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Key Documents

SML0547

Sigma-Aldrich

Loteprednol Etabonate

≥98% (HPLC)

Synonym(s):

(11b,17a)-17-[(Ethoxycarbonyl)oxy]-11-hydroxy-3-oxo-Androsta-1,4-diene-17-carboxylic acid chloromethyl ester, CDDD 5604, HGP 1, P 5604

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About This Item

Empirical Formula (Hill Notation):
C24H31ClO7
CAS Number:
Molecular Weight:
466.95
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

CCOC(=O)O[C@@]1(CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@]12C)C(=O)OCCl

InChI

1S/C24H31ClO7/c1-4-30-21(29)32-24(20(28)31-13-25)10-8-17-16-6-5-14-11-15(26)7-9-22(14,2)19(16)18(27)12-23(17,24)3/h7,9,11,16-19,27H,4-6,8,10,12-13H2,1-3H3/t16-,17-,18-,19+,22-,23-,24-/m0/s1

InChI key

DMKSVUSAATWOCU-HROMYWEYSA-N

Gene Information

human ... NR3C1(2908)

Biochem/physiol Actions

Loteprednol Etabonate is a "soft" steroid, typically used in topical applications for inflammatory conditions of the eye. Loteprednol Etabonate is an agonist of both glucocorticoid and mineralcorticoid receptors.
Loteprednol Etabonate is an anti-inflammatory corticosteroid (ophthalmology).
Loteprednol etabonate (LE) is a key site-active corticosteroid. It is produced by structural modifications of prednisolone-related compounds to form an inactive metabolite. Double-masked study states that loteprednol etabonate is used to treat giant papillary conjunctivitis, seasonal allergic conjunctivitis, postoperative inflammation and uveitis. LE has good ocular permeation properties.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Katherine A Lyseng-Williamson
Drugs, 73(9), 949-958 (2013-06-07)
Loteprednol etabonate ophthalmic gel 0.5% (Lotemax(®)) is approved in the USA for the treatment of post-operative inflammation and pain in patients who have undergone ocular surgery. The new gel formulation of loteprednol etabonate offers some potential advantages over the previously
Change in intraocular pressure during long-term use of loteprednol etabonate.
Novack GD, et al.
Journal of Glaucoma, 7(4), 266-269 (1998)
Brett P Bielory et al.
Current opinion in allergy and clinical immunology, 10(5), 469-477 (2010-08-20)
Corticosteroids are an effective short-term treatment option for seasonal allergic conjunctivitis (SAC). Their use has been limited due to their side effects and has led to the development of modified 'soft', 'smart' ophthalmic corticosteroid formulations that retain their anti-inflammatory mechanism
Marcus Ang et al.
Cornea, 39(8), 940-945 (2020-05-27)
To describe intraoperative and postoperative complications of Descemet membrane endothelial keratoplasty (DMEK) in Asian eyes. A: prospective comparative study of consecutive cases of DMEK cases between January 2016 and January 2018. A subgroup of consecutive patients were optimized with preoperative
Rajesh K Rajpal et al.
Journal of cataract and refractive surgery, 39(2), 158-167 (2012-12-12)
To examine the efficacy and safety of a new gel formulation loteprednol etabonate 0.5% in the treatment of inflammation and pain after cataract surgery. Seventeen United States clinical sites. Prospective double-masked parallel-group study. Patients with anterior chamber cell (ACC) grade

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