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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

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

CAS 64228-81-5

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 Formula	C₆₅H₈₂N₂O₁₈S₂
Molecular Weight	1243.5 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	26
Exact Mass	1242.50040612 g/mol
Monoisotopic Mass	1242.50040612 g/mol
Topological Polar Surface Area	258 Å²
Heavy Atom Count	87
Formal Charge	0
Complexity	1560
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	4
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	ATRACURIUM BESYLATE
Active Ingredient	ATRACURIUM BESYLATE
Company	AUROBINDO PHARMA LTD (Application Number: A206011); HOSPIRA INC (Application Number: A090761); MYLAN LABS LTD (Application Number: A206096); NANJING KING-FRIEND (Application Number: A091489); WEST-WARD PHARMS INT (Application Number: A074901)

2 of 2
Drug Name	ATRACURIUM BESYLATE PRESERVATIVE FREE
Active Ingredient	ATRACURIUM BESYLATE
Company	AUROBINDO PHARMA LTD (Application Number: A206010); HOSPIRA INC (Application Number: A090782); MYLAN LABS LTD (Application Number: A206001); NANJING KING-FRIEND (Application Number: A091488); WEST-WARD PHARMS INT (Application Number: A074900)

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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