Ivabradine oxalateProduct ingredient for Ivabradine

Name
Ivabradine oxalate
Drug Entry
Ivabradine

Ivabradine is a novel heart rate lowering medicine for the symptomatic management of stable angina pectoralis and symptomatic chronic heart failure. Ivabradine, brand name Corlanor, was approved by the FDA in April 2015 for the treatment of chronic heart failure in patients with an ejection fraction of ≤35%, in sinus rhythm with resting heart rate ≥70 beats per minute, who are not on beta-blockers due to contraindications or already receiving maximum beta-blocker dose. Recently a new indication was added to treat symptomatic heart failure from dilated cardiomyopathy for patients 6 months or more in ageLabel. Ivabradine acts by selectively inhibiting the "funny" channel pacemaker current (If) in the sinoatrial node in a dose-dependent fashion, resulting in a lower heart rate and thus more blood to flow to the myocardium. Although non-dihydropyridine calcium channel blockers and beta blockers also effectively lower heart rate, they exhibit adverse events due to their negative ionotropic effects. Therefore, as ivabradine is designed as a "pure" heart rate-lowering drug by selectively acting on the If channels, it may offer a more favorable side effect profile due to its lower likelihood of causing serious adverse effects.

Accession Number
DBSALT002999
Structure
Synonyms
Not Available
UNII
K6SGA5L3AB
CAS Number
1086026-42-7
Weight
Average: 558.628
Monoisotopic: 558.257730812
Chemical Formula
C29H38N2O9
InChI Key
BOHZBFAHOBOJOS-ZMBIFBSDSA-N
InChI
InChI=1S/C27H36N2O5.C2H2O4/c1-28(17-21-11-20-14-25(33-4)26(34-5)16-22(20)21)8-6-9-29-10-7-18-12-23(31-2)24(32-3)13-19(18)15-27(29)30;3-1(4)2(5)6/h12-14,16,21H,6-11,15,17H2,1-5H3;(H,3,4)(H,5,6)/t21-;/m1./s1
IUPAC Name
3-[3-({[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]methyl}(methyl)amino)propyl]-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one; oxalic acid
SMILES
OC(=O)C(O)=O.COC1=C(OC)C=C2[C@@H](CN(C)CCCN3CCC4=CC(OC)=C(OC)C=C4CC3=O)CC2=C1
ChemSpider
81368155
Predicted Properties
PropertyValueSource
Water Solubility0.0202 mg/mLALOGPS
logP3.17ALOGPS
logP2.72Chemaxon
logS-4.4ALOGPS
pKa (Strongest Basic)9.37Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area60.47 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity133.51 m3·mol-1Chemaxon
Polarizability54.51 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon