Description References
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Loteprednol etabonate

Description References
Product Name
Loteprednol etabonate
CAS No.
82034-46-6
Chemical Name
Loteprednol etabonate
Synonyms
Etabonate;Alrex;HGP 1;P 5604;Lotemax;CDDD 5604;Etocloteprednol;Lotemax|||Alrex;LOTEPREDNOL ETABONATE;Lotoprednol etabonate
CBNumber
CB9396463
Molecular Formula
C24H31ClO7
Formula Weight
466.95
MOL File
82034-46-6.mol
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Loteprednol etabonate Property

Melting point:
220.5-223.5
Boiling point:
600.1±55.0 °C(Predicted)
Density 
1.31±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: soluble5mg/mL, clear (warmed)
pka
14.06±0.70(Predicted)
form 
powder
color 
white to beige
Water Solubility 
<1mg/L(23 ºC)
Stability:
Hygroscopic
InChIKey
DMKSVUSAATWOCU-ICASLIHPSA-N
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Safety

WGK Germany 
3
HS Code 
2937.22.0000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0547
Product name
Loteprednol Etabonate
Purity
≥98% (HPLC)
Packaging
10mg
Price
$99.3
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0547
Product name
Loteprednol Etabonate
Purity
≥98% (HPLC)
Packaging
50mg
Price
$241.2
Updated
2024/03/01
TCI Chemical
Product number
L0327
Product name
Loteprednol Etabonate
Packaging
50MG
Price
$112
Updated
2024/03/01
TCI Chemical
Product number
L0327
Product name
Loteprednol Etabonate
Packaging
250MG
Price
$385
Updated
2024/03/01
Cayman Chemical
Product number
23305
Product name
Loteprednol etabonate
Purity
≥98%
Packaging
5mg
Price
$37
Updated
2024/03/01
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Loteprednol etabonate Chemical Properties,Usage,Production

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.

References

[1] http://www.webmd.com
[2] https://www.drugbank.ca
[3] http://www.bausch.com
[4] Timothy L. Comstock, Heleen H. DeCory (2012) Advances in Corticosteroid Therapy for Ocular Inflammation: Loteprednol Etabonate, International Journal of Inflammation, 2012, 789623
[5] N. Krug, JM. Hohlfeld, H. Geldmacher, M Larbig, R. Heermann, N. Lavallee, DT. Nguyen, U. Petzold, R. Hermann (2005) Effect of loteprednol etabonate nasal spray suspension on seasonal allergic rhinitis assessed by allergen challenge in an environmental exposure unit, Allergy, 60, 354-359

Description

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.

Chemical Properties

x

Originator

Pharmos (US)

Uses

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

Uses

An ophthalmic corticosteroid. Used as an anti-inflammatory.

Definition

ChEBI: Loteprednol etabonate is an etabonate ester, an 11beta-hydroxy steroid, a steroid ester, an organochlorine compound, a steroid acid ester and a 3-oxo-Delta(1),Delta(4)-steroid. It has a role as an anti-inflammatory drug. It is functionally related to a loteprednol.

Manufacturing Process

To a solution of hydrocortisone (15 g, 0.04 mol) in 120 ml of THF and 30 ml of methanol at room temperature is added a warm solution of sodium metaperiodate (25.7 g, 0.12 mol) in 100 ml of water. The reaction mixture is stirred at room temperature for 2 hours, then is concentrated under reduced pressure to remove the tetrahydrofuran and methanol. The solid is triturated with 50 ml of water, separated by filtration, washed with water and dried in vacuo at 50°C for 3 hours. The product, 11β,17α-dihydroxyandrost-4-en-3- one-17β-carboxylic acid (i.e., cortienic acid), is obtained in approximately 96% yield (13.76 g); melting point 231-234°C.
To a cold solution of 11β,17α-dihydroxyandrost-4-en-3-one-17β-carboxylic acid (5% weight/volume; 1 mol) and triethylamine (4 mol) in dichloromethane is added a 50% (weight/volume) solution of ethyl chloroformate (3.9 mol) in dichloromethane. The reaction mixture is allowed to warm to room temperature over a 2 hour period. The triethylamine hydrochloride precipitate which forms is removed by filtration and the filtration is washed successively with 3% sodium bicarbonate, 1% hydrochloric acid and water. The organic layer is separated, dried with magnesium sulfate, and filtered. The filtrate is concentrated in vacuo to a foam.
The foam is used in the next step below or chromatographed and crystallized for analysis. The product 17α-ethoxycarbonyloxy-11β-hydroxyandrost-4-en-3- one-17β-carboxylic acid, melting at 192-195°C C after chromatography and crystallization.
17α-Ethoxycarbonyloxy-11β-hydroxyandrost-4-en-3-one-17β-carboxylic acid is combined with an equivalent amount of 1 N sodium hydroxide in methanol and that solution is diluted to 100 times the original volume with ethyl ether. The suspension which results is refrigerated for 1 hour. Then, the crystals which form are removed by filtration, dried in an evacuated desiccator, and dissolved in hexamethylphosphoramide (10% weight/volume). A portion of the resultant solution containing 1 mole of the acid salt, i.e. of sodium 17αethoxycarbonyloxy-11β-hydroxyandrost-4-en-3-one-17β-carboxylate, is combined with 4 moles of chloromethyl iodide. The reaction mixture is maintained at room temperature for 3 hours, then is diluted to 10 times the original volume with ethyl acetate. The diluted reaction mixture is washed successively with 5% sodium thiosulfate, 3% sodium bicarbonate, and water. The organic layer is separated, dried with magnesium sulfate and filtered. The filtrate is concentrated in vacuo to a foam. The foam is purified by crystallization from ethyl ether or tetrahydrofuran/hexane. There is thus obtained chloromethyl-17α-ethoxycarbonyloxy-11β-hydroxyandrost-4-en-3- one-17β-carboxylate, melting at 197-200°C after crystallization.

brand name

Alrex (Bausch & Lomb); Lotemax (Bausch & Lomb); Lotemax (Pharmos);Lotemax (0.5%).

Therapeutic Function

Glucocorticoid

General Description

Loteprednol etabonate,chloromethyl 17α-[(ethoxycarbonyl)oxy]-11β-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate (Alrex,Lotemax), has a modified carboxylate at the C17 positionrather than the typical ketone functionality. This modificationmaintains affinity for the GR but allows facile metabolismto inactive metabolites. This limits the systemic actionof the drug. Loteprednol etabonate is used as anophthalmic suspension that has greatly reduced systemicaction because of rapid metabolism to the inactive carboxylate.

Biochem/physiol Actions

Loteprednol Etabonate is an anti-inflammatory corticosteroid (ophthalmology).

Loteprednol etabonate Preparation Products And Raw materials

Raw materials

Preparation Products

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Loteprednol etabonate Suppliers

Shandong Kehui Pharmaceutical Co. LTD
Tel
13276409687
Email
469553953@qq.com
Country
China
ProdList
30
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58
Jinan Kaypharm Chemical Co.,Ltd.
Tel
0531-86986780 13153183025
Fax
0531-86986781
Email
sales@kaypharm.cn
Country
China
ProdList
109
Advantage
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GUANGZHOU TOPWORK CHEMISTRY CO.,LTD.
Tel
020-87317062 13048089691
Email
852378519@qq.com
Country
China
ProdList
155
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58
Hangzhou LinghepharmTechnology Co.,Ltd.
Tel
+86-18571465433 18571465433
Email
sales@linghepharm.com
Country
China
ProdList
49
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58
Jinan Yunding Biotechnology Co., Ltd
Tel
15662712965
Email
1013429786@qq.com
Country
China
ProdList
22
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58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
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Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
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62
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
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59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
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View Lastest Price from Loteprednol etabonate manufacturers

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Loteprednol Etabonate 82034-46-6
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-09-19
Zhuozhou Wenxi import and Export Co., Ltd
Product
Loteprednol Etabonate 82034-46-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-11
Hebei Minshang Biological Technology Co. LTD
Product
Loteprednol etabonate 82034-46-6
Price
US $100.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1000t
Release date
2021-05-10

82034-46-6, Loteprednol etabonateRelated Search:


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  • 17α-(Ethoxycarbonyloxy)-11β-hydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid chloromethyl ester
  • 3-Oxo-11β-hydroxy-17α-(ethoxycarbonyloxy)androsta-1,4-diene-17-carboxylic acid chloromethyl ester
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  • (11b,17a)-17-[(Ethoxycarbonyl)oxy]-11-hydroxy-3-oxo-Androsta-1,4-diene-17-carboxylic acid chloromethyl ester
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  • 17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylic acid chloromethyl ester
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  • (11beta,17alpha)-17-[(Ethoxycarbonyl)oxy]-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylic Acid Chloromethyl Ester
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  • Loteprednol EtabonateQ: What is Loteprednol Etabonate Q: What is the CAS Number of Loteprednol Etabonate Q: What is the storage condition of Loteprednol Etabonate
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  • (8S,9S,10R,11S,13S,14S,17R)-chloromethyl 17-((ethoxycarbonyl)oxy)-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-carboxylate
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  • 82034-46-6
  • 82304-46-6
  • C24H31ClO7
  • C24H31O7CL
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  • Pharmaceuticals
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  • Steroid and Hormone
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  • 82034-46-6