KEGG   DRUG: D01450Help
Entry
D01450                      Drug                                   

Name
Bupivacaine hydrochloride hydrate (JP16);
Bupivacaine hydrochloride (USP);
Marcaine (TN)
Product
  Generic
  Other
Formula
C18H28N2O. HCl. H2O
Exact mass
342.2074
Mol weight
342.9039
Structure
Mol fileKCF fileDB searchJmolKegDraw
Activity
Anesthetic [local]
Remark
Therapeutic category: 
ATC code: 
Drug group: 
Target
voltage-gated sodium channel (SCN10A) blocker [HSA:6336] [KO:K04842];
voltage-gated sodium channel (SCN1A) blocker [HSA:6323] [KO:K04833];
voltage-gated sodium channel (SCN2A) blocker [HSA:6326] [KO:K04834];
voltage-gated sodium channel (SCN3A) blocker [HSA:6328] [KO:K04836];
voltage-gated sodium channel (SCN4A) blocker [HSA:6329] [KO:K04837];
voltage-gated sodium channel (SCN5A) blocker [HSA:6331] [KO:K04838];
voltage-gated sodium channel (SCN8A) blocker [HSA:6334] [KO:K04840];
voltage-gated sodium channel (SCN9A) blocker [HSA:6335] [KO:K04841]
Metabolism
Enzyme: CYP3A4 [HSA:1576]
Interaction
Drug interaction
Structure map
Sodium channel blocking drugs
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 N NERVOUS SYSTEM
  N01 ANESTHETICS
   N01B ANESTHETICS, LOCAL
    N01BB Amides
     N01BB01 Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
Therapeutic category of drugs in Japan [BR:br08301]
 1  Agents affecting nervous system and sensory organs
  12  Agents affecting peripheral nervous system
   121  Local anesthetics
    1214  Xylidines
     D01450  Bupivacaine hydrochloride hydrate (JP16); Bupivacaine hydrochloride (USP)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Na+ channel, SCN alpha, NaV1.x
    voltage-gated sodium channel (SCN1A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN2A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN3A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN4A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN5A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN8A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN9A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN10A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride hydrate (JAN); Bupivacaine hydrochloride (USP)
Cytochrome P450 interactions [BR:br08309]
 Substrates
  CYP3A4
   Bupivacaine
    D01450  Bupivacaine hydrochloride hydrate (JP16); Bupivacaine hydrochloride (USP)
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D01450  Bupivacaine hydrochloride hydrate
BRITE hierarchy
Other DBs
CAS: 
14252-80-3
PubChem: 
DrugBank: 
LigandBox: 
KCF data Show

ATOM        23
            1   C1y C    22.9876  -17.0670
            2   N1y N    22.9702  -18.4666
            3   C5a C    21.7746  -16.3556
            4   C1b C    21.7512  -19.1547
            5   N1b N    20.5615  -17.0496
            6   O5a O    21.7862  -14.9501
            7   C1b C    20.5498  -18.4549
            8   C8y C    19.4185  -16.3382
            9   C1b C    19.3369  -19.1487
            10  C8y C    18.1297  -17.0320
            11  C8y C    19.3602  -14.9325
            12  C1a C    19.3369  -20.5427
            13  C8x C    16.9225  -16.3206
            14  C1a C    18.1297  -18.4257
            15  C8x C    18.1471  -14.2270
            16  C8x C    16.9225  -14.9208
            17  C1a C    20.5679  -14.2445
            18  C1x C    24.1738  -19.1815
            19  C1x C    25.3947  -18.4968
            20  C1x C    25.4122  -17.0972
            21  C1x C    24.2086  -16.3822
            22  X   Cl   28.3695  -17.8451
            23  O0  O    31.5703  -17.8269
BOND        22
            1     1   2 1
            2     1   3 1
            3     2   4 1
            4     3   5 1
            5     3   6 2
            6     4   7 1
            7     5   8 1
            8     7   9 1
            9     8  10 1
            10    8  11 2
            11    9  12 1
            12   10  13 2
            13   10  14 1
            14   11  15 1
            15   13  16 1
            16   15  16 2
            17   11  17 1
            18    2  18 1
            19   18  19 1
            20   19  20 1
            21   20  21 1
            22    1  21 1

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