Erythromycin ethylsuccinate


Entry
D01361                      Drug                                   
Name
Erythromycin ethylsuccinate (JP18/USP);
E.E.S. (TN);
Eryped (TN);
Erythrocin W (TN)
Product
ERY-PED (Arbor Pharmaceuticals), E.E.S (Arbor Pharmaceuticals), ERYTHROMYCIN ETHYLSUCCINATE (Bryant Ranch Prepack), ERYTHROMYCIN ETHYLSUCCINATE (Wilshire Pharmaceuticals), ERYTHROMYCIN ETHYLSUCCINATE (Wilshire Pharmaceuticals)
  Generic
ERYTHROMYCIN ETHYLSUCCINATE (Amneal Pharmaceuticals NY LLC), ERYTHROMYCIN ETHYLSUCCINATE (ANI Pharmaceuticals), ERYTHROMYCIN ETHYLSUCCINATE (ANI Pharmaceuticals), ERYTHROMYCIN ETHYLSUCCINATE (Arbor Pharmaceuticals)
Formula
C43H75NO16
Exact mass
861.5086
Mol weight
862.0527
Structure
Simcomp
Class
Antibacterial
 DG01551  Macrolide antibiotic
  DG01874  14-membered ring macrolide antibiotic
Metabolizing enzyme substrate
 DG01633  CYP3A/CYP3A4 substrate
Metabolizing enzyme inhibitor
 DG02852  CYP3A/CYP3A4 inhibitor
Transporter inhibitor
 DG01622  ABCB1 inhibitor
Remark
Same as: C12796
Therapeutic category: 6141
ATC code: D10AF02 J01FA01 S01AA17
Chemical structure group: DG00436
Product (DG00436): D00140<JP/US> D01361<JP/US> D02009<JP/US> D02184<JP/US>
Efficacy
Antibacterial, Protein biosynthesis inhibitor
  Disease
Listeriosis [DS:H00332]
Pertussis [DS:H00319]
Diphtheria [DS:H00343]
Amebiasis [DS:H00360]
Syphilis [DS:H00354]
Legionnaires' disease [DS:H00311]
Comment
Active form of prodrug: Erythromycin [DR:D00140]
Target
50S ribosomal subunit
  Pathway
ko03010  Ribosome
Metabolism
Enzyme: CYP3A [HSA:1576 1577 1551]
Interaction
CYP inhibition: CYP3A [HSA:1576 1577 1551]
Transporter inhibition: ABCB1 [HSA:5243]
Structure map
map07020  Macrolides and ketolides
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 D DERMATOLOGICALS
  D10 ANTI-ACNE PREPARATIONS
   D10A ANTI-ACNE PREPARATIONS FOR TOPICAL USE
    D10AF Antiinfectives for treatment of acne
     D10AF02 Erythromycin
      D01361  Erythromycin ethylsuccinate (JP18/USP) <JP/US>
 J ANTIINFECTIVES FOR SYSTEMIC USE
  J01 ANTIBACTERIALS FOR SYSTEMIC USE
   J01F MACROLIDES, LINCOSAMIDES AND STREPTOGRAMINS
    J01FA Macrolides
     J01FA01 Erythromycin
      D01361  Erythromycin ethylsuccinate (JP18/USP) <JP/US>
 S SENSORY ORGANS
  S01 OPHTHALMOLOGICALS
   S01A ANTIINFECTIVES
    S01AA Antibiotics
     S01AA17 Erythromycin
      D01361  Erythromycin ethylsuccinate (JP18/USP) <JP/US>
USP drug classification [BR:br08302]
 Antibacterials
  Macrolides
   Erythromycin
    D01361  Erythromycin ethylsuccinate (JP18/USP)
 Dermatological Agents
  Topical Anti-infectives
   Antibacterials, dermatological
    Erythromycin
     D01361  Erythromycin ethylsuccinate (JP18/USP)
 Ophthalmic Agents
  Ophthalmic Anti-Infectives
   Antibacterials, Ophthalmic
    Erythromycin
     D01361  Erythromycin ethylsuccinate (JP18/USP)
Therapeutic category of drugs in Japan [BR:br08301]
 6  Agents against pathologic organisms and parasites
  61  Antibiotics
   614  Acting mainly on gram-positive bacteria and mycoplasma
    6141  Erythromycins
     D01361  Erythromycin ethylsuccinate (JP18/USP)
Drug groups [BR:br08330]
 Antibacterial
  DG01551  Macrolide antibiotic
   DG01874  14-membered ring macrolide antibiotic
    DG00436  Erythromycin
     D01361  Erythromycin ethylsuccinate
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG00436  Erythromycin
    D01361  Erythromycin ethylsuccinate
 Metabolizing enzyme inhibitor
  DG02852  CYP3A/CYP3A4 inhibitor
   DG00436  Erythromycin
    D01361  Erythromycin ethylsuccinate
 Transporter inhibitor
  DG01622  ABCB1 inhibitor
   DG00436  Erythromycin
    D01361  Erythromycin ethylsuccinate
Drug classes [BR:br08332]
 Antibacterial
  DG01551  Macrolide antibiotic
   D01361  Erythromycin ethylsuccinate
Antimicrobials [BR:br08307]
 Antibacterials
  Protein biosynthesis inhibitor
   Macrolide
    D01361  Erythromycin ethylsuccinate (JP18/USP) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D01361  Erythromycin ethylsuccinate
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D01361
 Drug transporters
  D01361
Prodrugs [br08324.html]
 D01361
Drug groups [BR:br08330]
 Antibacterial
  DG01551  Macrolide antibiotic
   DG01874  14-membered ring macrolide antibiotic
    DG00436  Erythromycin
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG00436  Erythromycin
 Metabolizing enzyme inhibitor
  DG02852  CYP3A/CYP3A4 inhibitor
   DG00436  Erythromycin
 Transporter inhibitor
  DG01622  ABCB1 inhibitor
   DG00436  Erythromycin
Antimicrobials abbreviations [BR:br08327]
 Antibacterials
  Protein biosynthesis inhibitor
   Macrolide
    DG00436  Erythromycin
Other DBs
CAS: 1264-62-6
PubChem: 7848424
ChEBI: 31555
LigandBox: D01361
NIKKAJI: J217.089B
KCF data

ATOM        60
            1   C1y C    26.6685   -9.4688
            2   C1z C    26.6685   -8.1507
            3   C1y C    25.5236  -10.1224
            4   O2a O    29.1257  -10.4999
            5   C1x C    25.5236   -7.4916
            6   O1a O    27.6627   -7.1957
            7   C1a C    27.9085   -8.5695
            8   C1y C    25.5236  -11.4405
            9   C1a C    24.5850   -9.1345
            10  C1y C    30.3129   -7.8458
            11  C1y C    25.5236   -6.1679
            12  O2a O    26.2385  -12.7531
            13  C1y C    24.3898  -12.0997
            14  C1y C    31.4424   -8.5142
            15  O2x O    30.3246   -6.5282
            16  C5x C    24.3898   -5.5143
            17  C1a C    26.6685   -5.5143
            18  C1y C    27.7044  -13.1571
            19  C7x C    23.2448  -11.4405
            20  C1a C    24.3898  -13.4176
            21  C1y C    32.6564   -7.8745
            22  O7a O    31.5013  -10.6489
            23  C1y C    31.4756   -5.8858
            24  C1y C    23.2448   -6.1679
            25  O5x O    24.3898   -4.1962
            26  C1x C    27.7044  -14.4698
            27  O2x O    28.8495  -12.4982
            28  O7x O    23.2448  -10.1224
            29  O6a O    22.2226  -12.3565
            30  C1x C    32.6027   -6.5617
            31  N1c N    33.7229   -8.5401
            32  C1a C    31.4946   -4.5703
            33  C1y C    23.2448   -7.4916
            34  C1a C    22.1055   -5.5143
            35  C1z C    28.8495  -15.1344
            36  C1y C    29.9831  -13.1571
            37  C1y C    22.1055   -9.4688
            38  C1z C    22.1055   -8.1507
            39  O1a O    24.3898   -8.1507
            40  C1y C    29.9831  -14.4698
            41  O2a O    28.8495  -16.4135
            42  C1a C    30.2457  -16.0840
            43  C1a C    31.1282  -12.5038
            44  C1b C    20.9659  -10.1224
            45  C1a C    20.8990   -8.6979
            46  O1a O    20.8990   -7.4861
            47  O1a O    31.1282  -15.1344
            48  C1a C    29.9106  -17.3407
            49  C1a C    20.9998  -11.2059
            50  C1a C    34.9280   -7.8560
            51  C7a C    32.6580  -11.3274
            52  O6a O    32.6580  -12.6811
            53  C1b C    33.7987  -10.6741
            54  C1b C    34.9498  -11.3443
            55  C1a C    33.7229   -9.8938
            56  C7a C    36.1516  -10.6561
            57  O7a O    37.3309  -11.3426
            58  O6a O    36.0870   -9.2405
            59  C1b C    38.5311  -10.6552
            60  C1a C    39.7112  -11.3421
BOND        62
            1     1   2 1
            2     1   3 1
            3     1   4 1 #Down
            4     2   5 1
            5     2   6 1 #Up
            6     2   7 1 #Down
            7     3   8 1
            8     3   9 1 #Down
            9    10   4 1 #Down
            10    5  11 1
            11    8  12 1 #Down
            12    8  13 1
            13   10  14 1
            14   10  15 1
            15   11  16 1
            16   11  17 1 #Down
            17   18  12 1 #Down
            18   13  19 1
            19   13  20 1 #Up
            20   14  21 1
            21   14  22 1 #Up
            22   15  23 1
            23   16  24 1
            24   16  25 2
            25   18  26 1
            26   18  27 1
            27   19  28 1
            28   19  29 2
            29   21  30 1
            30   21  31 1 #Down
            31   23  32 1 #Down
            32   24  33 1
            33   24  34 1 #Up
            34   26  35 1
            35   27  36 1
            36   28  37 1
            37   33  38 1
            38   33  39 1 #Up
            39   35  40 1
            40   35  41 1 #Down
            41   35  42 1
            42   36  43 1 #Up
            43   37  44 1 #Down
            44   38  45 1 #Down
            45   38  46 1 #Up
            46   40  47 1 #Down
            47   41  48 1
            48   44  49 1
            49   23  30 1
            50   36  40 1
            51   37  38 1
            52   31  50 1
            53   22  51 1
            54   51  52 2
            55   51  53 1
            56   53  54 1
            57   31  55 1
            58   54  56 1
            59   56  57 1
            60   56  58 2
            61   57  59 1
            62   59  60 1