KEGG   DRUG: Bupivacaine hydrochloride
Entry
D01450                      Drug                                   
Name
Bupivacaine hydrochloride (USP);
Bupivacaine hydrochloride hydrate (JP18);
Marcaine (TN)
Product
BUPIVACAINE HCL (HF Acquisition Co LLC), MARCAINE (Henry Schein), MARCAINE (Henry Schein), MARCAINE SPINAL (Hospira), SENSORCAINE (General Injectables & Vaccines), SENSORCAINE (General Injectables & Vaccines), SENSORCAINE (Henry Schein), SENSORCAINE (Henry Schein)
  Generic
BUPIVACAINE (Hospira), BUPIVACAINE HCI (HF Acquisition Co LLC), BUPIVACAINE HCL (Xellia Pharmaceuticals USA LLC), BUPIVACAINE HYDROCHLORIDE (A-S Medication Solutions), BUPIVACAINE HYDROCHLORIDE (Asclemed USA), BUPIVACAINE HYDROCHLORIDE (Asclemed USA), BUPIVACAINE HYDROCHLORIDE (Asclemed USA), BUPIVACAINE HYDROCHLORIDE (Asclemed USA), BUPIVACAINE HYDROCHLORIDE (Brookfield Pharmaceuticals), BUPIVACAINE HYDROCHLORIDE (Camber Pharmaceuticals), BUPIVACAINE HYDROCHLORIDE (Cardinal Health 107), BUPIVACAINE HYDROCHLORIDE (Eugia US LLC), BUPIVACAINE HYDROCHLORIDE (HF Acquisition Co LLC), BUPIVACAINE HYDROCHLORIDE (Henry Schein), BUPIVACAINE HYDROCHLORIDE (Henry Schein), BUPIVACAINE HYDROCHLORIDE (Hikma Pharmaceuticals USA), BUPIVACAINE HYDROCHLORIDE (Hikma Pharmaceuticals USA), BUPIVACAINE HYDROCHLORIDE (Huons), BUPIVACAINE HYDROCHLORIDE (Medical Purchasing Solutions), BUPIVACAINE HYDROCHLORIDE (Medical Purchasing Solutions), BUPIVACAINE HYDROCHLORIDE (Medical Purchasing Solutions), BUPIVACAINE HYDROCHLORIDE (Meitheal Pharmaceuticals), BUPIVACAINE HYDROCHLORIDE (Meitheal Pharmaceuticals), BUPIVACAINE HYDROCHLORIDE (NorthStar RxLLC), BUPIVACAINE HYDROCHLORIDE (Northstar Rx LLC), BUPIVACAINE HYDROCHLORIDE (Somerset Therapeutics), BUPIVACAINE HYDROCHLORIDE (Steriscience Specialties Private Limited), BUPIVACAINE HYDROCHLORIDE (Steriscience Specialties Private Limited), BUPIVACAINE HYDROCHLORIDE (Xellia Pharmaceuticals USA LLC), BUPIVACAINE HYDROCHLORIDE INJECTION, SOLUTION (HF Acquisition Co LLC), BUPIVACAINE HYDROCHLORIDE WITH DEXTROSE (B. Braun Medical), BUPIVICAINE HYDROCHLORIDE (HF Acquisition Co LLC), SENSORCAINE (Fresenius Kabi USA), SENSORCAINE (Fresenius Kabi USA), SENSORCAINE MPF (Henry Schein)
Formula
C18H28N2O. HCl. H2O
Exact mass
342.2074
Mol weight
342.90
Structure
Simcomp
Class
Neuropsychiatric agent
 DG02030  Anesthetics
  DG01675  Local anesthetic
   DG01673  Amide type local anesthetic
Metabolizing enzyme substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Remark
Therapeutic category: 1214
ATC code: N01BB01
Chemical structure group: DG00801
Product (DG00801): D07552<US> D01450<JP/US>
Product (mixture): D11569<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
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>
USP drug classification [BR:br08302]
 Anesthetics
  Local Anesthetics
   Bupivacaine
    D01450  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 (USP); Bupivacaine hydrochloride hydrate (JP18)
Drug groups [BR:br08330]
 Neuropsychiatric agent
  DG02030  Anesthetics
   DG01675  Local anesthetic
    DG01673  Amide type local anesthetic
     DG00801  Bupivacaine
      D01450  Bupivacaine hydrochloride
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00801  Bupivacaine
     D01450  Bupivacaine hydrochloride
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
New drug approvals in Japan [br08318.html]
 Drugs with new active ingredients
  D01450
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D01450
Drug groups [BR:br08330]
 Neuropsychiatric agent
  DG02030  Anesthetics
   DG01675  Local anesthetic
    DG01673  Amide type local anesthetic
     DG00801  Bupivacaine
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00801  Bupivacaine
Other DBs
CAS: 14252-80-3
PubChem: 7848513
ChEBI: 60789
LigandBox: D01450
LinkDB
KCF data

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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