atracurium

Names

[ Name ]:
atracurium

[Synonym ]:
5-[3-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl 3-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]propanoate
2,2'-{1,5-Pentanediylbis[oxy(3-oxo-3,1-propanediyl)]}bis[1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium]
Isoquinolinium, 2,2'-[1,5-pentanediylbis[oxy(3-oxo-3,1-propanediyl)]]bis[1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-
Atracurium
2,2'-{Pentane-1,5-diylbis[oxy(3-oxopropane-3,1-diyl)]}bis[1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium]
UNII-2GQ1IRY63P
Atracurium Dibesylate

Biological Activity

[Description]:

tracurium (BW-33A free acid) is a potent, competitive and non-depolarizing neuromuscular blocking agent.Atracurium also is an AChR receptor antagonist. Atracurium induces bronchoconstriction and neuromuscular blockade. Atracurium promotes astroglial differentiation[1][2][3][4][5].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR

Signaling Pathways >> Neuronal Signaling >> nAChR

Research Areas >> Inflammation/Immunology

[In Vitro]

Atracurium (10 µM; 72 h) promotes astroglial but not neuronal differentiation in HSR040622 and HSR040821 cells[4]. Atracurium (10 µM; 48 h) reduces tumor engraftment and increases survival of mice xenotransplanted with ex-vivo treated GSCs[4]. Atracurium (2.4 µM; 120 min) induces a complete fade of the tetanic contraction while only slightly affected the twitch in rat extensor digitorum longus muscle cells[5]. Cell Proliferation Assay[4] Cell Line: glioblastoma stem (GSC) cells Concentration: 3, 10, 20 µM Incubation Time: 72 h Result: Increased the percentage of GFP-positive cells in a dose-dependent manner from 5.3% in DMSO to 15.4%, 81.1%, and 86.8% in 3 μM, 10 μM, and 20 μM, respectively.

[In Vivo]

Atracurium (1, 5, 10, 20, 50 mg/kg; i.v.) induces bronchoconstriction in DBA/2 and SJL mice[2]. Atracurium (4.8 mg/kg; i.v.) induces neuromuscular blockade in rats[3]. Animal Model: 5-12 weeks, 15-20 g male mice[2] Dosage: 1, 5, 10, 20, 50 mg/kg Administration: I.v. Result: Induced bronchoconstriction and Atracurium-induced airway hyperresponsiveness in DBA/2 mice was eliminated in a dose-dependent manner by pretreatment with atropine or pancuronium. Animal Model: 290 ± 30 g Male Sprague±Dawley rats (60 mg/kg heat-killed Corynebacteriumparvum for i.v.)[3] Dosage: 4.8 mg/kg Administration: I.v. Result: Induced neuromuscular blockade in Corynebacteriumparvum-injected rats.

[References]

[1]. Basta SJ, et al. Clinical pharmacology of atracurium besylate (BW 33A): a new non-depolarizing muscle relaxant. Anesth Analg. 1982 Sep;61(9):723-9.

[2]. Levitt RC, et al. Genetic susceptibility to atracurium-induced bronchoconstriction. Am J Respir Crit Care Med. 1995 May;151(5):1537-42.

[3]. Mayer B, et al. Inflammatory liver disease shortens atracurium-induced neuromuscular blockade in rats. Eur J Anaesthesiol. 2001 Sep;18(9):599-604.

[4]. Spina R, et al. Atracurium Besylate and other neuromuscular blocking agents promote astroglial differentiation and deplete glioblastoma stem cells. Oncotarget. 2016 Jan 5;7(1):459-72.

[5]. Nascimento DC, et al. Cellular mechanisms of atracurium-induced tetanic fade in the isolated rat muscle. Basic Clin Pharmacol Toxicol. 2004 Jul;95(1):9-14.

Chemical & Physical Properties

[ Melting Point ]:
185-194ºC

[ Molecular Formula ]:
C₅₃H₇₂N₂O₁₂++

[ Molecular Weight ]:
929.144

[ Exact Mass ]:
928.507446

[ PSA ]:
126.44000

[ LogP ]:
1.04

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NX5841000

CHEMICAL NAME :: Isoquinolinium, 1,2,3,4-tetrahydro-2,2'-(1,5-pentanediylbis(oxy(3-oxo -3,1-propanediyl)))bis (1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-2-meth yl-

CAS REGISTRY NUMBER :: 64228-79-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C53-H72-N2-O12

MOLECULAR WEIGHT :: 929.27

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 520 ug/kg

TOXIC EFFECTS :: Cardiac - pulse rate

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 287,247,1983