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Landiolol hydrochloride

Product Name
Landiolol hydrochloride
CAS No.
144481-98-1
Chemical Name
Landiolol hydrochloride
Synonyms
propoxy);methyl 3-(4-((S);Ono 1101 hydrochloride;Landiolol hydrochloride;propanoate hydrochloride;Landiolol hydrochloride salt;-2,2-Dimethyl-1,3-dioxolan-4-yl);Landiolol hydrochloride USP/EP/BP;-2-hydroxy-3-((2-(morpholine-4-carboxamido);Carteolol Impurity 2(Carteolol EP Impurity B )
CBNumber
CB61179000
Molecular Formula
C25H40ClN3O8
Formula Weight
546.06
MOL File
144481-98-1.mol
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Landiolol hydrochloride Property

Melting point:
125.4°
storage temp. 
Refrigerator
solubility 
DMSO (Slightly), Ethanol (Slightly, Sonicated)
form 
Solid
color 
White to Off-White
InChIKey
DLPGJHSONYLBKP-WRNKUMIYNA-N
SMILES
C(C1C=CC(OC[C@@H](O)CNCCNC(N2CCOCC2)=O)=CC=1)CC(=O)OC[C@@H]1COC(C)(C)O1.Cl |&1:7,29,r|
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Safety

RTECS 
DA8346700
HS Code 
2934.99.4700
Toxicity
LD50 in mice (mg/kg): 290 i.v. (Iguchi)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical
Product number
L0296
Product name
Landiolol Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
50mg
Price
$131
Updated
2024/03/01
TCI Chemical
Product number
L0296
Product name
Landiolol Hydrochloride
Purity
>98.0%(HPLC)(T)
Packaging
250mg
Price
$439
Updated
2024/03/01
TRC
Product number
L173900
Product name
Landiolol Hydrochloride
Packaging
10mg
Price
$50
Updated
2021/12/16
TRC
Product number
L173900
Product name
Landiolol Hydrochloride
Packaging
50mg
Price
$90
Updated
2021/12/16
AK Scientific
Product number
J98964
Product name
LandiololHCl
Packaging
25mg
Price
$96
Updated
2021/12/16
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Landiolol hydrochloride Chemical Properties,Usage,Production

Description

Landiolol hydrochloride (14) was launched in Japan by Ono for the treatment of intraoperative tachyarrhythmia. It improves tachyarrhythmia by selectively blocking β1 receptors located mainly in the heart and by inhibiting the action of catecholamine.

Uses

Landiolol is an ultra-short acting beta blocker that is used to treat patients with cardiac arrhythmias and is also used to treat tachycardia during anasthesia.

Definition

ChEBI: Landiolol hydrochloride is a member of morpholines.

Pharmacokinetics

Landiolol hydrochloride has a β1/β2 ratio of 255, and, compared to propranolol, its β1-selectivity is 74–380 times greater while it has a 33–263 times greater β1 affinity than esmolol. This high β1-selectivity produces a more potent negative chronotropic effect and a less potent hypotensive effect. Work in rabbit animal models revealed a more rapid HR decrease with landiolol than with esmolol. In contrast, the decrease in mean arterial blood pressure (MAP) seen with esmolol was not observed with landiolol. Similar results were obtained in isolated rabbit and guinea pig hearts. Landiolol metabolism is mainly in the liver (approximately half) and plasma and is predominantly catalyzed by liver carboxylesterase and plasma pseudocholinesterase. In hepatically impaired patients, maximum concentration (Cmax) and area under the concentration (AUC)?time curve values were 42% and 44% higher, respectively. However, half-life did not differ compared with healthy patients, and no drug-related adverse events were observed[1].

Clinical Use

Landiolol hydrochloride, a highly cardio-selective beta-1 blocker with an ultra-short-acting half-life of 4 minutes, is widely used in Japan under the brand name Onoact®. β-blockers is useful in preventing refractory and urgent fatal arrhythmia and tachycardia in chronic phase.Recently, European Union health authorities have approved usage under the name Rapibloc®. Landiolol was originally approved by Japan for treatment of intraoperative tachyarrhythmias and was later approved for tachycardia atrial fibrillation (AF) and atrial flutter (AFL) during left ventricular (LV) dysfunction in November 2013. More recently, landiolol expanded its utility into usage for fatal arrhythmia requiring emergency treatment in 20196 and is fast becoming a reliable therapeutic choice for management of arrhythmia in acute phase[1].

Synthesis

The synthesis of landiolol appeared in an earlier patent in 1990. Esterification of 3- (4-hydroxyphenyl)propionic acid (141) with 2,2-dimethyl- 1,3-dioxolan-4-ylmethyl chloride (142) in DMSO gave desired ester 143 in 57% yield. Treatment of phenol 143 with bromo epoxide 144 in the present of K2CO3 afforded ether 145 in 76% yield. Epoxide 145 was then reacted with free amine 146 via a neucleophilic ring opening process to provide landiolol (14).

References

[1] Yujiro Matsuishi. “Evaluating the Therapeutic Efficacy and Safety of Landiolol Hydrochloride for Management of Arrhythmia in Critical Settings: Review of the Literature.” Vascular Health and Risk Management 16 (2020): 111–123.

Landiolol hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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Landiolol hydrochloride Suppliers

Chengdu Aupone Pharmaceutical Co.,Ltd.
Tel
18980796919
Email
236656639@qq.com
Country
China
ProdList
23
Advantage
58
Chongqing Chemieliva Pharmaceutical Co., Ltd.
Tel
023-67770219
Fax
+86 (23) 6777-0220
Email
jessica.hu@chemieliva.com
Country
China
ProdList
1444
Advantage
60
Wuhan Huajiu Pharmaceutical Technology Co.,Ltd.
Tel
027-59225746 18062681621
Fax
027-59225746
Email
730880265@qq.com
Country
China
ProdList
4785
Advantage
58
Jiangxi ravel Biotechnology Co.,Ltd
Tel
400-880-2824; 13184580281
Fax
400-880-2824
Email
hj@ruiweier.cn
Country
China
ProdList
2737
Advantage
58
Shanghai Star Pharmaceutical Chemical Technology Co., Ltd.
Tel
021-58521787 17701827760
Email
starpharmsh@gmail.com
Country
China
ProdList
208
Advantage
58
Tianjin Derchemist Science & Technology Co., Ltd.
Tel
22-58627059 13920586291
Fax
022-58620305
Email
zdcomcon@126.com
Country
China
ProdList
3401
Advantage
50
Biopole Pharmatech Co., Ltd.
Tel
0512-65974739-0 15151475053
Email
mengqi_biopole@163.com
Country
China
ProdList
45
Advantage
58
Hubei Zhongshan Medical Technology Co., Ltd
Tel
027-61907345 13397111514
Fax
3443707954
Email
w13397111514@163.com
Country
China
ProdList
1010
Advantage
58
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
9976
Advantage
60
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
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View Lastest Price from Landiolol hydrochloride manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Landiolol hydrochloride 144481-98-1
Price
US $0.00/g
Min. Order
1g
Purity
99.5%min
Supply Ability
1000g
Release date
2021-11-20
Hebei Weibang Biotechnology Co., Ltd
Product
Landiolol hydrochloride 144481-98-1
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-01
ShenZhen H&D Pharmaceutical Technology Co., LTD
Product
Landiolol(Hydrochloride) 144481-98-1
Price
US $0.00/mg
Min. Order
10mg
Purity
0.98
Supply Ability
10g
Release date
2024-04-08

144481-98-1, Landiolol hydrochlorideRelated Search:


  • [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-2-hydroxy-3-[2-(morpholine-4-carbonylamino)ethylamino]propoxy]phenyl]propanoate hydrochloride
  • Landiolol hydrochloride
  • Benzenepropanoic acid, 4-(2-hydroxy-3-((2-((4-morpholinylcarbonyl)amino)ethyl)amino)propoxy)-, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester, (S-(R*,R*))-, hydrochloride
  • Ono 1101 hydrochloride
  • -2,2-Dimethyl-1,3-dioxolan-4-yl)
  • -2-hydroxy-3-((2-(morpholine-4-carboxamido)
  • methyl 3-(4-((S)
  • propanoate hydrochloride
  • ((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-((S)-2-hydroxy-3-((2-(morpholine-4-carboxamido)ethyl)amino)propoxy)phenyl)propanoate hydrochloride
  • propoxy)
  • Landiolol hydrochloride USP/EP/BP
  • Landiolol hydrochloride salt
  • Benzenepropanoic acid, 4-[(2S)-2-hydroxy-3-[[2-[(4-morpholinylcarbonyl)amino]ethyl]amino]propoxy]-, [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl ester, hydrochloride (1:1)
  • Landiolol Hydrochloride (Benzenepropanoic acid, 4-[(2S)-2-hydroxy-3-[[2-[(4-mo rpholinylcarbonyl)amino]ethyl] amino]propoxy]-, [(4S)-2,2-dimethyl-1,3-dioxola n-4-yl]methyl ester, hydrochloride)
  • Carteolol Impurity 2(Carteolol EP Impurity B )
  • 144481-98-1
  • 44481-98-1
  • C25H40ClN3O8
  • C25H39N3O8HCl
  • APIs
  • API
  • 144481-98-1