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Also known as: 64228-81-5, Atracurium besilate, Tracrium, Atracurium (besylate), Bw-33a, Atracurium dibesylate
Molecular Formula
C65H82N2O18S2
Molecular Weight
1243.5  g/mol
InChI Key
XXZSQOVSEBAPGS-UHFFFAOYSA-L

Atracurium Besylate
A non-depolarizing neuromuscular blocking agent with short duration of action. Its lack of significant cardiovascular effects and its lack of dependence on good kidney function for elimination provide clinical advantage over alternate non-depolarizing neuromuscular blocking agents.
1 2D Structure

Atracurium Besylate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
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
2.1.2 InChI
InChI=1S/C53H72N2O12.2C6H6O3S/c1-54(22-18-38-32-48(62-7)50(64-9)34-40(38)42(54)28-36-14-16-44(58-3)46(30-36)60-5)24-20-52(56)66-26-12-11-13-27-67-53(57)21-25-55(2)23-19-39-33-49(63-8)51(65-10)35-41(39)43(55)29-37-15-17-45(59-4)47(31-37)61-6;2*7-10(8,9)6-4-2-1-3-5-6/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3;2*1-5H,(H,7,8,9)/q+2;;/p-2
2.1.3 InChI Key
XXZSQOVSEBAPGS-UHFFFAOYSA-L
2.1.4 Canonical SMILES
C[N+]1(CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC)CCC(=O)OCCCCCOC(=O)CC[N+]4(CCC5=CC(=C(C=C5C4CC6=CC(=C(C=C6)OC)OC)OC)OC)C.C1=CC=C(C=C1)S(=O)(=O)[O-].C1=CC=C(C=C1)S(=O)(=O)[O-]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 33 A 74

2. A 74, 33

3. Atracurium

4. Atracurium Besilate

5. Atracurium Dibesylate

6. Besilate, Atracurium

7. Bw 33a

8. Bw-33a

9. Bw33a

10. Relatrac

11. Tracrium

2.2.2 Depositor-Supplied Synonyms

1. 64228-81-5

2. Atracurium Besilate

3. Tracrium

4. Atracurium (besylate)

5. Bw-33a

6. Atracurium Dibesylate

7. Atracurii Besilas

8. Besilate D'atracurium

9. Besilato De Atracurio

10. Bw 33a

11. Chebi:2915

12. 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

13. Nsc-760047

14. 2,2'-((pentane-1,5-diylbis(oxy))bis(3-oxopropane-3,1-diyl))bis(1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium) Benzenesulfonate

15. Atracurium Besilate (inn)

16. Atracurium Besilate [inn]

17. 51w89

18. Tracrium Preservative Free

19. Cis-atracurium Besylate

20. Atracurii Besilas [inn-latin]

21. Hydro-1h-isoquinolin-2-ium-2-yl]propanoate

22. Bw 33 A

23. Besilate D'atracurium [inn-french]

24. Einecs 264-743-4

25. Atracurium Besylate Preservative Free

26. Besilato De Atracurio [inn-spanish]

27. 33 A 74

28. Unii-40ax66p76p

29. Atracurium Besylate [usan:usp]

30. Ncgc00017127-01

31. Tracrium (tn)

32. Benzenesulfonate;5-[3-[(1r,2r)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl 3-[(1r,2r)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-2-ium-2-yl]propanoate

33. 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-di

34. Cas-64228-81-5

35. Mfcd00797403

36. Dsstox_cid_2630

37. Atracurium Besylate (usp)

38. Dsstox_rid_76665

39. Dsstox_gsid_22630

40. Schembl41251

41. 2-(2-carboxyethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolinium Benzenesulfonate, Pentamethylene Ester

42. Pentamethylen Bis(3-(1,2,3,4-tetrahydro-6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-2-methyl-2-isochinolyl)propionat) Bis(benzolsulfonat)

43. Chembl1200527

44. Dtxsid6022630

45. Hy-b0292a

46. 40ax66p76p

47. Hms1568a11

48. Hms2095a11

49. Hms3651c21

50. Hms3712a11

51. Hms3884g12

52. Pharmakon1600-01505872

53. Bcp22694

54. Bcp22909

55. Benzenesulfonate; 5-[3-[(1r,2r)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-2-ium-2-yl]propanoyloxy]pentyl 3-[(1s,2s)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-2-ium-2-yl]propan

56. Tox21_110790

57. Nsc760047

58. S1832

59. Akos015895831

60. Ab07163

61. Atracurium Besylate, Mixture Of Isomers

62. Ccg-213566

63. Db00732

64. Nc00429

65. Nsc 760047

66. Ncgc00262598-01

67. Ncgc00262598-02

68. 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-methylisoquinolinium] Dibenzenesulfonate

69. As-14131

70. 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-, Dibenzenesulfonate

71. A2566

72. Ft-0657467

73. Ft-0659516

74. Sw197148-4

75. Atracurium Besylate, >=98% (hplc), Powder

76. D00758

77. Q165660

78. Sr-01000781272

79. Q-101018

80. Q-200864

81. Sr-01000781272-3

82. Atracurium Besilate Pound>>bw 33a Pound>>bw33a Pound>>bw-33a

83. Atracurium Besylate, European Pharmacopoeia (ep) Reference Standard

84. Atracurium Besylate, United States Pharmacopeia (usp) Reference Standard

85. Atracurium For Impurity F Identification, European Pharmacopoeia (ep) Reference Standard

86. Atracurium For Peak Identification, European Pharmacopoeia (ep) Reference Standard

87. 2,2'-((pentane-1,5-diylbis(oxy))bis(3-oxopropane-3,1-diyl))bis(1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium)benzenesulfonate

88. 2,2'-(3,3'-(pentane-1,5-diylbis(oxy))bis(3-oxopropane-3,1-diyl))bis(1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolinium) Benzenesulfonate

89. 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-isoquinolinium Benzenesulfonate

90. 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] Bisbenzenesulfonate

91. 2,2'-{pentane-1,5-diylbis[oxy(3-oxopropane-3,1-diyl)]}bis[1-{[3,4-bis(methyloxy)phenyl]methyl}-2-methyl-6,7-bis(methyloxy)-1,2,3,4-tetrahydroisoquinolinium] Bisbenzenesulfonate

2.3 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 1243.5 g/mol
Molecular Formula C65H82N2O18S2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count18
Rotatable Bond Count26
Exact Mass1242.50040612 g/mol
Monoisotopic Mass1242.50040612 g/mol
Topological Polar Surface Area258 Ų
Heavy Atom Count87
Formal Charge0
Complexity1560
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count4
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameAtracurium besylate
Drug LabelAtracurium besylate is an intermediate-duration, nondepolarizing, skeletal muscle relaxant for intravenous administration. Atracurium besylate is designated as 2-(2-Carboxyethyl)-1, 2, 3, 4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolinium b...
Active IngredientAtracurium besylate
Dosage FormInjectable
RouteInjection
Strength10mg/ml
Market StatusPrescription
CompanyHospira; Sagent Pharms; Eurohlth Intl

2 of 4  
Drug NameAtracurium besylate preservative free
Active IngredientAtracurium besylate
Dosage FormInjectable
RouteInjection
Strength10mg/ml
Market StatusPrescription
CompanyHospira; Sagent Pharms; Eurohlth Intl

3 of 4  
Drug NameAtracurium besylate
Drug LabelAtracurium besylate is an intermediate-duration, nondepolarizing, skeletal muscle relaxant for intravenous administration. Atracurium besylate is designated as 2-(2-Carboxyethyl)-1, 2, 3, 4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolinium b...
Active IngredientAtracurium besylate
Dosage FormInjectable
RouteInjection
Strength10mg/ml
Market StatusPrescription
CompanyHospira; Sagent Pharms; Eurohlth Intl

4 of 4  
Drug NameAtracurium besylate preservative free
Active IngredientAtracurium besylate
Dosage FormInjectable
RouteInjection
Strength10mg/ml
Market StatusPrescription
CompanyHospira; Sagent Pharms; Eurohlth Intl

4.2 Drug Indication

For use, as an adjunct to general anesthesia, to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 MeSH Pharmacological Classification

Neuromuscular Nondepolarizing Agents

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. (See all compounds classified as Neuromuscular Nondepolarizing Agents.)


Nicotinic Antagonists

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. (See all compounds classified as Nicotinic Antagonists.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Nondepolarizing Neuromuscular Blocker [EPC]; Neuromuscular Nondepolarizing Blockade [PE]
5.4 Biological Half-Life

The elimination half-life is approximately 20 minutes.


5.5 Mechanism of Action

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.


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17-Feb-2021
03-Oct-2024
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ABOUT THIS PAGE

Atracurium Besylate Manufacturers

A Atracurium Besylate manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Atracurium Besylate, including repackagers and relabelers. The FDA regulates Atracurium Besylate manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Atracurium Besylate API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Atracurium Besylate manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Atracurium Besylate Suppliers

A Atracurium Besylate supplier is an individual or a company that provides Atracurium Besylate active pharmaceutical ingredient (API) or Atracurium Besylate finished formulations upon request. The Atracurium Besylate suppliers may include Atracurium Besylate API manufacturers, exporters, distributors and traders.

click here to find a list of Atracurium Besylate suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Atracurium Besylate USDMF

A Atracurium Besylate DMF (Drug Master File) is a document detailing the whole manufacturing process of Atracurium Besylate active pharmaceutical ingredient (API) in detail. Different forms of Atracurium Besylate DMFs exist exist since differing nations have different regulations, such as Atracurium Besylate USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Atracurium Besylate DMF submitted to regulatory agencies in the US is known as a USDMF. Atracurium Besylate USDMF includes data on Atracurium Besylate's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Atracurium Besylate USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Atracurium Besylate suppliers with USDMF on PharmaCompass.

Atracurium Besylate CEP

A Atracurium Besylate CEP of the European Pharmacopoeia monograph is often referred to as a Atracurium Besylate Certificate of Suitability (COS). The purpose of a Atracurium Besylate CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Atracurium Besylate EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Atracurium Besylate to their clients by showing that a Atracurium Besylate CEP has been issued for it. The manufacturer submits a Atracurium Besylate CEP (COS) as part of the market authorization procedure, and it takes on the role of a Atracurium Besylate CEP holder for the record. Additionally, the data presented in the Atracurium Besylate CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Atracurium Besylate DMF.

A Atracurium Besylate CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Atracurium Besylate CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Atracurium Besylate suppliers with CEP (COS) on PharmaCompass.

Atracurium Besylate WC

A Atracurium Besylate written confirmation (Atracurium Besylate WC) is an official document issued by a regulatory agency to a Atracurium Besylate manufacturer, verifying that the manufacturing facility of a Atracurium Besylate active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Atracurium Besylate APIs or Atracurium Besylate finished pharmaceutical products to another nation, regulatory agencies frequently require a Atracurium Besylate WC (written confirmation) as part of the regulatory process.

click here to find a list of Atracurium Besylate suppliers with Written Confirmation (WC) on PharmaCompass.

Atracurium Besylate NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Atracurium Besylate as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Atracurium Besylate API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Atracurium Besylate as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Atracurium Besylate and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Atracurium Besylate NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Atracurium Besylate suppliers with NDC on PharmaCompass.

Atracurium Besylate GMP

Atracurium Besylate Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Atracurium Besylate GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Atracurium Besylate GMP manufacturer or Atracurium Besylate GMP API supplier for your needs.

Atracurium Besylate CoA

A Atracurium Besylate CoA (Certificate of Analysis) is a formal document that attests to Atracurium Besylate's compliance with Atracurium Besylate specifications and serves as a tool for batch-level quality control.

Atracurium Besylate CoA mostly includes findings from lab analyses of a specific batch. For each Atracurium Besylate CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Atracurium Besylate may be tested according to a variety of international standards, such as European Pharmacopoeia (Atracurium Besylate EP), Atracurium Besylate JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Atracurium Besylate USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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