2-[(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]-2-oxoethyl acetate

• ChemBase ID: 105014
• Molecular Formular: C23H31FO6
• Molecular Mass: 422.4870432
• Monoisotopic Mass: 422.21046693
• SMILES: O=C(OCC(=O)[C@]1(O)[C@]2(C[C@H](O)[C@]3(F)[C@@]4(C(=CC(=O)CC4)CC[C@H]3[C@@H]2CC1)C)C)C
• Canonical SMILES: CC(=O)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/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
• InChIKey: SYWHXTATXSMDSB-GSLJADNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethyl acetate; 2-[(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: fludrocortisone acetate
• Synonyms: 9α-Fluoro-11β,17α,21-trihydroxy-4-pregnene-3,20-dione acetate; Fludrocortisone acetate; (11β)-21-(Acetyloxy)-9-fluoro-11,17-dihydroxypregn-4-ene-3,20-dione; 9α-Fluorocortisol 21-Acetate; Alflorone Acetate; Cortineff; Fludrocortisone 21-Acetate; Florinef; NSC 15186; 9-Fluorocortisol acetate; 9-Fluorohydrocortisone acetate; 9α-Fluoro-11β,17α,21-trihydroxy-4-pregnene-3,20-dione acetate; 4-Pregnene-9α-fluoro-11β,17α,21-triol-3,20-dione acetate; FLUDROCORTISONE ACETATE

Database IDs

• CAS Number: 514-36-3
• EC Number: 208-180-4
• MDL Number: MFCD00864160
• PubChem SID: 162092097; 24894899
• PubChem CID: 225609

CALCULATED PROPERTIES

• Acid pKa: 12.574235
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7598988
• LogD (pH = 7.4): 1.7598959
• Log P: 1.7598988
• Molar Refractivity: 106.0795 cm^3
• Polarizability: 41.89201 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 224-226°C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TU5050000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63; R:22
• Safety Statements: 22-26-36; S:36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H361
• GHS Precautionary statements: P281

Product Information

• Purity: ≥98%
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02158054

Crystalline

Sigma Aldrich - F6127

Biochem/physiol Actions
Fludrocortisone acetate is a synthetic corticosteroid with more mineralocorticoid than glucocorticoid activity.

Toronto Research Chemicals - F428101

A mineralocorticoid.

REFERENCES

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