KEGG   DRUG: Bupivacaine hydrochlorideHelp
Entry
D01450                      Drug                                   

Name
Bupivacaine hydrochloride (USP);
Bupivacaine hydrochloride hydrate (JP17);
Marcaine (TN)
Product
  Generic
BUPIVACAINE HYDROCHLORIDE (AuroMedics Pharma LLC), BUPIVACAINE HYDROCHLORIDE (AuroMedics Pharma LLC), BUPIVACAINE HYDROCHLORIDE (Cardinal Health), BUPIVACAINE HYDROCHLORIDE (Cardinal Health), SENSORCAINE (Fresenius Kabi USA), SENSORCAINE (Fresenius Kabi USA), SENSORCAINE (General Injectables & Vaccines), BUPIVACAINE HYDROCHLORIDE (General Injectables & Vaccines), BUPIVACAINE HYDROCHLORIDE (General Injectables & Vaccines), SENSORCAINE MPF (General Injectables & Vaccines), SENSORCAINE (General Injectables & Vaccines), BUPIVACAINE (Hospira), BUPIVACAINE HYDROCHLORIDE (Hospira), BUPIVACAINE HYDROCHLORIDE (REMEDYREPACK), BUPIVACAINE HYDROCHLORIDE (REMEDYREPACK), BUPIVACAINE HYDROCHLORIDE AND EPINEPHRINE (Cardinal Health), BUPIVACAINE HYDROCHLORIDE AND EPINEPHRINE (Cardinal Health), SENSORCAINE (Fresenius Kabi USA)
Formula
C18H28N2O. HCl. H2O
Exact mass
342.2074
Mol weight
342.9039
Structure
Mol fileKCF fileDB searchJmolKegDraw
Class
Cardiovascular agent
 DG01592  COMT substrate
Neuropsychiatric agent
 DG01675  Local anesthetic
  DG01673  Amide type local anesthetic
Cyp substrate
 DG01633  CYP3A4 substrate
Remark
Therapeutic category: 
ATC code: 
Chemical group: 
Activity
Anesthetic (local)
Target
voltage-gated sodium channel (SCN10A) [HSA:6336] [KO:K04842];
voltage-gated sodium channel (SCN1A) [HSA:6323] [KO:K04833];
voltage-gated sodium channel (SCN2A) [HSA:6326] [KO:K04834];
voltage-gated sodium channel (SCN3A) [HSA:6328] [KO:K04836];
voltage-gated sodium channel (SCN4A) [HSA:6329] [KO:K04837];
voltage-gated sodium channel (SCN5A) [HSA:6331] [KO:K04838];
voltage-gated sodium channel (SCN8A) [HSA:6334] [KO:K04840];
voltage-gated sodium channel (SCN9A) [HSA:6335] [KO:K04841]
Metabolism
Enzyme: CYP3A4 [HSA:1576]
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
     N01BB01 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 (JP17)
Target-based classification of drugs [BR:br08310]
 Ion channels
  Voltage-gated cation channels
   Na+ channel, SCN alpha, NaV1.x
    voltage-gated sodium channel (SCN1A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN2A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN3A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN4A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN5A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN8A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN9A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride (USP)
    voltage-gated sodium channel (SCN10A)
     Bupivacaine
      D01450  Bupivacaine hydrochloride (USP)
Cytochrome P450 interactions [BR:br08309]
 CYP substrates
  CYP3A4
   Bupivacaine
    D01450  Bupivacaine hydrochloride (USP)
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D01450  Bupivacaine hydrochloride hydrate
Anesthetics and analgesics [br08369.html]
 Anesthetics
  D01450
BRITE hierarchy
Other DBs
CAS: 
14252-80-3
PubChem: 
DrugBank: 
LigandBox: 
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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