106861-44-3 Usage
Description
Mivacurium chloride, a mixture of three stereoisomers, is an intravenously administered, short-acting skeletal muscle relaxant introduced as an adjunct to general anesthesia. It is a non-depolarizing neuromuscular blocking agent with a shorter duration of action and a more rapid rate of spontaneous recovery than other non-depolarizing agents. Structurally, mivacurium chloride is closely related to doxacurium chloride and is an antagonist of nicotinic acetylcholine receptors (nAChRs) and muscarinic M2 and M3 receptors. It is a non-depolarizing neuromuscular blocking agent used to relax skeletal muscles during surgical procedures. The drug is hydrolyzed by plasma esterases, and anticholinesterase agents used as antidotes could prolong rather than reverse the effects of the drug.
Used in Pharmaceutical Industry:
Mivacurium chloride is used as a non-depolarizing neuromuscular blocking agent for providing muscle relaxation during surgical procedures. Its rapid onset and short duration of action make it suitable for use in various surgical settings.
Used in Anesthesia:
Mivacurium chloride is used as a muscle relaxant for inducing neuromuscular blockade in patients undergoing surgery. It helps in facilitating endotracheal intubation and maintaining muscle relaxation during the procedure.
Used in Pediatric Anesthesia:
Mivacurium chloride is used as a muscle relaxant in pediatric anesthesia, providing effective muscle relaxation for surgical procedures in children.
Chemical Properties:
Mivacurium chloride is an off-white solid.
Brand Name:
Mivacron (Abbott).
Manufacturing Process
To ()-5'-methoxylaudanosine (46.4 g) in methanol (240 mL) was added (-)-
dibenzoyltartaric acid monohydrate (45.2 g). The mixture was heated to
boiling, cooled at 5°C for 16 h and the (S)-(-)-5'-methoxylaudanosinium
dibenzoyltartrate salt (35.6 g, 80%) was filtered and discarded. The mother
liquors were made basic with concentrated aqueous NaOH and evaporated
under vacuum. The solid residue was partitioned between H2O and diethyl
ether. The ether phase was dried and evaporated to an oil (24.9 g). To the oil
in methanol (128 mL) was added (+)-dibenzoyltartaric acid monohydrate
(26.6 g). The mixture was heated to boiling and cooled at 5°C for 16 h.
Crystals were collected and recrystallized from methanol until a constant
specific rotation of [α]D20=+17.7° (1% EtOH) had been achieved. The yield of
(R)-(+)-5'-methoxylaudanosinium dibenzoyltartrate as white crystals was 29.4
g (66%). A portion of the salt (15.0 g) in methanol (200 mL) was made basic
with concentrated aqueous NaOH. The mixture was evaporated under vacuum
and the residue was partitioned between H2O and diethyl ether. The combined
ether layers were dried and evaporated under vacuum to yield 7.2 g (92%) of
(R)-(-)-5'-methoxylaudanosine as an oil.(R)-(-)-5'-Methoxylaudanosine (7.2 g), 3-chloropropanol (3.5 g), sodium
iodide (5.6 g) and sodium carbonate (0.5 g) were refluxed in 2-butanone (125
mL) for 16 h. The white suspension was filtered hot and solvent removed from
the filtrate under vacuum. The residual gum was trituated with hot ethyl
acetate to remove excess 3-iodopropanol, dissolved in 200 mL methanol and
passed through a column packed with Dowex RTM.1-X8 ion exchange resin
(60 g chloride form). The eluant was stripped of solvent under vacuum to give
N-3-hydroxypropyl-1-(R)-5'-methoxylaudanosinium chloride (8.4 g) as an
amophous solid. The material was assayed by HPLC as a 2.3/1 mixture of the trans/cis diastereomers.N-3-Hydroxypropyl-1-(R)-5'-methoxylaudanosinium chloride (2.3/1, trans/cis
by HPLC, 2.5 g) was dissolved in 60 mL 1,2-dichloroethane at about 70°C.
(E)-4-Octene-1,8-dioic acid chloride (0.5 g) (K. Sisido, K. Sei, and H. Nozaki,
J. Org. Chem., 1962, 27, 2681) was added and the mixture was stirred at
ambient temperature for 19 h. Solvent was removed under vacuum to give an
amorphous solid which was dissolved in chloroform (25 mL) and washed with
5% aqueous sodium chloride solution to remove unreacted quaternary salts.
The chloroform layer was dried and evaporated under vacuum to give an
amorphous solid. The acid ester impurities were substantially removed by
washing with hot 2-butanone. Residual solvent was evaporated under vacuum
and the resulting amorphous solid was dissolved in methanol, filtered and
lyophilized to give 1.9 g of (E)-(1R,1'R)-2,2'-[4-octenedioylbis
(oxytrimethylene)]bis[1,2,4,3-tetrahydro-6,7-dimethoxy-2-methyl-1-(3,4,5-
trimethoxybenzyl)isoquinolinium] dichloride, which was assayed by HPLC as
44.6% RS-RS (trans-trans) diester, 42.4% RR-RS (cis-trans) diester, 7.5% RRRR(cis-cis) diester, 4.0% RS (trans) acid ester and 1.5% RR (cis) (E)-
(1R,1'R)-2,2'-[4-Octenedioylbis(oxytrimethylene)]bis[1,2,3,4-tetrahydro-6,7-
dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)isoquinolinium]dichloride acid
ester, [α]D20=-62.7° (1.9% in water).
Therapeutic Function
Muscle relaxant
Biological Functions
Mivacurium chloride (Mivacron) is a newer agent
that is chemically related to atracurium. The primary
mechanism of inactivation is hydrolysis by plasma
cholinesterase. Although it is useful for patients with
renal or hepatic disease, some caution is warranted,
since these individuals may have reduced plasma
cholinesterase as a result of the disease.Mivacurium has
an onset of action (1.8 minutes) and duration of effect
(20 minutes) only twice that of succinylcholine, and in
this respect, it is the most similar to succinylcholine of
all of the nondepolarizing agents.
Check Digit Verification of cas no
The CAS Registry Mumber 106861-44-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,6,8,6 and 1 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 106861-44:
(8*1)+(7*0)+(6*6)+(5*8)+(4*6)+(3*1)+(2*4)+(1*4)=123
123 % 10 = 3
So 106861-44-3 is a valid CAS Registry Number.
