Barnidipine

Barnidipine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	C08CA12 (WHO) ;
Identifiers
	IUPAC name 3-(3R)-1-Benzylpyrrolidin-3-yl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate;
CAS Number	104713-75-9 ;
PubChem CID	443869;
ChemSpider	391959 ;
UNII	2VBY96ASWJ;
ChEMBL	ChEMBL2103761 ;
CompTox Dashboard (EPA)	DTXSID20909147 ;
Chemical and physical data
Formula	C27H29N3O6
Molar mass	491.544 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-][N+](=O)c1cccc(c1)[C@H]4C(/C(=O)OC)=C(\N\C(=C4\C(=O)O[C@H]3CCN(Cc2ccccc2)C3)C)C;
	InChI InChI=1S/C27H29N3O6/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/t22-,25-/m0/s1 ; Key:VXMOONUMYLCFJD-DHLKQENFSA-N ;
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Barnidipine (INN; also known as mepirodipine) is a calcium channel blocker which belongs to the dihydropyridine (DHP) group of calcium channel blockers. It is used in the treatment of hypertension.^[1]

Pharmacodynamics

Barnidipine is a pure S,S isomer, a lipophilic 1,4-dihydropyridine calcium channel blocker, which, like other compounds in the class, shows a high affinity for calcium channels, particularly the L-type slow channels of smooth muscle cells found in the vessel wall.^[2] Calcium channel blocking drugs have the characteristic of interfering with the flow of calcium ions into the interior of cells through the slow channels of the plasma membrane.

References

^ CID 443869 from PubChem
^ van Zwieten, PA. (1998). "Pharmacological profile of barnidipine: a single optical isomer dihydropyridine calcium antagonist". Blood Press Suppl. 1: 5–8. PMID 9660520.

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[1] CID 443869 from PubChem

[pmid_9660520-2] van Zwieten, PA. (1998). "Pharmacological profile of barnidipine: a single optical isomer dihydropyridine calcium antagonist". Blood Press Suppl. 1: 5–8. PMID 9660520.

[1]

[2]

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	C08CA12 (WHO)
Identifiers
IUPAC name 3-(3R)-1-Benzylpyrrolidin-3-yl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
CAS Number	104713-75-9^N
PubChem CID	443869
ChemSpider	391959^N
UNII	2VBY96ASWJ
ChEMBL	ChEMBL2103761^N
CompTox Dashboard (EPA)	DTXSID20909147
Chemical and physical data
Formula	C₂₇H₂₉N₃O₆
Molar mass	491.544 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [O-][N+](=O)c1cccc(c1)[C@H]4C(/C(=O)OC)=C(\N\C(=C4\C(=O)O[C@H]3CCN(Cc2ccccc2)C3)C)C
InChI InChI=1S/C27H29N3O6/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/t22-,25-/m0/s1^N Key:VXMOONUMYLCFJD-DHLKQENFSA-N^N
^NY (what is this?) (verify)