KEGG   DRUG: Ketoconazole
Entry
D00351                      Drug                                   

Name
Ketoconazole (JP18/USP);
Nizoral (TN);
Xolegel (TN)
  Abbr
KTC
Product
  Generic
KETACONAZOLE (Mylan Pharmaceuticals), KETOCONAZOLE (A-S Medication Solutions), KETOCONAZOLE (A-S Medication Solutions), KETOCONAZOLE (A-S Medication Solutions), KETOCONAZOLE (A-S Medication Solutions), KETOCONAZOLE (A-S Medication Solutions), KETOCONAZOLE (A-S Medication Solutions), KETOCONAZOLE (A-S Medication Solutions), KETOCONAZOLE (Bryant Ranch Prepack), KETOCONAZOLE (Bryant Ranch Prepack), KETOCONAZOLE (Bryant Ranch Prepack), KETOCONAZOLE (Bryant Ranch Prepack), KETOCONAZOLE (Bryant Ranch Prepack), KETOCONAZOLE (Bryant Ranch Prepack), KETOCONAZOLE (Bryant Ranch Prepack), KETOCONAZOLE (Burel Pharmaceuticals), KETOCONAZOLE (DIRECT RX), KETOCONAZOLE (Direct Rx), KETOCONAZOLE (E. Fougera & Co. a division of Fougera Pharmaceuticals), KETOCONAZOLE (Golden State Medical Supply), KETOCONAZOLE (Golden State Medical Supply), KETOCONAZOLE (Havix Group Inc d-b-a Aavis Pharmaceuticals), KETOCONAZOLE (IPG PHARMACEUTICALS), KETODAN (Medimetriks Pharmaceuticals), KETOCONAZOLE (NORTHSTAR RX LLC), KETOCONAZOLE (NuCare Pharmaceuticals), KETOCONAZOLE (NuCare Pharmaceuticals), KETOCONAZOLE (NuCare Pharmaceuticals), KETOCONAZOLE (NuCare Pharmaceuticals), KETOCONAZOLE (NuCare Pharmaceuticals), KETOCONAZOLE (PD-Rx Pharmaceuticals), KETOCONAZOLE (PD-Rx Pharmaceuticals), KETOCONAZOLE (Padagis Israel Pharmaceuticals), KETOCONAZOLE (Perrigo New York), KETOCONAZOLE (Preferred Pharmaceuticals), KETOCONAZOLE (Preferred Pharmaceuticals), KETOCONAZOLE (Preferred Pharmaceuticals), KETOCONAZOLE (Proficient Rx LP), KETOCONAZOLE (Proficient Rx LP), KETOCONAZOLE (REMEDYREPACK), KETOCONAZOLE (REMEDYREPACK), KETOCONAZOLE (REMEDYREPACK), KETOCONAZOLE (RPK Pharmaceuticals), KETOCONAZOLE (Strides Shasun Limited), KETOCONAZOLE (THIRTY MADISON), KETOCONAZOLE (TOLMAR), KETOCONAZOLE (Taro Pharmaceuticals U.S.A.), KETOCONAZOLE (Taro Pharmaceuticals U.S.A.), KETOCONAZOLE (Teva Pharmaceuticals USA), KETOCONAZOLE (Encube Ethicals Private Limited), KETOCONAZOLE (Xiromed)
Formula
C26H28Cl2N4O4
Exact mass
530.1488
Mol weight
531.4309
Structure
Simcomp
Class
Antifungal
 DG01883  Imidazole antifungal
Metabolizing enzyme inhibitor
 DG01641  CYP2C8 inhibitor
 DG01933  CYP2C19 inhibitor
 DG02852  CYP3A/CYP3A4 inhibitor
Transporter inhibitor
 DG01622  ABCB1 inhibitor
Remark
Therapeutic category: 2655
ATC code: D01AC08 G01AF11 H02CA03 J02AB02
Product: D00351<JP/US>
Efficacy
Antifungal, Ergosterol biosynthesis inhibitor
  Disease
Seborrheic dermatitis [DS:H01652]
Tinea (pityriasis) versicolor [DS:H01334]
Tinea pedis [DS:H01316]
Blastomycosis [DS:H01501]
Coccidioidomycosis [DS:H01319]
Histoplasmosis [DS:H01062]
Chromomycosis [DS:H01520]
Paracoccidioidomycosis [DS:H01329]
Comment
Imidazole derivative
Racemic mixture of two cis-enantiomers [The diagram shows the (2S,4R)-isomer.]
Target
sterol 14alpha-demethylase [KO:K05917]
  Pathway
hsa00140  Steroid hormone biosynthesis
ko00100  Steroid biosynthesis
Interaction
CYP inhibition: CYP3A [HSA:1576 1577 1551], CYP2C8 [HSA:1558], CYP2C19 [HSA:1557]
Transporter inhibition: ABCB1 [HSA:5243]
Structure map
map07026  Antifungal agents
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 D DERMATOLOGICALS
  D01 ANTIFUNGALS FOR DERMATOLOGICAL USE
   D01A ANTIFUNGALS FOR TOPICAL USE
    D01AC Imidazole and triazole derivatives
     D01AC08 Ketoconazole
      D00351  Ketoconazole (JP18/USP) <JP/US>
 G GENITO URINARY SYSTEM AND SEX HORMONES
  G01 GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
   G01A ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
    G01AF Imidazole derivatives
     G01AF11 Ketoconazole
      D00351  Ketoconazole (JP18/USP) <JP/US>
 H SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
  H02 CORTICOSTEROIDS FOR SYSTEMIC USE
   H02C ANTIADRENAL PREPARATIONS
    H02CA Anticorticosteroids
     H02CA03 Ketoconazole
      D00351  Ketoconazole (JP18/USP) <JP/US>
 J ANTIINFECTIVES FOR SYSTEMIC USE
  J02 ANTIMYCOTICS FOR SYSTEMIC USE
   J02A ANTIMYCOTICS FOR SYSTEMIC USE
    J02AB Imidazole derivatives
     J02AB02 Ketoconazole
      D00351  Ketoconazole (JP18/USP) <JP/US>
USP drug classification [BR:br08302]
 Antifungals
  Ketoconazole
   D00351  Ketoconazole (JP18/USP)
 Dermatological Agents
  Topical Anti-infectives
   Antifungals, dermatological
    Ketoconazole
     D00351  Ketoconazole (JP18/USP)
Therapeutic category of drugs in Japan [BR:br08301]
 2  Agents affecting individual organs
  26  Epidermides
   265  Antiparasitic dermatosis agents
    2655  Imidazoles
     D00351  Ketoconazole (JP18/USP)
Antimicrobials [BR:br08307]
 Antifungals
  Ergosterol biosynthesis inhibitor
   Imidazole
    D00351  Ketoconazole (JP18/USP) <JP/US>
Antimicrobials abbreviations [BR:br08327]
 Antifungals
  Ergosterol biosynthesis inhibitor
   Imidazole
    D00351  Ketoconazole (JP17/USP)
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00351  Ketoconazole
  D00351  Ketoconazole solution
  D00351  Ketoconazole lotion
  D00351  Ketoconazole cream
New drug approvals in Europe [br08329.html]
 European public assessment reports (EPAR) authorised medicine
  D00351
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D00351
 Drug transporters
  D00351
Rx-to-OTC switch list in the USA [br08315.html]
 D00351
Other DBs
CAS: 65277-42-1
PubChem: 7847417
ChEBI: 47519
ChEMBL: CHEMBL1324508 CHEMBL295698
DrugBank: DB01026
PDB-CCD: KLN[PDBj]
LigandBox: D00351
NIKKAJI: J231.018J J311.163F
KCF data

ATOM        36
            1   C1z C    16.6092  -16.9097
            2   C8y C    15.4102  -16.2195
            3   O2x O    17.0363  -18.2256
            4   C1b C    15.5740  -17.8163
            5   O2x O    17.7323  -16.0907
            6   C8y C    15.4102  -14.8332
            7   C8x C    14.2111  -16.9097
            8   C1y C    18.4225  -18.2256
            9   N4y N    14.1235  -17.8220
            10  C1x C    18.8611  -16.9097
            11  C8x C    14.2111  -14.1430
            12  X   Cl   16.6092  -14.1430
            13  C8x C    13.0121  -16.2195
            14  C1b C    19.8437  -18.9977
            15  C8x C    12.9946  -17.0033
            16  C8x C    13.6906  -19.1381
            17  C8y C    13.0121  -14.8332
            18  O2a O    21.2066  -18.0677
            19  C8x C    11.8716  -17.8220
            20  N5x N    12.3044  -19.1381
            21  X   Cl   11.8132  -14.1430
            22  C8y C    22.5987  -18.0736
            23  C8x C    23.2889  -19.2784
            24  C8x C    23.3006  -16.8745
            25  C8x C    24.6750  -19.2843
            26  C8x C    24.6809  -16.8803
            27  C8y C    25.3711  -18.0794
            28  N1y N    26.7513  -18.0853
            29  C1x C    27.4415  -19.2901
            30  C1x C    27.4475  -16.8920
            31  C1x C    28.8278  -19.2960
            32  C1x C    28.8336  -16.8920
            33  N1y N    29.5238  -18.0911
            34  C5a C    30.9101  -18.0270
            35  C1a C    31.5943  -19.3018
            36  O5a O    31.6060  -16.9037
BOND        40
            1     1   2 1 #Down
            2     1   3 1
            3     1   4 1 #Up
            4     1   5 1
            5     2   6 1
            6     2   7 2
            7     3   8 1
            8     4   9 1
            9     5  10 1
            10    6  11 2
            11    6  12 1
            12    7  13 1
            13    8  14 1 #Up
            14    9  15 1
            15    9  16 1
            16   11  17 1
            17   14  18 1
            18   15  19 2
            19   16  20 2
            20   17  21 1
            21   18  22 1
            22   22  23 2
            23   22  24 1
            24   23  25 1
            25   24  26 2
            26   25  27 2
            27   27  28 1
            28   28  29 1
            29   28  30 1
            30   29  31 1
            31   30  32 1
            32   31  33 1
            33   33  34 1
            34   34  35 1
            35   34  36 2
            36    8  10 1
            37   13  17 2
            38   19  20 1
            39   26  27 1
            40   32  33 1

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