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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H39N3O8
Molecular Weight 509.5925
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Landiolol

SMILES

CC1(C)OC[C@@H](COC(=O)CCC2=CC=C(OC[C@@H](O)CNCCNC(=O)N3CCOCC3)C=C2)O1

InChI

InChIKey=WMDSZGFJQKSLLH-RBBKRZOGSA-N
InChI=1S/C25H39N3O8/c1-25(2)35-18-22(36-25)17-34-23(30)8-5-19-3-6-21(7-4-19)33-16-20(29)15-26-9-10-27-24(31)28-11-13-32-14-12-28/h3-4,6-7,20,22,26,29H,5,8-18H2,1-2H3,(H,27,31)/t20-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula C25H39N3O8
Molecular Weight 509.5925
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Landiolol (Onoact) is an intravenously administered, ultra short-acting β1-blocker with an elimination half-life of 3-4 min and ≈8-fold greater cardioselectivity than esmolol in vitro. It is approved in Japan for the treatment of intraoperative and postoperative tachyarrhythmias, but in clinical practice is also used to prevent postoperative tachyarrhythmias, such as atrial fibrillation after coronary artery bypass grafting. Randomized controlled trials in patients undergoing open-heart surgery demonstrated that various dosages of landiolol (0.0005-0.04 mg/kg/min) [0.5-40 μg/kg/min] were more effective than diltiazem in converting postoperative atrial fibrillation to normal sinus rhythm during the first 8 h after surgery, and were more effective than placebo (or no landiolol) in preventing the development of atrial fibrillation during the first week after surgery (primary efficacy endpoints). Landiolol was generally well tolerated in clinical trials, with a relatively low risk of hypotension and bradycardia, although routine monitoring of cardiac function during landiolol administration is important. In general, adverse events such as reduced blood pressure resolve quickly after discontinuation of landiolol. Thus, as an ultra short-acting β1-blocker with a rapid onset of action and readily titratable and rapidly reversible effects, landiolol represents an important agent for the management of intraoperative and postoperative tachyarrhythmias.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Landiolol decreases a dysrhythmogenic dose of epinephrine in dogs during halothane anesthesia.
1999 Jun
[Clinical experience of landiolol for the treatment of intraoperative rapid atrial fibrillation].
2004 Apr
Patents

Patents

Sample Use Guides

landiolol dosage was in the range of 0.7 µg/kg/min-to-2.5 µg/kg/min
Route of Administration: Intravenous
In Vitro Use Guide
effects of landiolol on rat isolated aortic preparations under KCl contraction were investigated. Significant relaxations of isolated aortic preparations were obtained with landiolol 30-1000 micromol/L, suggesting a possible calcium antagonism with landiolol
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:04:12 GMT 2023
Edited
by admin
on Fri Dec 15 16:04:12 GMT 2023
Record UNII
62NWQ924LH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Landiolol
INN   MI   WHO-DD  
INN   USAN  
Official Name English
LANDIOLOL [USAN]
Common Name English
landiolol [INN]
Common Name English
[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-(4-{(2S)-2-hydroxy-3-[{2-[(morpholin-4-ylcarbonyl)amino]ethyl}amino]propoxy}phenyl)propanoate
Systematic Name English
AOP-200704
Code English
LDLL-600
Code English
LDLL600
Code English
LANDIOLOL [MI]
Common Name English
ONO-1101
Code English
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
Systematic Name English
AOP200704
Code English
Landiolol [WHO-DD]
Common Name English
(-)-2,2-dimethyl-1,3-dioxolan-4S-ylmethyl 3-[4-[3-[2-(morpholinocarbonylamino)ethylamino]-2S-hydroxypropoxy]phenyl]propionate
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
WHO-ATC C07AB14
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1545
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
WIKIPEDIA
LANDIOLOL
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID10158026
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL1742466
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
MESH
C077049
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
NCI_THESAURUS
C79125
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
MERCK INDEX
m6675
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY Merck Index
FDA UNII
62NWQ924LH
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
PUBCHEM
114905
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
DRUG BANK
DB12212
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
CAS
133242-30-5
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
INN
7516
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
EVMPD
SUB08396MIG
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
SMS_ID
100000082553
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
USAN
KL-159
Created by admin on Fri Dec 15 16:04:12 GMT 2023 , Edited by admin on Fri Dec 15 16:04:12 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
ENANTIOMER -> ENANTIOMER
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ACTIVE MOIETY