(22S)-Budesonide
A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (22S)-Budesonide are summarized together with 3D and 2D structures and relevant physico-chemical properties.
Table of Contents
What is the (22S)-Budesonide?
The molecule (22S)-Budesonide presents a molecular formula of C25H34O6 and its IUPAC name is (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.
Budesonide is a synthetic corticosteroid that is used to treat a variety of inflammatory conditions, including allergies, asthma, and Crohn's disease. It is a prodrug of the active metabolite, budesonide-17-monoacetate, which is more potent and has a longer half-life. Budesonide exists as an inhalation suspension, nebulizer solution, and oral suspension..
The mechanism of action of budesonide is not completely understood, but it is thought to work by inhibiting the production of inflammatory mediators, such as leukotrienes and prostaglandins. It also has been shown to have immunosuppressive effects..
Budesonide has been shown to be effective in the treatment of asthma, seasonal allergies, and Crohn's disease. It is generally well-tolerated, with the most common side effects being headache, nausea, and dizziness..
Budesonide is a relatively new medication and more research is needed to determine its long-term safety and efficacy..
3D structure
Cartesian coordinates
Geometry of (22S)-Budesonide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.
2D drawing
Molecule descriptors
| IUPAC name | (1S,2S,4R,6S,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one |
| InChI code | 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 |
| InChI Key | VOVIALXJUBGFJZ-AMTWPJRWSA-N |
| SMILES | CCC[C@H]1O[C@@H]2C[C@H]3[C@@H]4CCC5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1 |
Other names (synonyms)
IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.
One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.
Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.
In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.
- (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
- (22S)-BUDESONIDE
- (22S)-Budesonide
- (S)-16alpha,17-(Butylidenedioxy)-11beta,21-dihydroxypregna-1,4-diene-3,20-dione
- 168L5HT37P
- 51333-22-3
- 51372-28-2
- BUDESONIDE (11.BETA.,16.ALPHA.(S))
- BUDESONIDE, (S)-
- Budesonide (11beta,16alpha(S))
- Budesonide MMX
- PREGNA-1,4-DIENE-3,20-DIONE, 16,17-BUTYLIDENEBIS(OXY)-11,21-DIHYDROXY-, (11.BETA.,16.ALPHA.(S))
- Q27251792
Reference codes for other databases
There exist several different chemical codes commonly used in orded to identify molecules:- CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
- Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
- ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
- PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
- RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
- ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
- CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.
- ZINC4097286
- UNII-168L5HT37P
- DTXSID20860628
- EINECS 257-160-1
- SCHEMBL19635
Physico-Chemical properties
| IUPAC name | (1S,2S,4R,6S,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one |
| Molecular formula | C25H34O6 |
| Molecular weight | 430.534 |
| Melting point (ºC) | |
| Boiling point (ºC) | |
| Density (g/cm3) | |
| Molar refractivity | 115.18 |
| LogP | 2.7 |
| Topological polar surface area | 93.1 |
LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.
The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.
TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.
In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.
For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.