KEGG   DRUG: BupivacaineHelp
Entry
D07552                      Drug                                   

Name
Bupivacaine (USAN/INN);
Bucaine (TN);
Exparel (TN)
Product
Formula
C18H28N2O
Exact mass
288.2202
Mol weight
288.4277
Structure
Mol fileKCF fileDB search
Simcomp SIMCOMP
Class
Neuropsychiatric agent
 DG02030  Anesthetics
  DG01675  Local anesthetic
   DG01673  Amide type local anesthetic
 DG01675  Local anesthetic
  DG01673  Amide type local anesthetic
Enzyme substrate
 DG01633  CYP3A substrate
Remark
Same as: C07529
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
      D07552  Bupivacaine (USAN/INN) <US>
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated ion channels
   Sodium channels
    SCN1A
     D07552  Bupivacaine (USAN/INN) <US>
    SCN2A
     D07552  Bupivacaine (USAN/INN) <US>
    SCN3A
     D07552  Bupivacaine (USAN/INN) <US>
    SCN4A
     D07552  Bupivacaine (USAN/INN) <US>
    SCN5A
     D07552  Bupivacaine (USAN/INN) <US>
    SCN8A
     D07552  Bupivacaine (USAN/INN) <US>
    SCN9A
     D07552  Bupivacaine (USAN/INN) <US>
    SCN10A
     D07552  Bupivacaine (USAN/INN) <US>
    SCN11A
     D07552  Bupivacaine (USAN/INN) <US>
BRITE hierarchy
Other DBs
CAS: 2180-92-9
PubChem: 51091874
ChEBI: 3215 77431
ChEMBL: CHEMBL1098
LigandBox: D07552
NIKKAJI: J7.351B
LinkDB All DBs
KCF data Show

ATOM        21
            1   C1y C    25.9700  -17.6400
            2   N1y N    25.9700  -19.0400
            3   C5a C    24.7800  -16.9400
            4   C1b C    24.7800  -19.7400
            5   N1b N    23.5900  -17.6400
            6   O5a O    24.7800  -15.5400
            7   C1b C    23.5900  -19.0400
            8   C8y C    22.4000  -16.8700
            9   C1b C    22.3300  -19.7400
            10  C8y C    21.1400  -17.5700
            11  C8y C    22.4000  -15.4700
            12  C1a C    22.3300  -21.0700
            13  C8x C    19.9500  -16.8700
            14  C1a C    21.1400  -18.9700
            15  C8x C    21.1400  -14.7700
            16  C8x C    19.9500  -15.4700
            17  C1a C    23.5900  -14.7700
            18  C1x C    27.1600  -19.7400
            19  C1x C    28.4200  -19.0400
            20  C1x C    28.4200  -17.6400
            21  C1x C    27.2300  -16.9400
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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