Synonym
Nitrendipine, Bayotensin, Baypress, Nidrel, Deiten
IUPAC/Chemical Name
3-ethyl 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
InChi Key
PVHUJELLJLJGLN-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H20N2O6/c1-5-26-18(22)15-11(3)19-10(2)14(17(21)25-4)16(15)12-7-6-8-13(9-12)20(23)24/h6-9,16,19H,5H2,1-4H3
SMILES Code
CCOC(C1=C(C)NC(C)=C(C(OC)=O)C1C2=CC([N+]([O-])=O)=CC=C2)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Nitrendipine (BAY-E-5009), an analogue of Nifedipine (HY-B0284), is a dihydropyridine calcium channel blocker.
In vitro activity:
Using patch-clamp electrophysiology, the present study was designed to understand further the specific mechanism of interaction between nitrendipine and NMDA receptors. In these studies, nitrendipine reduced the frequency of openings and bursts, reduced the average duration of openings and bursts and reduced the single open time constant for the main conductance (48 pS) in a concentration (0.03-1 microM)- and voltage-dependent manner.
Reference: J Pharmacol Exp Ther. 1994 Oct;271(1):30-8. https://pubmed.ncbi.nlm.nih.gov/7965728/
In vivo activity:
At 3 weeks body weight was comparable, whereas systolic blood pressure was 157 +/- 9 mm Hg in nitrendipine-treated rats versus 191 +/- 10 mm Hg in controls (mean +/- SD, P < .00001). Fasting glucose was 6.8 +/- 2.7 mmol/L in nitrendipine-treated versus 8.9 +/- 1.5 mmol/L in control rats (P < .03). An intravenous glucose tolerance test (300 mg/kg) showed plasma glucose levels at 2, 5, 15, and 30 minutes to be significantly lower in the nitrendipine-treated group versus controls (two-way ANOVA, P < .03).
Reference: Hypertension. 1994 Jun;23(6 Pt 2):1051-3. https://pubmed.ncbi.nlm.nih.gov/8206592/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
30.0 |
83.25 |
|
| DMF:PBS (pH 7.2) (1:4) |
0.2 |
0.55 |
|
| DMSO |
49.0 |
135.97 |
|
| Ethanol |
2.0 |
5.55 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
360.36
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Skeen GA, White HS, Twyman RE. The dihydropyridine nitrendipine reduces N-methyl-D-aspartate (NMDA)-evoked currents of rodent cortical neurons through a direct interaction with the NMDA receptor-associated ion channel. J Pharmacol Exp Ther. 1994 Oct;271(1):30-8. PMID: 7965728.
2. Perry I, Buttrum SM, Nash GB. Effect of activation on adhesion of flowing neutrophils to cultured endothelium: time course and inhibition by a calcium channel blocker (nitrendipine). Br J Pharmacol. 1993 Dec;110(4):1630-4. doi: 10.1111/j.1476-5381.1993.tb14011.x. PMID: 7905773; PMCID: PMC2175889.
3. Aktay G, Emre MH, Polat A. Influence of dihydropyridine calcium antagonist nitrendipine on benzo(a)pyrene-induced oxidative stress. Arch Pharm Res. 2011 Jul;34(7):1171-5. doi: 10.1007/s12272-011-0715-x. Epub 2011 Aug 3. PMID: 21811924.
4. Bursztyn M, Raz I, Mekler J, Ben-Ishay D. Nitrendipine improves glucose tolerance and deoxyglucose uptake in hypertensive rats. Hypertension. 1994 Jun;23(6 Pt 2):1051-3. doi: 10.1161/01.hyp.23.6.1051. PMID: 8206592.
In vitro protocol:
1. Skeen GA, White HS, Twyman RE. The dihydropyridine nitrendipine reduces N-methyl-D-aspartate (NMDA)-evoked currents of rodent cortical neurons through a direct interaction with the NMDA receptor-associated ion channel. J Pharmacol Exp Ther. 1994 Oct;271(1):30-8. PMID: 7965728.
2. Perry I, Buttrum SM, Nash GB. Effect of activation on adhesion of flowing neutrophils to cultured endothelium: time course and inhibition by a calcium channel blocker (nitrendipine). Br J Pharmacol. 1993 Dec;110(4):1630-4. doi: 10.1111/j.1476-5381.1993.tb14011.x. PMID: 7905773; PMCID: PMC2175889.
In vivo protocol:
1. Aktay G, Emre MH, Polat A. Influence of dihydropyridine calcium antagonist nitrendipine on benzo(a)pyrene-induced oxidative stress. Arch Pharm Res. 2011 Jul;34(7):1171-5. doi: 10.1007/s12272-011-0715-x. Epub 2011 Aug 3. PMID: 21811924.
2. Bursztyn M, Raz I, Mekler J, Ben-Ishay D. Nitrendipine improves glucose tolerance and deoxyglucose uptake in hypertensive rats. Hypertension. 1994 Jun;23(6 Pt 2):1051-3. doi: 10.1161/01.hyp.23.6.1051. PMID: 8206592.
1: Siddiqui MA, Plosker GL. Fixed-dose combination enalapril/nitrendipine: a review of its use in mild-to-moderate hypertension. Drugs. 2004;64(10):1135-48. Review. PubMed PMID: 15139792.
2: Mancini M, Marotta T, Ferrara LA. Metabolic neutrality in nitrendipine therapy. J Cardiovasc Pharmacol. 1991;18 Suppl 1:S30-3. Review. PubMed PMID: 1723452.
3: Santiago TM, Lopez LM. Nitrendipine: a new dihydropyridine calcium-channel antagonist for the treatment of hypertension. DICP. 1990 Feb;24(2):167-75. Review. PubMed PMID: 2408259.
4: Hasegawa GR. Nicardipine, nitrendipine, and bepridil: new calcium antagonists for cardiovascular disorders. Clin Pharm. 1988 Feb;7(2):97-108. Review. PubMed PMID: 3280222.
5: Vanov SK, Pun EF, Taylor RJ. The safety of nitrendipine in the treatment of essential hypertension--a review of 61 clinical studies. Angiology. 1988 Jan;39(1 Pt 2):113-22. Review. PubMed PMID: 3277492.
6: Zanchetti A. Nitrendipine and ACE inhibitors. J Cardiovasc Pharmacol. 1988;12 Suppl 4:S80-5. Review. PubMed PMID: 2468881.
7: Hanbauer I, Sanna E. Presence in brain of an endogenous ligand for nitrendipine-binding sites that modulates Ca2+ channel activity. Ann N Y Acad Sci. 1988;522:96-105. Review. PubMed PMID: 2454061.
8: Ferrara LA, Marotta T. Nitrendipine and metabolic balance. J Cardiovasc Pharmacol. 1991;18 Suppl 5:S19-21. Review. PubMed PMID: 1725797.
9: Ruilope LM. Renal effects of nitrendipine. J Cardiovasc Pharmacol. 1991;18 Suppl 5:S10-3. Review. PubMed PMID: 1725795.
10: Byyny RL. Epidemiologic aspects of elderly hypertensive patients and the results of treatment with nitrendipine. J Cardiovasc Pharmacol. 1989;14 Suppl 10:S27-32; discussion S59-62. Review. PubMed PMID: 2483568.
11: Mac Carthy EP. Combination therapy of hypertension with beta-adrenoceptor blockers and the calcium channel antagonist nitrendipine. J Cardiovasc Pharmacol. 1988;12 Suppl 4:S76-9. Review. PubMed PMID: 2468880.
12: Eichelbaum M, Mikus G, Mast V, Fischer C, Kuhlmann U, Machleidt C. Pharmacokinetics and pharmacodynamics of nitrendipine in healthy subjects and patients with kidney and liver disease. J Cardiovasc Pharmacol. 1988;12 Suppl 4:S6-10. Review. PubMed PMID: 2468876.
13: Hulthén UL, Katzman PL. Review of long-term trials with nitrendipine. J Cardiovasc Pharmacol. 1988;12 Suppl 4:S11-5. Review. PubMed PMID: 2468850.
14: Kazda S, Hirth C, Stasch JP. Diuretic effect of nitrendipine contributes to its antihypertensive efficacy: a review. J Cardiovasc Pharmacol. 1988;12 Suppl 4:S1-5. Review. PubMed PMID: 2468846.
15: Goa KL, Sorkin EM. Nitrendipine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the treatment of hypertension. Drugs. 1987 Feb;33(2):123-55. Review. PubMed PMID: 3552592.
16: Trost BN, Weidmann P. Effects of nitrendipine and other calcium antagonists on glucose metabolism in man. J Cardiovasc Pharmacol. 1984;6 Suppl 7:S986-95. Review. PubMed PMID: 6085390.
