Nimodipine | BAY-E-9736 | CAS#66085-59-4 | Calcium Channel Blocker

MedKoo Cat#: 318367 | Name: Nimodipine

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Description:

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

Nimodipine is a dihydropyridine calcium channel blocker originally developed for the treatment of high blood pressure. It is not frequently used for this indication, but has shown good results in preventing a major complication of subarachnoid hemorrhage (a form of cerebral hemorrhage) termed vasospasm, which is now the main use of nimodipine.

Chemical Structure

Nimodipine

CAS#66085-59-4

Theoretical Analysis

MedKoo Cat#: 318367

Name: Nimodipine

CAS#: 66085-59-4

Chemical Formula: C21H26N2O7

Exact Mass: 418.1740

Molecular Weight: 418.44

Elemental Analysis: C, 60.28; H, 6.26; N, 6.69; O, 26.77

Price and Availability

Size	Price	Availability
500mg	USD 190.00	2 Weeks
1g	USD 350.00	2 Weeks
2g	USD 550.00	2 Weeks
5g	USD 950.00	2 Weeks
10g	USD 1,450.00	2 Weeks

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Synonym

Nimodipine, Nimotop, Periplum, BAY E 9736, BAY-E-9736, BAYE9736

IUPAC/Chemical Name

3-isopropyl 5-(2-methoxyethyl) 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

InChi Key

UIAGMCDKSXEBJQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H26N2O7/c1-12(2)30-21(25)18-14(4)22-13(3)17(20(24)29-10-9-28-5)19(18)15-7-6-8-16(11-15)23(26)27/h6-8,11-12,19,22H,9-10H2,1-5H3

SMILES Code

CC1=C(C(OCCOC)=O)C(C2=CC([N+]([O-])=O)=CC=C2)C(C(OC(C)C)=O)=C(C)N1

Appearance

Off-white to yellow 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:

Nimodipine is a dihydropyridine calcium channel blocker.

In vitro activity:

Nimodipine decreased both the peak amplitude and the integrated area of the AHP in an age- and concentration-dependent manner. At concentrations as low as 100 nM, nimodipine significantly reduced the AHP in aging CA1 neurons. In young CA1 neurons, nimodipine decreased the AHP only at 10 microM. Reference: J Neurophysiol. 1992 Dec;68(6):2100-9. https://pubmed.ncbi.nlm.nih.gov/1491260/

In vivo activity:

Cochlear perfusion of nimodipine resulted in reversible, dose-related suppression of the compound action potential of the auditory nerve (CAP; N1-P1), a prolongation of N1 latency at suprathreshold levels, an elevated CAP threshold, a decrease in N1 latency at a constant amplitude measured at CAP threshold, a reduction in cochlear microphonics (CM), and a reduction of the negative summating potential (SP) to a point where it became positive (i.e., a reversal of SP). Reference: Hear Res. 1990 Jul;46(3):277-87. https://pubmed.ncbi.nlm.nih.gov/2168361/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	71.69
	DMF:PBS (pH 7.2) (1:4)	0.2	0.48
	DMSO	62.7	149.87
	Ethanol	43.0	102.76

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 418.44 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. Moyer JR Jr, Thompson LT, Black JP, Disterhoft JF. Nimodipine increases excitability of rabbit CA1 pyramidal neurons in an age- and concentration-dependent manner. J Neurophysiol. 1992 Dec;68(6):2100-9. doi: 10.1152/jn.1992.68.6.2100. PMID: 1491260. 2. Honn KV, Onoda JM, Diglio CA, Carufel MM, Taylor JD, Sloane BF. Inhibition of tumor cell-platelet interactions and tumor metastasis by the calcium channel blocker, nimodipine. Clin Exp Metastasis. 1984 Jan-Mar;2(1):61-72. doi: 10.1007/BF00132307. PMID: 6543691. 3. Kuzmin A, Zvartau E, Gessa GL, Martellotta MC, Fratta W. Calcium antagonists isradipine and nimodipine suppress cocaine and morphine intravenous self-administration in drug-naive mice. Pharmacol Biochem Behav. 1992 Mar;41(3):497-500. doi: 10.1016/0091-3057(92)90363-k. PMID: 1533936. 4. Bobbin RP, Jastreboff PJ, Fallon M, Littman T. Nimodipine, an L-channel Ca2+ antagonist, reverses the negative summating potential recorded from the guinea pig cochlea. Hear Res. 1990 Jul;46(3):277-87. doi: 10.1016/0378-5955(90)90009-e. PMID: 2168361.

In vitro protocol:

In vivo protocol:

1. Kuzmin A, Zvartau E, Gessa GL, Martellotta MC, Fratta W. Calcium antagonists isradipine and nimodipine suppress cocaine and morphine intravenous self-administration in drug-naive mice. Pharmacol Biochem Behav. 1992 Mar;41(3):497-500. doi: 10.1016/0091-3057(92)90363-k. PMID: 1533936. 2. Bobbin RP, Jastreboff PJ, Fallon M, Littman T. Nimodipine, an L-channel Ca2+ antagonist, reverses the negative summating potential recorded from the guinea pig cochlea. Hear Res. 1990 Jul;46(3):277-87. doi: 10.1016/0378-5955(90)90009-e. PMID: 2168361.

1: Monzani D, Genovese E, Pini LA, Di Berardino F, Alicandri Ciufelli M, Galeazzi GM, Presutti L. Nimodipine in otolaryngology: from past evidence to clinical perspectives. Acta Otorhinolaryngol Ital. 2015 Jun;35(3):135-45. Review. PubMed PMID: 26246657; PubMed Central PMCID: PMC4510937. 2: Etminan N, Macdonald RL, Davis C, Burton K, Steiger HJ, Hänggi D. Intrathecal application of the nimodipine slow-release microparticle system eg-1962 for prevention of delayed cerebral ischemia and improvement of outcome after aneurysmal subarachnoid hemorrhage. Acta Neurochir Suppl. 2015;120:281-6. doi: 10.1007/978-3-319-04981-6_47. Review. PubMed PMID: 25366637. 3: Vergouwen MD, Vermeulen M, Roos YB. Effect of nimodipine on outcome in patients with traumatic subarachnoid haemorrhage: a systematic review. Lancet Neurol. 2006 Dec;5(12):1029-32. Review. PubMed PMID: 17110283. 4: Brown G, Carley S. Best evidence topic reports. Does nimodipine reduce mortality and secondary ischaemic events after subarachnoid haemorrhage? Emerg Med J. 2004 May;21(3):333. Review. PubMed PMID: 15107373; PubMed Central PMCID: PMC1726351. 5: Fritze J, Walden J. Clinical findings with nimodipine in dementia: test of the calcium hypothesis. J Neural Transm Suppl. 1995;46:439-53. Review. PubMed PMID: 8821080. 6: Mück W, Bode H. Bioanalytics of nimodipine--an overview of methods. Pharmazie. 1994 Feb-Mar;49(2-3):130-9. Review. PubMed PMID: 8171077. 7: Grobe-Einsler R. Clinical aspects of nimodipine. Clin Neuropharmacol. 1993;16 Suppl 1:S39-45. Review. PubMed PMID: 8519001. 8: de Jonge MC, Traber J. Nimodipine: cognition, aging, and degeneration. Clin Neuropharmacol. 1993;16 Suppl 1:S25-30. Review. PubMed PMID: 8518999. 9: Nimodipine for delayed cerebral ischaemia after subarachnoid haemorrhage. Drug Ther Bull. 1992 Oct 12;30(21):81-3. Review. PubMed PMID: 1425221. 10: Korolkovas A, Pancotti SL. [Nimodipine, a calcium antagonist with preferential cerebrovascular activity]. Arq Bras Cardiol. 1992 Jun;58(6):491-6. Review. Portuguese. PubMed PMID: 1340731. 11: Ernst E. Treating ischemic stroke: is nimodipine the answer? Clin Pharm. 1992 Apr;11(4):350-1. Review. PubMed PMID: 1563232. 12: Izquierdo I. Nimodipine and the recovery of memory. Trends Pharmacol Sci. 1990 Aug;11(8):309-10. Review. PubMed PMID: 2203191. 13: Adnet P, Moinardeau V, Riegel B, Lejeune JP, Fesard F, Debout J, Krivosic-Horber R. [Intravascular volume expansion and intravenous nimodipine in the treatment of cerebral vasospasm after surgical treatment of intracranial aneurysm]. Agressologie. 1990 Jun;31(6):385-8. Review. French. PubMed PMID: 2285112. 14: Bär PR, Traber J, Schuurman T, Gispen WH. CNS and PNS effects of nimodipine. J Neural Transm Suppl. 1990;31:55-71. Review. PubMed PMID: 2074438. 15: DiPalma JR. Nimodipine in subarachnoid hemorrhage. Am Fam Physician. 1989 Dec;40(6):143-5. Review. PubMed PMID: 2686374. 16: Hakim AM, Evans AC, Berger L, Kuwabara H, Worsley K, Marchal G, Biel C, Pokrupa R, Diksic M, Meyer E, et al. The effect of nimodipine on the evolution of human cerebral infarction studied by PET. J Cereb Blood Flow Metab. 1989 Aug;9(4):523-34. Review. PubMed PMID: 2661584. 17: Langley MS, Sorkin EM. Nimodipine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in cerebrovascular disease. Drugs. 1989 May;37(5):669-99. Review. PubMed PMID: 2663415. 18: Scriabine A, Schuurman T, Traber J. Pharmacological basis for the use of nimodipine in central nervous system disorders. FASEB J. 1989 May;3(7):1799-806. Review. PubMed PMID: 2565839. 19: Gilsbach JM. Nimodipine in the prevention of ischaemic deficits after aneurysmal subarachnoid haemorrhage. An analysis of recent clinical studies. Acta Neurochir Suppl (Wien). 1988;45:41-50. Review. PubMed PMID: 3066141. 20: Harders A, Gilsbach J. Haemodynamic effectiveness of nimodipine on spastic brain vessels after subarachnoid haemorrhage evaluated by the transcranial Doppler method. A review of clinical studies. Acta Neurochir Suppl (Wien). 1988;45:21-8. Review. PubMed PMID: 3066139.