Barnidipine hydrochlorideProduct ingredient for Barnidipine

Name
Barnidipine hydrochloride
Drug Entry
Barnidipine

Barnidipine is a long-acting novel calcium antagonist that belongs to the dihydropyridine (DHP) group of calcium channel blockers. Used in the treatment of hypertension, barnidipine displays high affinity for the calcium channels of the smooth muscle cells in the vascular wall 8 and selectivity against cardiovascular L-type calcium channels 1. Barnidipine contains two chiral centres thus can have four possible enantiomers. The active component is composed of a single optical isomer (3'S, 4S configuration), which is the most potent and longest-acting of the four enantiomers 3. Compared to several other calcium antagonists which are racemates, the barnidipine compound consisting of a single enantiomer may offer a high degree of pharmacological selectivity 3.

According to a dose-ranging, multicentre, placebo-controlled, double-blind study in patients with mild to moderate hypertension, the antihypertensive response from barnidipine treatment was maintained after a 1-year and 2-year follow-up period in 91% of the patients who had an initial response to the drug 1. In two European multicentre randomized, double-blind trials, barnidipine was shown to possess equivalent antihypertensive efficacy to amlodipine and nitrendipine, but produced fewer class-specific side-effects 4. It also demonstrated clinical efficacy which is similar to that of atenolol, enalapril and hydrochlorothiazide 1.

It is available in modified-release oral tablets under the brand name Vasexten to be taken once daily in the morning. Barnidipine has a gradual onset of action and is shown to be well tolerated in patients. It does not produce reflex tachycardia 1.

Accession Number
DBSALT003073
Structure
Synonyms
Barnidipine HCl / Barnidipine hydrochloride
External IDs
LY-198561
UNII
7LZ6R3AEM1
CAS Number
104757-53-1
Weight
Average: 528.0
Monoisotopic: 527.1823134
Chemical Formula
C27H30ClN3O6
InChI Key
XEMPUKIZUCIZEY-YSCHMLPRSA-N
InChI
InChI=1S/C27H29N3O6.ClH/c1-17-23(26(31)35-3)25(20-10-7-11-21(14-20)30(33)34)24(18(2)28-17)27(32)36-22-12-13-29(16-22)15-19-8-5-4-6-9-19;/h4-11,14,22,25,28H,12-13,15-16H2,1-3H3;1H/t22-,25-;/m0./s1
IUPAC Name
3-(3S)-1-benzylpyrrolidin-3-yl 5-methyl (4S)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
SMILES
Cl.COC(=O)C1=C(C)NC(C)=C([C@H]1C1=CC(=CC=C1)[N+]([O-])=O)C(=O)O[C@H]1CCN(CC2=CC=CC=C2)C1
ChemSpider
391958
ChEBI
31253
ChEMBL
CHEMBL2356712
Predicted Properties
PropertyValueSource
Water Solubility0.004 mg/mLALOGPS
logP4.12ALOGPS
logP3.51Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)16.97Chemaxon
pKa (Strongest Basic)8.11Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area111.01 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity136.36 m3·mol-1Chemaxon
Polarizability50.72 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon