CAS 51333-22-3|16,17-Butylidenebis(oxy)-11,21-dihydroxypregna-1,4-diene-3,20-dione|budesonide|(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[1...

General Information

Structure

Molecular Formula

C₂₅H₃₄O₆

Molecular Mass

430.53386

Exact Mass

430.23553881

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

LogD (pH = 7.4)

2.73

LogD (pH = 5.5)

2.73

Log P

2.73

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

13.75

Polar Surface Area

93.06

Polarizability

46.88

Molar Refractivity

116.11

LOG S

-4.73

Data Source

Names and Identifiers

Synonyms

16,17-Butylidenebis(oxy)-11,21-dihydroxypregna-1,4-diene-3,20-dioneBudesonideRespulesPreferidBidienBudesomideLisoflamBudesonideRhinocort(11β,16α)-16,17-[Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dioneOlfexBudenofalkNebuampulTurbuhalerSpirocortS 1320CortiventRhinocort AquaPrederidInflammidePulmicortBudesonEntocortPulmaxanMicronylDemotestNohalonBudamax(11beta,16alpha)-16,17-(Butylidenebis(oxy))-11,21-dihydroxypregna-1,4-diene-3,20-dionebudesonide

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[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-16-one (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^{13,18}]icosa-14,17-dien-16-one

IUPAC name

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

International Nonproprietary Name (INN)

budesonide

Names and Identifiers

Registration numbers

Properties

Safety Information

German water hazard class

RTECS

TU3723000

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

-20°C Freezer

Pharmacology Properties

Gene Information

human ... IFNG(3458), IL5(3567)rat ... Nr3c1(24413)

Mechanism of Action

Glucocorticoid steroid

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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.

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.

TRC

B689490

A non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.

ChEBI

CHEBI:3207

A glucocorticoid steroid having a highly oxygenated pregna-1,4-diene structure. It is used mainly in the treatment of asthma and non-infectious rhinitis and for treatment and prevention of nasal polyposis.

Molecule Details

References

PubChem Literature

From Data Sources

• Clissold, S.P., et al.: Drugs, 28, 485 (1979)

• Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979)

• Roth, G., et al.: J. Pharm. Sci., 69, 766 (1979)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1034

• Spencer, C.M. et al., Drugs, 1995, 50, 854, (rev, pharmacol)

• Hvizdos, K.M. et al., Drugs, 2000, 60, 1141-1178, (rev)

• Clissold, S.P. et al., Drugs, 1984, 28, 485; 1992, 44, 375, (rev)

• Albertsson, J. et al., Acta Cryst. B, 1978, 34, 3027-3036, (cryst struct)

• 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)

• Gauvreau, G.M. et al., Am. J. Resp. Crit. Care Med., 1996, 154, 1267, (pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BOM520

• McGavin, J.R. et al., Drugs, 2001, 61, 71-78, (rev)

• Wikby, A. et al., J. Chromatogr., 1978, 157, 65

• Thalen, A. et al., Arzneim.-Forsch., 1979, 29, 1687, (synth, pharmacol)

• Ryrfeldt, A. et al., Biochem. Pharmacol., 1989, 38, 17-22, (pharmacol)

• Korn, S.H. et al., Am. J. Resp. Crit. Care Med., 1997, 155, 1117, (pharmacol)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

IUPAC name

International Nonproprietary Name (INN)

budesonide

Molecule Details

Sigma Aldrich

B7777

PHR1178

TRC

B689490

A non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.

ChEBI

CHEBI:3207

References

PubChem Literature

From Data Sources

• Clissold, S.P., et al.: Drugs, 28, 485 (1979)

• Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979)

• Roth, G., et al.: J. Pharm. Sci., 69, 766 (1979)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 1034

• Spencer, C.M. et al., Drugs, 1995, 50, 854, (rev, pharmacol)

• Hvizdos, K.M. et al., Drugs, 2000, 60, 1141-1178, (rev)

• Clissold, S.P. et al., Drugs, 1984, 28, 485; 1992, 44, 375, (rev)

• Albertsson, J. et al., Acta Cryst. B, 1978, 34, 3027-3036, (cryst struct)

• 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)

• Gauvreau, G.M. et al., Am. J. Resp. Crit. Care Med., 1996, 154, 1267, (pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BOM520

• McGavin, J.R. et al., Drugs, 2001, 61, 71-78, (rev)

• Wikby, A. et al., J. Chromatogr., 1978, 157, 65

• Thalen, A. et al., Arzneim.-Forsch., 1979, 29, 1687, (synth, pharmacol)

• Ryrfeldt, A. et al., Biochem. Pharmacol., 1989, 38, 17-22, (pharmacol)

• Korn, S.H. et al., Am. J. Resp. Crit. Care Med., 1997, 155, 1117, (pharmacol)

Bioactivity

PubChem BioAssay

Properties

Safety Information

German water hazard class

RTECS

TU3723000

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

-20°C Freezer

Pharmacology Properties

Gene Information

human ... IFNG(3458), IL5(3567)rat ... Nr3c1(24413)

Mechanism of Action

Glucocorticoid steroid

Molecule

ID:132753