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

• ChemBase ID: 72610
• Molecular Formular: C25H34O6
• Molecular Mass: 430.53386
• Monoisotopic Mass: 430.23553881
• 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(O[C@@H](O1)CCC)C(=O)CO)C)O)C
• Canonical SMILES: CCC[C@@H]1O[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-VXKMTNQYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,6R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one; (1S,2S,4R,6R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
• IUPAC Traditional name: budesonide; @budesonide
• Synonyms: (11β,16α)-16,17-[(1R)-Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione; Dexbudesonide; (22R)-Budesonide (>90% de); Rhinocort; Pulmicort; Entocort; Symbicort; Budesonide

Database IDs

• CAS Number: 51372-29-3; 51333-22-3
• PubChem SID: 162037535
• PubChem CID: 40000

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: Chloroform; DMSO
• Apperance: Light Beige Solid
• Melting Point: 194-199°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1286

Research Area: Inflammation
Biological Activity:
Budesonide is a glucocorticoid steroid for the treatment of asthma, non-infectious rhinitis (including hay fever and other allergies), and for treatment and prevention of nasal polyposis. It has efficacy in the terminal ileum and the right colon. Budesonide in comparison with prednisolone has been associated with fewer bone density losses and unlike other corticosteroids has little influence on the hypothalamic-pituitary-adrenal axis, which also limits the need of tapering before discontinuation. Overall, it has a lower incidence of systemic manifestations than similar medications. [1]

Toronto Research Chemicals - B689500

Budesonide (B689490) epimer R. Budesonide 22R epimer is more active than 22S epimer. Used as an antiinflammatory agent.

REFERENCES

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