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MedKoo Cat#: 318167 | Name: Loteprednol Etabonate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

The compound is an ophthalmic corticosteroid, and categorized as an anti-inflammatory. Loteprednol Etabonate is the esther of Loteprednol. This results in an induction of the synthesis of certain anti-inflammatory proteins while inhibiting the synthesis of certain inflammatory mediators. Marketed by Bausch and Lomb as Lotemax in the U.S., ocular applications for this drug include the treatment of inflammation of the eye due to allergies, as well as chronic forms of keratitis, vernal keratoconjunctivitis, pingueculitis, and episcleritis.

Chemical Structure

Loteprednol Etabonate
Loteprednol Etabonate
CAS#82034-46-6

Theoretical Analysis

MedKoo Cat#: 318167

Name: Loteprednol Etabonate

CAS#: 82034-46-6

Chemical Formula: C24H31ClO7

Exact Mass: 466.1758

Molecular Weight: 466.96

Elemental Analysis: C, 61.73; H, 6.69; Cl, 7.59; O, 23.98

Price and Availability

Size Price Availability Quantity
25mg USD 265.00 2 weeks
50mg USD 485.00 2 weeks
100mg USD 850.00 2 Weeks
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Related CAS #
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Synonym
Loteprednol Etabonate; Lotemax; Alrex; HGP-1; Loterox; Locort;
IUPAC/Chemical Name
chloromethyl (8S,9S,10R,11S,13S,14S,17R)-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
InChi Key
DMKSVUSAATWOCU-HROMYWEYSA-N
InChi Code
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
SMILES Code
O=C([C@@]1(OC(OCC)=O)CC[C@@]2([H])[C@]3([H])CCC4=CC(C=C[C@]4(C)[C@@]3([H])[C@@H](O)C[C@]12C)=O)OCCl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Loteprednol etabonate (LE) is an orally active "soft" steroid belonging to a unique class of glucocorticoids.
In vitro activity:
In in vitro investigations using human cells, loteprednol inhibited the release of proinflammatory cytokines (e.g., TNF-alpha, GM-CSF, IL-4, IL-5) according to its relative binding potency to the glucocorticoid receptor. Reference: Drugs Today (Barc). 2000 May;36(5):313-20. https://pubmed.ncbi.nlm.nih.gov/12861354/
In vivo activity:
In in vivo animal studies, loteprednol effectively inhibited allergically induced vascular leakage in the nasal cavity of actively sensitized Brown Norway rats and rhinorrhea in actively sensitized domestic pigs following nasal challenge. In several models of allergic asthma, it was clearly demonstrated that loteprednol was able to suppress the allergically induced late phase eosinophilia in mice, rats and guinea pigs. Reference: Drugs Today (Barc). 2000 May;36(5):313-20. https://pubmed.ncbi.nlm.nih.gov/12861354/
Solvent mg/mL mM
Solubility
DMF 30.0 64.25
DMSO 74.3 159.19
Ethanol 17.0 36.41
Ethanol:PBS (pH 7.2) (1:1) 0.2 0.43
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 466.96 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Szelenyi I, Hochhaus G, Heer S, Kusters S, Marx D, Poppe H, Engel J. Loteprednol etabonate: a soft steroid for the treatment of allergic diseases of the airways. Drugs Today (Barc). 2000 May;36(5):313-20. doi: 10.1358/dot.2000.36.5.575043. PMID: 12861354.
In vitro protocol:
Szelenyi I, Hochhaus G, Heer S, Kusters S, Marx D, Poppe H, Engel J. Loteprednol etabonate: a soft steroid for the treatment of allergic diseases of the airways. Drugs Today (Barc). 2000 May;36(5):313-20. doi: 10.1358/dot.2000.36.5.575043. PMID: 12861354.
In vivo protocol:
Szelenyi I, Hochhaus G, Heer S, Kusters S, Marx D, Poppe H, Engel J. Loteprednol etabonate: a soft steroid for the treatment of allergic diseases of the airways. Drugs Today (Barc). 2000 May;36(5):313-20. doi: 10.1358/dot.2000.36.5.575043. PMID: 12861354.
1: Comstock TL, DeCory HH. Loteprednol Etabonate 0.5%/Tobramycin 0.3% Compared with Dexamethasone 0.1%/Tobramycin 0.3% for the Treatment of Blepharitis. Ocul Immunol Inflamm. 2016 Jan 20:1-8. [Epub ahead of print] PubMed PMID: 26788833. 2: Wu LQ, Chen X, Lou H, Cheng JW, Wei RL. Loteprednol etabonate in the treatment of allergic conjunctivitis: a meta-analysis. Curr Med Res Opin. 2015 Aug;31(8):1509-18. doi: 10.1185/03007995.2015.1058250. PubMed PMID: 26039179. 3: Price MO, Feng MT, Scanameo A, Price FW Jr. Loteprednol Etabonate 0.5% Gel Vs. Prednisolone Acetate 1% Solution After Descemet Membrane Endothelial Keratoplasty: Prospective Randomized Trial. Cornea. 2015 Aug;34(8):853-8. doi: 10.1097/ICO.0000000000000475. PubMed PMID: 26020827. 4: Nasr FH, Khoee S. Design, characterization and in vitro evaluation of novel shell crosslinked poly(butylene adipate)-co-N-succinyl chitosan nanogels containing loteprednol etabonate: A new system for therapeutic effect enhancement via controlled drug delivery. Eur J Med Chem. 2015 Sep 18;102:132-42. doi: 10.1016/j.ejmech.2015.07.045. Epub 2015 Aug 1. PubMed PMID: 26263245. 5: Boynton GE, Raoof D, Niziol LM, Hussain M, Mian SI. Prospective Randomized Trial Comparing Efficacy of Topical Loteprednol Etabonate 0.5% Versus Cyclosporine-A 0.05% for Treatment of Dry Eye Syndrome Following Hematopoietic Stem Cell Transplantation. Cornea. 2015 Jul;34(7):725-32. doi: 10.1097/ICO.0000000000000436. PubMed PMID: 25850708. 6: Han YK, Segall AI. A validated specific stability-indicating RP-HPLC assay method for the determination of loteprednol etabonate in eye drops. J Chromatogr Sci. 2015 May-Jun;53(5):761-6. doi: 10.1093/chromsci/bmu121. Epub 2014 Sep 18. PubMed PMID: 25234383. 7: Thanathanee O, Sriphon P, Anutarapongpan O, Athikulwongse R, Thongphiew P, Rangsin R, Suwan-apichon O. A randomized controlled trial comparing dexamethasone with loteprednol etabonate on postoperative photorefractive keratectomy. J Ocul Pharmacol Ther. 2015 Apr;31(3):165-8. doi: 10.1089/jop.2014.0107. Epub 2015 Jan 2. PubMed PMID: 25555173. 8: Lee H, Chung B, Kim KS, Seo KY, Choi BJ, Kim TI. Effects of topical loteprednol etabonate on tear cytokines and clinical outcomes in moderate and severe meibomian gland dysfunction: randomized clinical trial. Am J Ophthalmol. 2014 Dec;158(6):1172-1183.e1. doi: 10.1016/j.ajo.2014.08.015. Epub 2014 Aug 13. PubMed PMID: 25128594. 9: Salinger CL, Gordon M, Jackson MA, Perl T, Donnenfeld E. A retrospective analysis of the postoperative use of loteprednol etabonate gel 0.5% following laser-assisted in situ keratomileusis or photorefractive keratectomy surgery. Clin Ophthalmol. 2015 Nov 6;9:2089-97. doi: 10.2147/OPTH.S94332. eCollection 2015. PubMed PMID: 26609219; PubMed Central PMCID: PMC4644184. 10: Sheppard JD, Donnenfeld ED, Holland EJ, Slonim CB, Solomon R, Solomon KD, McDonald MB, Perry HD, Lane SS, Pflugfelder SC, Samudre SS. Effect of loteprednol etabonate 0.5% on initiation of dry eye treatment with topical cyclosporine 0.05%. Eye Contact Lens. 2014 Sep;40(5):289-96. doi: 10.1097/ICL.0000000000000049. PubMed PMID: 25083776. 11: Beyazyıldız E, Acar U, Beyazyıldız Ö, Pınarlı FA, Albayrak A, Uğurlu N, Tiryaki M, Delibaşi T. Comparison of prednisolone acetate and loteprednol etabonate for the treatment of benzalkonium chloride-induced dry eye syndrome in rats. J Ocul Pharmacol Ther. 2014 May;30(4):306-12. doi: 10.1089/jop.2013.0129. Epub 2014 Feb 4. PubMed PMID: 24494746. 12: Glogowski S, Lowe E, Siou-Mermet R, Ong T, Richardson M. Prolonged exposure to loteprednol etabonate in human tear fluid and rabbit ocular tissues following topical ocular administration of Lotemax gel, 0.5%. J Ocul Pharmacol Ther. 2014 Feb;30(1):66-73. doi: 10.1089/jop.2013.0142. Epub 2013 Dec 10. PubMed PMID: 24325539. 13: Marlowe ZT, Davio SR. Dose uniformity of loteprednol etabonate ophthalmic gel (0.5%) compared with branded and generic prednisolone acetate ophthalmic suspension (1%). Clin Ophthalmol. 2014;8:23-9. doi: 10.2147/OPTH.S55004. Epub 2013 Dec 10. PubMed PMID: 24357925; PubMed Central PMCID: PMC3862701. 14: Schopf L, Enlow E, Popov A, Bourassa J, Chen H. Ocular Pharmacokinetics of a Novel Loteprednol Etabonate 0.4% Ophthalmic Formulation. Ophthalmol Ther. 2014 Feb 4. [Epub ahead of print] PubMed PMID: 25134493; PubMed Central PMCID: PMC4254862. 15: Sheppard JD, Mansur A, Comstock TL, Hovanesian JA. An update on the surgical management of pterygium and the role of loteprednol etabonate ointment. Clin Ophthalmol. 2014 Jun 13;8:1105-18. doi: 10.2147/OPTH.S55259. eCollection 2014. Review. PubMed PMID: 24966664; PubMed Central PMCID: PMC4063821. 16: Rajpal RK, Fong R, Comstock TL. Loteprednol etabonate ophthalmic gel 0.5% following cataract surgery: integrated analysis of two clinical studies. Adv Ther. 2013 Oct;30(10):907-23. doi: 10.1007/s12325-013-0059-7. Epub 2013 Oct 18. PubMed PMID: 24136301. 17: Lyseng-Williamson KA. Loteprednol etabonate ophthalmic gel 0.5%: a review of its use in post-operative inflammation and pain following ocular surgery. Drugs. 2013 Jun;73(9):949-58. doi: 10.1007/s40265-013-0073-8. Review. PubMed PMID: 23740411. 18: Lane SS, Holland EJ. Loteprednol etabonate 0.5% versus prednisolone acetate 1.0% for the treatment of inflammation after cataract surgery. J Cataract Refract Surg. 2013 Feb;39(2):168-73. doi: 10.1016/j.jcrs.2012.10.039. Epub 2012 Dec 8. PubMed PMID: 23232255. 19: Rajpal RK, Roel L, Siou-Mermet R, Erb T. Efficacy and safety of loteprednol etabonate 0.5% gel in the treatment of ocular inflammation and pain after cataract surgery. J Cataract Refract Surg. 2013 Feb;39(2):158-67. doi: 10.1016/j.jcrs.2012.09.013. Epub 2012 Dec 3. PubMed PMID: 23218817. 20: Coffey MJ, Decory HH, Lane SS. Development of a non-settling gel formulation of 0.5% loteprednol etabonate for anti-inflammatory use as an ophthalmic drop. Clin Ophthalmol. 2013;7:299-312. doi: 10.2147/OPTH.S40588. Epub 2013 Feb 13. PubMed PMID: 23430378; PubMed Central PMCID: PMC3575187.