U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27ClO5
Molecular Weight 394.889
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOTEPREDNOL

SMILES

[H][C@@]12CC[C@](O)(C(=O)OCCl)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C

InChI

InChIKey=YPZVAYHNBBHPTO-MXRBDKCISA-N
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

HIDE SMILES / InChI

Molecular Formula C21H27ClO5
Molecular Weight 394.889
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Loteprednol (as the ester loteprednol etabonate) is a corticosteroid used to treat inflammations of the eye. It is marketed by Bausch and Lomb as Lotemax. It 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 conjunctivitis’s. Lotemax is less effective than prednisolone acetate 1% in two 28-day controlled clinical studies in acute anterior uveitis, where 72% of patients treated with Lotemax experienced resolution of anterior chamber cells, compared to 87% of patients treated with prednisolone acetate 1%. Lotemax is also indicated for the treatment of post-operative inflammation following ocular surgery. Corticosteroids inhibit the inflammatory response to a variety of inciting agents and probably delay or slow healing. They inhibit the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, deposition of collagen, and scar formation associated with inflammation. There is no generally accepted explanation for the mechanism of action of ocular corticosteroids. 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. Corticosteroids are capable of producing a rise in intraocular pressure (IOP). Loteprednol etabonate is structurally similar to other corticosteroids. However, the number 20 position ketone group is absent. It is highly lipid soluble, which enhances its penetration into cells. Loteprednol etabonate is synthesized through structural modifications of prednisolone-related compounds so that it will undergo a predictable transformation to an inactive metabolite. Based upon in vivo and in vitro preclinical metabolism studies, loteprednol etabonate undergoes extensive metabolism to inactive carboxylic acid metabolites. Lotemax possesses some adverse reactions associated with ophthalmic steroids include elevated intraocular pressure, which may be associated with optic nerve damage, visual acuity and field defects, posterior subcapsular cataract formation, secondary ocular infection from pathogens including herpes simplex, and perforation of the globe where there is thinning of the cornea or sclera.

Originator

Curator's Comment: Loteprednol etabonate is a glucocorticoid receptor agonist that was originally developed by Pharmos Corp as a topical treatment for various ocular inflammatory

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LOTEMAX

Approved Use

LOTEMAX is indicated for the treatment of steroid responsive inflammatory conditions of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe such as allergic conjunctivitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis, selected infective conjunctivitis, when the inherent hazard of steroid use is accepted to obtain an advisable diminution in edema and inflammation. LOTEMAX is less effective than prednisolone acetate 1% in two 28-day controlled clinical studies in acute anterior uveitis, where 72% of patients treated with LOTEMAX experienced resolution of anterior chamber cells, compared to 87% of patients treated with prednisolone acetate 1%. The incidence of patients with clinically significant increases in IOP (≥10 mmHg) was 1% with LOTEMAX and 6% with prednisolone acetate 1%. LOTEMAX should not be used in patients who require a more potent corticosteroid for this indication. LOTEMAX is also indicated for the treatment of post-operative inflammation following ocular surgery.

Launch Date

8.8940157E11
Primary
LOTEMAX

Approved Use

LOTEMAX is indicated for the treatment of steroid responsive inflammatory conditions of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe such as allergic conjunctivitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis, selected infective conjunctivitis, when the inherent hazard of steroid use is accepted to obtain an advisable diminution in edema and inflammation. LOTEMAX is less effective than prednisolone acetate 1% in two 28-day controlled clinical studies in acute anterior uveitis, where 72% of patients treated with LOTEMAX experienced resolution of anterior chamber cells, compared to 87% of patients treated with prednisolone acetate 1%. The incidence of patients with clinically significant increases in IOP (≥10 mmHg) was 1% with LOTEMAX and 6% with prednisolone acetate 1%. LOTEMAX should not be used in patients who require a more potent corticosteroid for this indication. LOTEMAX is also indicated for the treatment of post-operative inflammation following ocular surgery.

Launch Date

8.8940157E11
Primary
LOTEMAX

Approved Use

LOTEMAX is indicated for the treatment of steroid responsive inflammatory conditions of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe such as allergic conjunctivitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis, selected infective conjunctivitis, when the inherent hazard of steroid use is accepted to obtain an advisable diminution in edema and inflammation. LOTEMAX is less effective than prednisolone acetate 1% in two 28-day controlled clinical studies in acute anterior uveitis, where 72% of patients treated with LOTEMAX experienced resolution of anterior chamber cells, compared to 87% of patients treated with prednisolone acetate 1%. The incidence of patients with clinically significant increases in IOP (≥10 mmHg) was 1% with LOTEMAX and 6% with prednisolone acetate 1%. LOTEMAX should not be used in patients who require a more potent corticosteroid for this indication. LOTEMAX is also indicated for the treatment of post-operative inflammation following ocular surgery.

Launch Date

8.8940157E11
PubMed

PubMed

TitleDatePubMed
Loteprednol etabonate. Alrex, Lotemax, Loteprednol, Loterox.
2002
Comparison of the clinical efficacy and tolerability of olopatadine hydrochloride 0.1% ophthalmic solution and loteprednol etabonate 0.2% ophthalmic suspension in the conjunctival allergen challenge model.
2002 Jun
Asthma therapy in the new millennium.
2002 Jun
Bilateral nongranulomatous anterior uveitis associated with bimatoprost.
2003 Nov
Long-term safety of loteprednol etabonate 0.2% in the treatment of seasonal and perennial allergic conjunctivitis.
2004 Jan
A randomized, double-masked, placebo-controlled, multicenter comparison of loteprednol etabonate ophthalmic suspension, 0.5%, and placebo for treatment of keratoconjunctivitis sicca in patients with delayed tear clearance.
2004 Sep
Comparison of ketorolac tromethamine, diclofenac sodium, and loteprednol etabonate in an animal model of ocular inflammation.
2006 Jun
Treatment of ocular inflammatory conditions with loteprednol etabonate.
2008 Apr
Comparison of the safety and efficacy of loteprednol 0.5%/tobramycin 0.3% with dexamethasone 0.1%/tobramycin 0.3% in the treatment of blepharokeratoconjunctivitis.
2008 Jan
Post-penetrating keratoplasty glaucoma.
2008 Jul-Aug
Loteprednol and tobramycin in combination: a review of their impact on current treatment regimens.
2010 Apr
Intraocular pressure elevation from topical difluprednate use.
2010 Dec
Rate and risk factors for cataract formation and extraction after Descemet stripping endothelial keratoplasty.
2010 Nov
Patents

Sample Use Guides

Apply one to two drops of LOTEMAX (loteprednol etabonate ophthalmic suspension) into the conjunctival sac of the affected eye four times daily. During the initial treatment within the first week, the dosing may be increased, up to 1 drop every hour, if necessary.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:27:53 UTC 2023
Edited
by admin
on Fri Dec 15 16:27:53 UTC 2023
Record UNII
Z8CBU6KR16
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOTEPREDNOL
INN   VANDF   WHO-DD  
INN  
Official Name English
LOTEPREDNOL [VANDF]
Common Name English
Loteprednol [WHO-DD]
Common Name English
loteprednol [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
NDF-RT N0000175576
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
WHO-VATC QS01BA14
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
WHO-ATC S01BA14
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
NDF-RT N0000175450
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
Code System Code Type Description
INN
6654
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
EVMPD
SUB08599MIG
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
DRUG BANK
DB00873
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
WIKIPEDIA
LOTEPREDNOL
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID10156128
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
PUBCHEM
9865442
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
FDA UNII
Z8CBU6KR16
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
CAS
129260-79-3
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
RXCUI
237027
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C72818
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
LACTMED
Loteprednol
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
MESH
C063378
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
ChEMBL
CHEMBL1200865
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
CHEBI
50848
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
DAILYMED
Z8CBU6KR16
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
SMS_ID
100000082058
Created by admin on Fri Dec 15 16:27:53 UTC 2023 , Edited by admin on Fri Dec 15 16:27:53 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY