(1S,2S,4R,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: 132753
• Molecular Formular: C25H34O6
• Molecular Mass: 430.53386
• Monoisotopic Mass: 430.23553881
• SMILES: CCCC1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@@]5([C@H]4[C@H](C[C@@]3([C@@]2(O1)C(=O)CO)C)O)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-propyl-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: budesonide; (1S,2S,4R,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
• 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; 16,17-Butylidenebis(oxy)-11,21-dihydroxypregna-1,4-diene-3,20-dione; Budesonide; Budamax; Demotest; Inflammide; Lisoflam; Nohalon; Olfex; Prederid; Pulmaxan

Database IDs

• CAS Number: 51333-22-3
• EC Number: 257-139-7
• MDL Number: MFCD00083259
• PubChem SID: 162227030; 24278277
• PubChem CID: 5281004

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; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 238-246°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: TU3723000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... IFNG(3458), IL5(3567)rat ... Nr3c1(24413)
• Mechanism of Action: Glucocorticoid steroid

Product Information

• Purity: ≥99%
• Grade: certified reference material
• Packaging: pkg of 500 mg
• Description: Stereoisomers 1:1
• Application(s): Used for the management of asthma, non-infectious rhinitis and for treatment of inflammatory bowel disease
• Pharmacopeia Traceability: traceable to BP 793; traceable to PhEur B1157300; traceable to USP 1078201
• Empirical Formula (Hill Notation): C25H34O6

DETAILS

Sigma Aldrich - B7777

Biochem/physiol Actions
Budesonide is a second generation glucocorticoid with low systemic absorption. It is used as an anti-inflammatory agent in the treatment of asthma, rhinitis, and inflammatory bowel disease. It inhibits the expression of chemokine mRNA and production of eotaxin and RANTES protein in primary human bronchial epithelial cells. Budesonide is currently in clinical trials for the prevention of lung cancer. It shows inhibitory effects on benzo[a]pyrene-induced carcinogenesis of the lung in mice.

Sigma Aldrich - PHR1178

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
Biochem/physiol Actions
Budesonide is a second generation glucocorticoid with low systemic absorption. It is used as an anti-inflammatory agent in the treatment of asthma, rhinitis, and inflammatory bowel disease. It inhibits the expression of chemokine mRNA and production of eotaxin and RANTES protein in primary human bronchial epithelial cells. Budesonide is currently in clinical trials for the prevention of lung cancer. It shows inhibitory effects on benzo[a]pyrene-induced carcinogenesis of the lung in mice.

Toronto Research Chemicals - B689490

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)
• Albertsson, J. et al., Acta Cryst. B, 1978, 34, 3027-3036, (cryst struct)
• Wikby, A. et al., J. Chromatogr., 1978, 157, 65
• Thalen, A. et al., Arzneim.-Forsch., 1979, 29, 1687, (synth, pharmacol)
• Brattsand, R. et al., J. Steroid Biochem., 1982, 16, 779, (pharmacol)
• Thalen, A. et al., Acta Pharm. Suec., 1984, 21, 109; 145; 1987, 24, 97, (synth, pmr)
• Clissold, S.P. et al., Drugs, 1984, 28, 485; 1992, 44, 375, (rev)
• Ryrfeldt, A. et al., Biochem. Pharmacol., 1989, 38, 17-22, (pharmacol)
• Spencer, C.M. et al., Drugs, 1995, 50, 854, (rev, pharmacol)
• Gauvreau, G.M. et al., Am. J. Resp. Crit. Care Med., 1996, 154, 1267, (pharmacol)
• Korn, S.H. et al., Am. J. Resp. Crit. Care Med., 1997, 155, 1117, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1034
• Hvizdos, K.M. et al., Drugs, 2000, 60, 1141-1178, (rev)
• McGavin, J.R. et al., Drugs, 2001, 61, 71-78, (rev)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BOM520