KEGG   DRUG: D01287Help
Entry
D01287                      Drug                                   

Name
Levobupivacaine hydrochloride (JAN/USAN);
Chirocaine (TN)
Formula
C18H28N2O. HCl
Exact mass
324.1968
Mol weight
324.8887
Structure
Mol fileKCF fileDB searchJmolKegDraw
Activity
Local anesthetic;
Analgesic
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], CYP1A2 [HSA:1544]
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
     N01BB10 Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
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
     D01287  Levobupivacaine hydrochloride (JAN/USAN)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Na+ channel, SCN alpha, NaV1.x
    voltage-gated sodium channel (SCN1A)
     Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
    voltage-gated sodium channel (SCN2A)
     Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
    voltage-gated sodium channel (SCN3A)
     Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
    voltage-gated sodium channel (SCN4A)
     Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
    voltage-gated sodium channel (SCN5A)
     Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
    voltage-gated sodium channel (SCN8A)
     Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
    voltage-gated sodium channel (SCN9A)
     Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
    voltage-gated sodium channel (SCN10A)
     Levobupivacaine
      D01287  Levobupivacaine hydrochloride (JAN/USAN)
Cytochrome P450 interactions [BR:br08309]
 Substrates
  CYP1A2
   Levobupivacaine
    D01287  Levobupivacaine hydrochloride (JAN/USAN)
  CYP3A4
   Levobupivacaine
    D01287  Levobupivacaine hydrochloride (JAN/USAN)
BRITE hierarchy
Other DBs
CAS: 
27262-48-2
PubChem: 
DrugBank: 
LigandBox: 
KCF data Show

ATOM        22
            1   C1y C    26.0358  -18.8835
            2   N1y N    26.0184  -20.2817
            3   C5a C    24.8241  -18.1727
            4   C1x C    27.2477  -18.1843
            5   C1x C    27.2301  -20.9866
            6   C1b C    24.8008  -20.9692
            7   N1b N    23.6122  -18.8661
            8   O5a O    24.8357  -16.7687
            9   C1x C    28.4535  -18.8951
            10  C1x C    28.4478  -20.2991
            11  C1b C    23.6005  -20.2701
            12  C8y C    22.4004  -18.1553
            13  C1b C    22.3888  -20.9633
            14  C8y C    21.1828  -18.8485
            15  C8y C    22.4121  -16.7511
            16  C1a C    22.3888  -22.3558
            17  C8x C    19.9768  -18.1377
            18  C1a C    21.1828  -20.2409
            19  C8x C    21.2002  -16.0462
            20  C1a C    23.3966  -15.7433
            21  C8x C    19.9768  -16.7395
            22  X   Cl   31.4327  -19.6720
BOND        22
            1     1   2 1
            2     1   3 1 #Down
            3     1   4 1
            4     2   5 1
            5     2   6 1
            6     3   7 1
            7     3   8 2
            8     4   9 1
            9     5  10 1
            10    6  11 1
            11    7  12 1
            12   11  13 1
            13   12  14 1
            14   12  15 2
            15   13  16 1
            16   14  17 2
            17   14  18 1
            18   15  19 1
            19   15  20 1
            20   17  21 1
            21    9  10 1
            22   19  21 2

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