Entry

D01450                      Drug

Name

Bupivacaine hydrochloride (USP);
Bupivacaine hydrochloride hydrate (JP18);
Marcaine (TN)

Product

BUPIVACAINE HCL (HF Acquisition Co LLC), XARACOLL (INNOCOLL PHARMACEUTICALS), SENSORCAINE (General Injectables & Vaccines), MARCAINE (General Injectables & Vaccines), SENSORCAINE (General Injectables & Vaccines), MARCAINE (General Injectables & Vaccines), MARCAINE (Henry Schein), SENSORCAINE (Henry Schein), SENSORCAINE (Henry Schein), MARCAINE (Henry Schein), DURAPREN 0.75% (IT3 Medical LLC), DURAPREN 0.5% (IT3 Medical LLC), MARCAINE SPINAL (Hospira)

Generic

BUPIVACAINE HCI (HF Acquisition Co LLC), BUPIVACAINE HYDROCHLORIDE (A-S Medication Solutions), BUPIVACAINE HYDROCHLORIDE (Asclemed USA), BUPIVACAINE HYDROCHLORIDE (Asclemed USA), BUPIVACAINE HYDROCHLORIDE (AuroMedics Pharma LLC), BUPIVACAINE HYDROCHLORIDE (AuroMedics Pharma LLC), BUPIVACAINE HYDROCHLORIDE (Baxter Healthcare Corporation), BUPIVACAINE HYDROCHLORIDE (Cardinal Health), SENSORCAINE (Fresenius Kabi USA), BUPIVACAINE HYDROCHLORIDE (General Injectables & Vaccines), BUPIVACAINE HYDROCHLORIDE (General Injectables & Vaccines), SENSORCAINE MPF (General Injectables & Vaccines), BUPIVACAINE HYDROCHLORIDE (HF Acquisition Co LLC), BUPIVACAINE HYDROCHLORIDE (Henry Schein), BUPIVACAINE HYDROCHLORIDE (Henry Schein), SENSORCAINE MPF (Henry Schein), BUPIVACAINE HYDROCHLORIDE (Hikma Pharmaceuticals USA), BUPIVACAINE HYDROCHLORIDE (Hikma Pharmaceuticals USA), BUPIVACAINE HYDROCHLORIDE (Huons), BURAPREN 0.5% (IT3 Medical LLC), BURAPREN 0.75% (IT3 Medical LLC), BUPIVACAINE HYDROCHLORIDE (Medical Purchasing Solutions), BUPIVACAINE HYDROCHLORIDE (Medical Purchasing Solutions), BUPIVACAINE HYDROCHLORIDE (Medical Purchasing Solutions), BUPIVACAINE (Hospira), BUPIVACAINE HYDROCHLORIDE WITH DEXTROSE (B. Braun Medical), POINT OF CARE KIT KM (NuCare Pharmaceuticals), POINT OF CARE LM DEP 2 (NuCare Pharmaceuticals), BUPIVICAINE HYDROCHLORIDE (HF Acquisition Co LLC)

Formula

C18H28N2O. HCl. H2O

Exact mass

342.2074

Mol weight

342.9039

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

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