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Mivacurium chloride

Product Name
Mivacurium chloride
CAS No.
106861-44-3
Chemical Name
Mivacurium chloride
Synonyms
(S)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline;Mivacron;BW-B1090U;rac-Mivacron;rac-BW-B 1090;rac-BW-B 1090U;Lomiwa Reservoir;BMS-512148 (2S)-1;MIVACURIUM CHLORIDE;Mivacarium Chloride
CBNumber
CB7218031
Molecular Formula
C58H80ClN2O14+
Formula Weight
1064.73
MOL File
106861-44-3.mol
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Mivacurium chloride Property

alpha 
20D -62.7° (c = 1.9 in water)
storage temp. 
Hygroscopic, -20°C Freezer, Under Inert Atmosphere
solubility 
DMSO: Soluble; Water: Soluble
form 
A solid
color 
White to off-white
Stability:
Hygroscopic
InChI
InChI=1/C58H80N2O14.ClH/c1-59(25-21-41-35-47(63-3)49(65-5)37-43(41)45(59)29-39-31-51(67-7)57(71-11)52(32-39)68-8)23-17-27-73-55(61)19-15-13-14-16-20-56(62)74-28-18-24-60(2)26-22-42-36-48(64-4)50(66-6)38-44(42)46(60)30-40-33-53(69-9)58(72-12)54(34-40)70-10;/h13-14,31-38,45-46H,15-30H2,1-12H3;1H/q+2;/p-1/b14-13+;/t45-,46-,59?,60?;/s3
InChIKey
KFWHZSUNFAPZPW-NVIAPQDINA-M
SMILES
C(C1C=C(OC)C(OC)=C(OC)C=1)[C@H]1[N+](CCC2=CC(OC)=C(OC)C=C12)(C)CCCOC(=O)CC/C=C/CCC(=O)OCCC[N+]1(CCC2=CC(OC)=C(OC)C=C2[C@H]1CC1C=C(OC)C(OC)=C(OC)C=1)C.[Cl-] |&1:13,59,r|
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
23610
Product name
Mivacurium (chloride)
Purity
≥95%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
23610
Product name
Mivacurium (chloride)
Purity
≥95%
Packaging
5mg
Price
$93
Updated
2024/03/01
Cayman Chemical
Product number
23610
Product name
Mivacurium (chloride)
Purity
≥95%
Packaging
10mg
Price
$146
Updated
2024/03/01
TRC
Product number
M385000
Product name
MivacuriumChloride(MixtureofIsomers)
Packaging
2.5mg
Price
$55
Updated
2021/12/16
Usbiological
Product number
017687
Product name
Mivacurium Chloride
Packaging
2.5mg
Price
$425
Updated
2021/12/16
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Mivacurium chloride Chemical Properties,Usage,Production

Description

Mivacurium chloride,a mixture of three stereoisomers, is an intravenously administered, short-acting skeletal muscle relaxant introduced as an adjunct to general anesthesia. Structurally mivacurium chloride is closely related to doxacurium chloride introduced in 1991 by Wellcome as a muscle relaxant. It is a nondepolarizing neuromuscular blocking agent reportedly with a shorter duration of action and a more rapid rate of spontaneous recovery than other nondepolarizing agents. In extensive clinical trials mivacurium chloride was well tolerated with few side effects.

Description

Mivacurium is an antagonist of nicotinic acetylcholine receptors (nAChRs) and muscarinic M2 and M3 receptors (ED50s = 0.08, 0.3, and 0.1 mg/kg for ex vivo human skeletal muscle nAChRs, guinea pig cardiac M2 receptors, and guinea pig bronchial M3 receptors, respectively). It inhibits acetylcholine-induced activation of neuronal nAChRs (IC50s = 69.04, 3.71, 1.52, and 2.90 for human α3β2-, α3β4-, α4β2-, and α7-containing nAChRs expressed in Xenopus oocytes). Mivacurium also inhibits adult human muscular α1β1εδ-containing nAChRs (IC50 = 3.69 nM in Xenopus oocytes expressing the human recombinant receptor). In vivo, mivacurium inhibits bradycardia and bronchoconstriction induced by vagal stimulation or acetylcholine in guinea pigs. It also induces neuromuscular blockade (ED95 = 80 μg/kg) in sheep with a more rapid onset time than atracurium and vecuronium . Formulations containing mivacurium have been used for pediatric anesthesia.

Chemical Properties

Off-White Solid

Originator

Wellcome (United Kingdom)

Uses

Non-depolarizing neuromuscular blocking agent. Muscle relaxant (skeletal)

Definition

ChEBI: Mivacurium chloride is a member of isoquinolines.

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).

brand name

Mivacron (Abbott).

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.

General Description

Mivacurium chloride, 1,2,3,4-tetrahydro-2-(3-hydroxypropyl)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)isoquinolinium chloride, (E)-4-octandioate (Mivacron), is a mixture of three stereoisomers,the trans-trans, cis-trans, and cis-cis diesters, each ofwhich has neuromuscular blocking properties. The cis-cisisomer is about one tenth as potent as the other isomers.Mivacurium chloride is a short-acting nondepolarizing drugused as an adjunct to anesthesia to relax skeletal muscle.The drug is hydrolyzed by plasma esterases, and it is likelythat anticholinesterase agents used as antidotes could prolongrather than reverse the effects of the drug.

Mivacurium chloride Preparation Products And Raw materials

Raw materials

3-Chloro-1-propanol PAPAVERINE HYDROCHLORIDE 2-Butanone CHLOROETHANE

Preparation Products

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Mivacurium chloride Suppliers

Canada 1 China 99 Europe 2 Germany 1 India 3 Italy 2 Spain 2 United States 13 Global 123
Wuhan Brin Technology Co., Ltd.
Tel
3456065315 13260619011
Email
3456065315@qq.com
Country
China
ProdList
1972
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58
Beijing Jingzi Pharmaceutical Technology Co., Ltd.
Tel
15011485209
Email
17241816@qq.com
Country
China
ProdList
81
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
9976
Advantage
60
Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
Advantage
62
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Chemsky（shanghai）International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
China Langchem Inc.
Tel
0086-21-58956006
Fax
0086-21-58956100
Country
China
ProdList
7811
Advantage
57
Hunan Hui Bai Shi Biotechnology Co., Ltd.
Tel
0731-85526065 13308475853
Email
ivy@hnhbsj.com
Country
China
ProdList
4554
Advantage
62
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
14055
Advantage
65
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View Lastest Price from Mivacurium chloride manufacturers

Guangzhou Tosun Pharmaceutical Limited
Product
Mivacurium Chloride 106861-44-3
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
above 98%
Supply Ability
10g/month
Release date
2023-05-10
Hebei Mingeng Biotechnology Co., Ltd
Product
Mivacurium Dichloride 106861-44-3
Price
US $200.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg/Month
Release date
2022-11-21
Dideu Industries Group Limited
Product
Mivacurium chloride 106861-44-3
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-07-07

106861-44-3, Mivacurium chlorideRelated Search:

BENZALKONIUM CHLORIDE Thionyl chloride Calcium chloride Benzalkonium chloride Dequalinium chloride Choline chloride Cetylpyridinium chloride Trospium chloride Sodium chloride Potassium chloride Polyvinyl chloride Ammonium chloride CIS-3-OCTENE DL-LAUDANOSINE (R)-(+)-Tetrahydropapaverine (R)-1-(3-Methoxyphenyl)ethylamine Methylene Chloride 1-BENZYL-6,7-DIMETHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE

  • MIVACURIUM CHLORIDE
  • rac Mivacurium Chloride
  • rac-BW-B 1090
  • rac-Mivacron
  • rel-(1R,1'R)-2,2'-[[(4E)-1,8-Dioxo-4-octene-1,8-diyl]bis(oxy-3,1-propanediyl)]bis[1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]- isoquinolinium Chloride
  • [R-[R*,R*-(E)]]2,2'-(1,8-Dioxo-4-octene-1,8-diyl)bis(oxy-3,1-propanediyl)bis[1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxyphenyl)isoquinolinium] dichloride
  • rac-BW-B 1090U
  • -1，2，3，4-Te．trahydro-2-(3-hydroxypropyl)-6，7-dimethoxy-2-methyl-1-(3，4，5-trimethoxy-benzyl)isoquinolinium chloride，(E)-4-octenedioate(2：1)
  • BW-B1090U
  • Mivacron
  • (1R,1'R)-2,2'-[[(4E)-1,8-Dioxo-4-octene-1,8-diyl]bis(oxy-3,1-propanediyl)]bis[1,2,3,4-tetrahydro-6,7-diMethoxy-2-Methyl-1-[(3,4,5-triMethoxyphenyl)Methyl]-isoquinoliniuM Chloride
  • Mivacurium Chloride (mixture of isomers)
  • Mivacurium Chloride (Mixture of Diastereomers)
  • (S)-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
  • (R)-3-(6,7-dimethoxy-1-(3,4,5-trimethoxybenzyl)-3,4-dihydroisoquinolin-2(1H)-yl)propan-1-ol
  • Mivacurium Chloride Impurity 6
  • (R)-3-(2-chloro-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydro-2l5-isoquinolin-2-yl)propyl acetate
  • Mivacurium Chloride Impurity 7
  • (R,E)-9-(3-(2-chloro-6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydro-2l5-isoquinolin-2-yl)propoxy)-9-oxonon-5-enoic acid
  • Micuronium Chloride impurity
  • Micuronium Chloride isomers
  • Z-Micuronium Chloride
  • Mivacurium dichloride
  • Mivacurium chloride USP/EP/BP
  • Mivacarium Chloride
  • Mivacurium Chloride ( isomers)
  • BMS-512148 (2S)-1
  • Dapagliflozin ((2S)-1
  • Micuronium chloride
  • Lomiwa Reservoir
  • (1R,1'R)-2,2'-((((E)-Oct-4-enedioyl)bis(oxy))bis(propane-3,1-diyl))bis(6,7-dimethoxy-2-methyl-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-2-ium) chloride
  • 106861-44-3
  • 10686-44-3
  • C58H80Cl2N2O14
  • Intermediates & Fine Chemicals
  • Neurochemicals
  • Pharmaceuticals
  • API