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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:
82034-46-6
Molecular Weight:
466.95
MDL number:
MFCD00870765
UNSPSC Code:
51111800
PubChem Substance ID:
329825544
NACRES:
NA.77

Quality Level

100

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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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
Mesut Erdurmus et al.
Cornea, 28(7), 759-764 (2009-07-04)
The aim of the present study was to evaluate the frequency of steroid-induced intraocular pressure (IOP) elevation and/or glaucoma in patients with keratoconus (KCN) compared with patients with Fuchs endothelial dystrophy after penetrating keratoplasty (PK). A retrospective review of the
Brett P Bielory et al.
Acta ophthalmologica, 90(5), 399-407 (2011-11-10)
Seasonal allergic conjunctivitis (SAC) is an inflammatory response of the conjunctiva triggered by exposure to seasonal allergens. Treatment options for SAC include artificial tears, antihistamines, decongestants, mast cell stabilizers, nonsteroidal anti-inflammatory drugs, dual antihistamine/mast cell stabilizers, immunotherapy and corticosteroids. Topical
Edeline Lu et al.
Optometry (St. Louis, Mo.), 82(7), 413-420 (2011-05-06)
The aim of this study was to present a case of a patient who showed a significant increase in intraocular pressure (IOP) with topical administration of loteprednol etabonate 0.2%. A 29-year-old man administered 1 drop of loteprednol etabonate 0.2% (Alrex(®))
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