(1S,2S,4R,8S,9S,11S,12R,13S)-8-(2-chloroacetyl)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

• ChemBase ID: 132188
• Molecular Formular: C24H32ClFO5
• Molecular Mass: 454.9592832
• Monoisotopic Mass: 454.19223002
• SMILES: C[C@]12CCC(=O)C=C1CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]1[C@]2(OC(O1)(C)C)C(=O)CCl)C)O)F
• Canonical SMILES: ClCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1CCC1=CC(=O)CC[C@]21C)F)(C)C
• InChI: InChI=1S/C24H32ClFO5/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,26)17(28)11-22(16,4)24(19,31-20)18(29)12-25/h9,15-17,19,28H,5-8,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1
• InChIKey: MUQNGPZZQDCDFT-JNQJZLCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12R,13S)-8-(2-chloroacetyl)-12-fluoro-11-hydroxy-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icos-17-en-16-one
• IUPAC Traditional name: halog
• Synonyms: Halcinonide; (11β,16α)-21-Chloro-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione; Adcortin; Alcinonide; Halciderm; Halcimat; Halcinonide; Halog; SQ 18566; Halcinonide

Database IDs

• CAS Number: 3093-35-4
• EC Number: 221-439-6
• MDL Number: MFCD00866006
• PubChem SID: 162226465
• PubChem CID: 443943

CALCULATED PROPERTIES

• Acid pKa: 13.632763
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.3008862
• LogD (pH = 7.4): 3.300886
• Log P: 3.3008862
• Molar Refractivity: 113.5475 cm^3
• Polarizability: 44.833042 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: TU5010200
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63
• Safety Statements: 36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• 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

DETAILS

Toronto Research Chemicals - H102000

Anti-inflammatory (topical).

REFERENCES

• Kirshbaum, J., et al.: Anal. Profiles Drug Subs., 8, 251 (1979)