KEGG   DRUG: Bupivacaine hydrochlorideHelp
Entry
D01450                      Drug                                   

Name
Bupivacaine hydrochloride (USP);
Bupivacaine hydrochloride hydrate (JP17);
Marcaine (TN)
Product
  Generic
  Other
Formula
C18H28N2O. HCl. H2O
Exact mass
342.2074
Mol weight
342.9039
Structure
Mol fileKCF fileDB search
Simcomp SIMCOMP
Class
Cardiovascular agent
 DG01592  COMT substrate
Neuropsychiatric agent
 DG02030  Anesthetics
  DG01675  Local anesthetic
   DG01673  Amide type local anesthetic
 DG01675  Local anesthetic
  DG01673  Amide type local anesthetic
Cyp substrate
 DG01633  CYP3A substrate
Remark
Therapeutic category: 1214
ATC code: N01BB01
Chemical structure group: DG00801
Product (DG00801): D07552<US> D01450<JP/US>
Efficacy
Anesthetic (local)
Target
SCN1A [HSA:6323] [KO:K04833]
SCN2A [HSA:6326] [KO:K04834]
SCN3A [HSA:6328] [KO:K04836]
SCN4A [HSA:6329] [KO:K04837]
SCN5A [HSA:6331] [KO:K04838]
SCN8A [HSA:6334] [KO:K04840]
SCN9A [HSA:6335] [KO:K04841]
SCN10A [HSA:6336] [KO:K04842]
SCN11A [HSA:11280] [KO:K04843]
  Pathway
hsa04728  Dopaminergic synapse
Metabolism
Enzyme: CYP3A4 [HSA:1576]
Interaction
Drug interaction
Structure map
map07231  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 (USP) <JP/US>
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 (USP); Bupivacaine hydrochloride hydrate (JP17)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated ion channels
   Sodium channels
    SCN1A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
    SCN2A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
    SCN3A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
    SCN4A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
    SCN5A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
    SCN8A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
    SCN9A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
    SCN10A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
    SCN11A
     D01450  Bupivacaine hydrochloride (USP) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D01450  Bupivacaine hydrochloride hydrate
Drug classes of therapeutic agents [br08360.html]
 Anesthetics, analgesics and anti-inflammatory drugs
  D01450
New drug approvals in Japan [br08318.html]
 Drugs with new active ingredients
  D01450
BRITE hierarchy
Other DBs
CAS: 14252-80-3
PubChem: 7848513
ChEBI: 60789
DrugBank: DB00297
LigandBox: D01450
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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