KEGG   DRUG: Chloramphenicol
Entry
D00104                      Drug                                   
Name
Chloramphenicol (JP18/USP/INN);
Amphicol (TN);
Chloromycetin (TN);
Econochlor (TN)
Formula
C11H12Cl2N2O5
Exact mass
322.0123
Mol weight
323.1294
Structure
Simcomp
Source
Streptomyces venezuelae [TAX:54571], Streptomyces omiyaensis [TAX:68247]
Class
Antibacterial
 DG01576  Amphenicol type antibacterial
Metabolizing enzyme inhibitor
 DG01933  CYP2C19 inhibitor
Remark
Same as: C00918
Therapeutic category: 1317 1325 2521 2634 6151
ATC code: D06AX02 D10AF03 G01AA05 J01BA01 S01AA01 S02AA01 S03AA08
Chemical structure group: DG00399
Product (DG00399): D00104<JP> D02185<JP/US>
Product (mixture): D04106<JP> D04753<JP>
Efficacy
Antibacterial, Antirickettsial, Protein biosynthesis inhibitor
Comment
Natural product
Amphenicol derivative
Target
50S ribosomal subunit
  Pathway
ko03010  Ribosome
Interaction
CYP inhibition: CYP2C19 [HSA:1557]
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 (JP18/USP/INN) <JP>
  D10 ANTI-ACNE PREPARATIONS
   D10A ANTI-ACNE PREPARATIONS FOR TOPICAL USE
    D10AF Antiinfectives for treatment of acne
     D10AF03 Chloramphenicol
      D00104  Chloramphenicol (JP18/USP/INN) <JP>
 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 (JP18/USP/INN) <JP>
 J ANTIINFECTIVES FOR SYSTEMIC USE
  J01 ANTIBACTERIALS FOR SYSTEMIC USE
   J01B AMPHENICOLS
    J01BA Amphenicols
     J01BA01 Chloramphenicol
      D00104  Chloramphenicol (JP18/USP/INN) <JP>
 S SENSORY ORGANS
  S01 OPHTHALMOLOGICALS
   S01A ANTIINFECTIVES
    S01AA Antibiotics
     S01AA01 Chloramphenicol
      D00104  Chloramphenicol (JP18/USP/INN) <JP>
  S02 OTOLOGICALS
   S02A ANTIINFECTIVES
    S02AA Antiinfectives
     S02AA01 Chloramphenicol
      D00104  Chloramphenicol (JP18/USP/INN) <JP>
  S03 OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS
   S03A ANTIINFECTIVES
    S03AA Antiinfectives
     S03AA08 Chloramphenicol
      D00104  Chloramphenicol (JP18/USP/INN) <JP>
USP drug classification [BR:br08302]
 Antibacterials
  Antibacterials, Other
   Chloramphenicol
    D00104  Chloramphenicol (JP18/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 (JP18/USP/INN)
   132  Otic and nasal agents
    1325  Otolaryngologic antibiotics
     D00104  Chloramphenicol (JP18/USP/INN)
 2  Agents affecting individual organs
  25  Urogenital and anal organ agents
   252  Genital organ agents
    2521  Antibiotics
     D00104  Chloramphenicol (JP18/USP/INN)
  26  Epidermides
   263  Suppurative dermatosis agents
    2634  Antibiotics for external use
     D00104  Chloramphenicol (JP18/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 (JP18/USP/INN)
Classification of Japanese OTC drugs [BR:br08313]
 Agents for integumentary system
  56 Purulent skin remedies
   D00104  Chloramphenicol (JP18/USP/INN)
Risk category of Japanese OTC drugs [BR:br08312]
 Second-class OTC drugs
  Inorganic and organic chemicals
   Chloramphenicol
    D00104  Chloramphenicol (JP18/USP/INN)
Drug groups [BR:br08330]
 Antibacterial
  DG01576  Amphenicol type antibacterial
   DG00399  Chloramphenicol
    D00104  Chloramphenicol
 Metabolizing enzyme inhibitor
  DG01933  CYP2C19 inhibitor
   D00104  Chloramphenicol
Antimicrobials [BR:br08307]
 Antibacterials
  Protein biosynthesis inhibitor
   Amphenicol
    D00104  Chloramphenicol (JP18/USP/INN) <JP>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00104  Chloramphenicol
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D00104
Prodrugs [br08324.html]
 D00104
Drug groups [BR:br08330]
 Antibacterial
  DG01576  Amphenicol type antibacterial
   DG00399  Chloramphenicol
Antimicrobials abbreviations [BR:br08327]
 Antibacterials
  Protein biosynthesis inhibitor
   Amphenicol
    DG00399  Chloramphenicol
Prodrugs [br08324.html]
 DG00399
Other DBs
CAS: 56-75-7
PubChem: 7847172
ChEBI: 17698
PDB-CCD: CLM[PDBj]
LigandBox: D00104
NIKKAJI: J2.802I
KCF data

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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