Loteprednol etabonate



Loteprednol etabonate is a corticosteroid used to treat allergic conjunctivitis as well as inflammation and pain after ocular surgery.

Brand Names
Alrex, Eysuvis, Inveltys, Lotemax, Zylet
Generic Name
Loteprednol etabonate
DrugBank Accession Number

Loteprednol Etabonate (LE) is a topical corticoid anti-inflammatory. 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, it can be used for the treatment and management of seasonal allergic rhinitis.

Most prescription LE products, however, tend to be indicated for the treatment of post-operative inflammation and pain following ocular surgery Label. A number of such new formulations that have been approved include Kala Pharmaceutical's Inveltys - the first twice-daily (BID) ocular corticosteroid approved for this indication, designed specifically to enhance patient compliance and simplified dosing compared to all other similar ocular steroids that are dosed four times daily 6.

Moreover, LE was purposefully engineered to be a 'soft drug', one that is designed to be active locally at the site of administration and then rapidly metabolized to inactive components after eliciting its actions at the desired location, thereby subsequently minimizing the chance for adverse effects 4.

Small Molecule
Average: 466.96
Monoisotopic: 466.175831
Chemical Formula
  • Loteprednol etabonate
External IDs
  • CDDD 5604
  • CDDD-5604
  • HGP 1
  • HGP-1
  • KPI-121
  • P 5604
  • P-5604



A number of prescription loteprednol etabonate ophthalmic products are specifically indicated for the treatment of post-operative inflammation and pain following ocular surgery Label.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofDry eye syndrome (des)••••••••••••••••••••••
Treatment ofEye pain••••••••••••
Treatment ofEye inflammation••••••••••••
Contraindications & Blackbox Warnings
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Loteprednol etabonate (LE) belongs to a unique class of corticosteroids with potent anti-inflammatory effects designed to be active at the site of action 1,5. Animal studies have shown that LE has a binding affinity to steroid receptors that is 4.3 times greater than dexamethasone 5. This particular class of steroids consists of bioactive molecules whose in-vivo transformation to non-toxic substances can be predicted from their chemistry and knowledge of enzymatic pathways in the body 5. Cortienic acid is an inactive metabolite of hydrocortisone and analogs of cortienic acid are also devoid of corticosteroid activity 5. Specifically, LE is an ester derivative of one of these analogs, cortienic acid etabonate 5. In particular, LE possesses a metabolically labile 17 beta-chloromethyl ester function which was designed in order to be hydrolyzed to an inactive carboxylic acid moiety 1. This inactive metabolite is more hydrophilic and is thus readily eliminated from the body 1. LE also exhibits good ocular permeation properties and good skin permeation properties 1.

Mechanism of action

Corticosteroids like loteprednol etabonate inhibit the inflammatory response to a variety of inciting agents and likely delay or slow healing Label,5,1. They inhibit the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, deposition of collagen, and scar formation that are commonly associated with inflammation Label,1. While glucocorticoids are known to bind to and activate the glucocorticoid receptor, the molecular mechanisms involved in glucocorticoid/glucocorticoid receptor-dependent modulation of inflammation are not clearly established Label,5,1. Moreover, corticosteroids are thought to inhibit prostaglandin production through several independent mechanisms Label,1. In particular, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins 8. 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 8. Arachidonic acid is released from membrane phospholipids by phospholipase A2 8.

The use of LE subsequently treats post-operative inflammation and pain following ocular surgery by managing the prostaglandin release, recruitment and travel of neutrophils and macrophages, and production of other inflammatory mediators that are intrinsically associated with the physical trauma of surgery 1.

AGlucocorticoid receptor

Loteprednol etabonate (LE) demonstrates good ocular permeation properties as it is lipid soluble, allowing the agent to penetrate into cells with relative ease Label,1.

Results from the ocular administration of loteprednol in normal, healthy volunteers have shown that there are low or undetectable concentrations of either unchanged material or its metabolite 5. Following twice-daily unilateral topical ocular dosing of LE for 14 days in healthy subjects, the plasma concentrations of loteprednol etabonate were below the limit of quantitation (1 ng/mL) at all time points Label. These finds suggest that limited, if any, systemic absorption of LE occurs 5.

Volume of distribution

The only data available regarding the volume of distribution of loteprednol etabonate (LE) is the volume of distribution the agent demonstrated when administered to dogs - a value of 3.7 L/kg 3. It has been shown, however, that the topical ocular administration of LE distributes preferentially into the cellular components of blood 8.

Protein binding

Strong protein binding of approximately 98% for loteprednol etabonate facilitates little pharmacodynamic action and/or adverse effects on the part of the agent in the systemic circulation 2.


Loteprednol etabonate (LE) is readily and extensively metabolized to two inactive metabolites, PJ-90 (Δ1-cortienic acid) and PJ-91 (Δ1-cortienic acid etabonate) Label,8. Metabolism occurs locally in ocular tissues, and to the extent that loteprednol etabonate reaches the systemic circulation, likely the liver and other tissues into which it distributes 8.

In particular, studies have demonstrated that LE (chloromethyl 17alpha-ethoxycarbonyloxy-11beta-hydroxy-3-oxoandrosta-1,4-diene) is rapidly hydrolyzed at the location of its 17beta-chloromethyl ester function by paraoxonase 1 in human plasma at the site of administration at the level of the affected eye tissue to the 17beta-carboxylate PJ-91 metabolite and PJ-90 metabolite 2,4. Both metabolites are considered inactive Label,4,4.

Hover over products below to view reaction partners

Route of elimination

Following systemic administration to rats, loteprednol etabonate is eliminated primarily via the biliary/faecal route, with most of the dose eliminated in the form of the metabolite, PJ-90 8.


The terminal half-life of loteprednol etabonate as determined when administered intravenously at a dose of 5 mg/kg in the dog animal model is 2.8 hours 3.


Loteprednol etabonate was slowly hydrolyzed in liver at clearance rates of 0.21 +/- 0.04 and 2.41 +/- 0.13 ml/h/kg in the liver and plasma, respectively 2.

Adverse Effects
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The most common adverse drug reactions reported during clinical trials for the medication were eye pain and posterior capsular opacification, both of which may also be the consequence of the very surgical procedures performed on the eye(s) Label.

The agent is not absorbed systemically following topical ophthalmic administration and maternal use is not expected to result in fetal exposure to the drug Label.

The medication is not absorbed systemically by the mother following topical ophthalmic administration, and breastfeeding is not expected to result in exposure of the child to the agent Label.

Long-term animal studies have not been conducted to evaluate the carcinogenic potential of loteprednol etabonate. Loteprednol etabonate was not genotoxic in vitro in the Ames test, the mouse lymphoma thymidine kinase (tk) assay, or in a chromosome aberration test in human lymphocytes, or in vivo in the single dose mouse micronucleus assay Label.

Overdose is not expected to be likely to occur after ocular administration 8.

Not Available
Pharmacogenomic Effects/ADRs
Not Available


Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.


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International/Other Brands
Eysuvis / Loteflam (Cipla Pharmaceuticals Limited)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlrexSuspension / drops2 mg/1mLOphthalmicBausch & Lomb Incorporated1998-03-09Not applicableUS flag
AlrexSuspension / drops2 mg/1mLOphthalmicStat Rx USA1998-03-09Not applicableUS flag
AlrexSuspension0.2 % w/vOphthalmicBausch & Lomb Inc2009-06-24Not applicableCanada flag
AlrexSuspension / drops2 mg/1mLOphthalmicPhysicians Total Care, Inc.2002-10-17Not applicableUS flag
EysuvisSuspension / drops2.5 mg/1mLOphthalmicALCON LABORATORIES, INC.2020-11-18Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Loteprednol EtabonateGel5 mg/1gOphthalmicArmas Pharmaceuticals Inc.2023-10-25Not applicableUS flag
Loteprednol EtabonateGel5 mg/1gOphthalmicBausch & Lomb Americas Inc.2023-06-30Not applicableUS flag
Loteprednol EtabonateGel5 mg/1gOphthalmicBausch & Lomb Incorporated2021-02-17Not applicableUS flag
Loteprednol EtabonateSuspension / drops5 mg/1mLOphthalmicOceanside Pharmaceuticals2019-07-01Not applicableUS flag
Loteprednol EtabonateSuspension / drops5 mg/1mLOphthalmicArmas Pharmaceuticals Inc.2023-10-26Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
LOTEBRA % 0.5+ % 0.3 GÖZ DAMLASI, SÜSPANSİYON, 5 MLLoteprednol etabonate (0.5 %) + Tobramycin (0.3 %)Suspension / dropsOphthalmicABDİ İBRAHİM İLAÇ SAN. VE TİC. A.Ş.2014-05-08Not applicableTurkey flag
LOTEMICIN®Loteprednol etabonate (5 mg) + Tobramycin (3 mg)SuspensionConjunctival; OphthalmicLABORATORIOS POEN S.A.U.2008-04-03Not applicableColombia flag
LOTEMICIN®Loteprednol etabonate (5 mg) + Tobramycin (3 mg)SuspensionOphthalmicQUIBI S.A. EN REESTRUCTURACION2022-09-30Not applicableColombia flag
TOBRALOT 5 MG+3 MG/ML GÖZ DAMLASI, SÜSPANSİYON, 1 ADETLoteprednol etabonate (5 mg/mL) + Tobramycin (3 mg/ml)Suspension / dropsOphthalmicVEM İLAÇ SAN. VE TİC. A.Ş.2019-11-30Not applicableTurkey flag
ZyletLoteprednol etabonate (5 mg/1mL) + Tobramycin (3 mg/1mL)Suspension / dropsOphthalmicBausch & Lomb Incorporated2004-12-14Not applicableUS flag


Drug Categories
Chemical TaxonomyProvided by Classyfire
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Organic compounds
Super Class
Lipids and lipid-like molecules
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androgens and derivatives / 3-oxo delta-1,4-steroids / 11-beta-hydroxysteroids / Delta-1,4-steroids / Carbonic acid diesters / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives
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11-beta-hydroxysteroid / 11-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl chloride / Alkyl halide / Androgen-skeleton / Androstane-skeleton
show 20 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
organochlorine compound, 11beta-hydroxy steroid, steroid ester, etabonate ester, 3-oxo-Delta(1),Delta(4)-steroid, steroid acid ester (CHEBI:31784)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

CAS number
InChI Key
chloromethyl (1R,3aS,3bS,9aR,9bS,10S,11aS)-1-[(ethoxycarbonyl)oxy]-10-hydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1-carboxylate


General References
  1. 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. [Article]
  2. Samir A, Bodor N, Imai T: Identification of esterase involved in the metabolism of two corticosteroid soft drugs. Biochem Pharmacol. 2017 Mar 1;127:82-89. doi: 10.1016/j.bcp.2016.12.010. Epub 2016 Dec 22. [Article]
  3. Hochhaus G, Chen LS, Ratka A, Druzgala P, Howes J, Bodor N, Derendorf H: Pharmacokinetic characterization and tissue distribution of the new glucocorticoid soft drug loteprednol etabonate in rats and dogs. J Pharm Sci. 1992 Dec;81(12):1210-5. [Article]
  4. Druzgala P, Wu WM, Bodor N: Ocular absorption and distribution of loteprednol etabonate, a soft steroid, in rabbit eyes. Curr Eye Res. 1991 Oct;10(10):933-7. [Article]
  5. Electronic Medicines Compendium: Loteprednol etabonate Monograph [Link]
  6. Inveltys FDA Approval Press Release [Link]
  7. FDA Approved Drug Products: Eysuvis (loteprednol etabonate) ophthalmic suspension [Link]
  8. Australian Register of Therapeutic Goods: Loteprednol etabonate Product Information [File]
Human Metabolome Database
PubChem Compound
PubChem Substance
Therapeutic Targets Database
RxList Drug Page
Drugs.com Drug Page
FDA label
Download (153 KB)
Download (22 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
4CompletedPreventionCorneal Edema / Endothelial Corneal Dystrophy1somestatusstop reasonjust information to hide
4CompletedPreventionCorneal Edema / Fuchs' Dystrophy1somestatusstop reasonjust information to hide
4CompletedTreatmentAllergic Conjunctivitis (AC)2somestatusstop reasonjust information to hide
4CompletedTreatmentBilateral Conjunctivitis (Disorder)1somestatusstop reasonjust information to hide
4CompletedTreatmentBlepharokeratoconjunctivitis1somestatusstop reasonjust information to hide


  • Bausch and lomb inc
  • Pharmos corp
  • Alchymars SPA
  • Bausch & Lomb Inc.
  • Physicians Total Care Inc.
Dosage Forms
SuspensionConjunctival0.20 %w/v
SuspensionOphthalmic0.2 % w/v
Suspension / dropsOphthalmic2 mg/1mL
SuspensionOphthalmic5 mg
Solution / dropsOphthalmic0.5 %
Suspension / dropsOphthalmic2.5 mg/1mL
SuspensionTopical10 mg/1mL
SuspensionOphthalmic0.5 %
GelOphthalmic5 mg/1g
OintmentOphthalmic5 mg/1g
Solution / dropsIntraocular
SuspensionOphthalmic0.5 % w/v
Suspension / dropsOphthalmic5 mg/1mL
Suspension / dropsOphthalmic0.5 %
Suspension / dropsOphthalmic5 mg/ml
GelOphthalmic0.5 % w/w
OintmentOphthalmic0.5 % w/w
GelOphthalmic3.8 mg/1g
SolutionOphthalmic5 mg/ml
SuspensionConjunctival; Ophthalmic
SuspensionConjunctival; Ophthalmic0.002 g
SuspensionConjunctival; Ophthalmic5 mg
OintmentOphthalmic; Topical500 mg
SuspensionConjunctival; Ophthalmic500000 mg
SuspensionOphthalmic2 mg
Suspension / dropsOphthalmic
Not Available
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5540930No1996-07-302013-10-25US flag
US4996335No1991-02-262012-03-09US flag
CA2174550No2002-10-012014-10-21Canada flag
US5800807No1998-09-012017-01-29US flag
US9056057No2015-06-162033-05-03US flag
US9532955No2017-01-032033-05-03US flag
US9827191No2017-11-282033-05-03US flag
US10058511No2018-08-282033-05-03US flag
US9737491No2017-08-222033-05-03US flag
US9393213No2016-07-192033-05-03US flag
US10596107No2020-03-242036-12-23US flag
US10646437No2020-05-122033-05-03US flag
US10688045No2020-06-232033-05-03US flag
US10857096No2020-12-082033-05-03US flag
US10864219No2020-12-152033-05-03US flag
US10646436No2020-05-122033-05-03US flag
US10945948No2021-03-162033-05-03US flag
US10940108No2021-03-092033-05-03US flag
US10993908No2021-05-042033-05-03US flag
US11219596No2013-05-032033-05-03US flag
US11219597No2013-05-032033-05-03US flag
US11534395No2016-01-262036-01-26US flag
US11596599No2013-05-032033-05-03US flag
US11642317No2013-05-032033-05-03US flag
US11872318No2013-05-032033-05-03US flag


Experimental Properties
melting point (°C)220-224 °CNot Available
water solubility5 mg/mLNot Available
logP3.4Not Available
Predicted Properties
Water Solubility0.00693 mg/mLALOGPS
pKa (Strongest Acidic)14.88Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area99.13 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity118.17 m3·mol-1Chemaxon
Polarizability48.43 Å3Chemaxon
Number of Rings4Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Human Intestinal Absorption+0.9884
Blood Brain Barrier+0.9294
Caco-2 permeable+0.5426
P-glycoprotein substrateSubstrate0.7489
P-glycoprotein inhibitor INon-inhibitor0.6379
P-glycoprotein inhibitor IINon-inhibitor0.6419
Renal organic cation transporterNon-inhibitor0.7633
CYP450 2C9 substrateNon-substrate0.862
CYP450 2D6 substrateNon-substrate0.914
CYP450 3A4 substrateSubstrate0.794
CYP450 1A2 substrateNon-inhibitor0.8987
CYP450 2C9 inhibitorNon-inhibitor0.8866
CYP450 2D6 inhibitorNon-inhibitor0.872
CYP450 2C19 inhibitorNon-inhibitor0.9233
CYP450 3A4 inhibitorNon-inhibitor0.5687
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8468
Ames testNon AMES toxic0.8574
BiodegradationNot ready biodegradable0.9614
Rat acute toxicity2.2305 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9647
hERG inhibition (predictor II)Non-inhibitor0.5773
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)


Mass Spec (NIST)
Not Available
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0292-0940000000-f369442eba5344b3ecb4
MS/MS Spectrum - , positiveLC-MS/MSsplash10-06di-0794200000-c3979b4c8c9d5097df0e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0002900000-62dfb69d936690e92bf8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002r-9004000000-2d1482861070b8faead7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0292-0829700000-9158889016aca21bf495
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03ea-9003000000-dcafaf883320564db016
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-9026000000-1405ccd82cb3a2173a13
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0c00-0933100000-dfc7a4af1f7b55b6e9db
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
DeepCCS 1.0 (2019)
DeepCCS 1.0 (2019)
DeepCCS 1.0 (2019)


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Pharmacological action
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
Uniprot ID
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
  1. Druzgala P, Hochhaus G, Bodor N: Soft drugs--10. Blanching activity and receptor binding affinity of a new type of glucocorticoid: loteprednol etabonate. J Steroid Biochem Mol Biol. 1991 Feb;38(2):149-54. [Article]
  2. Bodor N, Buchwald P: Corticosteroid design for the treatment of asthma: structural insights and the therapeutic potential of soft corticosteroids. Curr Pharm Des. 2006;12(25):3241-60. [Article]
  3. Szelenyi I, Hochhaus G, Heer S, Kusters S, Marx D, Poppe H, Engel J: Loteprednol etabonate: a soft steroid for the treatment of allergic diseases of the airways. Drugs Today (Barc). 2000 May;36(5):313-20. [Article]
  4. Samudre SS, Lattanzio FA Jr, Williams PB, Sheppard JD Jr: Comparison of topical steroids for acute anterior uveitis. J Ocul Pharmacol Ther. 2004 Dec;20(6):533-47. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]


Pharmacological action
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
Uniprot ID
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
  1. NCI/NIH [Link]
  2. Electronic Medicines Compendium: Loteprednol etabonate Monograph [Link]
Pharmacological action
General Function
Protein homodimerization activity
Specific Function
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxyl...
Gene Name
Uniprot ID
Uniprot Name
Serum paraoxonase/arylesterase 1
Molecular Weight
39730.99 Da
  1. Samir A, Bodor N, Imai T: Identification of esterase involved in the metabolism of two corticosteroid soft drugs. Biochem Pharmacol. 2017 Mar 1;127:82-89. doi: 10.1016/j.bcp.2016.12.010. Epub 2016 Dec 22. [Article]

Drug created at June 13, 2005 13:24 / Updated at July 15, 2024 23:36