Loteprednol etabonate

Base Information

• Chemical Name: Loteprednol etabonate
• CAS No.: 82034-46-6
• Molecular Formula: C24H31ClO7
• Molecular Weight: 466.959
• Hs Code.: 2937229000
• European Community (EC) Number: 639-474-4
• UNII: YEH1EZ96K6
• DSSTox Substance ID: DTXSID2046468
• Nikkaji Number: J418.181F
• Wikidata: Q3837481
• NCI Thesaurus Code: C47589
• RXCUI: 52177
• Pharos Ligand ID: UV6VMJYUSXYX
• Metabolomics Workbench ID: 54455
• ChEMBL ID: CHEMBL1200865
• Mol file: 82034-46-6.mol

Synonyms:17-ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate, Chloromethyl;Alrex;CEHOAC;Chloromethyl 17 ethoxycarbonyloxy 11 hydroxy 3 oxoandrosta 1,4 diene 17 carboxylate;chloromethyl 17-ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate;Etabonate, Loteprednol;Lotemax;loteprednol;loteprednol etabonate

Chemical Property of Loteprednol etabonate

Chemical Property:

• Vapor Pressure: 6.65E-17mmHg at 25°C
• Melting Point: 220.5-223.5 °C
• Refractive Index: 1.57
• Boiling Point: 600.1 °C at 760 mmHg
• PKA: 14.06±0.70(Predicted)
• Flash Point: 316.7 °C
• PSA: 99.13000
• Density: 1.31 g/cm³
• LogP: 3.91650
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble5mg/mL, clear (warmed)
• Water Solubility.: <1mg/L(23 oC)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 466.1758310
• Heavy Atom Count: 32
• Complexity: 882

Purity/Quality:

99% ^*data from raw suppliers

Chloromethyl 17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)OC1(CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)C(=O)OCCl
• Isomeric SMILES: CCOC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)C(=O)OCCl
• Recent ClinicalTrials: Comparing Treatment of Dry Eye With Intracanlicular Dexamethasone, Restasis, and/or Lotemax
• Recent EU Clinical Trials: A Randomized, Multicenter, Double-Blind, Parallel-Group Clinical Safety and Efficacy Evaluation of Loteprednol Etabonate Ophthalmic Gel, 0.5% versus Vehicle for the Treatment of Inflammation and Pain Following Cataract Surgery
• Description: Loteprednol (as Loteprednol Etabonate) is a topical anti-inflammatory corticosteroid. Loteprednol etabonate (LE) has a 17α-chloromethyl ester, in lieu of a ketone group, and a 17β-etabonate group. LE is highly lipophilic and binds with high affinity to the glucocorticoid receptor. Any unbound LE is metabolized to inactive metabolites. Loteprednol etabonate is used in ophthalmic solution 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, uveitis, acne rosacea, superficial punctate keratitis, herpes zoster keratitis, iritis, cyclitis, and selected infective conjunctivitis. It is used in ophthalmic ointment for the treatment of post-operative inflammation and pain following ocular surgery. As a nasal spray, it is used for the treatment and management of seasonal allergic rhinitis. Loteprednol etabonate was introduced in the US as Lotemax (opththalmic suspension at 0.5%) for the treatment of steroid-responsive inflammatory conditions of the palpebral and bulbar conjunctiva, cornea and anterior segment of the ocular globe, and as Alrex (opththalmic suspension at 0.2%) for the symptomatic treatment of seasonal allergic conjunctivitis. Loteprednol etabonate is a novel soft corticosteroid with a superior efficacy and an improved safety profile compared to prior ophthalmic steroids due to its metabolic lability and a fast enzymatic transformation to inactive metabolite. A combination of Lotemax with the antibiotic Tobramycin is currently under development.
• Uses: An ophthalmic corticosteroid. Used as an anti-inflammatory Biological Activity Chemical Information Tech Support & FAQs Biological Activity Loteprednol etabonate is an anti-inflammatory corticosteroid used in ophthalmology. It is used for the treatment of steroid responsive inflammatory conditions of the eye su An ophthalmic corticosteroid. Used as an anti-inflammatory.
• Therapeutic Function: Glucocorticoid

Technology Process of Loteprednol etabonate

There total 9 articles about Loteprednol etabonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.8%

chlorosulfuric acid chloromethyl ester (49715-04-0) + 17α-ethoxycarbonyloxy-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid → Loteprednol etabonate (82034-46-6)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 2h; Time;

Reference yield: 92.6%

C24H33NO6 + N,N-dimethyl-formamide (68-12-2,33513-42-7) → Loteprednol etabonate (82034-46-6)

Guidance literature:

With dipotassium peroxodisulfate; potassium chloride; for 3.5h; Reflux;

Reference yield: 89.0%

Chloroiodomethane (593-71-5) + 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride (133991-62-5) → Loteprednol etabonate (82034-46-6)

Guidance literature:

17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride; With sodium ethanolate; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 24h; Large scale;

Chloroiodomethane; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 2h; Large scale;

upstream raw materials:

prednisolon

Chloroiodomethane

17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic ethoxycarboxylic anhydride

chlorosulfuric acid chloromethyl ester

Downstream raw materials:

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 0^2,7. 0^11,15]heptadeca-3,6-diene-14-carboxylic acid

Refernces

• 1、 -. "A method for synthesizing loteprednol etabonate and a method for synthesizing intermediate (by machine translation)". . . Retrieved 2017/05/05.
• 2、 -. "Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor". . . Retrieved 2008/06/13.