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Atracurium Besylate

HCID 47320
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
64228-81-5
Standard SMILES
COc1ccc(CC2c3cc(OC)c(OC)cc3CC[N+]2(C)CCC(=O)OCCCCCOC(=O)CC[N+]2(C)CCc3cc(OC)c(OC)cc3C2Cc2ccc(OC)c(OC)c2)cc1OC.O=S(=O)([O-])c1ccccc1.O=S(=O)([O-])c1ccccc1
InChIKey
XXZSQOVSEBAPGS-UHFFFAOYSA-L
Molecular formula
C65H82N2O18S2
Average molar mass
1,243.5 g/mol
Monoisotopic mass
1,242.50040612

Names & identifiers

Preferred name
Atracurium Besylate
IUPAC
benzenesulfonate;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
English name
Atracurium besylate
Molecular formula
C65H82N2O18S2
Molecular weight
1243.48

Names & synonyms

Atracurium besylate64228-81-5Atracurium besilateAtracurium DibesylateBesilato de atracurioAtracurii besilasBesilate d'atracuriumBW 33ABW-33ATracrium Preservative FreeAtracurium Besylate Preservative FreeDTXSID6022630
Show more names
Atracurim besylate51W89TracurTRACRIUM51W-89:NimbexWellcome 33A74Atracurium BesyLtracurium Besylate
benzenesulfonate;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]propanoateNSC-760047WELLCOME 33-A-74CHEBI:2915DTXCID30263040AX66P76Patracurio besilatobenzenesulfonate;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

Database identifiers

Properties

Computed structural propertiesFilling in

Topological polar surface area
258 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
18
Rotatable bonds
26
Heavy atoms
87
Formal charge
0
Complexity
1,560

Experimental & physicochemical properties

SolubilityMiscible
Melting Point85-90

Physicochemical properties

Melting point
85 · 85-90°C
storage temp.
2 · Inert atmosphere,2-8°C
solubility
2 O: · H2O: ~27 mg/mL
form
powder
color
white
Major Application
pharmaceutical (small molecule)
InChIKey
YXSLJKQTIDHPOT-UHFFFAOYSA-N
SMILES
[O-]S(=O)(=O)c1ccccc1.[O-]S(=O)(=O)c2ccccc2.COc3ccc(CC4c5cc(OC)c(OC)cc5CC[N+]4(C)CCC(=O)OCCCCCOC(=O)CC[N+]6(C)CCc7cc(OC)c(OC)cc7C6Cc8ccc(OC)c(OC)c8)cc3OC
CAS DataBase Reference
64228 · 64228-81-5(CAS DataBase Reference)
FDA UNII
40 AX66P76P · 40AX66P76P
UNSPSC Code
41116107 · 41116107

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

Danger

H300 (24.3%): Fatal if swallowed [Danger Acute toxicity, oral];H301 (70.3%): Toxic if swallowed [Danger Acute toxicity, oral];H310 (25.7%): Fatal in contact with skin [Danger Acute toxicity, dermal];H330 (25.7%): Fatal if inhaled [Danger Acute toxicity, inhalation]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 74 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 2 (24.3%);Acute Tox. 3 (70.3%);Acute Tox. 2 (25.7%);Acute Tox. 2 (25.7%)

Toxicology

Effects During Pregnancy and Lactation · 1 item

◉ Summary of Use during Lactation;No information is available on the use of atracurium during breastfeeding. Because it is short acting, highly polar and poorly absorbed orally, it is not likely to reach the breastmilk in high concentration or to reach the bloodstream of the infant. When a combination of anesthetic agents is used for a procedure, follow the recommendations for the most problematic medication used during the procedure. Consider using an atracurium product that has no benzyl alcohol preservative.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information was not found as of the revision date.

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Atracurium is a nondepolarizing skeletal muscle relaxant. Atracurium can be used most advantageously if muscle twitch response to peripheral nerve stimulation is monitored to assess degree of muscle relaxation. The duration of neuromuscular block produced by Atracurium is approximately one third to one half the duration of block by d-tubocurarine, metocurine, and pancuronium at initially equipotent doses. As with other nondepolarizing neuromuscular blockers, the time to onset of paralysis decreases and the duration of maximum effect increases with increasing doses of Atracurium. Repeated administration of maintenance doses of Atracurium has no cumulative effect on the duration of neuromuscular block if recovery is allowed to begin prior to repeat dosing. Moreover, the time needed to recover from repeat doses does not change with additional doses. Repeat doses can therefore be administered at relatively regular intervals with predictable results.

Mechanism of Action · 1 item

Atracurium antagonizes the neurotransmitter action of acetylcholine by binding competitively with cholinergic receptor sites on the motor end-plate. This antagonism is inhibited, and neuromuscular block reversed, by acetylcholinesterase inhibitors such as neostigmine, edrophonium, and pyridostigmine.

Biological Half-LifeThe elimination half-life is approximately 20 minutes.
FDA Pharmacological Classification · 2 items

ATRACURIUM BESYLATE

Neuromuscular Nondepolarizing Blockade [PE]; Nondepolarizing Neuromuscular Blocker [EPC]

MeSH Pharmacological Classification · 2 items

Drugs that interrupt transmission at the skeletal neuromuscular junction without causing depolarization of the motor end plate. They prevent acetylcholine from triggering muscle contraction and are used as muscle relaxants during electroshock treatments, in convulsive states, and as anesthesia adjuvants.

Drugs that bind to nicotinic cholinergic receptors (RECEPTORS, NICOTINIC) and block the actions of acetylcholine or cholinergic agonists. Nicotinic antagonists block synaptic transmission at autonomic ganglia, the skeletal neuromuscular junction, and at central nervous system nicotinic synapses.

Related reactions

2 records
New reaction record
HRID 1808316 reaction equation
HRID 1808316As reactantuspto-grants-2013_01
HRID 2067921 reaction equation
HRID 2067921As reactantuspto-grants-2012_10

Compound notes

Loading…

On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS
64228-81-5
PubChem CID
47320
DTXSID
DTXSID6022630
ChEMBL
CHEMBL1200527
ChEBI
CHEBI:2915
EC Number
264-743-4
NACRES
24 · NA.24
Protein binding
82 % · 82%
Volume of distribution
0.16 · 0.16(L/kg)
Biological half-life
20 minutes · Approx 20 minutes / Unchanged
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
280 · P280-P305+P351+P338
Safety Statements
24 · 24/25
WGK Germany
3 · 3
HS Code
29334900 · 29334900
Storage Class
11 · 11 - Combustible Solids

Safety data

wgk
3
hs_code
29334900
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302
Precautionary statements
P280-P305+P351+P338

Uses & manufacturing

Uses · 2 items

Use (kg; approx.) in Germany (2009): >75;Consumption (g per capita; approx.) in Germany (2009): 0.000916;Calculated removal (%): 99.7

Use (kg; approx.) in Germany (2009): >10;Consumption (g per capita; approx.) in Germany (2009): 0.000122;Calculated removal (%): 99.7

Applications · 3 items

Uses1. It is a kind of non-depolarizing muscle relaxants with the 2.5 times of effect as high as tubocurarine 2.5 times but with a short duration. It is used for a variety of surgical procedures, especially for intubation and caesarean section. 2. It is a skeletal muscle relaxant for general anesthesia.

UsesA neuromuscular blocking agent

General DescriptionAtracurium besylate, 2-(2-carboxyethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolinium benzenesulfonate pentamethyleneester (Tracrium), is a nondepolarizing neuromuscular blockingagent that is approximately 2.5 times more potent thand-tubocurarine. Its duration of action (half-life, 0.33 hours)is much shorter than that of d-tubocurarine.

Upstream & downstream products

Upstream raw materials

Triethylamine hydrochlorideMethyl benzenesulfonateSalmeterol xinafoateAnhydrous benzenePAPAVERINEAcryloyl chloridePyrogallol1,5-Pentanediol6-Benzylaminopurinespectrum(+/-)-Tetrahydropapaverine(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]indene-2,5-diol1,5-Diaminopentane dihydrochloride

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东雨禾医药科技有限公司15263077727 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
广州市亿邦医药科技有限公司+86 (20) 28996708,29078958,28139708,29076128,28133708,28139728,28139738,28133718,021-31663278,021-31663578,021-60538387
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
上海药坦药物研究开发有限公司15512780135 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
上海攀鸿化工科技有限公司021-56491756 13512199871 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
Beckmann-Kenko GmbH+49 4241 9308 88 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
Wuhan Demeikai Biotechnology Co., Ltd+8618942921723 · [email protected]
百盛HK进出口有限公司+86-18068513926
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
Wuhan NCE Biomedical Co.,Ltd.4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海诺宝化工有限公司+86(0)21 60484900
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
东阳市鸿森科技有限公司+86-0579-86846643 18072368515 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
台州市科德化工有限公司0576-84613060 13093829633;13736603231 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
南京伶亚生物医药科技有限公司18068075658 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海皓之翔生物科技有限公司(原上海拓青化工有限公司)526763801 13301653310 · [email protected]

Additional notes

DefinitionChEBI: The bisbenzenesulfonate salt of atracurium.