100ML) + Furaltadone (0.45 G/100ML) + Lidocaine (4 G/100ML) + Neomycin (0.375 G/100ML) + Polymyxin B (1 MU/100ML)LiquidAuricular (otic)บริษัท เอส.เอ็ม.ฟาร์มาซูติคอล จำกัด2001-02-14Not applicableThailand flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Florinef AcetateFludrocortisone acetate (0.1 mg/1)TabletOralPhysicians Total Care, Inc.1993-11-022011-05-31US flag

Categories

ATC Codes
S02CA07 — Fludrocortisone and antiinfectivesS01CA06 — Fludrocortisone and antiinfectivesH02AA02 — FludrocortisoneS03CA05 — Fludrocortisone and antiinfectives
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 17-hydroxysteroids / 3-oxo delta-4-steroids / Halogenated steroids / Delta-4-steroids / Cyclohexenones / Tertiary alcohols / Alpha-hydroxy ketones
show 8 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound
show 24 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
11beta-hydroxy steroid, 17alpha-hydroxy steroid, 3-oxo Delta(4)-steroid, 20-oxo steroid, fluorinated steroid, mineralocorticoid, 21-hydroxy steroid, C21-steroid (CHEBI:50885) / C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C07004) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030103)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
U0476M545B
CAS number
127-31-1
InChI Key
AAXVEMMRQDVLJB-BULBTXNYSA-N
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
IUPAC Name
(1R,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)CC[C@]12C

References

Synthesis Reference

U.S. Patent 2,957,013

General References
  1. Agarwal MK, Coupry F, Philippe M: Physiological activity and receptor binding of 9 alpha fluorohydrocortisone. Biochem Biophys Res Commun. 1977 Sep 23;78(2):747-53. doi: 10.1016/0006-291x(77)90242-x. [Article]
  2. Lan NC, Graham B, Bartter FC, Baxter JD: Binding of steroids to mineralocorticoid receptors: implications for in vivo occupancy by glucocorticoids. J Clin Endocrinol Metab. 1982 Feb;54(2):332-42. doi: 10.1210/jcem-54-2-332. [Article]
  3. Diederich S, Eigendorff E, Burkhardt P, Quinkler M, Bumke-Vogt C, Rochel M, Seidelmann D, Esperling P, Oelkers W, Bahr V: 11beta-hydroxysteroid dehydrogenase types 1 and 2: an important pharmacokinetic determinant for the activity of synthetic mineralo- and glucocorticoids. J Clin Endocrinol Metab. 2002 Dec;87(12):5695-701. doi: 10.1210/jc.2002-020970. [Article]
  4. Abboud R, Akil M, Charcosset C, Greige-Gerges H: Interaction of glucocorticoids and progesterone derivatives with human serum albumin. Chem Phys Lipids. 2017 Oct;207(Pt B):271-278. doi: 10.1016/j.chemphyslip.2017.04.007. Epub 2017 Apr 21. [Article]
  5. SANDBERG AA, SLAUNWHITE WR Jr, CARTER AC: Transcortin: a corticosteroid-binding protein of plasma. III. The effects of various steroids. J Clin Invest. 1960 Dec;39:1914-26. doi: 10.1172/JCI104216. [Article]
  6. Mitsky VP, Workman RJ, Nicholson WE, Vernikos J, Robertson RM, Robertson D: A sensitive radioimmunoassay for fludrocortisone in human plasma. Steroids. 1994 Sep;59(9):555-8. doi: 10.1016/0039-128x(94)90074-4. [Article]
  7. Oelkers W, Buchen S, Diederich S, Krain J, Muhme S, Schoneshofer M: Impaired renal 11 beta-oxidation of 9 alpha-fluorocortisol: an explanation for its mineralocorticoid potency. J Clin Endocrinol Metab. 1994 Apr;78(4):928-32. [Article]
  8. Abel SM, Back DJ, Maggs JL, Park BK: Cortisol metabolism by human liver in vitro--IV. Metabolism of 9 alpha-fluorocortisol by human liver microsomes and cytosol. J Steroid Biochem Mol Biol. 1993 Dec;46(6):833-9. doi: 10.1016/0960-0760(93)90326-r. [Article]
  9. Hamitouche N, Comets E, Ribot M, Alvarez JC, Bellissant E, Laviolle B: Population Pharmacokinetic-Pharmacodynamic Model of Oral Fludrocortisone and Intravenous Hydrocortisone in Healthy Volunteers. AAPS J. 2017 May;19(3):727-735. doi: 10.1208/s12248-016-0041-9. Epub 2017 Jan 12. [Article]
  10. Banda J, Lakshmanan R, Vvs SP, Gudla SP, Prudhivi R: A highly sensitive method for the quantification of fludrocortisone in human plasma using ultra-high-performance liquid chromatography tandem mass spectrometry and its pharmacokinetic application. Biomed Chromatogr. 2015 Aug;29(8):1213-9. doi: 10.1002/bmc.3410. Epub 2015 Jan 22. [Article]
  11. Charmandari E, Nicolaides NC, Chrousos GP: Adrenal insufficiency. Lancet. 2014 Jun 21;383(9935):2152-67. doi: 10.1016/S0140-6736(13)61684-0. Epub 2014 Feb 4. [Article]
  12. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  13. 32. (2012). In Rang and Dale's Pharmacology (7th ed.). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
  14. DPD Approved Drugs: Florinef [Link]
  15. MedSafe NZ: Florinef [Link]
  16. UK Approved Drugs: Fludrocortisone [Link]
  17. CaymanChem: Fludrocortisone acetate MSDS [Link]
Human Metabolome Database
HMDB0014825
KEGG Drug
D07967
KEGG Compound
C07004
PubChem Compound
31378
PubChem Substance
46508616
ChemSpider
29111
RxNav
4452
ChEBI
50885
ChEMBL
CHEMBL1201388
ZINC
ZINC000004097304
Therapeutic Targets Database
DAP001105
PharmGKB
PA164743961
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
ZK5
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fludrocortisone
PDB Entries
1gs4

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCongenital Adrenal Hyperplasia (CAH)1
4CompletedPreventionSeptic Shock1
4CompletedTreatmentSyncope, Vasovagal, Neurally-Mediated1
4RecruitingTreatmentNeurogenic Orthostatic Hypotension (nOH)1
4Unknown StatusDiagnosticHypertension1

Pharmacoeconomics

Manufacturers
  • King pharmaceuticals inc
  • Barr laboratories inc
  • Impax laboratories inc
Packagers
  • Amerisource Health Services Corp.
  • Avkare Incorporated
  • Barr Pharmaceuticals
  • Bristol-Myers Squibb Co.
  • Cardinal Health
  • E.R. Squibb and Sons LLC
  • Global Pharmaceuticals
  • Heartland Repack Services LLC
  • Impax Laboratories Inc.
  • Kaiser Foundation Hospital
  • Medisca Inc.
  • Physicians Total Care Inc.
  • Resource Optimization and Innovation LLC
  • Vangard Labs Inc.
Dosage Forms
FormRouteStrength
TabletOral.1 mg/1
TabletOral.1 mg / tab
TabletOral0.1 mg/1
Solution / dropsAuricular (otic)
LiquidAuricular (otic)
TabletOral0.1 mg/0.1mg
TabletOral0.1 mg
Prices
Unit descriptionCostUnit
Fludrocortisone acetate powder73.14USD g
Florinef acetate 0.1 mg tablet1.49USD tablet
Fludrocortisone Acetate 0.1 mg tablet0.81USD tablet
Fludrocortisone 0.1 mg tablet0.75USD tablet
Florinef 0.1 mg Tablet0.25USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.224 mg/mLALOGPS
logP1.35ALOGPS
logP1.32Chemaxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.55Chemaxon
pKa (Strongest Basic)-3.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area94.83 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity96.93 m3·mol-1Chemaxon
Polarizability39.53 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9927
Blood Brain Barrier+0.9731
Caco-2 permeable+0.8415
P-glycoprotein substrateSubstrate0.7911
P-glycoprotein inhibitor INon-inhibitor0.8385
P-glycoprotein inhibitor IINon-inhibitor0.9351
Renal organic cation transporterNon-inhibitor0.7774
CYP450 2C9 substrateNon-substrate0.8799
CYP450 2D6 substrateNon-substrate0.909
CYP450 3A4 substrateSubstrate0.7138
CYP450 1A2 substrateNon-inhibitor0.9306
CYP450 2C9 inhibitorNon-inhibitor0.9023
CYP450 2D6 inhibitorNon-inhibitor0.9201
CYP450 2C19 inhibitorNon-inhibitor0.9285
CYP450 3A4 inhibitorNon-inhibitor0.8772
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.903
Ames testNon AMES toxic0.8895
CarcinogenicityNon-carcinogens0.9479
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.1686 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9591
hERG inhibition (predictor II)Inhibitor0.5213
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0c11-2923000000-2aa4b6ff5d62976e9db5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-20dbead22f786ba4e1d2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0009000000-d5df7f0ebcc9f21cc864
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0359000000-45a2f0b486160d8bdb78
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-1009000000-2d5b34feb5786e3db7ce
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03gi-0292000000-45127d63a1a334cdd2a0
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0v4i-0309000000-6c1d4ff96c0d4fd7bde0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-195.0727039
predicted
DarkChem Lite v0.1.0
[M-H]-187.58272
predicted
DeepCCS 1.0 (2019)
[M+H]+198.7076039
predicted
DarkChem Lite v0.1.0
[M+H]+189.47812
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.5833039
predicted
DarkChem Lite v0.1.0
[M+Na]+195.6023
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 Da
References
  1. Agarwal MK, Coupry F, Philippe M: Physiological activity and receptor binding of 9 alpha fluorohydrocortisone. Biochem Biophys Res Commun. 1977 Sep 23;78(2):747-53. doi: 10.1016/0006-291x(77)90242-x. [Article]
  2. Lan NC, Graham B, Bartter FC, Baxter JD: Binding of steroids to mineralocorticoid receptors: implications for in vivo occupancy by glucocorticoids. J Clin Endocrinol Metab. 1982 Feb;54(2):332-42. doi: 10.1210/jcem-54-2-332. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Agarwal MK, Coupry F, Philippe M: Physiological activity and receptor binding of 9 alpha fluorohydrocortisone. Biochem Biophys Res Commun. 1977 Sep 23;78(2):747-53. doi: 10.1016/0006-291x(77)90242-x. [Article]
  2. Lan NC, Graham B, Bartter FC, Baxter JD: Binding of steroids to mineralocorticoid receptors: implications for in vivo occupancy by glucocorticoids. J Clin Endocrinol Metab. 1982 Feb;54(2):332-42. doi: 10.1210/jcem-54-2-332. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  2. Vienna presentation 2012 [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation...
Gene Name
HSD11B2
Uniprot ID
P80365
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 2
Molecular Weight
44126.06 Da
References
  1. Diederich S, Eigendorff E, Burkhardt P, Quinkler M, Bumke-Vogt C, Rochel M, Seidelmann D, Esperling P, Oelkers W, Bahr V: 11beta-hydroxysteroid dehydrogenase types 1 and 2: an important pharmacokinetic determinant for the activity of synthetic mineralo- and glucocorticoids. J Clin Endocrinol Metab. 2002 Dec;87(12):5695-701. doi: 10.1210/jc.2002-020970. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the rea...
Gene Name
HSD11B1
Uniprot ID
P28845
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 1
Molecular Weight
32400.665 Da
References
  1. Diederich S, Eigendorff E, Burkhardt P, Quinkler M, Bumke-Vogt C, Rochel M, Seidelmann D, Esperling P, Oelkers W, Bahr V: 11beta-hydroxysteroid dehydrogenase types 1 and 2: an important pharmacokinetic determinant for the activity of synthetic mineralo- and glucocorticoids. J Clin Endocrinol Metab. 2002 Dec;87(12):5695-701. doi: 10.1210/jc.2002-020970. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Abboud R, Akil M, Charcosset C, Greige-Gerges H: Interaction of glucocorticoids and progesterone derivatives with human serum albumin. Chem Phys Lipids. 2017 Oct;207(Pt B):271-278. doi: 10.1016/j.chemphyslip.2017.04.007. Epub 2017 Apr 21. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name
SERPINA6
Uniprot ID
P08185
Uniprot Name
Corticosteroid-binding globulin
Molecular Weight
45140.49 Da
References
  1. SANDBERG AA, SLAUNWHITE WR Jr, CARTER AC: Transcortin: a corticosteroid-binding protein of plasma. III. The effects of various steroids. J Clin Invest. 1960 Dec;39:1914-26. doi: 10.1172/JCI104216. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55