Loteprednol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Loteprednol
Accession Number
DB00873  (APRD01078)
Type
Small Molecule
Groups
Approved, Experimental
Description
Not Available
Structure
Thumb
3D
Similar Structures
Synonyms
  • Loteprednol
Categories
UNII
Z8CBU6KR16
CAS number
129260-79-3
Weight
Average: 394.889
Monoisotopic: 394.154701681
Chemical Formula
C21H27ClO5
InChI Key
YPZVAYHNBBHPTO-MXRBDKCISA-N
InChI
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
IUPAC Name
chloromethyl (1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1-carboxylate
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

Pharmacology

Indication
Not Available
Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Loteprednol.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Loteprednol.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Loteprednol.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Loteprednol.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Loteprednol.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Loteprednol.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Loteprednol.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Loteprednol.
4-HydroxytestosteroneThe risk or severity of edema formation can be increased when 4-Hydroxytestosterone is combined with Loteprednol.
5-androstenedioneThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Loteprednol.
Food Interactions
Not Available

References

General References
Not Available
External Links
Not Available
ATC Codes
S01BA14 — Loteprednol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailablePharmacokinetics1
1CompletedSupportive CareOcular Pain1
1CompletedTreatmentHealthy Volunteers1
1RecruitingOtherInflammation Following Ocular Surgery1
2CompletedPreventionConjunctivitis, Seasonal Allergic1
2CompletedTreatmentDry Eye Syndromes / Keratoconjunctivitis Sicca1
2CompletedTreatmentEye Dryness1
2CompletedTreatmentKeratoconjunctivitis Sicca1
2CompletedTreatmentBacterial blepharitis1
3Active Not RecruitingTreatmentCataracts1
3CompletedTreatmentCataracts / Inflammatory Reaction / Pain NOS2
3CompletedTreatmentConjunctivitis, Seasonal Allergic1
3CompletedTreatmentBacterial blepharitis / Conjunctivitis / Corneal Inflammation1
3CompletedTreatmentDry Eye Syndromes / Keratoconjunctivitis Sicca2
3CompletedTreatmentInflammatory Reaction / Pain NOS2
3CompletedTreatmentOcular Infections, Irritations and Inflammations1
3CompletedTreatmentPost Surgical Ocular Inflammation and Pain1
3CompletedTreatmentOcular inflammatory conditions2
4Active Not RecruitingTreatmentConjunctivitis, Giant Papillary / Conjunctivitis, Seasonal Allergic / Inflammatory Reaction1
4Active Not RecruitingTreatmentMeibomian Gland Dysfunction (MGD) / Posterior Blepharitis1
4CompletedPreventionCorneal Edema / Fuchs' Dystrophy1
4CompletedTreatmentBlepharokeratoconjunctivitis1
4CompletedTreatmentCataract Extraction1
4CompletedTreatmentChalazion / Hordeolum1
4CompletedTreatmentConjunctivitis1
4CompletedTreatmentConjunctivitis, Seasonal Allergic1
4CompletedTreatmentDry Eye Syndrome (DES)1
4CompletedTreatmentDry Eye Syndrome (DES) / Keratoconjunctivitis Sicca1
4CompletedTreatmentEpithelial Defect After Phototherapeutic Keratectomy1
4CompletedTreatmentInflammatory Reaction1
4CompletedTreatmentOcular Hypertension / Open-angle Glaucoma (OAG)1
4Not Yet RecruitingTreatmentMust be PRK Candidate1
4Unknown StatusPreventionCataract operation / Pseudophakia1
4Unknown StatusTreatmentContact Lenses Dryness1
4WithdrawnTreatmentDry Eye Syndrome (DES)1
Not AvailableCompletedNot AvailableInflammatory Reaction / Pseudophakia1
Not AvailableCompletedNot AvailableOcular Hypertension1
Not AvailableCompletedPreventionEye Dryness1
Not AvailableCompletedTreatmentDiabetic Macular Edema (DME) / Retinal Vein Occlusions(RVO)1
Not AvailableUnknown StatusTreatmentDry Eye Syndrome (DES)1
Not AvailableUnknown StatusTreatmentEye Dryness1
Not AvailableUnknown StatusTreatmentPost-operative Healing Following Blepharoplasty and Ptosis Repair1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0336 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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 masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
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
show 4 more
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
show 18 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
organochlorine compound, 11beta-hydroxy steroid, 17alpha-hydroxy steroid, androstanoid, 3-oxo-Delta(1),Delta(4)-steroid, steroid acid ester (CHEBI:50848)

Drug created on August 24, 2018 09:59 / Updated on December 14, 2018 13:19