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MedKoo Cat#: 318366 | Name: Nilvadipine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nilvadipine is a calcium channel blocker (CCB) used for the treatment of hypertension and chronic major cerebral artery occlusion. Pathohistochemical studies have revealed that the volume of the infarction in the middle cerebral artery occlusion model could be decreased by nilvadipine. Nilvadipine has also been studied as a possible treatment for Alzheimer's Disease.

Chemical Structure

Nilvadipine
CAS#75530-68-6

Theoretical Analysis

MedKoo Cat#: 318366

Name: Nilvadipine

CAS#: 75530-68-6

Chemical Formula: C19H19N3O6

Exact Mass: 385.1274

Molecular Weight: 385.37

Elemental Analysis: C, 59.22; H, 4.97; N, 10.90; O, 24.91

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
1g USD 950.00 2 Weeks
5g USD 1,650.00 2 Weeks
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Related CAS #
No Data
Synonym
Nilvadipine, Escor, Nivadil, FR-34235, FK-235
IUPAC/Chemical Name
5-isopropyl 3-methyl 2-cyano-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
InChi Key
FAIIFDPAEUKBEP-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H19N3O6/c1-10(2)28-19(24)15-11(3)21-14(9-20)17(18(23)27-4)16(15)12-6-5-7-13(8-12)22(25)26/h5-8,10,16,21H,1-4H3
SMILES Code
CC1=C(C(OC(C)C)=O)C(C2=CC([N+]([O-])=O)=CC=C2)C(C(OC)=O)=C(C#N)N1
Appearance
Solid powder
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Nilvadipine is a potent calcium channel antagonist, and the IC50 value is around 0.1 nM.
In vitro activity:
The chemotactic activities of inflammatory cell products for rat aortic smooth muscle cells (SMC) were examined in modified Boyden chambers. The chemotaxis, irrespective of the attractants used, was strongly inhibited by nilvadipine, a potent calcium antagonist, and the IC50 values were around 1 x 10(-10) M. Reference: Atherosclerosis. 1988 Aug;72(2-3):213-9. https://pubmed.ncbi.nlm.nih.gov/2850808/
In vivo activity:
The antiatherogenic activity of FR34235 (Nilvadipine), a calcium antagonist, was examined in rabbits with carotid arteries sheathed with polyethylene cuffs, and compared with that of nifedipine, verapamil and diltiazem. FR34235 dose-dependently inhibited the cuff-induced intimal thickening, and was more potent than the other calcium antagonists, whose order of potency was nifedipine, diltiazem and verapamil. Reference: Atherosclerosis. 1987 Apr;64(2-3):255-61. https://pubmed.ncbi.nlm.nih.gov/3606723/
Solvent mg/mL mM comments
Solubility
DMF 30.0 77.85
DMSO 52.3 135.80
DMSO:PBS (pH 7.2) (1:10) 0.1 0.26
Ethanol 18.0 46.71
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 385.37 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.

Recalculate based on batch purity %
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. Iwasaki Y, Asai M, Yoshida M, Nigawara T, Kambayashi M, Oiso Y, Nakashima N. Nilvadipine inhibits nuclear factor-kappaB-dependent transcription in hepatic cells. Clin Chim Acta. 2004 Dec;350(1-2):151-7. doi: 10.1016/j.cccn.2004.07.012. PMID: 15530472. 2. Nomoto A, Mutoh S, Hagihara H, Yamaguchi I. Smooth muscle cell migration induced by inflammatory cell products and its inhibition by a potent calcium antagonist, nilvadipine. Atherosclerosis. 1988 Aug;72(2-3):213-9. doi: 10.1016/0021-9150(88)90083-4. PMID: 2850808. 3. Yamazaki H, Ohguro H, Maeda T, Maruyama I, Takano Y, Metoki T, Nakazawa M, Sawada H, Dezawa M. Preservation of retinal morphology and functions in royal college surgeons rat by nilvadipine, a Ca(2+) antagonist. Invest Ophthalmol Vis Sci. 2002 Apr;43(4):919-26. PMID: 11923229. 4. Nomoto A, Hirosumi J, Sekiguchi C, Mutoh S, Yamaguchi I, Aoki H. Antiatherogenic activity of FR34235 (Nilvadipine), a new potent calcium antagonist. Effect on cuff-induced intimal thickening of rabbit carotid artery. Atherosclerosis. 1987 Apr;64(2-3):255-61. doi: 10.1016/0021-9150(87)90253-x. PMID: 3606723.
In vitro protocol:
1. Iwasaki Y, Asai M, Yoshida M, Nigawara T, Kambayashi M, Oiso Y, Nakashima N. Nilvadipine inhibits nuclear factor-kappaB-dependent transcription in hepatic cells. Clin Chim Acta. 2004 Dec;350(1-2):151-7. doi: 10.1016/j.cccn.2004.07.012. PMID: 15530472. 2. Nomoto A, Mutoh S, Hagihara H, Yamaguchi I. Smooth muscle cell migration induced by inflammatory cell products and its inhibition by a potent calcium antagonist, nilvadipine. Atherosclerosis. 1988 Aug;72(2-3):213-9. doi: 10.1016/0021-9150(88)90083-4. PMID: 2850808.
In vivo protocol:
1. Yamazaki H, Ohguro H, Maeda T, Maruyama I, Takano Y, Metoki T, Nakazawa M, Sawada H, Dezawa M. Preservation of retinal morphology and functions in royal college surgeons rat by nilvadipine, a Ca(2+) antagonist. Invest Ophthalmol Vis Sci. 2002 Apr;43(4):919-26. PMID: 11923229. 2. Nomoto A, Hirosumi J, Sekiguchi C, Mutoh S, Yamaguchi I, Aoki H. Antiatherogenic activity of FR34235 (Nilvadipine), a new potent calcium antagonist. Effect on cuff-induced intimal thickening of rabbit carotid artery. Atherosclerosis. 1987 Apr;64(2-3):255-61. doi: 10.1016/0021-9150(87)90253-x. PMID: 3606723.
1: Lawlor B, Kennelly S, O'Dwyer S. Correction. NILVAD protocol: a European multicenter double-blind placebo-controlled trial of nilvadipine in mild-to-moderate Alzheimer's disease. BMJ Open. 2015 Sep 28;5(9):e006364. doi: 10.1136/bmjopen-2014-006364corr1. PubMed PMID: 26416510; PubMed Central PMCID: PMC4593160. 2: Lawlor B, Kennelly S, O'Dwyer S, Cregg F, Walsh C, Coen R, Kenny RA, Howard R, Murphy C, Adams J, Daly L, Segurado R, Gaynor S, Crawford F, Mullan M, Lucca U, Banzi R, Pasquier F, Breuilh L, Riepe M, Kalman J, Wallin A, Borjesson A, Molloy W, Tsolaki M, Olde Rikkert M. NILVAD protocol: a European multicentre double-blind placebo-controlled trial of nilvadipine in mild-to-moderate Alzheimer's disease. BMJ Open. 2014 Oct 9;4(10):e006364. doi: 10.1136/bmjopen-2014-006364. Erratum in: BMJ Open. 2015;5(9):e006364. PubMed PMID: 25300460; PubMed Central PMCID: PMC4194801. 3: Kuroki T, Mori A, Nakahara T, Sakamoto K, Ishii K. Histological protection by nilvadipine against neurotoxicity induced by NOC12, a nitric oxide donor, in the rat retina. Biol Pharm Bull. 2014;37(2):306-10. PubMed PMID: 24492726. 4: Nakazawa M, Suzuki Y, Ito T, Metoki T, Kudo T, Ohguro H. Long-term effects of nilvadipine against progression of the central visual field defect in retinitis pigmentosa: an extended study. Biomed Res Int. 2013;2013:585729. doi: 10.1155/2013/585729. Epub 2013 Nov 12. PubMed PMID: 24319686; PubMed Central PMCID: PMC3844269. 5: Kennelly S, Abdullah L, Kenny RA, Mathura V, Luis CA, Mouzon B, Crawford F, Mullan M, Lawlor B. Apolipoprotein E genotype-specific short-term cognitive benefits of treatment with the antihypertensive nilvadipine in Alzheimer's patients--an open-label trial. Int J Geriatr Psychiatry. 2012 Apr;27(4):415-22. doi: 10.1002/gps.2735. Epub 2011 May 10. PubMed PMID: 21560164. 6: Kennelly SP, Abdullah L, Paris D, Parish J, Mathura V, Mullan M, Crawford F, Lawlor BA, Kenny RA. Demonstration of safety in Alzheimer's patients for intervention with an anti-hypertensive drug Nilvadipine: results from a 6-week open label study. Int J Geriatr Psychiatry. 2011 Oct;26(10):1038-45. doi: 10.1002/gps.2638. Epub 2010 Oct 29. PubMed PMID: 21905098. 7: Sakai T, Sako K, Hayashi M. Factors affecting the absorption of nilvadipine from disintegration-controlled matrix tablet in dogs. Biol Pharm Bull. 2011;34(11):1731-6. PubMed PMID: 22040887. 8: Nakazawa M, Ohguro H, Takeuchi K, Miyagawa Y, Ito T, Metoki T. Effect of nilvadipine on central visual field in retinitis pigmentosa: a 30-month clinical trial. Ophthalmologica. 2011;225(2):120-6. doi: 10.1159/000320500. Epub 2010 Oct 16. PubMed PMID: 20948238. 9: Ishida S, Koto T, Nagai N, Oike Y. Calcium channel blocker nilvadipine, but not diltiazem, inhibits ocular inflammation in endotoxin-induced uveitis. Jpn J Ophthalmol. 2010 Nov;54(6):594-601. doi: 10.1007/s10384-010-0862-5. Epub 2010 Dec 30. PubMed PMID: 21191722. 10: Sato T, Hanyu H, Akai T, Takasaki A, Sakurai H, Iwamoto T. [A patient with early Alzheimer's disease who showed improvement of cognitive function and cerebral perfusion by combined therapy of nilvadipine and PPAR gamma agonists]. Nihon Ronen Igakkai Zasshi. 2008 Jul;45(4):428-33. Japanese. PubMed PMID: 18753719. 11: Dohmen W. [Investigation on the blood pressure-independent nephroprotective effect of nilvadipine in type 2 diabetics]. MMW Fortschr Med. 2008 Jan 17;149 Suppl 4:167-71. German. PubMed PMID: 18402242. 12: Haginaka J, Futagami A. Addition of N-carbobenzyloxy-L-tryptophan as a co-template molecule to molecularly imprinted polymer monoliths for (+)-nilvadipine. J Chromatogr A. 2008 Mar 28;1185(2):258-62. doi: 10.1016/j.chroma.2008.01.059. Epub 2008 Jan 31. PubMed PMID: 18262193. 13: Matsuda H, Araki N, Kuji I, Ohkubo T, Imabayashi E, Shimazu K. Effect of nilvadipine on regional cerebral blood flow in a patient with early Alzheimer disease. Clin Nucl Med. 2008 Jan;33(1):34-5. PubMed PMID: 18097255. 14: Takeuchi K, Nakazawa M, Mizukoshi S. Systemic administration of nilvadipine delays photoreceptor degeneration of heterozygous retinal degeneration slow (rds) mouse. Exp Eye Res. 2008 Jan;86(1):60-9. Epub 2007 Sep 22. PubMed PMID: 17976582. 15: Shinohara Y, Tohgi H, Hirai S, Terashi A, Fukuuchi Y, Yamaguchi T, Okudera T. Effect of the Ca antagonist nilvadipine on stroke occurrence or recurrence and extension of asymptomatic cerebral infarction in hypertensive patients with or without history of stroke (PICA Study). 1. Design and results at enrollment. Cerebrovasc Dis. 2007;24(2-3):202-9. Epub 2007 Jun 27. PubMed PMID: 17596689. 16: Hanyu H, Hirao K, Shimizu S, Iwamoto T, Koizumi K, Abe K. Favourable effects of nilvadipine on cognitive function and regional cerebral blood flow on SPECT in hypertensive patients with mild cognitive impairment. Nucl Med Commun. 2007 Apr;28(4):281-7. PubMed PMID: 17325591. 17: Sasaki T, Nakatani Y, Sugiyama K. The inhibitory effect of nilvadipine on calcium channels in retinal ganglion cells in goldfish. J Ocul Pharmacol Ther. 2006 Dec;22(6):455-9. PubMed PMID: 17238813. 18: Tanaka N, Imai K, Okimoto K, Ueda S, Tokunaga Y, Ohike A, Ibuki R, Higaki K, Kimura T. Development of novel sustained-release system, disintegration-controlled matrix tablet (DCMT) with solid dispersion granules of nilvadipine. J Control Release. 2005 Nov 28;108(2-3):386-95. Epub 2005 Oct 25. PubMed PMID: 16253377. 19: Himeda T, Kanbara S, Oki C, Kato H, Araki T. Effects of chronic administration with nilvadipine against immunohistochemical changes related to aging in the mouse hippocampus. Metab Brain Dis. 2005 Jun;20(2):141-53. PubMed PMID: 15938132. 20: Iwasaki Y, Asai M, Yoshida M, Nigawara T, Kambayashi M, Oiso Y, Nakashima N. Nilvadipine inhibits nuclear factor-kappaB-dependent transcription in hepatic cells. Clin Chim Acta. 2004 Dec;350(1-2):151-7. PubMed PMID: 15530472.