| Common Name |
Loteprednol
| Description |
Loteprednol (as Loteprednol Etabonate) is a topical corticoid antiinflammatory. It is used in ophthalmic solution for the treatment of steroid responsive inflammatory conditions of the eye such as allergic conjunctivitis, uveitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis, and selected infective conjunctivitides. As a nasal spray, is used for the treatment and management of seasonal allergic rhinitis.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
Loteprednol etabonateHMDB
CEHOACMeSH
Chloromethyl 17 ethoxycarbonyloxy 11 hydroxy 3 oxoandrosta 1,4 diene 17 carboxylateMeSH
Etabonate, loteprednolMeSH
Chloromethyl 17-ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylateMeSH
17-Ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate, chloromethylMeSH
LotemaxMeSH
AlrexMeSH
| Chemical Formlia |
C21H27ClO5
| Average Molecliar Weight |
394.889
| Monoisotopic Molecliar Weight |
394.154701681
| IUPAC Name |
chloromethyl (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-14-carboxylate
| Traditional Name |
loteprednol
| CAS Registry Number |
82034-46-6
| SMILES |
[H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
| InChI Identifier |
InChI=1S/C21H27ClO5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,18(25)27-11-22)20(15,2)10-16(24)17(14)19/h5,7,9,14-17,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,17+,19-,20-,21-/m0/s1
| InChI Key |
YPZVAYHNBBHPTO-MXRBDKCISA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of mascliine characteristics. They also show profound effects on scalp and body hair in humans.
| Kingdom |
Organic compounds
| Super Class |
Lipids and lipid-like moleclies
| Class |
Steroids and steroid derivatives
| Sub Class |
Androstane steroids
| Direct Parent |
Androgens and derivatives
| Alternative Parents |
3-oxo delta-1,4-steroids
17-hydroxysteroids
11-beta-hydroxysteroids
Delta-1,4-steroids
Tertiary alcohols
Secondary alcohols
Cyclic ketones
Cyclic alcohols and derivatives
Carboxylic acid esters
Monocarboxylic acids and derivatives
Organochlorides
Organic oxides
Hydrocarbon derivatives
Alkyl chlorides
| Substituents |
Androgen-skeleton
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-1,4-steroid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organochloride
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Alkyl chloride
Alcohol
Organohalogen compound
Organic oxide
Aliphatic homopolycyclic compound
| Molecliar Framework |
Aliphatic homopolycyclic compounds
| External Descriptors |
organochlorine compound (CHEBI:50848 )
11beta-hydroxy steroid (CHEBI:50848 )
17alpha-hydroxy steroid (CHEBI:50848 )
androstanoid (CHEBI:50848 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:50848 )
steroid acid ester (CHEBI:50848 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Allergic Agents
Anti-inflammatory Agents
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Pharmaceutical
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point220 – 224 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.36e-02 g/LNot Available
LogP3.4Not Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.034 mg/mLALOGPS
logP2.2ALOGPS
logP2.52ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.01ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity102.65 m3·mol-1ChemAxon
Polarizability41.29 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00873
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00873
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB00873
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
8041134
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Loteprednol
| NuGOwiki Link |
HMDB15011
| Metagene Link |
HMDB15011
| METLIN ID |
Not Available
| PubChem Compound |
9865442
| PDB ID |
Not Available
| ChEBI ID |
50848
Product: CL-387786
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Pavesio CE, Decory HH: Treatment of ocular inflammatory conditions with loteprednol etabonate. Br J Ophthalmol. 2008 Apr;92(4):455-9. doi: 10.1136/bjo.2007.132621. Epub 2008 Feb 1. [PubMed:18245274 ]
|
PMID: 3132318
