2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-(2H11)cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate

• ChemBase ID: 164743
• Molecular Formular: C32H44O7
• Molecular Mass: 540.68756
• Monoisotopic Mass: 540.30870375
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1C[C@@H]1[C@]2(OC(O1)C1CCCCC1)C(=O)COC(=O)C(C)C)C)O)C
• Canonical SMILES: O=C(C(C)C)OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1CCC1=CC(=O)C=C[C@]21C)C1CCCCC1
• InChI: InChI=1S/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29?,30-,31-,32+/m0/s1
• InChIKey: LUKZNWIVRBCLON-FOMURGDPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-(^2H₁₁)cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate
• IUPAC Traditional name: 2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-(^2H₁₁)cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate
• Synonyms: (11β,16α)-16,17-[[(R/S)-(Cyclohexyl-d11)-methylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-pregna-1,4-diene-3,20-dione; Alvesco-d11; Omnaris-d11; RPR 251526-d11; Ciclesonide-d11 (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162258878
• PubChem CID: 71314861

CALCULATED PROPERTIES

• Acid pKa: 14.7785225
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 5.3232727
• LogD (pH = 7.4): 5.3232727
• Log P: 5.3232727
• Molar Refractivity: 146.2789 cm^3
• Polarizability: 57.75212 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C432692

A labelled glucocorticoid microemulsion nasal preparation allergy inhibitor rhinitis.This compound is a mixture of diastereomers at the cyclohexyl acetal.

REFERENCES

• Fukuoka, E., et al.: Chem. Pharm. Bull., 35, 2943 (1987)
• Schmitt, E., et al.: J. Pharm. Sci., 88, 291 (1987)
• Hancock, B., et al.: Pharm. Res., 17, 397 (1987)
• Hogan, S., et al.: Pharm. Res., 18, 112 (2001).