Bupivacaine hydrochloride is 2-Piperidinecarboxamide,
1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, monohydrate, a white
crystalline powder that is freely soluble in 95 percent ethanol, soluble in
water, and slightly soluble in chloroform or acetone. It has the following
(-)-3,4-Dihydroxy-α-[(methylamino)methyl] benzyl alcohol. It has the
following structural formula:
MARCAINE is available in sterile
isotonic solutions with and without epinephrine (as bitartrate) 1:200,000 for
injection via local infiltration, peripheral nerve block, and caudal and lumbar
epidural blocks. Solutions of MARCAINE may be autoclaved if they do not contain
epinephrine. Solutions are clear and colorless.
Bupivacaine is related chemically
and pharmacologically to the aminoacyl local anesthetics. It is a homologue of
mepivacaine and is chemically related to lidocaine. All three of these
anesthetics contain an amide linkage between the aromatic nucleus and the
amino, or piperidine group. They differ in this respect from the procaine-type
local anesthetics, which have an ester linkage.
MARCAINE - Sterile isotonic
solutions containing sodium chloride. In multiple-dose vials, each mL also contains
1 mg methylparaben as antiseptic preservative. The pH of these solutions is
adjusted to between 4 and 6.5 with sodium hydroxide or hydrochloric acid.
MARCAINE with epinephrine
1:200,000 (as bitartrate) - Sterile isotonic solutions containing sodium chloride. Each
mL contains bupivacaine hydrochloride and 0.0091 mg epinephrine bitartrate,
with 0.5 mg sodium metabisulfite, 0.001 mL monothioglycerol, and 2 mg ascorbic
acid as antioxidants, 0.0017 mL 60% sodium lactate buffer, and 0.1 mg edetate
calcium disodium as stabilizer. In multiple-dose vials, each mL also contains 1
mg methylparaben as antiseptic preservative. The pH of these solutions is
adjusted to between 3.4 and 4.5 with sodium hydroxide or hydrochloric acid. The
specific gravity of MARCAINE 0.5% with epinephrine 1:200,000 (as bitartrate) at
25°C is 1.008 and at 37°C is 1.008.
What are the possible side effects of bupivacaine (Marcaine HCl, Marcaine Spinal, Sensorcaine, Sensorcaine-MPF)?
Get emergency medical help if you have any of these signs of an allergic reaction: hives; difficulty breathing; swelling of your face, lips, tongue, or throat.
Tell your caregivers at once if you have any of these serious side effects:
- weak or shallow breathing;
- fast heart rate, gasping, feeling unusually hot;
- slow heart rate, weak pulse;
- feeling restless or anxious, ringing in the ears, metallic taste, speech problems, numbness or tingling around your mouth, tremors, feeling light-headed, or...
Read All Potential Side Effects and See Pictures of Marcaine »
Last reviewed on RxList: 2/21/2012
This monograph has been modified to include the generic and brand name in many instances.