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LEVOBUNOLOL

Product Name
LEVOBUNOLOL
CAS No.
47141-42-4
Chemical Name
LEVOBUNOLOL
Synonyms
W 6421A;AK-Beta;Betegan;l-Bunolol;Liquifilm;LEVOBUNOLOL;Levobunololum;LEVOBUNOLOL USP/EP/BP;[(-)-5-[3,(t-Butylamino)-2-hydroxy-propoxy]-3,4-di,HCl;5-[3-(tert-Butylamino)-2β-hydroxypropyloxy]-3,4-dihydronaphthalen-1(2H)-one
CBNumber
CB5210167
Molecular Formula
C17H25NO3
Formula Weight
291.39
MOL File
47141-42-4.mol
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LEVOBUNOLOL Property

Melting point:
209-211°C
storage temp. 
-20°C Freezer, Under Inert Atmosphere
CAS DataBase Reference
47141-42-4(CAS DataBase Reference)
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Safety

Toxicity
LD50 in male, female rats, mice (mg/kg): 700, 800, 1530, 1220 orally; 25, 28, 78, 84 i.v.; LD50 in male, female hamsters, dogs (mg/kg): 435, 500, 100, 100 orally (Kaplan, 1980)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

American Custom Chemicals Corporation
Product number
API0003156
Product name
LEVOBUNOLOL
Purity
95.00%
Packaging
1G
Price
$630
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
11354
Product name
LevobunololHCl
Packaging
1.25g
Price
$1560
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0003156
Product name
LEVOBUNOLOL
Purity
95.00%
Packaging
2.5G
Price
$1947
Updated
2021/12/16
AHH
Product number
MT-53190
Product name
Levobunolol
Purity
98%
Packaging
5g
Price
$510
Updated
2021/12/16
Chemenu
Product number
CM129099
Product name
(S)-5-(3-(tert-butylamino)-2-hydroxypropoxy)-3,4-dihydronaphthalen-1(2H)-one
Purity
95%
Packaging
1g
Price
$327
Updated
2021/12/16
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LEVOBUNOLOL Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Betagan,Allergan,India

Uses

Levobunolol hydrochloride is an antiglaucoma agent in ophthalmie solutions.

Uses

As a non-selective adrenoceptor antagonist, Levobunolol is used as an anticonvulsant.

Definition

ChEBI: A cyclic ketone that is 3,4-dihydronaphthalen-1-one substituted at position 5 by a 3-(tert-butylamino)-2-hydroxypropoxy group (the S-enantiomer). A non-selective beta-adrenergic antagonist used (as its hydrochlo ide salt) for treatment of glaucoma.

Manufacturing Process

9.62 g (59 mmoles) 5-hydroxy-3,4-dihydro-1(2H)-naphthalenone, 67 ml toluene, 0.36 g (1.1 mmoles) tetra-n-butylammonium bromide, 4.51 g (68 mmoles) 85% potassium hydroxide and 20 ml (254 mmoles) (R)-(-)- epichlorhydrine were placed in an appropriate flask fitted with efficient mechanical stirring, and the mixture was heated under reflux for two hours. The mixture was allowed to cool to 30°C, 50 ml toluene and 50 ml water were added and the mixture was vigorously stirred. The organic phase was removed and the aqueous phase extracted with 25 ml toluene. The combined organic phases were concentrated at reduced pressure, 31 ml (300 mmoles) tert-butylamine, 45 ml ethanol and 3 ml deionized water were added, and the solution was heated under reflux for one hour. The mixture was allowed to cool to 40°C and the volatile products were distilled at reduced pressure. Toluene (9 ml) was added to the residue and volatiles were distilled at reduced pressure. (S)-5-(2,3-Epoxypropoxy)-3,4-dihydro-1(2H)- naphthalenone with an optical purity greater than 95% was obtained. Toluene (75 ml) was added to the product, and then, 10 ml of 35% (w/v) hydrochloric acid and 110 ml water, and the mixture was stirred for fifteen minutes. The organic phase was decanted and the aqueous one was extracted with 50 ml toluene. The aqueous phase was basified by addition of a solution of 5.1 g sodium hydroxide in 150 ml water and extracted twice with toluene (100 and 50 ml, respectively). The combined organic extracts were dried with anhydrous sodium sulfate, decolorized with active charcoal and filtered.
To the above toluenic solution containing levobunolol as free base, 16 ml ethanol and the stoichiometric amount of hydrogen chloride were added. The stirred mixture was cooled below 10°C and kept at this temperature for one hour. The precipitated solid was filtered, washed with toluene, recrystallized twice from 43 ml ethanol and dried to give 10.0 g (51% yield) of (-)-3,4- dihydro-5-(3-(tert-butylamino)-2-hydroxypropoxy)-1(2H)-naphthalenone hydrochloride (levobunolol hydrochloride) having a rotary power at 25°C below -19°.

brand name

Akbeta(Akorn); Betagan(Allergan).

Therapeutic Function

Beta-adrenergic blocker

LEVOBUNOLOL Preparation Products And Raw materials

Raw materials

Preparation Products

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LEVOBUNOLOL Suppliers

LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Chemsky (shanghai) International Co.,Ltd
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
15402
Advantage
60
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
Advantage
58
Shanghai Han-Xiang Chemical Co., Ltd.
Tel
15971444841
Fax
18327183813
Email
amber@biochempartner.com
Country
China
ProdList
3061
Advantage
58
Shaanxi Dideu Medichem Co. Ltd
Tel
+86-029-89586680 +86-18192503167
Fax
+86-29-88380327
Email
1026@dideu.com
Country
China
ProdList
7724
Advantage
58
Energy Chemical
Tel
021-58432009 400-005-6266
Fax
021-58436166
Email
marketing@energy-chemical.com
Country
China
ProdList
44918
Advantage
58
TargetMol Chemicals Inc.
Tel
15002134094
Email
marketing@targetmol.cn
Country
China
ProdList
19707
Advantage
58
TargetMol Chemicals Inc.
Tel
+8613564774135
Email
zijue.cai@tsbiochem.com
Country
United States
ProdList
19885
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
Hangzhou MolCore BioPharmatech Co.,Ltd.
Tel
+86-057181025280; +8617767106207
Fax
0571-85806285
Email
sales@molcore.com
Country
China
ProdList
49734
Advantage
58

47141-42-4, LEVOBUNOLOLRelated Search:


  • LEVOBUNOLOL
  • 5-[(2S)-3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-1(2H)-naphthalenone
  • 5-[(S)-3-[(1,1-Dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydronaphthalen-1(2H)-one
  • 5-[3-(tert-Butylamino)-2β-hydroxypropyloxy]-3,4-dihydronaphthalen-1(2H)-one
  • (S)-5-[3-[(1,1-DiMethylethyl)aMino]-2-hydroxypropoxy]- 3,4-dihydro-1(2H)-naphthalenone
  • l-Bunolol
  • W 6421A
  • 5-[(2S)-3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-2H-naphthalen-1-one
  • [(-)-5-[3,(t-Butylamino)-2-hydroxy-propoxy]-3,4-di,HCl
  • 1(2H)-Naphthalenone, 5-[(2S)-3-[(1,1-dimethylethyl)amino]-2-hydroxypropoxy]-3,4-dihydro-
  • LEVOBUNOLOL USP/EP/BP
  • AK-Beta
  • Betegan
  • Levobunololum
  • Liquifilm
  • 47141-42-4
  • 27912-17-4
  • Intermediates & Fine Chemicals
  • Pharmaceuticals