(1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl hexanoate

• ChemBase ID: 105400
• Molecular Formular: C27H40O4
• Molecular Mass: 428.6041
• Monoisotopic Mass: 428.29265976
• SMILES: O=C1C=C2[C@]([C@H]3CC[C@@]4([C@@](OC(=O)CCCCC)(C(=O)C)CC[C@H]4[C@@H]3CC2)C)(C)CC1
• Canonical SMILES: CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C(=O)C
• InChI: InChI=1S/C27H40O4/c1-5-6-7-8-24(30)31-27(18(2)28)16-13-23-21-10-9-19-17-20(29)11-14-25(19,3)22(21)12-15-26(23,27)4/h17,21-23H,5-16H2,1-4H3/t21-,22+,23+,25+,26+,27+/m1/s1
• InChIKey: DOMWKUIIPQCAJU-LJHIYBGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl hexanoate; (1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadec-6-en-14-yl hexanoate
• IUPAC Traditional name: proge; (1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl hexanoate
• Synonyms: 17α-Hydroxyprogesterone caproate; 17α-Hydroxyprogesterone hexanoate; 17-α-Hydroxypregn-4-ene-3,20-dione hexanoate; 17α-HYDROXYPROGESTERONE CAPROATE; Delalutin; Pharlon; Proge; Proluton.; Hydroxyprogesterone caproate

Database IDs

• CAS Number: 630-56-8
• EC Number: 211-138-8
• MDL Number: MFCD00072134
• PubChem SID: 24895697; 162092117
• PubChem CID: 169870

CALCULATED PROPERTIES

• Acid pKa: 17.807032
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.8765464
• LogD (pH = 7.4): 5.8765464
• Log P: 5.8765464
• Molar Refractivity: 121.6867 cm^3
• Polarizability: 48.209354 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 2-8°C
• RTECS: TU5085000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61
• Safety Statements: 53-22-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Mechanism of Action: Gonadotropin secretion inhibitor; Progestogen

Product Information

• Application(s): Progestogen

DETAILS

MP Biomedicals - 02190038

Crystalline

Sigma Aldrich - H5520

Biochem/physiol Actions
Shows significant reduction of pre-term delivery by mothers with a history of premature delivery, with no detectable harm to the infant.1

REFERENCES

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 583B, (nmr)
• Ringold, H.J. et al., J.A.C.S., 1956, 78, 816, (synth)
• Birmingham, M.K. et al., Steroids, 1963, 1, 463, (ir)
• Florey, K., Anal. Profiles Drug Subst., 1975, 4, 209, (rev, caproate)
• Duax, W.L., Steroids, 1979, 34, 501, (cryst struct)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1183
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HNT500; PMG600