Product Name

  • Name

    Loteprednol etabonate

  • EINECS 200-010-0
  • CAS No. 82034-46-6
  • Article Data4
  • CAS DataBase
  • Density 1.31 g/cm3
  • Solubility <1mg/L(23 oC)
  • Melting Point 220.5-223.5 °C
  • Formula C24H31ClO7
  • Boiling Point 600.1 °C at 760 mmHg
  • Molecular Weight 466.959
  • Flash Point 316.7 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 82034-46-6 (Loteprednol etabonate)
  • Hazard Symbols
  • Synonyms Alrex;CDDD 5604;HGP 1;Lotemax;
  • PSA 99.13000
  • LogP 3.91650

Synthetic route

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

17α-ethoxycarbonyloxy-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid

17α-ethoxycarbonyloxy-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid

Loteprednol etabonate
82034-46-6

Loteprednol etabonate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane at 20℃; for 2h; Time;92.8%
C24H33NO6

C24H33NO6

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

Loteprednol etabonate
82034-46-6

Loteprednol etabonate

Conditions
ConditionsYield
With dipotassium peroxodisulfate; potassium chloride for 3.5h; Reflux;92.6%
Chloroiodomethane
593-71-5

Chloroiodomethane

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

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

Loteprednol etabonate
82034-46-6

Loteprednol etabonate

Conditions
ConditionsYield
Stage #1: 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;
Stage #2: Chloroiodomethane In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 2h; Large scale;		89%
prednisolon
50-24-8

prednisolon

Loteprednol etabonate
82034-46-6

Loteprednol etabonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium periodate / methanol; water / 0.5 h / Heating; Large scale
2.1: triethylamine / dichloromethane / 0.5 h / 0 - 10 °C / Large scale
3.1: sodium ethanolate / N,N,N,N,N,N-hexamethylphosphoric triamide / 24 h / 20 °C / Large scale
3.2: 2 h / 20 °C / Large scale
View Scheme
Multi-step reaction with 4 steps
1: sodium periodate / tetrahydrofuran; methanol; water / 2 h / 20 °C
2: sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 3 h / 20 °C
3: diethylamine / water / pH 2 - 3
4: sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 2 h / 20 °C
View Scheme
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
37927-29-0

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid

Loteprednol etabonate
82034-46-6

Loteprednol etabonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 3 h / 20 °C
2: diethylamine / water / pH 2 - 3
3: sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 2 h / 20 °C
View Scheme
C26H30N2O6

C26H30N2O6

Loteprednol etabonate
82034-46-6

Loteprednol etabonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydrogencarbonate; glycidyl methyl ether / 15 h / 50 - 60 °C / Inert atmosphere
2: triethylamine / dichloromethane / 2 h / 0 - 5 °C / Inert atmosphere
3: potassium chloride; dipotassium peroxodisulfate / 3.5 h / Reflux
View Scheme
C26H30N2O6

C26H30N2O6

Loteprednol etabonate
82034-46-6

Loteprednol etabonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium acetate; epichlorohydrin / 15 h / 50 - 60 °C / Inert atmosphere
2: triethylamine / dichloromethane / 2 h / 0 - 5 °C / Inert atmosphere
3: potassium chloride; dipotassium peroxodisulfate / 3.5 h / Reflux
View Scheme
1,4-androstadien-11β-hydroxy-3-one-17α-hydroxynitrile

1,4-androstadien-11β-hydroxy-3-one-17α-hydroxynitrile

Loteprednol etabonate
82034-46-6

Loteprednol etabonate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate; copper(I) trifluoromethanesolfonate toluene complex / tetrahydrofuran / 5 h / Inert atmosphere; Reflux
2: potassium hydrogencarbonate; glycidyl methyl ether / 15 h / 50 - 60 °C / Inert atmosphere
3: triethylamine / dichloromethane / 2 h / 0 - 5 °C / Inert atmosphere
4: potassium chloride; dipotassium peroxodisulfate / 3.5 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: caesium carbonate; copper(l) iodide / 2-methyltetrahydrofuran / 5 h / Inert atmosphere; Reflux
2: potassium acetate; epichlorohydrin / 15 h / 50 - 60 °C / Inert atmosphere
3: triethylamine / dichloromethane / 2 h / 0 - 5 °C / Inert atmosphere
4: potassium chloride; dipotassium peroxodisulfate / 3.5 h / Reflux
View Scheme
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

(8S,10S,13S,14S,17R)-17-Ethoxycarbonyloxy-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester
207670-55-1

(8S,10S,13S,14S,17R)-17-Ethoxycarbonyloxy-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester

Conditions
ConditionsYield
With sulfuryl dichloride; triethylamine In toluene at -20 - 22℃; for 4h;89%
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

(8S,9S,10R,13S,14S,17R)-17-Ethoxycarbonyloxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester

(8S,9S,10R,13S,14S,17R)-17-Ethoxycarbonyloxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester

Conditions
ConditionsYield
With acetic anhydride; dimethyl sulfoxide at 22℃; for 72h;72%
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

chloromethyl 1β,11β-epoxy-17α-ethoxycarbonyloxy-2-oxo-10α-androsta-4-ene-17β-carboxylate

chloromethyl 1β,11β-epoxy-17α-ethoxycarbonyloxy-2-oxo-10α-androsta-4-ene-17β-carboxylate

Conditions
ConditionsYield
In water; acetonitrile at 25℃; for 472h; Photolysis;21%
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

A

chloromethyl 17α-ethoxycarbonyloxy-11β-hydroxy-1-methyl-3-oxo-6(5->10α)-abeo-19-norandrosta-1,4-diene-17β-carboxylate

chloromethyl 17α-ethoxycarbonyloxy-11β-hydroxy-1-methyl-3-oxo-6(5->10α)-abeo-19-norandrosta-1,4-diene-17β-carboxylate

B

chloromethyl 17α-ethoxycarbonyloxy-11β-hydroxy-5α-methyl-2-oxo-19-norandrosta-1(10),3-diene-17β-carboxylate

chloromethyl 17α-ethoxycarbonyloxy-11β-hydroxy-5α-methyl-2-oxo-19-norandrosta-1(10),3-diene-17β-carboxylate

Conditions
ConditionsYield
In water at 25℃; for 472h; Photolysis;A 0.4%
B 1.2%
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

A

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
37927-29-0

(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid

B

17α-ethoxycarbonyloxy-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid

17α-ethoxycarbonyloxy-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid

Conditions
ConditionsYield
With heptakis(2,6-di-O-methyl)cyclomaltoheptaose; water at 37℃; Kinetics; Activation energy; Further Variations:; Temperatures; Reagents; Solvents; Hydrolysis;
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

(8S,9R,10S,11S,13S,14S,17R)-9,11-Dichloro-17-ethoxycarbonyloxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester

(8S,9R,10S,11S,13S,14S,17R)-9,11-Dichloro-17-ethoxycarbonyloxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / SO2Cl2, Et3N / toluene / 4 h / -20 - 22 °C
2: 54 percent / SO2Cl2, pyridine / chlorobenzene / 3 h / -10 - 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 89 percent / SO2Cl2, Et3N / toluene / 4 h / -20 - 22 °C
2: 34 percent / Cl2, H2O, pyridine / CCl4; benzene / 10 h / 5 °C
View Scheme
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

(8S,9R,10S,11S,13S,14S,17R)-9-Chloro-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester

(8S,9R,10S,11S,13S,14S,17R)-9-Chloro-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / SO2Cl2, Et3N / toluene / 4 h / -20 - 22 °C
2: 16 percent / Cl2, H2O, pyridine / CCl4; benzene / 10 h / 5 °C
View Scheme
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

chloromethyl 9,11α-epoxy-17α-ethoxycarbonyloxy-3-oxoandrosta-1,4-diene-17β-carboxylate
207670-56-2

chloromethyl 9,11α-epoxy-17α-ethoxycarbonyloxy-3-oxoandrosta-1,4-diene-17β-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / SO2Cl2, Et3N / toluene / 4 h / -20 - 22 °C
2: 7.68 g / 3-chloroperoxybenzoic acid / CHCl3 / 120 h / 22 °C
View Scheme
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

cyanomethyl 9,11α-epoxy-17α-ethoxycarbonyloxy-3-oxoandrosta-1,4-diene-17β-carboxylate

cyanomethyl 9,11α-epoxy-17α-ethoxycarbonyloxy-3-oxoandrosta-1,4-diene-17β-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / SO2Cl2, Et3N / toluene / 4 h / -20 - 22 °C
2: 7.68 g / 3-chloroperoxybenzoic acid / CHCl3 / 120 h / 22 °C
3: 14 percent / lithium perchlorate / acetonitrile / 75 h / 70 °C
View Scheme
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

azidomethyl 9,11α-epoxy-17α-ethoxycarbonyloxy-3-oxoandrosta-1,4-diene-17β-carboxylate

azidomethyl 9,11α-epoxy-17α-ethoxycarbonyloxy-3-oxoandrosta-1,4-diene-17β-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / SO2Cl2, Et3N / toluene / 4 h / -20 - 22 °C
2: 7.68 g / 3-chloroperoxybenzoic acid / CHCl3 / 120 h / 22 °C
3: 33 percent / LiN3 / acetonitrile / 50 h / 70 °C
View Scheme
Loteprednol etabonate
82034-46-6

Loteprednol etabonate

loteprednol etabonate monohydrate

loteprednol etabonate monohydrate

Conditions
ConditionsYield
With water In acetone at 50℃; under 112511 Torr; Solvent; Pressure; Supercritical conditions;

Loteprednol etabonate Specification

The IUPAC name of Loteprednol etabonate is 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. With the CAS registry number 82034-46-6, it is also named as Chloromethyl 11beta,17-dihydroxy-3-oxoandrosta-1,4-diene-17beta-carboxylate, 17-(ethyl carbonate). The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals; Steroids; APIs.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.17; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 7; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 8; (6)Index of Refraction: 1.57; (7)Molar Refractivity: 116.47 cm3; (8)Molar Volume: 354.6 cm3; (9)Polarizability: 46.17×10-24 cm3; (10)Surface Tension: 53.2 dyne/cm; (11)Flash Point: 316.7 °C; (12)Enthalpy of Vaporization: 102.49 kJ/mol; (13)Boiling Point: 600.1 °C at 760 mmHg; (14)Vapour Pressure: 6.65E-17 mmHg at 25°C; (15)Rotatable Bond Count: 7; (16)Tautomer Count: 3; (17)Exact Mass: 466.175831; (18)MonoIsotopic Mass: 466.175831; (19)Topological Polar Surface Area: 99.1; (20)Heavy Atom Count: 32; (21)Complexity: 882; (22)Defined Atom StereoCenter Count: 7.

Preparation of Loteprednol etabonate: It can be obtained by the following reaction.

Uses of Loteprednol etabonate: It is an ophthalmic corticosteroid which can be used as an anti-inflammatory drug. The drug has little or no effect on intraocular pressure.

People can use the following data to convert to the molecule structure.
1. SMILES:ClCOC(=O)[C@@]1(OC(=O)OCC)CC[C@H]2[C@H]4[C@H]([C@@H](O)C[C@]12C)[C@]/3(/C=C\C(=O)\C=C\3CC4)C
2. InChI:InChI=1/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

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