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

• ChemBase ID: 179848
• Molecular Formular: C24H34O6
• Molecular Mass: 418.52316
• Monoisotopic Mass: 418.23553881
• SMILES: [C@]12([C@@](C(=O)COC(=O)CC)(CC[C@H]1[C@H]1[C@@H]([C@@]3(C(=CC(=O)CC3)CC1)C)[C@H](C2)O)O)C
• Canonical SMILES: CCC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C24H34O6/c1-4-20(28)30-13-19(27)24(29)10-8-17-16-6-5-14-11-15(25)7-9-22(14,2)21(16)18(26)12-23(17,24)3/h11,16-18,21,26,29H,4-10,12-13H2,1-3H3/t16-,17-,18-,21+,22-,23-,24-/m0/s1
• InChIKey: MRECAIZOMKKXOZ-RPPPWEFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,10S,11S,14R,15S,17S)-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 propanoate
• IUPAC Traditional name: 2-[(1S,2R,10S,11S,14R,15S,17S)-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 propanoate
• Synonyms: Hydrocortisone propionate

Database IDs

• CAS Number: 6677-98-1
• PubChem SID: 164235758
• PubChem CID: 111228

CALCULATED PROPERTIES

• Acid pKa: 12.610237
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.4168277
• LogD (pH = 7.4): 2.416825
• Log P: 2.4168277
• Molar Refractivity: 111.1784 cm^3
• Polarizability: 43.965054 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: ACTH antagonist; ACTH secretion inhibitor; Calcium mobilizer; Corticosteroid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

Product Information

• Application(s): Antiinflammatory; Immunosuppressive

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 584C, (nmr)
• Reichstein, T., Helv. Chim. Acta, 1937, 20, 953, (isol)
• v. Euw, J. et al., Helv. Chim. Acta, 1942, 25, 988, (struct)
• Zaffaroni, A. et al., J.A.C.S., 1951, 73, 1390, (biosynth)
• Wendler, N.L. et al., J.A.C.S., 1951, 73, 3818, (synth)
• U.K. Pat., 1954, 712 948; CA, 49, 12546i, (cypionate)
• U.S. Pat., 1956, 2 736 733; CA, 50, 13107, (tebutate)
• Ger. Pat., 1958, 1 037 451; CA, 54, 22730, (Hydrocortamate)
• Heller, E., Z. Naturforsch., B, 1959, 14, 298, (ir)
• Danish Pat., 1960, 88 839; CA, 55, 21181, (xanthogenate)
• U.S. Pat., 1960, 2 936 313; CA, 54, 19783, (phosphate)
• Shirasaka, M., Chem. Pharm. Bull., 1961, 9, 152, (synth)
• Gardi, R. et al., Gazz. Chim. Ital., 1963, 93, 431, (valerate)
• Biles, J.A., J. Pharm. Sci., 1963, 52, 1066, (tebutate, struct)
• Vitali, R. et al., Gazz. Chim. Ital., 1966, 96, 1115, (butyrate)
• Saucy, G. et al., Helv. Chim. Acta, 1966, 49, 1529; 1967, 50, 1394, (synth, ir, uv, pmr)
• van der Sijde, D. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 721, (synth)
• Smit, A. et al., Rec. Trav. Chim. (J. R. Neth. Chem. Soc.), 1966, 85, 731, (synth, struct, pmr)
• U.K. Pat., 1968, 1 111 320; CA, 70, 2447
• Kooreman, H.J. et al., Synth. Commun., 1971, 1, 81, (butyrate)
• Bhacca, N.S. et al., J.A.C.S., 1973, 95, 8421, (cmr)
• Haskins, N.J. et al., Biomed. Mass Spectrom., 1974, 1, 423, (ms)
• Fiegel, G., Arzneim.-Forsch., 1975, 25, 560, (use)
• Swartz, H., Invest. Med. Int., 1976, 3, 255, (rev, butyrate)
• De Angelis, L., Drugs of Today (Barcelona), 1979, 15, 435, (Hydrocortisone bendazac)
• Ger. Pat., 1979, 2 826 257; CA, 93, 26657, (butyrate, propionate)
• Genard, P., Org. Mass Spectrom., 1979, 12, 396, (pmr)
• U.K. Pat., 1979, 2 023 145; CA, 93, 114834, (aceponate)
• Castellano, E.E. et al., Acta Cryst. B, 1980, 36, 3063, (cryst. struct)
• Florey, K., Anal. Profiles Drug Subst., 1983, 12, 277, (rev, synth, pharmacol, anal)
• Laurent, H. et al., Arch. Pharm. (Weinheim, Ger.), 1984, 317, 421, (Hydrocortisone bendazac)
• Tanaka, S. et al., Chem. Pharm. Bull., 1986, 34, 1235, (butyrate, propionate)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6346; 6986; 7335
• Minagawa, K. et al., J.C.S. Perkin 1, 1988, 587, (synth)
• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 734
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BAV275; HHR000; CNS750; HHQ800; HHQ825; HHQ850; HHQ875