Miconazole

Details

• Internal ID: d08e5832-e0aa-4dda-a488-cb6a4171bc4f
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Benzylethers
• IUPAC Name: 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole
• SMILES (Canonical): C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl
• SMILES (Isomeric): C1=CC(=C(C=C1Cl)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl
• InChI: InChI=1S/C18H14Cl4N2O/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/h1-8,11,18H,9-10H2
• InChI Key: BYBLEWFAAKGYCD-UHFFFAOYSA-N
• Popularity: 6,393 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₄Cl₄N₂O
• Molecular Weight: 416.10 g/mol
• Exact Mass: 415.983074 g/mol
• Topological Polar Surface Area (TPSA): 27.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 6.45
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• 22916-47-8
• Monistat
• Monistat IV
• Daktarin IV
• Miconazol
• Miconazolo
• Miconazolum
• Minostate
• 1-[2-(2,4-Dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole
• MJR 1762
• Miconazolum [INN-Latin]
• Vusion
• Monistat-Derm
• Oravig
• Florid(nitrate)
• 1-(2-((2,4-Dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
• Miconazol [INN-Spanish]
• NSC 170986
• Brentan
• R 18134
• CCRIS 7924
• 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]imidazole
• UNII-7NNO0D7S5M
• EINECS 245-324-5
• 7NNO0D7S5M
• MFCD00216019
• 1H-Imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-
• BRN 0965511
• DTXSID6023319
• 1-(2,4-Dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole
• 1H-Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-
• CHEMBL91
• Monistat (TN)
• R18134 nitrate
• DTXCID803319
• Dactarin
• CHEBI:82892
• Miconazole [USP:INN:BAN:JAN]
• 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl) imidazole
• Imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)-
• 22916-47-8 (free)
• Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-
• NSC170986
• NSC-170986
• MCZ
• Miconazolo [DCIT]
• NCGC00016770-01
• Micozole
• Zimycan
• Miconazol (INN-Spanish)
• Miconazolum (INN-Latin)
• imidazole, 1-(2,4-dichloro-beta-((2,4-dichlorobenzyl)oxy) phenethyl)-
• Femizol-M
• Miconazole-7
• MICONAZOLE (MART.)
• MICONAZOLE [MART.]
• Monazole 7
• 1-[2-(2,4-dichlorophenyl)-2-{[(2,4-dichlorophenyl)methyl]oxy}ethyl]-1H-imidazole
• 1H-imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl) methoxy)ethyl)-
• MICONAZOLE (EP IMPURITY)
• MICONAZOLE [EP IMPURITY]
• C18H14Cl4N2O
• MICONAZOLE (EP MONOGRAPH)
• MICONAZOLE (USP IMPURITY)
• MICONAZOLE [EP MONOGRAPH]
• MICONAZOLE [USP IMPURITY]
• Miconazole (USP:INN:BAN:JAN)
• MICONAZOLE (USP MONOGRAPH)
• MICONAZOLE [USP MONOGRAPH]
• Aflorix(nitrate)
• 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
• 1-[2-[(2,4-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
• Albistat(nitrate)
• Andergin(nitrate)
• Conofite(nitrate)
• (+/-)-1-(2,4-DICHLORO-B-((2,4-DICHLOROBENZYL)OXY)PHENETHYL)IMIDAZOLE
• (+/-)-Miconazole nitrate salt
• 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-1h-imidazole
• imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl) methoxy)ethyl)- (9CI)
• Monista (nitrate)
• 1H-IMIDAZOLE, 1-2-((2,4-DICHLOROPHENYL)-2-((2,4-DICHLOROPHENYL))METHOXY)ETHYL)-, (+/-)-
• Micantin (nitrate)
• (+-)-Miconazole
• Novo-Miconazole Vaginal Ovules
• Gyno-Daktar(nitrate)
• Lotrimin AF(nitrate)
• Epi-Monistat(nitrate)
• Monistat 7 Vaginal Suppositories
• Miconazole nitrate salt
• Zimybase
• rac-miconazole
• 1-(2,4-Dichloro-beta-[(2,4-dichlorobenzyl)oxy]phenethyl)imidazole
• SR-01000000271
• 1-(2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
• (RS)-miconazole
• 1-(2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl)-1H-imidazole
• 1-[2-(2,4-Dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole
• Prestwick_335
• Oravig (TN)
• Miconazole (Monistat)
• Spectrum_000965
• MICONAZOLE [MI]
• MICONAZOLE [INN]
• MICONAZOLE [JAN]
• Prestwick0_000067
• Prestwick1_000067
• Prestwick2_000067
• Prestwick3_000067
• Spectrum2_001048
• Spectrum3_000507
• Spectrum4_000061
• Spectrum5_001297
• MICONAZOLE [VANDF]
• bmse000924
• (+-)-1-(2,4-Dichloro-beta-((2,4-dichlorobenzyl)oxy)phenethyl)imidazole
• cid_4189
• SCHEMBL2866
• MICONAZOLE [WHO-DD]
• Oprea1_091955
• BSPBio_000253
• BSPBio_002033
• KBioGR_000581
• KBioSS_001445
• MLS002222203
• DivK1c_000156
• SPBio_000976
• SPBio_002174
• BPBio1_000279
• CHEBI:6923
• GTPL2449
• Miconazole (JP17/USP/INN)
• MICONAZOLE [ORANGE BOOK]
• SCHEMBL13934598
• BDBM31772
• KBio1_000156
• KBio2_001445
• KBio2_004013
• KBio2_006581
• KBio3_001533
• A01AB09
• A07AC01
• D01AC02
• G01AF04
• J02AB01
• S02AA13
• NINDS_000156
• HMS1568M15
• HMS2090B21
• HMS2095M15
• HMS2232B14
• HMS3374J10
• HMS3656E14
• HMS3712M15
• HY-B0454
• Tox21_110601
• DL-448
• s2536
• 1-(2,4-dichlorophenyl)-1-[(2,4-dichlorophenyl)methoxy]-2-imidazolylethane
• AKOS001574474
• AKOS016842489
• CCG-220067
• DB01110
• DS-1881
• 1H-Imidazole, 1-2-((2,4-dichlorophenyl)-2-((2,4-dichlorophenyl))methoxy)ethyl)-, (+-)-
• IDI1_000156
• NCGC00018294-02
• NCGC00018294-04
• NCGC00018294-06
• NCGC00018294-08
• NCI60_001353
• NCI60_001380
• SMR001307249
• SY107559
• SBI-0051448.P003
• CAS-22916-47-8
• AB00053500
• FT-0628942
• SW196614-4
• D00416
• R18134
• AB00053500-23
• AB00053500-24
• AB00053500-25
• AB00053500_26
• AB00053500_27
• AB00053500_28
• EN300-7370602
• A878389
• AE-641/01941016
• Q410534
• J-014898
• SR-01000000271-5
• BRD-A82396632-001-03-0
• BRD-A82396632-008-02-7
• 1-[2,4dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole
• 1-[2,4-Dichloro-beta-([2,4-dichlorobenzyl]oxy)-phenethyl]imidazole
• 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)-phenethyl]imidazole
• 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]-imidazole
• 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxy)phenethyl]imidazole
• Imidazole,4-dichloro-.beta.-[(2,4-dichlorobenzyl)oxy]phenethyl]-
• 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)-imidazol
• 1-[2,4-Dichloro-.beta.-[(2,4-dichlorobenzyl)oxy]phenethyl]imidazole
• 1-[2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole
• 1H-Imidazole,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-
• Imidazole, 1-(2,4-dichloro-.beta.-((2,4-dichlorobenzyl)oxy)phenethyl)-
• 1-((2RS)-2-(2,4-Dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
• 1-[2-(2,4-dichlorobenzyl)oxy-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid
• 1-[2-(2,4-Dichlorophenyl)-2-[(2,4-dichlorophenyl)-methoxy]ethyl]-1H-imidazole
• 1-[2-[(2,4-Dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole #
• imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl) methoxy)ethyl)-
• Imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,4-dichlorophenyl)methoxy)ethyl)- (9CI)
• rac-1-(2-(2,4-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole
• 75319-47-0
• Monistat, Daktarin IV, Miconazolo, Miconazolum, Dactarin, Miconazol, Minostate, Brentan, Florid(nitrate)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9900	99.00%
Caco-2	-	0.6702	67.02%
Blood Brain Barrier	+	0.6114	61.14%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8448	84.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9501	95.01%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.9000	90.00%
BSEP inhibitior	+	0.9606	96.06%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.7943	79.43%
CYP3A4 substrate	-	0.6614	66.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	+	0.8861	88.61%
CYP2C9 inhibition	+	0.9390	93.90%
CYP2C19 inhibition	+	0.9591	95.91%
CYP2D6 inhibition	+	0.9413	94.13%
CYP1A2 inhibition	+	0.9472	94.72%
CYP2C8 inhibition	+	0.9817	98.17%
CYP inhibitory promiscuity	+	0.9961	99.61%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7938	79.38%
Carcinogenicity (trinary)	Non-required	0.4617	46.17%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9862	98.62%
Skin irritation	-	0.8442	84.42%
Skin corrosion	-	0.9546	95.46%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9289	92.89%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.9342	93.42%
skin sensitisation	-	0.8665	86.65%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.6956	69.56%
Acute Oral Toxicity (c)	III	0.8025	80.25%
Estrogen receptor binding	+	0.9236	92.36%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.7545	75.45%
Glucocorticoid receptor binding	+	0.6960	69.60%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.7910	79.10%
Honey bee toxicity	-	0.8674	86.74%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.8700	87.00%
Fish aquatic toxicity	+	0.7609	76.09%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3522	P05093	Cytochrome P450 17A1	243 nM	Ki	via Super-PRED
CHEMBL1978	P11511	Cytochrome P450 19A1	600 nM	IC50	via Super-PRED
CHEMBL3849	Q16850	Cytochrome P450 51	200 nM	IC50	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	8.9 nM	Potency	via Super-PRED
CHEMBL1835	P24557	Thromboxane-A synthase	263 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.49%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	94.29%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.96%	86.33%
CHEMBL5896	O75164	Lysine-specific demethylase 4A	92.75%	99.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.51%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.51%	89.62%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	89.96%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.63%	94.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	88.14%	100.00%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	87.82%	86.00%
CHEMBL4208	P20618	Proteasome component C5	86.71%	90.00%
CHEMBL2721	P43005	Excitatory amino acid transporter 3	86.47%	93.50%
CHEMBL2581	P07339	Cathepsin D	85.34%	98.95%
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	85.10%	97.98%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.64%	86.92%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	83.73%	95.34%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	83.58%	97.23%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.32%	95.78%
CHEMBL2424504	P29375	Lysine-specific demethylase 5A	82.98%	99.23%
CHEMBL1929	P47989	Xanthine dehydrogenase	82.06%	96.12%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	82.03%	90.24%
CHEMBL4973	P43004	Excitatory amino acid transporter 2	81.61%	98.75%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.63%	93.10%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.10%	99.15%

Plants that contains it

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Cross-Links

• PubChem: 4189
• LOTUS: LTS0018211
• wikiData: Q410534