105979-17-7

105979-17-7 structure
105979-17-7 structure
  • Name: Benidipine
  • Chemical Name: 5-O-[(3R)-1-benzylpiperidin-3-yl] 3-O-methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  • CAS Number: 105979-17-7
  • Molecular Formula: C28H31N3O6
  • Molecular Weight: 505.56
  • Catalog: API Circulatory system medication Prevention and treatment of angina pectoris
  • Create Date: 2018-07-08 17:52:36
  • Modify Date: 2024-01-06 23:01:46
  • Benidipine is a potent and orally active calcium channel antagonist[1]. Benidipine shows anti-apoptosis effects in ischaemic/reperfused myocardial cells[2]. Benidipine increases the activity of endothelial cell-type nitric oxide synthase and improves coronary circulation in hypertensive rats[3].

Name 5-O-[(3R)-1-benzylpiperidin-3-yl] 3-O-methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Synonyms Benidipene
(+/-)-(R*)-3-[(R*)-1-benzyl-3-piperidyl] methyl-1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate hydrochloride
(3R)-1-Benzylpiperidin-3-yl methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl (3R)-1-(phenylmethyl)-3-piperidinyl ester, (4R)-
methyl (3R)-1-(phenylmethyl)piperidin-3-yl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
MFCD00906929
(3R)-1-Benzyl-3-piperidinyl methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro-3,5-pyridinedicarboxylate
Coniel
(R*,R*)-(±)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid Methyl 1-(Phenylmethyl)-3-piperidinyl Ester
Benidipine
H007
UNII:4G9T91JS7E
Description Benidipine is a potent and orally active calcium channel antagonist[1]. Benidipine shows anti-apoptosis effects in ischaemic/reperfused myocardial cells[2]. Benidipine increases the activity of endothelial cell-type nitric oxide synthase and improves coronary circulation in hypertensive rats[3].
Related Catalog
In Vivo Benidipine (3, 5, 10 µg/kg; i.v.) shows significant anti-apoptosis effects in a haemodynamically independent manner[2]. Benidipine (5 mg/kg; i.v.; every other day for 6 weeks) increases the activity of endothelial cell-type nitric oxide synthase (eNOS) and improves coronary circulation in hypertensive rats[3]. Benidipine (1, 3, 10 mg/kg; p.o.; once daily for 1 week) significant cardioprotective effects against ischemia-reperfusion injury[4]. Animal Model: Sham MI (myocardial ischaemia)/R (ischmia reperfused injury) rabbits and MI/R rabbits[2] Dosage: 3, 5, 10 µg/kg Administration: I.v. Result: Caused a significant decreased in HR ( heart rate), MABP (mean arterial blood pressure), PRI (pressure-rateindex) at 10 µg/kg, decreased apoptotic positive cells to7.4% at 3 µg/kg and not significantly different from that seen in the group treated with higher dose. Animal Model: Renovascular hypertensive rats (RHR)[3] Dosage: 5 mg/kg (dissolved in peanut oil) Administration: I.v.; every other day for 6 weeks Result: Significantly decreased the blood pressure and coronary vascular resistance index, but increased nitrite production and eNOS mRNA expression and significantly increased the coronary flow at rest, the capillary density. Animal Model: Rats (heart model (Langendorff perfusion))[4] Dosage: 1, 3, 10 mg/kg Administration: P.o.; once daily for 1 week Result: Significantly increased the post-ischemic recovery of LVDP and LV dP/dt max (LVDP: 87.5±10.1 vs 64.6±11.9%; LV dP/dt max: 97.8±10.4 vs 70.2±15.7%; p<0.05) at 3 mg/kg.
References

[1]. Yao K, et al. Pharmacological, pharmacokinetic, and clinical properties of benidipine hydrochloride, a novel, long-acting calcium channel blocker. J Pharmacol Sci. 2006 Apr;100(4):243-61.

[2]. Gao F, et al. Anti-apoptotic effect of benidipine, a long-lasting vasodilating calcium antagonist, in ischaemic/reperfused myocardial cells. Br J Pharmacol. 2001 Feb;132(4):869-78.

[3]. Kobayashi N, et al. Benidipine stimulates nitric oxide synthase and improves coronary circulation in hypertensive rats. Am J Hypertens. 1999 May;12(5):483-91.

[4]. Masanori S, et al. Orally administered benidipine and manidipine prevent ischemia-reperfusion injury in the rat heart. Circ J. 2004 Mar;68(3):241-6.

Density 1.3±0.1 g/cm3
Boiling Point 625.2±55.0 °C at 760 mmHg
Molecular Formula C28H31N3O6
Molecular Weight 505.56
Flash Point 331.9±31.5 °C
Exact Mass 505.221283
PSA 113.69000
LogP 4.92
Vapour Pressure 0.0±1.8 mmHg at 25°C
Index of Refraction 1.622
WGK Germany 3