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51372-28-2 molecular structure
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(1S,2S,4R,6S,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

ChemBase ID: 1092
Molecular Formular: C25H34O6
Molecular Mass: 430.53386
Monoisotopic Mass: 430.23553881
SMILES and InChIs

SMILES:
O1[C@]2([C@@]3([C@H]([C@H]4[C@H]([C@@H](O)C3)[C@@]3(C(=CC(=O)C=C3)CC4)C)C[C@H]2O[C@@H]1CCC)C)C(=O)CO
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-AMTWPJRWSA-N

Cite this record

CBID:1092 http://www.chembase.cn/molecule-1092.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2S,4R,6S,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
(1S,2S,4R,6S,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
IUPAC Traditional name
budesonide
pulmicort
Brand Name
Bidien
Budeson
Cortivent
Desowen
Entocort
Entocort EC
Micronyl
Preferid
Pulmicort
Pulmicort Nebuamp
Pulmicort Respules
Pulmicort Turbuhaler
Rhinocort
Rhinocort Aqua
Rhinocort Turbuhaler
Spirocort
Tridesilon
Synonyms
budesonide
Budesonide
(11β,16α)-16,17-[(1S)-Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione
(22S)-Budesonide (85:15 = S:R)
CAS Number
51372-28-2
51333-22-3
PubChem SID
160964555
PubChem CID
63006

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
B689505 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.743137  H Acceptors
H Donor LogD (pH = 5.5) 2.73389 
LogD (pH = 7.4) 2.7338898  Log P 2.73389 
Molar Refractivity 116.1098 cm3 Polarizability 45.44829 Å3
Polar Surface Area 93.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.42  LOG S -3.97 
Solubility (Water) 4.57e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
insoluble expand Show data source
Methanol expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
196-198°C expand Show data source
Hydrophobicity(logP)
1.9 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB01222 external link
Item Information
Drug Groups approved; investigational
Description A glucocorticoid used in the management of asthma, the treatment of various skin disorders, and allergic rhinitis. [PubChem]
Indication For the treatment of mild to moderate active Crohn's disease. Also for the treatment of asthma, non-infectious rhinitis (including hay fever and other allergies), and for treatment and prevention of nasal polyposis.
Pharmacology Budesonide is a synthetic corticosteroid used in Crohn's disease to decrease the symptoms and inflammation associated with the disease, especially at times of flare up. Budesonide has a high topical glucocorticosteroid (GCS) activity and a substantial first pass elimination. The formulation contains granules which are coated to protect dissolution in gastric juice, but which dissolve at pH >5.5, ie, normally when the granules reach the duodenum. Thereafter, a matrix of ethylcellulose with budesonide controls the release of the drug into the intestinal lumen in a time-dependent manner.
Toxicity Single oral doses of 200 and 400 mg/kg were lethal in female and male mice, respectively. The signs of acute toxicity were decreased motor activity, piloerection and generalized edema.
Affected Organisms
Humans and other mammals
Biotransformation Following absorption, budesonide is subject to high first pass metabolism (80-90%). In vitro experiments in human liver microsomes demonstrate that budesonide is rapidly and extensively biotransformed, mainly by CYP3A4, to its 2 major metabolites, 6b-hydroxy budesonide and 16a- hydroxy prednisolone. The glucocorticoid activity of these metabolites is negligible (<1/100) in relation to that of the parent compound.
Absorption Absorption is complete following oral administration.
Half Life 2.0 and 3.6 hours
Protein Binding 85-90%
Elimination Budesonide is excreted in urine and feces in the form of metabolites.
Distribution * 3 L/kg [asthmatic children 4 to 6 years of age]
Clearance * 0.5 L/min [Athmatic children 4 to 6 years of age]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - B689505 external link
Budesonide (B689490) epimer S. Budesonide 22R epimer is more active than 22S epimer. Used as an antiinflammatory agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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