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MW 418.4 Da, Purity >98%. L-type Ca2+ channel blocker. Potent cerebrovasodilator. Cognitive enhancer. More lipophilic than nifedipine (ab120135).

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Images

Chemical Structure - Nimodipine, L-type Ca2+ channel blocker (AB120138), expandable thumbnail
  • Functional Studies - Nimodipine, L-type Ca2+ channel blocker (AB120138), expandable thumbnail

Publications

Key facts

CAS number
66085-59-4
Purity
> 98%
Form
Solid
Molecular weight
418.4 Da
Molecular formula
C21H26N2O7
PubChem identifier
4497
Nature
Synthetic

Target data

Alternative names

(R)-limonene 6-monooxygenase, (S)-limonene 6-monooxygenase, (S)-limonene 7-monooxygenase, 1,8-cineole 2-exo-monooxygenase, 2700049B16Rik, 3110031N04Rik, A3AR, A3R, AA3R_HUMAN, ABC member 16, MDR/TAP subfamily, ABC16, ABCB1, ABCBB_HUMAN, AD 026, ADORA 3, AI838772, AIS, ANDR_HUMAN, ANKTM 1, AR, AR JP, AR8, ARA3, ATP binding cassette sub family B (MDR/TAP) member 11, ATP-binding cassette sub-family B member 11, AW493413, Adenosine A3 receptor, Adenosine receptor A3, Albendazole monooxygenase, Albendazole sulfoxidase, Androgen nuclear receptor variant 2, Androgen receptor, Androgen receptor (dihydrotestosterone receptor; testicular feminization; spinal and bulbar muscular atrophy; Kennedy disease), Ankyrin-like with transmembrane domains protein 1, Arachidonic acid epoxygenase, Aryl hydrocarbon hydroxylase, BAR, BK channel, BK channel beta subunit, BK channel subunit beta-1, BK channel subunit beta-2, BK channel subunit beta-4, BKCA alpha, BKCA alpha subunit, BKTM, BKbeta, BKbeta1, BKbeta2, BKbeta4, BRIC2, BXR, Bile acid receptor, Bile salt export pump, Bsep, CAC1C_HUMAN, CACH 2, CACN 2, CACNL1A1, CANN6, CAPC, CB-R, CB1, CB1A, CB1K5, CB1R, CCHL1A1, CNR, CNR1_HUMAN, CP 12, CP1A2_HUMAN, CP2C9_HUMAN, CP2J2_HUMAN, CP33, CP34, CP3A4_HUMAN, CPC12, CPC8, CPC9, CPCJ, CPJ2, CYP1A2, CYP2C, CYP2C10, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIA2, CYPIIC9, CYPIIIA3, CYPIIIA4, CYPIIJ2, CaV1.2, Calcium activated potassium channel beta 4 subunit, Calcium activated potassium channel subfamily M subunit beta 1, Calcium activated potassium channel subfamily M subunit beta 2, Calcium activated potassium channel subfamily M subunit beta 4, Calcium channel, Calcium channel L type alpha 1 polypeptide isoform 1 cardiac muscle, Calcium channel cardic dihydropyridine sensitive alpha 1 subunit, Calcium channel voltage dependent L type alpha 1C subunit, Calcium-activated potassium channel, Calcium-activated potassium channel subunit alpha-1, Calcium-activated potassium channel subunit beta, Calcium-activated potassium channel subunit beta-1, Calcium-activated potassium channel subunit beta-2, Calcium-activated potassium channel subunit beta-4, Cannabinoid receptor 1, Central cannabinoid receptor, Charybdotoxin receptor subunit beta-1, Charybdotoxin receptor subunit beta-2, Charybdotoxin receptor subunit beta-4, Cytochrome P(3)450, Cytochrome P-450MP, Cytochrome P450 1A2, Cytochrome P450 2C9, Cytochrome P450 2J2, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 4, Cytochrome P450 HLp, Cytochrome P450 MP-4, Cytochrome P450 MP-8, Cytochrome P450 NF-25, Cytochrome P450 PB-1, Cytochrome P450 family 1 polypeptide 2, Cytochrome P450 family 1 subfamily A polypeptide 2, Cytochrome P450 family 2 subfamily J polypeptide 2, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily I aromatic compound inducible polypeptide 2, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450 subfamily IIJ (arachidonic acid epoxygenase) polypeptide 2, Cytochrome P450 subfamily IIJ polypeptide 2, Cytochrome P450, family 2, subfamily C, polypeptide 9, Cytochrome P450-P3, Cytochrome P450-PCN1, Cytokeratin-associated protein in cancer, DHPR alpha 1, DHPR alpha 1 subunit, DHTR, Dihydro testosterone receptor, Dihydrotestosterone receptor (DHTR), Dioxin inducable P3 450, Drosophila slowpoke like, E3 ubiquitin ligase, E3 ubiquitin-protein ligase parkin, ERR a, ERR-alpha, ERR1 protein, ERR1_HUMAN, ESRL 1, ESRR A, Estrogen receptor related 1, Estrogen receptor-like 1, Estrogen-related receptor alpha, Estrra, FLJ11090, FRA6E, Farnesoid X-activated receptor, Farnesol receptor HRR-1, GPCR 2, Glucocorticoid inducible P450, HLP, HRR 1, HUMARA, HYSP1, Hbeta1, Hbeta2, Hbeta3, Hbeta4, K(VCA)alpha, K(VCA)beta, K(VCA)beta-1, K(VCA)beta-2, K(VCA)beta-4, KCMA1_HUMAN, KCMB1_HUMAN, KCMB2_HUMAN, KCMB4_HUMAN, KCNMA, KCNMA1, KCNMB 1, KCNMB 2, KCa1.1, KD, Kennedy disease (KD), L type, LPRS 2, LQT8, LRC26_HUMAN, Large conductance Ca2+ activated K+ channel beta 1 subunit, Large conductance Ca2+ activated K+ channel beta2 subunit, Large conductance calcium activated potassium channel beta 2 subunit, Large conductance calcium dependent potassium ion channel beta 4 subunit, Leucine-rich repeat-containing protein 26, Lrrc26, MGC104252, MGC112732, MGC126680, MGC149605, MGC22431, MGC57945, MGC88320, Maxi K channel, Maxi K channel beta subunit, Maxi K channel subunit beta-1, Maxi K channel subunit beta-2, Maxi K channel subunit beta-4, Maxi Potassium channel alpha, MaxiK, MaxiK channel beta 2 subunit, Microsomal monooxygenase, NF 25, NR1I2_HUMAN, NR3B1, NR3C3, NR3C4, Nifedipine oxidase, Nuclear receptor subfamily 1 group I member 2, Nuclear receptor subfamily 3 group B member 1, Nuclear receptor subfamily 3 group C member 3, Nuclear receptor subfamily 3 group C member 4, Nuclear receptor subfamily 3 group C member 4 (NR3C4), ONR 1, OTTHUMP00000010550, OTTHUMP00000016838, OTTHUMP00000020135, OTTHUMP00000214579, OTTHUMP00000215173, OTTHUMP00000215174, OTTHUMP00000215175, Orphan nuclear receptor PAR 1, Orphan nuclear receptor PXR, P(3)450, P3 450, P450 4, P450 III steroid inducible, P450 MP, P450 P3, P450 PB 1, P450 PCN1, P450 form 4, P450(PA), P450, family III, P450C2C, P450C3, P450IIC19, P450IIC9, PAR, PAR q, PARK 2, PDJ, PFIC 2, PGR, PGY4, PR, PRA, PRB, PRGR_HUMAN, PRKN 2, PRKN2_HUMAN, PRR, Parkin 2, Parkinson disease (autosomal recessive juvenile) 2, Parkinson disease (autosomal recessive, juvenile) 2, parkin, Parkinson disease protein 2, Parkinson juvenile disease protein 2, Parkinson protein 2 E3 ubiquitin protein ligase, Parkinson protein 2, E3 ubiquitin protein ligase (parkin), Potassium large conductance calcium activated channel subfamily M beta member 1, Potassium large conductance calcium activated channel subfamily M beta member 2, Potassium large conductance calcium activated channel subfamily M beta member 4, Pregnane X receptor, Progesterone receptor, Progestin receptor form A, Progestin receptor form B, Quinine 3-monooxygenase, RIP 14, RP11 552M11.7, RP24-311F12.2, RXR-interacting protein 14, Retinoid X receptor-interacting protein 14, S-mephenytoin 4-hydroxylase, SAKCA, SBMA, SCAN1, SLO, SMAX1, SXR, Sister of P glycoprotein, Slo homolog, Slo-alpha, Slo-beta, Slo-beta-1, Slo-beta-2, Slo-beta-4, Slo1, Slowpoke homolog, Spgp, Spinal and bulbar muscular atrophy, Spinal and bulbar muscular atrophy (SBMA), Steroid and xenobiotic receptor, Steroid hormone receptor ERR1, TFM, TGPCR1, TRPA1_HUMAN, TS, TYDP, TYDP1_HUMAN, Taurochenodeoxycholate 6-alpha-hydroxylase, Testicular Feminization (TFM), Transformation-sensitive protein p120, Transient receptor potential cation channel subfamily A member 1, Tyr-DNA phosphodiesterase 1, Tyrosyl-DNA phosphodiesterase 1, Ubiquitin E3 ligase PRKN, Voltage dependent L type calcium channel alpha 1C subunit, Voltage gated L type calcium channel Cav1.2 alpha 1 subunit, splice variant 10*, Voltage gated calcium channel alpha subunit Cav1.2, Voltage-dependent L-type calcium channel subunit alpha-1C, Voltage-gated calcium channel subunit alpha Cav1.2, Xenobiotic monooxygenase, alpha-1 polypeptide, androgen receptor splice variant 4b, bA350O14.10, bA552M11.5, cardiac muscle, cytochrome P-450 S-mephenytoin 4-hydroxylase, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, cytokeratin-associated protein, estrogen receptor related receptor alpha, flavoprotein-linked monooxygenase, hERR1, hSlo, hslo beta, isoform 1, pregnane X nuclear receptor variant 2, progressive familial intrahepatic cholestasis 2, subfamily M subunit alpha-1, subfamily M subunit beta-1, subfamily M subunit beta-2, subfamily M subunit beta-4

Recommended products

MW 418.4 Da, Purity >98%. L-type Ca2+ channel blocker. Potent cerebrovasodilator. Cognitive enhancer. More lipophilic than nifedipine (ab120135).

Key facts

Purity
> 98%
PubChem identifier
4497
Solubility

Soluble in DMSO to 100 mM.

Soluble in ethanol to 10 mM.

Biochemical name
Nimodipine
Biological description

L-type Ca2+ channel blocker. Potent cerebrovasodilator. Cognitive enhancer. More lipophilic than nifedipine (ab120135).

Canonical SMILES
CC1=C(C(C(=C(N1)C)C(=O)OC(C)C)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)OCCOC
InChI
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
InChIKey
UIAGMCDKSXEBJQ-UHFFFAOYSA-N
IUPAC name
3-O-(2-methoxyethyl) 5-O-propan-2-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Storage

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
Ambient
Appropriate long-term storage conditions
Ambient
Storage information
The product can be stored for up to 12 months

Notes

Nimodipine is light sensitive and it is recommended that the compound is protected from light.

Supplementary info

This supplementary information is collated from multiple sources and compiled automatically.
Activity summary

Parkin also known as PARK2 is a protein with a mass of approximately 52 kDa. This protein functions as an E3 ubiquitin ligase and it is an important part of the ubiquitin-proteasome system which tags proteins for degradation. Parkin is expressed across several tissues with significant levels found in the brain particularly in dopaminergic neurons. The progesterone receptor weighing around 98 kDa binds progesterone and activates transcription of target genes. It is expressed in reproductive tissues like the uterus and breast. CACNA1C (Cav1.2) forms an L-type calcium channel subunit and weighs around 260 kDa. It is found in the heart and brain. Cannabinoid Receptor I known as CB1 weighing about 52 kDa is a G-protein coupled receptor highly expressed in the central nervous system.

Biological function summary

These targets show distinct roles in cellular functions. Parkin participates in mitochondrial quality control often forming a complex with PINK1 to mediate mitophagy. The progesterone receptor regulates genes involved in reproductive tissue development and maintenance. CACNA1C plays a pivotal role in calcium entry into cells influencing cardiac muscle contraction. Cannabinoid Receptor I inhibits adenylate cyclase affecting neurotransmitter release. Cytochrome P450 1A2 and 3A4/CYP3A4 perform important functions in drug metabolism. These enzymes contribute to the oxidative metabolism of a variety of substrates. Maxi Potassium channel alpha/SLO and its beta subunits like KCNMB1 affect neuron excitability by conducting potassium ions. TDP1 repairs DNA single-strand breaks. The adenosine A3 receptor influences anti-inflammatory pathways.

Pathways

Parkin and related proteins such as Ubiquitin C are involved in the ubiquitin-dependent catabolic pathway correlating with the autophagy process for cellular quality control. The progesterone receptor takes part in the steroid hormone signaling pathway working alongside estrogen receptors for gene expression control. The calcium signaling pathway includes CACNA1C and closely associates with other calcium channels like RyR2. Cannabinoid Receptor I aligns with the endocannabinoid signaling pathway. Cytochrome P450 isoenzymes CYP1A2 and CYP3A4 interact in the xenobiotic metabolism pathway involving substrates like drugs and carcinogens. Maxi potassium channel proteins regulate neural signaling pathways.

Associated diseases and disorders

Parkin mutations are implicated in autosomal recessive juvenile Parkinson's disease with PINK1 as a related protein. Mutations in the progesterone receptor can result in reproductive system disorders including certain breast cancers closely linked to estrogen receptor pathways. Variants in CACNA1C associate with disorders like Timothy syndrome which affects the heart and brain. Cannabinoid Receptor I disruption can influence neuropsychiatric conditions such as pharmacologically targeting this receptor impacts alleviation of symptoms in schizophrenia. Cytochrome P450 enzymes like CYP3A4 alterations can contribute to adverse drug reactions. Dysfunctions in the maxi potassium channels relate to epilepsy and other neural disorders with KCNMB1 being another contributing factor.

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2 product images

  • Chemical Structure - Nimodipine, L-type Ca2+ channel blocker (ab120138), expandable thumbnail

    Chemical Structure - Nimodipine, L-type Ca2+ channel blocker (ab120138)

    2D chemical structure image of ab120138, Nimodipine, L-type Ca2+ channel blocker

  • Functional Studies - Nimodipine, L-type Ca2+ channel blocker (ab120138), expandable thumbnail

    Functional Studies - Nimodipine, L-type Ca2+ channel blocker (ab120138)

    ab2770 staining aryl hydrocarbon receptor in MDA-MB-231 cells treated with nimodipine (ab120138), by ICC/IF. Increase in aryl hydrocarbon receptor expression correlates with increased concentration of nimodipine, as described in literature.
    The cells were incubated at 37°C for 6h in media containing different concentrations of ab120138 (nimodipine) in DMSO, fixed with 100% methanol for 5 minutes at -20°C and blocked with PBS containing 10% goat serum, 0.3 M glycine, 1% BSA and 0.1% tween for 2h at room temperature. Staining of the treated cells with ab2770 (1/100 dilution) was performed overnight at 4°C in PBS containing 1% BSA and 0.1% tween. A DyLight 488 goat anti-mouse polyclonal antibody (Goat Anti-Mouse IgG H&L (DyLight® 488) preadsorbed ab96879) at 1/250 dilution was used as the secondary antibody. Nuclei were counterstained with DAPI and are shown in blue.

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