1002. Barnidipine

Nomenclature

CAS number: 104713-75-9
(4S)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid methyl (3S)-1-(phenylmethyl)-3-pyrrolidinyl ester; (+)-(3′S,4S)-1-benzyl-3-pyrrolidinyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate; (3S)-1-benzyl-3-pyrrolidinyl methyl (4S)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate; mepirodipine.
C27H29N3O6; mol wt 491.54.
C 65.97%, H 5.95%, N 8.55%, O 19.53%.

Description and references

Dihydropyridine calcium channel blocker. Prepn (stereochemistry unspecified): T. Kojima, T. Takenaka, DE 2904552; eidem, US 4220649 (1979, 1980 both to Yamanouchi). Prepn and bioactivity of enantiomers: K. Tamazawa et al., J. Med. Chem. 29, 2504 (1986). GC-MS determn in plasma: T. Teramura et al., J. Chromatogr. 528, 191 (1990). Review of pharmacology and therapeutic efficacy: H. Satoh, Cardiovasc. Drug Rev. 9, 340-356 (1991).

Chemical structure

Properties

mp 137-139°. [α]D20 +64.8° (c = 1 in methanol).

Derivative

Hydrochloride.

Nomenclature

CAS number: 104757-53-1
YM-09730-5; Hypoca (Yamanouchi).
C27H29N3O6.HCl; mol wt 528.00.
C 61.42%, H 5.73%, N 7.96%, O 18.18%, Cl 6.71%.

Properties

mp 226-228°. [α]D20 +116.4° (c = 1 in methanol). Insol in water. LD50 orally in male, female rats: 105, 113 mg/kg (Satoh).

Therapeutic Category

Antihypertensive; antianginal.

Keywords

Antianginal; Antihypertensive; Dihydropyridine Derivatives; Calcium Channel Blocker; Dihydropyridine Derivatives