Synonym
Nisoldipine, Bay K 5552, Sular, Baymycard, Nisocor, Syscor
IUPAC/Chemical Name
3-isobutyl 5-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
InChi Key
VKQFCGNPDRICFG-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H24N2O6/c1-11(2)10-28-20(24)17-13(4)21-12(3)16(19(23)27-5)18(17)14-8-6-7-9-15(14)22(25)26/h6-9,11,18,21H,10H2,1-5H3
SMILES Code
CC1=C(C(C(=C(N1)C)C(=O)OCC(C)C)C2=CC=CC=C2[N+](=O)[O-])C(=O)OC
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:
Nisoldipine(BAY-k 5552; Sular) is a calcium channel blocker.
In vitro activity:
Nisoldipine inhibited I(Kr) with an IC(50) of 23 microM, and I(Ks) with an IC(50) of 40 microM. The drug also had weak inhibitory effects on inward- and outward-directed I(K1); the IC(50) determined for outward-directed current was 80 microM. Investigation of nisoldipine action on I(Ks) showed that inhibition occurred in the absence of previous pulsing, and with little change in the time courses of activation and deactivation.
Reference: Br J Pharmacol. 2003 Nov;140(5):863-70. https://pubmed.ncbi.nlm.nih.gov/14530219/
In vivo activity:
The corresponding pharmacokinetic parameters were applied to evaluate the effects of m-nisoldipine on the four CYP isoforms in vivo. In addition, RT-qPCR was performed to determine the effects of m-nisoldipine on the mRNA expression of CYPs in rat liver. Results indicated that high dose and middle dose of m-nisoldipine showed significant effects on all four CYPs and CYP2C11, respectively. Moreover, for CYP2D1 and CYP1A2, there were no significant effects found at either low or middle dose of m-nisoldipine.
Reference: Xenobiotica. 2018 Jul;48(7):676-683. https://pubmed.ncbi.nlm.nih.gov/28756727/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
30.0 |
77.24 |
|
| DMSO |
69.0 |
177.65 |
|
| DMSO:PBS (pH 7.2) (1:10) |
0.1 |
0.26 |
|
| Ethanol |
3.0 |
7.72 |
|
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
388.41
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. Chen X, Liu H, Pan Z, Miao Q, Zhang Y. The inhibitory effects of m-nisoldipine on the 5-hydroxytryptamine-induced proliferation of pulmonary artery smooth muscle cells via Ca2+ antagonism and antioxidant mechanisms. Eur J Pharmacol. 2012 Jul 5;686(1-3):32-40. doi: 10.1016/j.ejphar.2012.04.044. Epub 2012 May 2. PMID: 22575515.
2. Missan S, Zhabyeyev P, Dyachok O, Jones SE, McDonald TF. Block of cardiac delayed-rectifier and inward-rectifier K+ currents by nisoldipine. Br J Pharmacol. 2003 Nov;140(5):863-70. doi: 10.1038/sj.bjp.0705518. Epub 2003 Oct 6. PMID: 14530219; PMCID: PMC1574108.
3. Sun Y, Liu Y, Zhang X, Wan C, Lyu T, Zhang L. Effects of m-nisoldipine on the activity and mRNA expression of four CYP isozymes in rats. Xenobiotica. 2018 Jul;48(7):676-683. doi: 10.1080/00498254.2017.1358831. Epub 2017 Aug 4. PMID: 28756727.
4. Verma M, Bali A, Singh N, Jaggi AS. Investigating the role of nisoldipine in foot-shock-induced post-traumatic stress disorder in mice. Fundam Clin Pharmacol. 2016 Apr;30(2):128-36. doi: 10.1111/fcp.12174. Epub 2016 Jan 18. PMID: 26662718.
In vitro protocol:
1. Chen X, Liu H, Pan Z, Miao Q, Zhang Y. The inhibitory effects of m-nisoldipine on the 5-hydroxytryptamine-induced proliferation of pulmonary artery smooth muscle cells via Ca2+ antagonism and antioxidant mechanisms. Eur J Pharmacol. 2012 Jul 5;686(1-3):32-40. doi: 10.1016/j.ejphar.2012.04.044. Epub 2012 May 2. PMID: 22575515.
2. Missan S, Zhabyeyev P, Dyachok O, Jones SE, McDonald TF. Block of cardiac delayed-rectifier and inward-rectifier K+ currents by nisoldipine. Br J Pharmacol. 2003 Nov;140(5):863-70. doi: 10.1038/sj.bjp.0705518. Epub 2003 Oct 6. PMID: 14530219; PMCID: PMC1574108.
In vivo protocol:
1. Sun Y, Liu Y, Zhang X, Wan C, Lyu T, Zhang L. Effects of m-nisoldipine on the activity and mRNA expression of four CYP isozymes in rats. Xenobiotica. 2018 Jul;48(7):676-683. doi: 10.1080/00498254.2017.1358831. Epub 2017 Aug 4. PMID: 28756727.
2. Verma M, Bali A, Singh N, Jaggi AS. Investigating the role of nisoldipine in foot-shock-induced post-traumatic stress disorder in mice. Fundam Clin Pharmacol. 2016 Apr;30(2):128-36. doi: 10.1111/fcp.12174. Epub 2016 Jan 18. PMID: 26662718.
1: White WB. Pharmacologic agents in the management of hypertension--nisoldipine coat-core. J Clin Hypertens (Greenwich). 2007 Apr;9(4):259-66. Review. PubMed PMID: 17396068.
2: Hamilton SF, Houle LM, Thadani U. Rapid-release and coat-core formulations of nisoldipine in treatment of hypertension, angina, and heart failure. Heart Dis. 1999 Nov-Dec;1(5):279-88. Review. PubMed PMID: 11720635.
3: Heinig R. Clinical pharmacokinetics of nisoldipine coat-core. Clin Pharmacokinet. 1998 Sep;35(3):191-208. Review. Erratum in: Clin Pharmacokinet 1998 Nov;35(5):390. PubMed PMID: 9784933.
4: Opie LH. What does nisoldipine coat core (CC) add to current therapy that is clinically meaningful? Am J Cardiol. 1997 May 22;79(10A):29-32; discussion 47-8. Review. PubMed PMID: 9186064.
5: Langtry HD, Spencer CM. Nisoldipine coat-core. A review of its pharmacodynamic and pharmacokinetic properties and clinical efficacy in the management of ischaemic heart disease. Drugs. 1997 May;53(5):867-84. Review. PubMed PMID: 9129871.
6: Fodor JG. Nisoldipine CC: efficacy and tolerability in hypertension and ischemic heart disease. Cardiovasc Drugs Ther. 1997 Jan;10 Suppl 3:873-9. Review. PubMed PMID: 9126676.
7: Langan J, Rodríguez-Mañas L, Sareli P, Heinig R. Nisoldipine CC: clinical experience in hypertension. Cardiology. 1997;88 Suppl 1:56-62; discussion 63-5. Review. PubMed PMID: 9118169.
8: Lewis BS. Efficacy and safety of nisoldipine coat core in the management of angina pectoris, systemic hypertension, and ischemic ventricular dysfunction. Am J Cardiol. 1995 Apr 27;75(13):46E-53E. Review. PubMed PMID: 7726125.
9: Pouleur H, Rousseau MF. Nisoldipine in severe ischaemic left ventricular dysfunction. Eur Heart J. 1993 Jul;14 Suppl A:45-7. Review. PubMed PMID: 8370362.
10: Mitchell J, Frishman W, Heiman M. Nisoldipine: a new dihydropyridine calcium-channel blocker. J Clin Pharmacol. 1993 Jan;33(1):46-52. Review. PubMed PMID: 8429113.
11: Eber B, Schumacher M, Zweiker R, Pokan R, Klein W. [Nisoldipine in comparison with long-term nitrates]. Acta Med Austriaca. 1992;19(5):137-9. Review. German. PubMed PMID: 1298142.
12: Duncker DJ, Van Woerkens LJ, Serruys PW, Roelandt JR, Hugenholtz PG, Verdouw PD. Actions of nisoldipine in cardiovascular disease. Can J Cardiol. 1989 Jun-Aug;5(5):266-74. Review. PubMed PMID: 2667729.
13: Friedel HA, Sorkin EM. Nisoldipine. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the treatment of angina pectoris, hypertension and related cardiovascular disorders. Drugs. 1988 Dec;36(6):682-731. Review. PubMed PMID: 3065058.
14: Melcher A, Dens J, Curry P, Hagel H. Nisoldipine CC: clinical experience in ischaemic heart disease. Cardiology. 1997;88 Suppl 1:17-23; discussion 24-5. Review. PubMed PMID: 9118164.
15: Plosker GL, Faulds D. Nisoldipine coat-core. A review of its pharmacology and therapeutic efficacy in hypertension. Drugs. 1996 Aug;52(2):232-53. Review. PubMed PMID: 8841741.
16: Glasser SP. Nisoldipine coat core as concomitant therapy in chronic stable angina pectoris. Am J Cardiol. 1995 Apr 27;75(13):68E-70E. Review. PubMed PMID: 7726128.
17: Zannad F. Clinical pharmacology of nisoldipine coat core. Am J Cardiol. 1995 Apr 27;75(13):41E-45E. Review. PubMed PMID: 7726124.
18: Knorr AM. Why is nisoldipine a specific agent in ischemic left ventricular dysfunction? Am J Cardiol. 1995 Apr 27;75(13):36E-40E. Review. PubMed PMID: 7726122.
19: Krivonkin KIu, Belousov IuB. [Clinical pharmacology of nisoldipine, a new calcium antagonist]. Kardiologiia. 1991 Sep;31(9):100-5. Review. Russian. PubMed PMID: 1753601.
20: Knorr A. The pharmacology of nisoldipine. Cardiovasc Drugs Ther. 1987 Dec;1(4):393-402. Review. PubMed PMID: 3154674.
