MW 479.1 Da, Purity >99%. Imidazole antifungal agent. Inhibits fungal membrane ergosterol biosynthesis. Increases reactive oxygen species production.
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- Toxicological sciences : an official journal of th 126:298-3052012Antifungal miconazole induces cardiotoxicity via inhibition of APE/Ref-1-related pathway in rat neonatal cardiomyocytes.Applications:Unspecified applicationReactive species:Unspecified reactive speciesKyung-Jong Won et. al.PubMed 22262564
- Veterinary dermatology 20:429-342010In vitro and in vivo evaluation of a potentiated miconazole aural solution in chronic Malassezia otitis externa in dogs.Applications:Unspecified applicationReactive species:Unspecified reactive speciesPatrick Hensel,Michaela Austel,Richard E Wooley,Deborah Keys,Branson W RitchiePubMed 20178480
- Life sciences 76:2091-1012005Effect of miconazole on intracellular Ca2+ levels and proliferation in human osteosarcoma cells.Applications:Unspecified applicationReactive species:Unspecified reactive speciesHong-Tai Chang,Wei-Chung Chen,Jin-Shyr Chen,Yih-Chau Lu,Shu-Shong Hsu,Jue-Long Wang,He-Hsiung Cheng,Jin-Shiung Cheng,Bang-Ping Jiann,An-Jen Chiang,Jong-Khing Huang,Chung-Ren JanPubMed 15826876
Key facts
- CAS number
22832-87-7
- Purity
> 99%
- Form
Solid
- Molecular weight
479.1 Da
- Molecular formula
C18H15Cl4N3O4
- PubChem identifier
68553
- Nature
Synthetic
Alternative names
1,8-cineole 2-exo-monooxygenase, 2700049B16Rik, 3110031N04Rik, AI838772, AW493413, Albendazole monooxygenase, Albendazole sulfoxidase, BAZ2B_HUMAN, 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, Bromodomain adjacent to zinc finger domain 2B, Bromodomain adjacent to zinc finger domain protein 2B, CAPC, CP33, CP34, CP3A4_HUMAN, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIIIA3, CYPIIIA4, 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-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, Charybdotoxin receptor subunit beta-1, Charybdotoxin receptor subunit beta-2, Charybdotoxin receptor subunit beta-4, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 HLp, Cytochrome P450 NF-25, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450-PCN1, Cytokeratin-associated protein in cancer, Cytosolic NADP-isocitrate dehydrogenase, DKFZp434H071, DKFZp762I0516, DNA replication inhibitor, Drosophila slowpoke like, Epididymis luminal protein 216, Epididymis secretory protein Li 26, FLJ11090, FLJ45644, GEMI_HUMAN, GMNN, Geminin, Geminin DNA replication inhibitor, Glucocorticoid inducible P450, HEL-216, HEL-S-26, HLP, HS90A_HUMAN, HSP 84, HSP 86, HSP 90, HSP 90 b, HSP90A, HSP90AA1, HSP90AB1, HSPC1, HSPC2, HSPCAL1, HSPCAL4, Hbeta1, Hbeta2, Hbeta3, Hbeta4, Heat shock 86 kDa, Heat shock protein 90kDa alpha cytosolic class A member 1, Heat shock protein 90kDa alpha cytosolic class B member 1, Heat shock protein HSP 90-alpha, Heat shock protein HSP 90-beta, ICDH, IDCD, IDH, IDH1, IDHC_HUMAN, IDP, IDPC, IMD42, Isocitrate dehydrogenase (NADP(+)) 1 cytosolic, Isocitrate dehydrogenase 1 (NADP+) soluble, Isocitrate dehydrogenase [NADP] cytoplasmic, 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, 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, MGC129539, MGC22431, MGC57945, 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, NADP dependent isocitrate dehydrogenase cytosolic, NADP dependent isocitrate dehydrogenase peroxisomal, NADP(+)-specific ICDH, NF 25, NR1F3, Nifedipine oxidase, Nuclear receptor ROR-gamma, Nuclear receptor RZR-gamma, Nuclear receptor subfamily 1 group F member 3, OTTHUMP00000039393, OTTHUMP00000162897, OTTHUMP00000162898, Oxalosuccinate decarboxylase, P450 III steroid inducible, P450 PCN1, P450, family III, P450C3, PICD, 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, Quinine 3-monooxygenase, RAR related orphan nuclear receptor variant 2, RAR related orphan receptor C, isoform a, RAR related orphan receptor gamma, RAR-related orphan receptor C, RORG_HUMAN, RP24-311F12.2, RP3 369A17.3, RZR GAMMA, RZRG, Renal carcinoma antigen NY-REN-38, Retinoic acid binding receptor gamma, Retinoid-related orphan receptor-gamma, Rorc, SAKCA, SCAN1, SLO, Slo homolog, Slo-alpha, Slo-beta, Slo-beta-1, Slo-beta-2, Slo-beta-4, Slo1, Slowpoke homolog, TOR, TYDP, TYDP1_HUMAN, Taurochenodeoxycholate 6-alpha-hydroxylase, Tyr-DNA phosphodiesterase 1, Tyrosyl-DNA phosphodiesterase 1, WALp4, bA350O14.10, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, cytokeratin-associated protein, hSlo, hWALp4, hslo beta, subfamily M subunit alpha-1, subfamily M subunit beta-1, subfamily M subunit beta-2, subfamily M subunit beta-4
Recommended products
MW 479.1 Da, Purity >99%. Imidazole antifungal agent. Inhibits fungal membrane ergosterol biosynthesis. Increases reactive oxygen species production.
Alternative names
1,8-cineole 2-exo-monooxygenase, 2700049B16Rik, 3110031N04Rik, AI838772, AW493413, Albendazole monooxygenase, Albendazole sulfoxidase, BAZ2B_HUMAN, 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, Bromodomain adjacent to zinc finger domain 2B, Bromodomain adjacent to zinc finger domain protein 2B, CAPC, CP33, CP34, CP3A4_HUMAN, CYP3, CYP3A, CYP3A3, CYP3A4, CYPIIIA3, CYPIIIA4, 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-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, Charybdotoxin receptor subunit beta-1, Charybdotoxin receptor subunit beta-2, Charybdotoxin receptor subunit beta-4, Cytochrome P450 3A3, Cytochrome P450 3A4, Cytochrome P450 HLp, Cytochrome P450 NF-25, Cytochrome P450 family 3 subfamily A polypeptide 4, Cytochrome P450 subfamily IIIA polypeptide 4, Cytochrome P450-PCN1, Cytokeratin-associated protein in cancer, Cytosolic NADP-isocitrate dehydrogenase, DKFZp434H071, DKFZp762I0516, DNA replication inhibitor, Drosophila slowpoke like, Epididymis luminal protein 216, Epididymis secretory protein Li 26, FLJ11090, FLJ45644, GEMI_HUMAN, GMNN, Geminin, Geminin DNA replication inhibitor, Glucocorticoid inducible P450, HEL-216, HEL-S-26, HLP, HS90A_HUMAN, HSP 84, HSP 86, HSP 90, HSP 90 b, HSP90A, HSP90AA1, HSP90AB1, HSPC1, HSPC2, HSPCAL1, HSPCAL4, Hbeta1, Hbeta2, Hbeta3, Hbeta4, Heat shock 86 kDa, Heat shock protein 90kDa alpha cytosolic class A member 1, Heat shock protein 90kDa alpha cytosolic class B member 1, Heat shock protein HSP 90-alpha, Heat shock protein HSP 90-beta, ICDH, IDCD, IDH, IDH1, IDHC_HUMAN, IDP, IDPC, IMD42, Isocitrate dehydrogenase (NADP(+)) 1 cytosolic, Isocitrate dehydrogenase 1 (NADP+) soluble, Isocitrate dehydrogenase [NADP] cytoplasmic, 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, 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, MGC129539, MGC22431, MGC57945, 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, NADP dependent isocitrate dehydrogenase cytosolic, NADP dependent isocitrate dehydrogenase peroxisomal, NADP(+)-specific ICDH, NF 25, NR1F3, Nifedipine oxidase, Nuclear receptor ROR-gamma, Nuclear receptor RZR-gamma, Nuclear receptor subfamily 1 group F member 3, OTTHUMP00000039393, OTTHUMP00000162897, OTTHUMP00000162898, Oxalosuccinate decarboxylase, P450 III steroid inducible, P450 PCN1, P450, family III, P450C3, PICD, 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, Quinine 3-monooxygenase, RAR related orphan nuclear receptor variant 2, RAR related orphan receptor C, isoform a, RAR related orphan receptor gamma, RAR-related orphan receptor C, RORG_HUMAN, RP24-311F12.2, RP3 369A17.3, RZR GAMMA, RZRG, Renal carcinoma antigen NY-REN-38, Retinoic acid binding receptor gamma, Retinoid-related orphan receptor-gamma, Rorc, SAKCA, SCAN1, SLO, Slo homolog, Slo-alpha, Slo-beta, Slo-beta-1, Slo-beta-2, Slo-beta-4, Slo1, Slowpoke homolog, TOR, TYDP, TYDP1_HUMAN, Taurochenodeoxycholate 6-alpha-hydroxylase, Tyr-DNA phosphodiesterase 1, Tyrosyl-DNA phosphodiesterase 1, WALp4, bA350O14.10, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 3, cytochrome P450, subfamily IIIA (niphedipine oxidase), polypeptide 4, cytokeratin-associated protein, hSlo, hWALp4, hslo beta, subfamily M subunit alpha-1, subfamily M subunit beta-1, subfamily M subunit beta-2, subfamily M subunit beta-4
Key facts
- CAS number
22832-87-7
- Purity
> 99%
- Form
Solid
- Molecular weight
479.1 Da
- Molecular formula
C18H15Cl4N3O4
- PubChem identifier
68553
- Nature
Synthetic
- Solubility
Soluble in DMSO to 100 mM. Soluble in ethanol to 10 mM.
- Biochemical name
Miconazole nitrate
- Biological description
Imidazole antifungal agent. Inhibits fungal membrane ergosterol biosynthesis. Increases reactive oxygen species production.
- Canonical SMILES
C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl.[N+](=O)(O)[O-]
- InChI
InChI=1S/C18H14Cl4N2O.HNO3/c19-13-2-1-12(16(21)7-13)10-25-18(9-24-6-5-23-11-24)15-4-3-14(20)8-17(15)22;2-1(3)4/h1-8,11,18H,9-10H2;(H,2,3,4)
- InChIKey
MCCACAIVAXEFAL-UHFFFAOYSA-N
- IUPAC name
1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole;nitric acid
Storage
- Shipped at conditions
Ambient - Can Ship with Ice
- Appropriate short-term storage conditions
Ambient
- Appropriate long-term storage conditions
Ambient
- Storage information
Store under desiccating conditions, The product can be stored for up to 12 months
Supplementary info
This supplementary information is collated from multiple sources and compiled automatically.
- Activity summary
Hsp90 is a molecular chaperone involved in protein folding and stabilization with an approximate mass of 90 kDa. It localizes in the cytoplasm and nucleus widely expressed in most tissues. Cytochrome P450 3A4 (CYP3A4) is an important enzyme in drug metabolism with a vital role in hepatic and intestinal detoxification processes. Maxi Potassium channels including alpha subunit SLO and beta subunits KCNMB1 KCNMB2 and KCNMB4 regulate membrane potential and electric excitability in smooth muscle and neurons. TDP1 is involved in DNA repair mechanisms while Geminin is critical for cell cycle regulation. Retinoic Acid Receptor-related Orphan Receptor gamma (ROR gamma) regulates immune responses and BAZ2B functions within chromatin remodeling. IDH1 participates in the Krebs cycle and LRRC26 modulates large-conductance potassium channels.
- Biological function summary
Hsp90 acts to stabilize many proteins required for cell growth and survival. It functions as part of a complex known as the Hsp90 chaperone machine. CYP3A4 metabolizes a wide range of substances affecting drug pharmacokinetics significantly. Maxi Potassium channels impact cellular excitability linking to neurotransmitter release and muscle contraction regulation. TDP1 repairs stalled topoisomerase I-DNA complexes contributing to genomic stability. Geminin inhibits DNA replication re-initiation during the cell cycle while ROR gamma influences T-cell differentiation. BAZ2B is essential in maintaining chromatin accessibility and IDH1 catalyzes the oxidative decarboxylation of isocitrate to alpha-ketoglutarate in cellular respiration. LRRC26 regulates potassium channel activity impacting smooth muscle tone.
- Pathways
Hsp90 supports various signal transduction pathways including heat shock response and protein kinase signaling. CYP3A4 plays a central role in the xenobiotic metabolism pathway interacting with proteins like NADPH-cytochrome P450 reductase. Maxi Potassium channels integrate into pathways controlling vascular tension and neuronal activity associating with proteins involved in calcium signaling. TDP1 participates in DNA repair pathways working alongside proteins like PARP1. Geminin blocks replication licensing within cell cycle control pathways. ROR gamma features prominently in immune cell signaling pathways interacting with cytokines. BAZ2B is part of the chromatin remodeling pathway while IDH1 finds itself in the TCA cycle linked with malate dehydrogenase. LRRC26 is involved in ion channel regulation pathways.
- Associated diseases and disorders
Hsp90 inhibitors are explored in cancer therapy due to their effects on oncogenic protein stability. CYP3A4 is implicated in drug interactions and toxicity issues impacting liver disease outcomes. Dysfunction in Maxi Potassium channels relates to cardiovascular diseases such as hypertension. TDP1 mutations cause neurodegenerative disorder spinocerebellar ataxia with axonal neuropathy. Geminin dysregulation associates with cancer progression especially in breast cancer often involving p53 pathways. ROR gamma contributes to autoimmune disease development including rheumatoid arthritis. BAZ2B alterations link to certain neurological disorders. IDH1 mutations often appear in gliomas affecting tumor metabolism. LRRC26 mutations can lead to auditory disorders by impacting potassium channel function in sensory hair cells.
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Chemical Structure - (±)-Miconazole nitrate, Imidazole antifungal agent (ab141195)
2D chemical structure image of ab141195, Miconazole nitrate, Imidazole antifungal agent
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