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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
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

1998
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

1998
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

1998
PubMed

PubMed

TitleDatePubMed
Loteprednol etabonate. Alrex, Lotemax, Loteprednol, Loterox.
2002
Long-term safety of loteprednol etabonate 0.2% in the treatment of seasonal and perennial allergic conjunctivitis.
2004 Jan
Treatment of ocular inflammatory conditions with loteprednol etabonate.
2008 Apr
Post-penetrating keratoplasty glaucoma.
2008 Jul-Aug
Intraocular pressure elevation from topical difluprednate use.
2010 Dec
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
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
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NDF-RT N0000175576
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WHO-VATC QS01BA14
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WHO-ATC S01BA14
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NDF-RT N0000175450
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Code System Code Type Description
INN
6654
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PRIMARY
EVMPD
SUB08599MIG
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DRUG BANK
DB00873
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WIKIPEDIA
LOTEPREDNOL
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EPA CompTox
DTXSID10156128
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PUBCHEM
9865442
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FDA UNII
Z8CBU6KR16
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PRIMARY
CAS
129260-79-3
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RXCUI
237027
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PRIMARY RxNorm
NCI_THESAURUS
C72818
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LACTMED
Loteprednol
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MESH
C063378
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ChEMBL
CHEMBL1200865
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PRIMARY
CHEBI
50848
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PRIMARY
DAILYMED
Z8CBU6KR16
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PRIMARY
SMS_ID
100000082058
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PRIMARY