KEGG   DRUG: ChloramphenicolHelp
Entry
D00104                      Drug                                   

Name
Chloramphenicol (JP17/USP/INN);
CP;
Amphicol (TN);
Chloromycetin (TN);
Econochlor (TN)
Formula
C11H12Cl2N2O5
Exact mass
322.0123
Mol weight
323.1294
Structure
Mol fileKCF fileDB searchJmolKegDraw
Simcomp SIMCOMP
Source
Streptomyces venezuelae [TAX:54571], Streptomyces omiyaensis [TAX:68247]
Class
Antibacterial
 DG01576  Amphenicol type antibacterial
Cyp substrate
 DG01639  CYP2C19 substrate
Cyp inhibitor
 DG01933  CYP2C19 inhibitor
 DG01522  CYP3A4 inhibitor
 DG01915  CYP3A5 inhibitor
Remark
Efficacy
Antibacterial, Antirickettsial, Protein biosynthesis inhibitor
Comment
Natural product
Amphenicol derivative
Target
50S ribosomal subunit
  Pathway
Ribosome
Metabolism
Enzyme: CYP2C19 [HSA:1557]
Interaction
CYP inhibition: CYP2C19 [HSA:1557], CYP3A4 [HSA:1576], CYP3A5 [HSA:1577], CYP3A7 [HSA:1551]
Drug interaction
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 D DERMATOLOGICALS
  D06 ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
   D06A ANTIBIOTICS FOR TOPICAL USE
    D06AX Other antibiotics for topical use
     D06AX02 Chloramphenicol
      D00104  Chloramphenicol (JP17/USP/INN)
  D10 ANTI-ACNE PREPARATIONS
   D10A ANTI-ACNE PREPARATIONS FOR TOPICAL USE
    D10AF Antiinfectives for treatment of acne
     D10AF03 Chloramphenicol
      D00104  Chloramphenicol (JP17/USP/INN)
 G GENITO URINARY SYSTEM AND SEX HORMONES
  G01 GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
   G01A ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
    G01AA Antibiotics
     G01AA05 Chloramphenicol
      D00104  Chloramphenicol (JP17/USP/INN)
 J ANTIINFECTIVES FOR SYSTEMIC USE
  J01 ANTIBACTERIALS FOR SYSTEMIC USE
   J01B AMPHENICOLS
    J01BA Amphenicols
     J01BA01 Chloramphenicol
      D00104  Chloramphenicol (JP17/USP/INN)
 S SENSORY ORGANS
  S01 OPHTHALMOLOGICALS
   S01A ANTIINFECTIVES
    S01AA Antibiotics
     S01AA01 Chloramphenicol
      D00104  Chloramphenicol (JP17/USP/INN)
  S02 OTOLOGICALS
   S02A ANTIINFECTIVES
    S02AA Antiinfectives
     S02AA01 Chloramphenicol
      D00104  Chloramphenicol (JP17/USP/INN)
  S03 OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
   S03A ANTIINFECTIVES
    S03AA Antiinfectives
     S03AA08 Chloramphenicol
      D00104  Chloramphenicol (JP17/USP/INN)
USP drug classification [BR:br08302]
 Antibacterials
  Antibacterials, Other
   Chloramphenicol
    D00104  Chloramphenicol (JP17/USP/INN)
Therapeutic category of drugs in Japan [BR:br08301]
 1  Agents affecting nervous system and sensory organs
  13  Agents affecting sensory organs
   131  Ophthalmic agents
    1317  Ophthalmic antibiotics
     D00104  Chloramphenicol (JP17/USP/INN)
   132  Otic and nasal agents
    1325  Otolaryngologic antibiotics
     D00104  Chloramphenicol (JP17/USP/INN)
 2  Agents affecting individual organs
  25  Urogenital and anal organ agents
   252  Genital organ agents
    2521  Antibiotics
     D00104  Chloramphenicol (JP17/USP/INN)
  26  Epidermides
   263  Suppurative dermatosis agents
    2634  Antibiotics for external use
     D00104  Chloramphenicol (JP17/USP/INN)
 6  Agents against pathologic organisms and parasites
  61  Antibiotics
   615  Acting mainly on gram-positive bacteria, gram-negative bacteria, rickettsia and chlamydia
    6151  Chloramphenicols
     D00104  Chloramphenicol (JP17/USP/INN)
Classification of Japanese OTC drugs [BR:br08313]
 Agents for integumentary system
  56 Purulent skin remedies
   D00104  Chloramphenicol (JP17/USP/INN)
Risk category of Japanese OTC drugs [BR:br08312]
 Second-class OTC drugs
  Inorganic and organic chemicals
   Chloramphenicol
    D00104  Chloramphenicol (JP17/USP/INN)
Antiinfectives [BR:br08307]
 Antibacterials
  Protein biosynthesis inhibitor
   50S subunit inhibitor
    Amphenicols
     Chloramphenicol
      D00104  Chloramphenicol (JP17/USP/INN)
Cytochrome P450 interactions [BR:br08309]
 CYP inhbitors
  CYP2C19
   Chloramphenicol
    D00104  Chloramphenicol (JP17/USP/INN)
  CYP3A4
   Chloramphenicol
    D00104  Chloramphenicol (JP17/USP/INN)
  CYP3A5
   Chloramphenicol
    D00104  Chloramphenicol (JP17/USP/INN)
  CYP3A7
   Chloramphenicol
    D00104  Chloramphenicol (JP17/USP/INN)
 CYP substrates
  CYP2C19
   Chloramphenicol
    D00104  Chloramphenicol (JP17/USP/INN)
  CYP3A4
   Chloramphenicol
    D00104  Chloramphenicol (JP17/USP/INN)
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00104  Chloramphenicol
Antibacterials [br08350.html]
 D00104
BRITE hierarchy
Other DBs
CAS: 
56-75-7
PubChem: 
ChEBI: 
ChEMBL: 
DrugBank: 
PDB-CCD: 
LigandBox: 
NIKKAJI: 
KCF data Show

ATOM        20
            1   C8y C    21.4200  -17.2900
            2   C1c C    21.4200  -18.6900
            3   C8x C    20.2300  -16.5900
            4   C8x C    22.6800  -16.5900
            5   C1c C    22.6100  -19.3900
            6   O1a O    20.2300  -19.3900
            7   C8x C    20.2300  -15.1900
            8   C8x C    22.6800  -15.1900
            9   N1b N    23.8700  -18.6900
            10  C1b C    22.6100  -20.7900
            11  C8y C    21.4200  -14.4900
            12  C5a C    25.0600  -19.3900
            13  O1a O    21.4200  -21.4900
            14  N2b N    21.4200  -13.0900 #+
            15  C1c C    26.2500  -18.6900
            16  O5a O    25.0600  -20.7900
            17  O3a O    20.2300  -12.3900
            18  O3a O    22.6100  -12.3900 #-
            19  X   Cl   27.5100  -19.3900
            20  X   Cl   26.2500  -17.2900
BOND        20
            1     1   2 1
            2     1   3 2
            3     1   4 1
            4     2   5 1
            5     2   6 1 #Down
            6     3   7 1
            7     4   8 2
            8     5   9 1
            9     5  10 1
            10    7  11 2
            11    9  12 1
            12   10  13 1
            13   11  14 1
            14   12  15 1
            15   12  16 2
            16   14  17 2
            17   14  18 1
            18   15  19 1
            19   15  20 1
            20    8  11 1

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