loteprednol etabonate Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
prednisone and prednisolone derivatives 1611 82034-46-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • loteprednol etabonate
  • lenoxin
  • lotemax
An androstadiene derivative corticosteroid that is used as an ANTI-ALLERGIC AGENT for the treatment of inflammatory and allergic eye conditions.
  • Molecular weight: 466.96
  • Formula: C24H31ClO7
  • CLOGP: 3.34
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 1
  • TPSA: 99.13
  • ALOGS: -4.83
  • ROTB: 7

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BA (Bioavailability) 0 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
March 9, 1998 FDA BAUSCH AND LOMB

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Eye irritation 242.58 20.91 73 2800 18376 53327817
Ocular hyperaemia 116.96 20.91 44 2829 21747 53324446
Eye pain 115.68 20.91 48 2825 30677 53315516
Intraocular pressure increased 104.32 20.91 30 2843 6408 53339785
Vision blurred 71.77 20.91 49 2824 85555 53260638
Eye pruritus 60.80 20.91 24 2849 13445 53332748
Corneal oedema 59.98 20.91 15 2858 1882 53344311
Foreign body sensation in eyes 58.91 20.91 15 2858 2024 53344169
Cataract 55.32 20.91 34 2839 49586 53296607
Lacrimation increased 54.21 20.91 24 2849 17879 53328314
Dacryostenosis acquired 53.24 20.91 11 2862 586 53345607
Dry eye 45.17 20.91 26 2847 33618 53312575
Photophobia 40.40 20.91 19 2854 16239 53329954
Eye inflammation 39.34 20.91 13 2860 4384 53341809
Punctate keratitis 35.92 20.91 8 2865 609 53345584
Keratitis 32.48 20.91 10 2863 2687 53343506
Visual acuity reduced 31.84 20.91 18 2855 22467 53323726
Endophthalmitis 29.68 20.91 10 2863 3577 53342616
Corneal scar 28.18 20.91 5 2868 117 53346076
Diffuse lamellar keratitis 24.41 20.91 3 2870 3 53346190
Cystoid macular oedema 23.93 20.91 7 2866 1580 53344613
Corneal disorder 23.14 20.91 7 2866 1774 53344419
Instillation site pain 22.89 20.91 6 2867 906 53345287
Hypopyon 22.64 20.91 6 2867 945 53345248
Glaucoma 22.43 20.91 13 2860 16990 53329203
Eye discharge 22.39 20.91 9 2864 5271 53340922
Eye swelling 21.97 20.91 14 2859 21680 53324513
Visual impairment 21.65 20.91 23 2850 72889 53273304

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Eye irritation 78.97 28.24 21 894 6497 32506114
Eye pain 64.73 28.24 21 894 12927 32499684
Intraocular pressure increased 58.06 28.24 16 899 5642 32506969
Vision blurred 45.61 28.24 23 892 44163 32468448
Corneal oedema 39.73 28.24 9 906 1429 32511182
Dacryostenosis acquired 35.59 28.24 6 909 203 32512408
Ulcerative keratitis 33.84 28.24 8 907 1528 32511083
Corneal dystrophy 31.35 28.24 5 910 119 32512492
Corneal striae 30.00 28.24 4 911 25 32512586
Diffuse lamellar keratitis 30.00 28.24 4 911 25 32512586

Pharmacologic Action:

SourceCodeDescription
FDA MoA N0000175450 Corticosteroid Hormone Receptor Agonists
FDA EPC N0000175576 Corticosteroid
MeSH PA D018926 Anti-Allergic Agents
CHEBI has role CHEBI:35679 hypolipidemic agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Herpes zoster keratoconjunctivitis indication 42448002
Punctate keratitis indication 42513006 DOID:12197
Iritis indication 65074000 DOID:1406
Perforation of cornea indication 74895004
Iridocyclitis indication 77971008
Corneal abrasion indication 85848002
Uveitis indication 128473001 DOID:13141
Ocular rosacea indication 200933006
Herpes zoster keratitis indication 397573005
Rosacea indication 398909004 DOID:8881
Anterior uveitis indication 410692006 DOID:1407
Allergic conjunctivitis indication 473460002 DOID:11204
Post-Op Ocular Inflammation indication
Ocular hypertension contraindication 4210003 DOID:9282
Glaucoma contraindication 23986001 DOID:1686
Herpes simplex dendritic keratitis contraindication 29943008
Fungal infection of eye contraindication 31194008
Tuberculosis of eye contraindication 49107007
Herpes zoster ophthalmicus contraindication 87513003
Viral eye infection contraindication 312132001
Vaccinia keratitis contraindication 397552005

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.33 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
1% INVELTYS KALA PHARMS INC N210565 Aug. 22, 2018 RX SUSPENSION/DROPS OPHTHALMIC 10058511 May 3, 2033 A METHOD FOR DELIVERING A PHARMACEUTICAL AGENT ACROSS A MUCOSAL BARRIER
1% INVELTYS KALA PHARMS INC N210565 Aug. 22, 2018 RX SUSPENSION/DROPS OPHTHALMIC 10864219 May 3, 2033 A METHOD FOR TREATING OCULAR INFLAMMATION
1% INVELTYS KALA PHARMS INC N210565 Aug. 22, 2018 RX SUSPENSION/DROPS OPHTHALMIC 11219597 May 3, 2033 A METHOD OF REDUCING POST-SURGICAL PAIN FOLLOWING OCULAR SURGERY
1% INVELTYS KALA PHARMS INC N210565 Aug. 22, 2018 RX SUSPENSION/DROPS OPHTHALMIC 11219597 May 3, 2033 A METHOD OF TREATING POSTOPERATIVE INFLAMMATION FOLLOWING OCULAR SURGERY
1% INVELTYS KALA PHARMS INC N210565 Aug. 22, 2018 RX SUSPENSION/DROPS OPHTHALMIC 9056057 May 3, 2033 A METHOD FOR DELIVERING A COMPOSITION TO A MUCUS MEMBRANE
1% INVELTYS KALA PHARMS INC N210565 Aug. 22, 2018 RX SUSPENSION/DROPS OPHTHALMIC 9532955 May 3, 2033 A METHOD FOR DELIVERING A COMPOSITION TO A MUCUS MEMBRANE
1% INVELTYS KALA PHARMS INC N210565 Aug. 22, 2018 RX SUSPENSION/DROPS OPHTHALMIC 9737491 May 3, 2033 A METHOD FOR DELIVERING A PHARMACEUTICAL AGENT ACROSS A MUCOSAL BARRIER
1% INVELTYS KALA PHARMS INC N210565 Aug. 22, 2018 RX SUSPENSION/DROPS OPHTHALMIC 9827191 May 3, 2033 A METHOD FOR TREATING INFLAMMATION AND/OR OTHER DISORDERS IN AN EYE OF A PATIENT
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 10058511 May 3, 2033 A METHOD FOR DELIVERING A PHARMACEUTICAL AGENT ACROSS A MUCOSAL BARRIER
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 10857096 May 3, 2033 A METHOD FOR TREATING DRY EYE IN A PATIENT
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 10940108 May 3, 2033 A METHOD FOR TREATING DRY EYE IN A PATIENT
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 10945948 May 3, 2033 A METHOD FOR TREATING DRY EYE IN A PATIENT
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 10993908 May 3, 2033 ADMINISTRATION TO THE EYE OF A PATIENT FOR TREATMENT OF DRY EYE CONDITION
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 11219596 May 3, 2033 A METHOD FOR TREATING DRY EYE IN A PATIENT
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 9056057 May 3, 2033 A METHOD FOR DELIVERING A COMPOSITION TO A MUCUS MEMBRANE
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 9532955 May 3, 2033 A METHOD FOR DELIVERING A COMPOSITION TO A MUCUS MEMBRANE
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 9737491 May 3, 2033 A METHOD FOR DELIVERING A PHARMACEUTICAL AGENT ACROSS A MUCOSAL BARRIER
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC 9827191 May 3, 2033 A METHOD FOR TREATING DRY EYE IN A PATIENT
0.38% LOTEMAX SM BAUSCH AND LOMB INC N208219 Feb. 22, 2019 RX GEL OPHTHALMIC 10596107 Dec. 23, 2036 TREATMENT OF POST-OPERATIVE INFLAMMATION AND PAIN FOLLOWING OCULAR SURGERY

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.38% LOTEMAX SM BAUSCH AND LOMB INC N208219 Feb. 22, 2019 RX GEL OPHTHALMIC Feb. 22, 2022 NEW STRENGTH
0.25% EYSUVIS KALA PHARMS INC N210933 Oct. 26, 2020 RX SUSPENSION/DROPS OPHTHALMIC Oct. 26, 2023 NEW PRODUCT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Glucocorticoid receptor Nuclear hormone receptor AGONIST DRUGBANK CHEMBL

External reference:

IDSource
4021086 VUID
N0000179334 NUI
D01689 KEGG_DRUG
129260-79-3 SECONDARY_CAS_RN
4021086 VANDF
4024100 VANDF
C0126177 UMLSCUI
CHEBI:50848 CHEBI
CHEMBL1200865 ChEMBL_ID
D000069559 MESH_DESCRIPTOR_UI
DB14596 DRUGBANK_ID
7085 IUPHAR_LIGAND_ID
6654 INN_ID
YEH1EZ96K6 UNII
444025 PUBCHEM_CID
9865442 PUBCHEM_CID
DB00873 DRUGBANK_ID
Z8CBU6KR16 UNII
202988 RXNORM
11633 MMSL
1692 MMSL
315769 MMSL
4997 MMSL
007442 NDDF
007443 NDDF
108857005 SNOMEDCT_US
387047007 SNOMEDCT_US
419711001 SNOMEDCT_US
CHEMBL1201389 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ALREX HUMAN PRESCRIPTION DRUG LABEL 1 16590-007 SUSPENSION/ DROPS 2 mg OPHTHALMIC NDA 20 sections
Loteprednol Etabonate HUMAN PRESCRIPTION DRUG LABEL 1 17478-830 GEL 5 mg OPHTHALMIC ANDA 23 sections
LOTEMAX HUMAN PRESCRIPTION DRUG LABEL 1 24208-299 SUSPENSION/ DROPS 5 mg OPHTHALMIC NDA 18 sections
ALREX HUMAN PRESCRIPTION DRUG LABEL 1 24208-353 SUSPENSION/ DROPS 2 mg OPHTHALMIC NDA 20 sections
Zylet HUMAN PRESCRIPTION DRUG LABEL 2 24208-358 SUSPENSION/ DROPS 5 mg OPHTHALMIC NDA 21 sections
Lotemax HUMAN PRESCRIPTION DRUG LABEL 1 24208-443 OINTMENT 5 mg OPHTHALMIC NDA 22 sections
LOTEMAX HUMAN PRESCRIPTION DRUG LABEL 1 24208-503 GEL 5 mg OPHTHALMIC NDA 22 sections
Lotemax SM HUMAN PRESCRIPTION DRUG LABEL 1 24208-507 GEL 3.80 mg OPHTHALMIC NDA 22 sections
Loteprednol Etabonate HUMAN PRESCRIPTION DRUG LABEL 1 24208-508 GEL 5 mg OPHTHALMIC NDA authorized generic 22 sections
Loteprednol Etabonate HUMAN PRESCRIPTION DRUG LABEL 1 50383-265 SUSPENSION/ DROPS 5 mg OPHTHALMIC ANDA 17 sections
ALREX HUMAN PRESCRIPTION DRUG LABEL 1 54868-4277 SUSPENSION/ DROPS 2 mg OPHTHALMIC NDA 20 sections
LOTEMAX HUMAN PRESCRIPTION DRUG LABEL 1 54868-4278 SUSPENSION/ DROPS 5 mg OPHTHALMIC NDA 18 sections
Loteprednol Etabonate Human Prescription Drug Label 1 62756-232 SUSPENSION/ DROPS 5 mg OPHTHALMIC ANDA 16 sections
Loteprednol Etabonate HUMAN PRESCRIPTION DRUG LABEL 1 68682-299 SUSPENSION/ DROPS 5 mg OPHTHALMIC NDA authorized generic 18 sections
Inveltys HUMAN PRESCRIPTION DRUG LABEL 1 71571-121 SUSPENSION 10 mg TOPICAL NDA 24 sections
Eysuvis HUMAN PRESCRIPTION DRUG LABEL 1 71571-333 SUSPENSION/ DROPS 2.50 mg OPHTHALMIC NDA 23 sections