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INJECTABLE;INJECTION - EQ 10MG BASE/ML, INJECTABLE;INJECTION - EQ 2MG BASE/ML

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Synnat Cisatracurium Besylate

Synopsis

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Chemistry

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Also known as: 96946-42-8, Nimbex, Cisatracurium besilate, Cisatracurium (besylate), 51w89, Cisatracurium besylate [usan]

Molecular Formula

C₆₅H₈₂N₂O₁₈S₂

Molecular Weight

1243.5 g/mol

InChI Key

XXZSQOVSEBAPGS-DONVQRBFSA-L

FDA UNII

Y78PS7MEDE

Cisatracurium Besylate is the besylate salt form of cisatracurium, a non-depolarizing skeletal muscle relaxant of the benzylisoquinolinium class, with skeletal muscle relaxing activity. Cisatracurium besylate acts as a competitive acetylcholine antagonist that binds to nicotinic receptors at the neuromuscular junction. This blocks neuromuscular transmission and causes neuromuscular relaxation.

1 2D Structure

Cisatracurium Besylate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

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/t42-,43-,54-,55-;;/m1../s1

2.1.3 InChI Key

XXZSQOVSEBAPGS-DONVQRBFSA-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-]

2.1.5 Isomeric SMILES

C[N@@+]1(CCC2=CC(=C(C=C2[C@H]1CC3=CC(=C(C=C3)OC)OC)OC)OC)CCC(=O)OCCCCCOC(=O)CC[N@+]4(CCC5=CC(=C(C=C5[C@H]4CC6=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 Other Identifiers

2.2.1 UNII

Y78PS7MEDE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 51w89

2. Cisatracurium

3. Cisatracurium Besilate

4. Nimbex

2.3.2 Depositor-Supplied Synonyms

1. 96946-42-8

2. Nimbex

3. Cisatracurium Besilate

4. Cisatracurium (besylate)

5. 51w89

6. Cisatracurium Besylate [usan]

7. Cisatracurium (as Besilate)

8. 80ys8o1mbs

9. Cisatracurium Besilate [inn]

10. Chebi:3721

11. (1r,1'r,2r,2'r)-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

12. 96946-42-8 (besylate)

13. (1r,2r)-2-(2-carboxyethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinolinium Benzenesulfonate, Pentamethylene Ester

14. (1r-cis,1'r-cis)-atracurium Besylate

15. 51-w89

16. 51w-89

17. 51-w-89

18. Cisatracurium Besilate (inn)

19. Nimbex Preservative Free

20. Cis-atracurium Besylate

21. Unii-80ys8o1mbs

22. Nimbium

23. Atracurium Besylate 1r-cis,1r'-cis Form

24. Nimbex Forte

25. Ncgc00017127-01

26. Cas-64228-81-5

27. Nimbex (tn)

28. Cisatracurium Besylate Preservative Free

29. Cis-atracurium Besilate

30. 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-,(1r,1'r,2r,2'r)-, Dibenzenesulfonate

31. Y78ps7mede

32. Schembl40669

33. Cisatracurium Besylate (usp)

34. Cisatracurium Dibenzenesulfonate

35. Cisatracurium Besylate (nimbex)

36. Chembl1200641

37. Cisatracurium Besylate (~90%)

38. Dtxsid10895045

39. Hms3715p04

40. Hms3884l07

41. Cisatracurium Besylate [mi]

42. 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

43. Ex-a2646

44. Mfcd00871018

45. S2113

46. Cisatracurium Besylate [vandf]

47. Akos026750111

48. Cisatracurium Besilate [mart.]

49. Ccg-221271

50. Cisatracurium Besilate [who-dd]

51. Cisatracurium Besylate [usp-rs]

52. (1r,2r,1'r,2'r)-atracurium Besylate

53. Bs-17985

54. Hy-13596

55. 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, (1r-(1alpha,2alpha(1'r(sup *),2'r(sup *))))-

56. Cisatracurium Besylate [orange Book]

57. Cisatracurium Besilate [ep Monograph]

58. Sw222230-1

59. Cisatracurium Besylate [usp Monograph]

60. 51 W89

61. D00759

62. Q267669

63. W-60404

64. Z2216208615

65. Atracurium Besylate, (1r,1'r,2r,2'r)-(+/-)-

66. Cisatracurium Besilate, Europepharmacopoeia (ep) Reference Standard

67. Cisatracurium Besylate, United States Pharmacopeia (usp) Reference Standard

68. Cisatracurium For Peak Identification, Europepharmacopoeia (ep) Reference Standard

69. Cisatracurium For System Suitability, Europepharmacopoeia (ep) Reference Standard

70. (1r,1'r,2r,2'r)-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

71. (1r,2r)-1-[(3,4-dimethoxyphenyl)methyl]-2-(3-{[5-({3-[(1r,2r)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl]propanoyl}oxy)pentyl]oxy}-3-oxopropyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium Dibenzenesulfonate

72. (1r,2r,1'r,2'r)-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

73. (1r-cis,1'r-cis)-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

74. 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-, (1r,1'r,2r,2'r)-, Benzenesulfonate (1:2)

75. 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-, (1r,1'r,2r,2'r)-, Dibenzenesulfonate

76. 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-, (1r,1'r,2r,2'r)-rel, Dibenzenesulfonate

77. 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, (1r-(1.alpha.,2.alpha.(1'r*,2'r*)))-

78. 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-, Dibenzenesulphonate, (1r-(1.alpha.,2.alpha.(1'r*,2'r*)))-

2.4 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	4
Undefined Atom Stereocenter Count	0
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 6
Drug Name	Cisatracurium besylate
Active Ingredient	Cisatracurium besylate
Dosage Form	Injectable
Route	Injection
Strength	eq 2mg base/ml
Market Status	Prescription
Company	Sandoz

2 of 6
Drug Name	Nimbex
Drug Label	NIMBEX (cisatracurium besylate) is a nondepolarizing skeletal muscle relaxant for intravenous administration. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action. Cisatracurium besylate is one of 10...
Active Ingredient	Cisatracurium besylate
Dosage Form	Injectable
Route	Injection
Strength	eq 2mg base/ml
Market Status	Prescription
Company	Abbvie

3 of 6
Drug Name	Nimbex preservative free
Drug Label	Cisatracurium besylate is a nondepolarizing skeletal muscle relaxant for intravenous administration. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action. Cisatracurium besylate is one of 10isomers...
Active Ingredient	Cisatracurium besylate
Dosage Form	Injectable
Route	Injection
Strength	eq 2mg base/ml; eq 10mg base/ml
Market Status	Prescription
Company	Abbvie

4 of 6
Drug Name	Cisatracurium besylate
Active Ingredient	Cisatracurium besylate
Dosage Form	Injectable
Route	Injection
Strength	eq 2mg base/ml
Market Status	Prescription
Company	Sandoz

5 of 6
Drug Name	Nimbex
Drug Label	NIMBEX (cisatracurium besylate) is a nondepolarizing skeletal muscle relaxant for intravenous administration. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action. Cisatracurium besylate is one of 10...
Active Ingredient	Cisatracurium besylate
Dosage Form	Injectable
Route	Injection
Strength	eq 2mg base/ml
Market Status	Prescription
Company	Abbvie

6 of 6
Drug Name	Nimbex preservative free
Drug Label	Cisatracurium besylate is a nondepolarizing skeletal muscle relaxant for intravenous administration. Compared to other neuromuscular blocking agents, it is intermediate in its onset and duration of action. Cisatracurium besylate is one of 10isomers...
Active Ingredient	Cisatracurium besylate
Dosage Form	Injectable
Route	Injection
Strength	eq 2mg base/ml; eq 10mg base/ml
Market Status	Prescription
Company	Abbvie

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Neuromuscular Blocking Agents

Drugs that interrupt transmission of nerve impulses at the skeletal neuromuscular junction. They can be of two types, competitive, stabilizing blockers (NEUROMUSCULAR NONDEPOLARIZING AGENTS) or noncompetitive, depolarizing agents (NEUROMUSCULAR DEPOLARIZING AGENTS). Both prevent acetylcholine from triggering the muscle contraction and they are used as anesthesia adjuvants, as relaxants during electroshock, in convulsive states, etc. (See all compounds classified as Neuromuscular Blocking Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

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

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