(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-(2H7)propyl(6-2H)-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

• ChemBase ID: 163082
• Molecular Formular: C25H34O6
• Molecular Mass: 430.53386
• Monoisotopic Mass: 430.23553881
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]1([C@@H](C2)OC(O1)CCC)C(=O)CO)C)C
• Canonical SMILES: CCCC1O[C@H]2[C@](O1)(C(=O)CO)[C@@]1([C@@H](C2)[C@@H]2CCC3=CC(=O)C=C[C@@]3([C@H]2[C@H](C1)O)C)C
• InChI: InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21?,22+,23-,24-,25+/m0/s1
• InChIKey: VOVIALXJUBGFJZ-KWVAZRHASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-(^2H₇)propyl(6-^2H)-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• IUPAC Traditional name: (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-(^2H₇)propyl(6-^2H)-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• Synonyms: (11β,16α)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione; Bidien; Budenofalk; Budesomide; Budeson; Cortivent; Entocort; Micronyl; Nebuampul; Preferid; Pulmicort; Respules; Rhinocort; Rhinocort Aqua; S 1320; Spirocort; Turbuhaler; Budesonide-d8

Database IDs

• PubChem SID: 162257217
• PubChem CID: 12796588

CALCULATED PROPERTIES

• Acid pKa: 13.743137
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.73389
• LogD (pH = 7.4): 2.7338898
• Log P: 2.73389
• Molar Refractivity: 116.1098 cm^3
• Polarizability: 45.44829 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO
• Apperance: White Solid
• Melting Point: 214-217°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B689492

Labelled Budesonide, a non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.

REFERENCES

• Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979)
• Roth, G., et al.: J. Pharm. Sci., 69, 766 (1979)
• Clissold, S.P., et al.: Drugs, 28, 485 (1979)