Azithromycin


Entry
D07486                      Drug                                   
Name
Azithromycin (INN);
Azasite (TN);
Azithromycin (TN)
Product
  Generic
AZITHROMYCIN (Bryant Ranch Prepack), ZITHROMAX (DIRECT RX), AZITHROMYCIN (NuCare Pharmaceuticals), AZITHROMYCIN (NuCare Pharmaceuticals), AZITHROMYCIN (Proficient Rx LP), AZITHROMYCIN (Proficient Rx LP), AZITHROMYCIN (RPK Pharmaceuticals), AZITHROMYCIN (RPK Pharmaceuticals), AZITHROMYCIN (Wockhardt USA LLC.), AZITHROMYCIN (Wockhardt USA LLC.)
Formula
C38H72N2O12
Exact mass
748.5085
Mol weight
748.9845
Structure
Simcomp
Class
Antibacterial
 DG01551  Macrolide antibiotic
  DG01875  15-Membered ring macrolide antibiotic
Transporter substrate
 DG01665  ABCB1 substrate
Transporter inhibitor
 DG01622  ABCB1 inhibitor
Remark
Same as: C06838
ATC code: J01FA10 S01AA26
Chemical structure group: DG00606
Product (DG00606): D07486<US> D02134<JP/US> D06390<US>
Efficacy
Antibacterial, Protein biosynthesis inhibitor
  Disease
Urethritis and cervicitis due to Chlamydia trachomatis [DS:H00347]
Target
50S ribosomal subunit
  Pathway
ko03010  Ribosome
Metabolism
Transporter: ABCB1 [HSA:5243]
Interaction
Transporter inhibition: ABCB1 [HSA:5243]
Structure map
map07020  Macrolides and ketolides
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 J ANTIINFECTIVES FOR SYSTEMIC USE
  J01 ANTIBACTERIALS FOR SYSTEMIC USE
   J01F MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
    J01FA Macrolides
     J01FA10 Azithromycin
      D07486  Azithromycin (INN) <US>
 S SENSORY ORGANS
  S01 OPHTHALMOLOGICALS
   S01A ANTIINFECTIVES
    S01AA Antibiotics
     S01AA26 Azithromycin
      D07486  Azithromycin (INN) <US>
USP drug classification [BR:br08302]
 Antibacterials
  Macrolides
   Azithromycin
    D07486  Azithromycin (INN)
 Ophthalmic Agents
  Ophthalmic Anti-Infectives
   Antibacterials, Ophthalmic
    Azithromycin
     D07486  Azithromycin (INN)
Drug groups [BR:br08330]
 Antibacterial
  DG01551  Macrolide antibiotic
   DG01875  15-Membered ring macrolide antibiotic
    DG00606  Azithromycin
     D07486  Azithromycin
 Transporter substrate
  DG01665  ABCB1 substrate
   DG00606  Azithromycin
    D07486  Azithromycin
 Transporter inhibitor
  DG01622  ABCB1 inhibitor
   DG00606  Azithromycin
    D07486  Azithromycin
Drug classes [BR:br08332]
 Antibacterial
  DG01551  Macrolide antibiotic
   D07486  Azithromycin
Antimicrobials [BR:br08307]
 Antibacterials
  Protein biosynthesis inhibitor
   Macrolide
    D07486  Azithromycin (INN) <US>
Drug metabolizing enzymes and transporters [br08309.html]
 Drug transporters
  D07486
Drug groups [BR:br08330]
 Antibacterial
  DG01551  Macrolide antibiotic
   DG01875  15-Membered ring macrolide antibiotic
    DG00606  Azithromycin
 Transporter substrate
  DG01665  ABCB1 substrate
   DG00606  Azithromycin
 Transporter inhibitor
  DG01622  ABCB1 inhibitor
   DG00606  Azithromycin
Antimicrobials abbreviations [BR:br08327]
 Antibacterials
  Protein biosynthesis inhibitor
   Macrolide
    DG00606  Azithromycin
Other DBs
CAS: 83905-01-5
PubChem: 51091811
ChEBI: 2955
PDB-CCD: ZIT[PDBj]
LigandBox: D07486
NIKKAJI: J134.080H
KCF data

ATOM        52
            1   C1y C    21.6300  -16.2400
            2   C1y C    20.3700  -16.8700
            3   O2a O    23.1700  -17.2200
            4   C1z C    21.6300  -14.9100
            5   C1y C    20.3700  -18.2000
            6   C1a C    19.6000  -15.8900
            7   C1y C    24.5000  -16.4500
            8   C1x C    20.8600  -14.3500
            9   C1a C    22.8200  -15.4700
            10  O1a O    22.8200  -14.2100
            11  O2a O    21.1400  -20.1600
            12  C1y C    19.2500  -18.8300
            13  C1y C    25.2700  -17.7100
            14  O2x O    25.2700  -15.1900
            15  C1y C    21.3500  -13.0900
            16  C1y C    22.7500  -20.8600
            17  C7x C    18.1300  -18.2000
            18  C1a C    19.1800  -20.1600
            19  C1y C    26.6700  -17.7100
            20  O1a O    24.5000  -18.9700
            21  C1y C    26.6700  -15.1900
            22  C1x C    20.5100  -12.2500
            23  C1a C    22.3300  -12.5300
            24  C1x C    22.7500  -22.3300
            25  O2x O    24.0100  -20.1600
            26  O7x O    18.1300  -16.8700
            27  O6a O    17.1500  -19.1800
            28  C1x C    27.3700  -16.4500
            29  N1c N    27.3700  -18.9700
            30  C1a C    27.3700  -14.0000
            31  N1y N    19.3200  -12.2500
            32  C1z C    24.0100  -23.0300
            33  C1y C    25.2000  -20.8600
            34  C1y C    17.0100  -16.1700
            35  C1a C    28.7700  -19.8800
            36  C1a C    28.7000  -18.2700
            37  C1y C    18.2000  -12.8800
            38  C1a C    19.3200  -10.8500
            39  C1y C    25.2000  -22.3300
            40  O2a O    23.9400  -24.3600
            41  C1a C    26.4600  -20.1600
            42  C1z C    17.0100  -14.8400
            43  C1b C    15.8200  -16.8000
            44  C1y C    18.2000  -14.2100
            45  C1a C    17.0100  -12.1800
            46  O1a O    26.4600  -23.0300
            47  C1a C    25.1300  -25.0600
            48  C1a C    15.6800  -15.3300
            49  O1a O    15.8200  -13.7200
            50  C1a C    15.8200  -18.1300
            51  O1a O    19.3200  -14.9100
            52  C1a C    22.7500  -23.7300
BOND        54
            1     1   2 1
            2     1   3 1 #Down
            3     1   4 1
            4     2   5 1
            5     2   6 1
            6     7   3 1 #Down
            7     4   8 1
            8     4   9 1 #Down
            9     4  10 1 #Up
            10    5  11 1 #Down
            11    5  12 1
            12    7  13 1
            13    7  14 1
            14    8  15 1
            15   16  11 1 #Down
            16   12  17 1
            17   12  18 1 #Up
            18   13  19 1
            19   13  20 1 #Up
            20   14  21 1
            21   15  22 1
            22   15  23 1 #Down
            23   16  24 1
            24   16  25 1
            25   17  26 1
            26   17  27 2
            27   19  28 1
            28   19  29 1 #Down
            29   21  30 1 #Down
            30   22  31 1
            31   24  32 1
            32   25  33 1
            33   26  34 1
            34   29  35 1
            35   29  36 1
            36   31  37 1
            37   31  38 1
            38   32  39 1
            39   32  40 1 #Down
            40   33  41 1 #Up
            41   34  42 1
            42   34  43 1 #Down
            43   37  44 1
            44   37  45 1 #Up
            45   39  46 1 #Down
            46   40  47 1
            47   42  48 1 #Down
            48   42  49 1 #Up
            49   43  50 1
            50   44  51 1 #Up
            51   21  28 1
            52   33  39 1
            53   42  44 1
            54   32  52 1 #Up