ChemFOnt: Showing chemical card for Clobetasol (CFc000009444)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:35 UTC

Chemfont ID

CFc000009444

Molecule Identification

Common Name

Clobetasol

Definition

Clobetasol is only found in individuals that have used or taken this drug. It is a derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in treatment of psoriasis but may cause marked adrenocortical suppression. [PubChem]The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A₂ inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A₂. Initially, however, clobetasol, like other corticosteroids, bind to the glucocorticoid receptor, which complexes, enteres the cell nucleus and modifies genetic transcription (transrepression/transactivation).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(11beta,16beta)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	ChEBI
Clobetasolum	ChEBI
Clobecort amex	Kegg
(11b,16b)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	Generator
(11Β,16β)-21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	Generator
Clobetasol 17 propionate	HMDB
Clobetasol 17-propionate	HMDB
Clobetasol propionate	HMDB
Clobex	HMDB
Clofenazon	HMDB
Cormax	HMDB
Dermovate	HMDB
Embeline	HMDB
Embeline e	HMDB
OLUX	HMDB
Temovate	HMDB

Chemical Formula

C₂₂H₂₈ClFO₄

Average Molecular Weight

410.907

Monoisotopic Molecular Weight

410.166015296

IUPAC Name

(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

Traditional Name

clobetasol

CAS Registry Number

25122-46-7

SMILES

[H][C@@]12C[C@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

InChI Key

FCSHDIVRCWTZOX-DVTGEIKXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
Hydroxysteroid
Halo-steroid
9-halo-steroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
Delta-1,4-steroid
Alpha-haloketone
Cyclic alcohol
Alpha-hydroxy ketone
Tertiary alcohol
Alpha-chloroketone
Cyclic ketone
Secondary alcohol
Fluorohydrin
Halohydrin
Ketone
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Alkyl fluoride
Organofluoride
Organochloride
Organohalogen compound
Alkyl chloride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:205919 )
17alpha-hydroxy steroid (CHEBI:205919 )
glucocorticoid (CHEBI:205919 )
20-oxo steroid (CHEBI:205919 )
fluorinated steroid (CHEBI:205919 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:205919 )
chlorinated steroid (CHEBI:205919 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015148)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.04	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.54 m³·mol⁻¹	ChemAxon
Polarizability	41.97 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015148

DrugBank ID

DB11750

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clobetasol propionate

METLIN ID

Not Available

PubChem Compound

5311051

PDB ID

Not Available

ChEBI ID

205919

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Clobetasol (CFc000009444)

MOL for CFc000009444 (Clobetasol)

3D MOL for CFc000009444 (Clobetasol)

3D SDF for CFc000009444 (Clobetasol)

3D-SDF for CFc000009444 (Clobetasol)

PDB for CFc000009444 (Clobetasol)

3D PDB for CFc000009444 (Clobetasol)

SMILES for CFc000009444 (Clobetasol)

INCHI for CFc000009444 (Clobetasol)

Structure for CFc000009444 (Clobetasol)

3D Structure for CFc000009444 (Clobetasol)