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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Record UNII
62NWQ924LH
Record Status Validated (UNII)
Record Version