ChemicalBook Product Catalog API Anesthetic Agents Local anesthetics Bupivacaine hydrochloride

Bupivacaine hydrochloride

Product NameBupivacaine hydrochloride
CAS14252-80-3
MFC18H28N2O.ClH
MW324.89
EINECS627-065-3
MOL File14252-80-3.mol

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)

Usage And Synthesis

Chemical Properties

White Solid

Uses

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

Uses

antineoplastic

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.