Bupivacaine hydrochloride Chemical Properties

Melting point:

249-2510C

storage temp. 

Refrigerator

solubility 

Soluble in water, freely soluble in alcohol.

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

InChI

InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H

InChIKey

SIEYLFHKZGLBNX-UHFFFAOYSA-N

SMILES

C1(CCCCN1CCCC)C(=O)NC1C(C)=CC=CC=1C.Cl

CAS DataBase Reference

14252-80-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

T+

Risk Statements 

26/27/28

Safety Statements 

22-36/37/39-45

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

TK6125000

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2933399090

Toxicity

LD50 in mice (mg/kg): 7.8 i.v., 82 s.c. (Henn, Brattsand)

Bupivacaine hydrochloride Usage And Synthesis

Chemical Properties

White Solid

Uses

antineoplastic

Uses

Bupivacaine Hydrochloride is the salt form of Bupivacaine (B689561); is a sodium channel blocker, local anesthetic.

Definition

ChEBI: Bupivacaine hydrochloride (anhydrous) is a racemate composed of equimolar amounts of dextrobupivacaine hydrochloride and levobupivacaine hydrochloride. The monohydrate form is commonly used as a local anaesthetic. It has a role as an adrenergic antagonist, an amphiphile, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor and a local anaesthetic. It contains a levobupivacaine hydrochloride (anhydrous), a dextrobupivacaine hydrochloride (anhydrous) and a bupivacaine(1+).

brand name

Marcaine (Hospira); Sensorcaine (AstraZeneca).

Biological Functions

Bupivacaine hydrochloride (Marcaine, Sensorcaine) has particularly long action, and some nerve blocks last more than 24 hours; this is often an advantage for postoperative analgesia. Its use for epidural anesthesia in obstetrics has attracted interest because it can relieve the pain of labor at concentrations as low as 0.125% while permitting some motor activity of abdominal muscles to aid in expelling the fetus. The lower concentration minimizes the possibility of cardiac toxicity. Fetal drug concentrations remain low, and drug-induced neurobehavioral changes are not observed in the newborn. Bupivacaine also is approved for spinal anesthesia and is approximately four times more potent and more toxic than mepivacaine and lidocaine. It can be used with or without epinephrine.

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