(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

• ChemBase ID: 569
• Molecular Formular: C21H29FO5
• Molecular Mass: 380.4503632
• Monoisotopic Mass: 380.19990225
• SMILES: F[C@]12[C@H]([C@H]3[C@@]([C@](O)(CC3)C(=O)CO)(C[C@@H]2O)C)CCC2=CC(=O)CC[C@]12C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)CC[C@]12C)F
• 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
• InChIKey: AAXVEMMRQDVLJB-BULBTXNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: fludrocortisone
• Brand Name: 9 .Alpha. Ff; 9 Alpha Ff; 9 alpha-Fludrocortisone; 9 alpha-Fluorocortisol; 9.Alpha.-Fluorocortisol; 9.Alpha.-Fluorohydrocortisone; Alflorone; Astonin-H; F-COL; F-Cortef; Florinef; Fludrocortisona [INN-Spanish]; Fludrocortisone Acetate; Fludrocortisonum [INN-Latin]; Fludrocortone; Fludrone; Fludronef; Fluodrocortisone; Fluohydrisone; Fluohydrocortisone; Fluorocortisol; Fluorocortisone; ZK5
• Synonyms: Fludrocortisone; (11β)-9-Fluoro-11,17,21-trihydroxypregn-4-ene-3,20-dione; 9α-Fluorohydrocortisone; 9α-Fluoro-17-hydroxycorticosterone; Fluohydrisone; Astonin H-d5; NSC 11318

Database IDs

• CAS Number: 127-31-1
• PubChem SID: 46508616; 160964032
• PubChem CID: 31378

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.550707
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.3187733
• LogD (pH = 7.4): 1.3187703
• Log P: 1.3187734
• Molar Refractivity: 96.928 cm^3
• Polarizability: 38.038094 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.35
• LOG S: -3.23
• Solubility (Water): 2.24e-01 g/l

PROPERTIES

Physical Property

• Solubility: 140 mg/L; Chloroform; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 244-246°C (dec.)
• Hydrophobicity(logP): 0.3

Safety Information

• Storage Condition: Refrigerator

DETAILS

DrugBank - DB00687

• Drug Groups: approved
• Description: A synthetic mineralocorticoid with anti-inflammatory activity. [PubChem]
• Indication: For partial replacement therapy for primary and secondary adrenocortical insufficiency in Addison's disease and for the treatment of salt-losing adrenogenital syndrome.
• Pharmacology: Fludrocortisone is a synthetic adrenocortical steroid possessing very potent mineralocorticoid properties and high glucocorticoid activity. It is indicated as partial replacement therapy for primary and secondary adrenocortical insufficiency in Addison’s disease and for the treatment of salt-losing adrenogenital syndrome. The physiologic action of fludrocortisone acetate is similar to that of hydrocortisone. However, the effects of fludrocortisone acetate, particularly on electrolyte balance, but also on carbohydrate metabolism, are considerably heightened and prolonged. Mineralocorticoids act on the distal tubules of the kidney to enhance the reabsorption of sodium ions from the tubular fluid into the plasma; they increase the urinary excretion of both potassium and hydrogen ions.
• Toxicity: Effects of overexposure include irritation, cardiac edema, increased blood volume, hypertension, cardiac arrhythmias, enlargement of the heart, headaches, and weakness of the extremities.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, some renal.
• Half Life: 3.5 hours
• Protein Binding: High
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - F428100

A mineralocorticoid.

REFERENCES

• Florey, K., et al.: Anal. Profiles Drug Subs., 3, 281 (1974)