NP-MRD: Showing NP-Card for miconazole (NP0153933)

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Record Information

Version

2.0

Created at

2022-09-02 10:40:38 UTC

Updated at

2022-09-02 10:40:38 UTC

NP-MRD ID

NP0153933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

miconazole

Description

Miconazole, also known as monistat or oravig, belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene). Miconazole is a drug which is used for topical application in the treatment of tinea pedis (athlete’s foot), tinea cruris, and tinea corporis caused by trichophyton rubrum, trichophyton mentagrophytes, and epidermophyton floccosum, in the treatment of cutaneous candidiasis (moniliasis), and in the treatment of tinea versicolor. It is used for ring worm of the body, groin (jock itch), and feet (athlete's foot). Miconazole is a very strong basic compound (based on its pKa). Miconazole is a potentially toxic compound. In the UK, miconazole may be used to treat neonatal oral thrush, while the alternative nystatin is only licensed for patients over the age of one month, but drug interactions are possible. Miconazole is also used in Ektachrome film developing in the final rinse of the Kodak E-6 process and similar Fuji CR-56 process, replacing formaldehyde. Common side effects include itchiness or irritation of the area in which it was applied. miconazole is found in Micromonospora echinospora. Miconazole was patented in 1968 and approved for medical use in 1971.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -6.5586   -3.6523   -0.3012 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.1293   -2.6537   -0.0243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0480   -2.6960   -0.8750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8990   -1.9245   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355   -1.0757    0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6593   -0.2082    0.6836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620   -0.3181   -0.2261 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    0.5784    0.1582 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3720    1.6839   -0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3306    2.7189   -0.6919 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    2.8188   -1.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1509    3.9926   -0.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2468    4.5777    0.0931 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696    3.8258    0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6392   -0.2040    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3972   -0.3898   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185   -1.1815   -0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -1.8305    0.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4059   -2.8133   -0.0036 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2504   -1.6774    1.2672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1246   -0.8832    1.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2826   -0.6919    2.8165 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9083   -1.0215    1.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8321    0.0705    2.6237 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0549   -1.7992    1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0873   -3.3660   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0607   -1.9608   -1.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0571    0.8429    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3191   -0.5385    1.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1468    0.9639    1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    1.2249   -1.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6531    2.1452   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1309    2.1812   -1.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374    4.3818   -0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2387    4.0060    0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0517    0.1000   -1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0887   -1.2982   -1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851   -2.1827    2.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9002   -1.7457    1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 25  2  0
 25 23  1  0
 23 24  1  0
 23  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 21  2  0
 21 22  1  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 16  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
 14 10  1  0
 16 15  1  0
 25 39  1  0
  6 28  1  0
  6 29  1  0
  8 30  1  1
  9 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 20 38  1  0
 17 37  1  0
 16 36  1  0
  4 27  1  0
  3 26  1  0
M  END

1110
  Mrv0541 02231215152D          

 25 27  0  0  1  0            999 V2000
    3.7934   -0.6188    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -3.0938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    3.0938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3494    2.7133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2694    1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6043    1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5244    2.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    3.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    2.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 19  1  0  0  0  0
  3 21  1  0  0  0  0
  4 25  1  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
  6 15  1  0  0  0  0
  6 16  1  0  0  0  0
  7 16  2  0  0  0  0
  7 20  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 12  2  0  0  0  0
 10 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  2  0  0  0  0
 14 21  2  0  0  0  0
 14 22  1  0  0  0  0
 15 20  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
 21 23  1  0  0  0  0
 22 24  2  0  0  0  0
 23 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

> <INCHI_IDENTIFIER>
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

> <FORMULA>
C18H14Cl4N2O

> <MOLECULAR_WEIGHT>
416.129

> <EXACT_MASS>
413.986023908

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
39.54459918917317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
5.956368360333332

> <ALOGPS_LOGS>
-5.74

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.767291901565906

> <JCHEM_POLAR_SURFACE_AREA>
27.05

> <JCHEM_REFRACTIVITY>
103.06760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.63e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
miconazole

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1110                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       7.081  -1.155   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       9.748  -5.775   0.000  0.00  0.00          Cl+0
HETATM    3 Cl   UNK     0       8.415   5.775   0.000  0.00  0.00          Cl+0
HETATM    4 Cl   UNK     0       3.080   5.775   0.000  0.00  0.00          Cl+0
HETATM    5  O   UNK     0       8.415   1.155   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      11.082   2.695   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      11.852   5.065   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081   3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.836   3.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.328   3.600   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -3.465   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082  -3.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -4.235   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.312   5.065   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.081   5.005   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.747   2.695   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.747   5.775   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.414   3.465   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.414   5.005   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   19                                                            
CONECT    3   21                                                            
CONECT    4   25                                                            
CONECT    5    8   11                                                       
CONECT    6    9   15   16                                                  
CONECT    7   16   20                                                       
CONECT    8    5    9   10                                                  
CONECT    9    6    8                                                       
CONECT   10    8   12   13                                                  
CONECT   11    5   14                                                       
CONECT   12    1   10   17                                                  
CONECT   13   10   18                                                       
CONECT   14   11   21   22                                                  
CONECT   15    6   20                                                       
CONECT   16    6    7                                                       
CONECT   17   12   19                                                       
CONECT   18   13   19                                                       
CONECT   19    2   17   18                                                  
CONECT   20    7   15                                                       
CONECT   21    3   14   23                                                  
CONECT   22   14   24                                                       
CONECT   23   21   25                                                       
CONECT   24   22   25                                                       
CONECT   25    4   23   24                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
Monistat	Kegg
Oravig	Kegg
MCZ	HMDB
Dactarin	HMDB
Esteve brand OF miconazole	HMDB
Janssen-cilag brand OF miconazole	HMDB
Miconazole nitrate	HMDB
Johnston and johnston brand OF miconazole nitrate	HMDB
Miconazole esteve brand	HMDB
Janssen cilag brand OF miconazole	HMDB
Brentan	HMDB
Miconasil nitrate	HMDB
Miconazole janssen-cilag brand	HMDB
Nitrate, miconasil	HMDB
Nitrate, miconazole	HMDB
Miconazole	MeSH

Chemical Formula

C₁₈H₁₄Cl₄N₂O

Average Mass

416.1290 Da

Monoisotopic Mass

413.98602 Da

IUPAC Name

1-[2-(2,4-dichlorophenyl)-2-[(2,4-dichlorophenyl)methoxy]ethyl]-1H-imidazole

Traditional Name

miconazole

CAS Registry Number

Not Available

SMILES

ClC1=CC(Cl)=C(COC(CN2C=CN=C2)C2=C(Cl)C=C(Cl)C=C2)C=C1

InChI Identifier

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Micromonospora echinospora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzylethers

Direct Parent

Benzylethers

Alternative Parents

Substituents

Benzylether
1,3-dichlorobenzene
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
N-substituted imidazole
Imidazole
Azole
Heteroaromatic compound
Ether
Dialkyl ether
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:82892 )
ether (CHEBI:82892 )
dichlorobenzene (CHEBI:82892 )
a small molecule (CPD-4501 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.86	ALOGPS
logP	5.96	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	6.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.05 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.07 m³·mol⁻¹	ChemAxon
Polarizability	39.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon