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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

Novachemistry
Tel
44-20819178-90 02081917890
Fax
(0)2080432064
Email
info@novachemistry.com
Country
United Kingdom
ProdList
4381
Advantage
58
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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