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DSSTox_CID_3566

DSSTox_CID_3566

Synopsis, Chemistry

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INJECTABLE;INJECTION - 100MG/10ML (10MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, INJECTABLE;INJECTION - 10MG/ML (10MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, INJECTABLE;INJECTION - 50MG/5ML (10MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

INJECTABLE;INJECTION - 100MG/10ML (10MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
INJECTABLE;INJECTION - 10MG/ML (10MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
INJECTABLE;INJECTION - 50MG/5ML (10MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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Also known as: 119302-91-9, Zemuron, Esmeron, Rocuronium (bromide), Org 9426, Org-9426

Molecular Formula

C₃₂H₅₃BrN₂O₄

Molecular Weight

609.7 g/mol

InChI Key

OYTJKRAYGYRUJK-FMCCZJBLSA-M

FDA UNII

I65MW4OFHZ

An androstanol non-depolarizing neuromuscular blocking agent. It has a mono-quaternary structure and is a weaker nicotinic antagonist than PANCURONIUM.

1 2D Structure

DSSTox_CID_3566

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-hydroxy-10,13-dimethyl-2-morpholin-4-yl-16-(1-prop-2-enylpyrrolidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate;bromide

2.1.2 InChI

InChI=1S/C32H53N2O4.BrH/c1-5-14-34(15-6-7-16-34)28-20-26-24-9-8-23-19-29(36)27(33-12-17-37-18-13-33)21-32(23,4)25(24)10-11-31(26,3)30(28)38-22(2)35;/h5,23-30,36H,1,6-21H2,2-4H3;1H/q+1;/p-1/t23-,24+,25-,26-,27-,28-,29-,30-,31-,32-;/m0./s1

2.1.3 InChI Key

OYTJKRAYGYRUJK-FMCCZJBLSA-M

2.1.4 Canonical SMILES

CC(=O)OC1C(CC2C1(CCC3C2CCC4C3(CC(C(C4)O)N5CCOCC5)C)C)[N+]6(CCCC6)CC=C.[Br-]

2.1.5 Isomeric SMILES

CC(=O)O[C@H]1[C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(C[C@@H]([C@H](C4)O)N5CCOCC5)C)C)[N+]6(CCCC6)CC=C.[Br-]

2.2 Other Identifiers

2.2.1 UNII

I65MW4OFHZ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(17-(acetoyl)-3-hydroxy-2-(4-morpholinyl)androstan-16-yl)-1-(2-propenyl)pyrrolidinium

2. Androstane-3,17-diol, 2-(4-morpholinyl)-16-(1-(2-propen-1-yl)-1-pyrrolidiniumyl)-, 17-acetate, (2beta,3alpha,5alpha,16beta,17beta)-

3. Esmeron

4. Esmerone

5. Org 9426

6. Org-9426

7. Org9426

8. Pyrrolidinium, 1-((2beta,3alpha,5alpha,16beta,17beta)-17-(acetyloxy)-3-hydroxy-2-(4-morpholinyl)androstan-16-yl)-1-(2-propenyl)-, Bromide

9. Rocuronium

10. Zemuron

2.3.2 Depositor-Supplied Synonyms

1. 119302-91-9

2. Zemuron

3. Esmeron

4. Rocuronium (bromide)

5. Org 9426

6. Org-9426

7. Chebi:8885

8. I65mw4ofhz

9. 1-allyl-1-(3alpha,17beta-dihydroxy-2beta-morpholino-5alpha-androstan-16beta-yl)pyrrolidinium Bromide, 17-acetate

10. [(2s,3s,5s,8r,9s,10s,13s,14s,16s,17r)-3-hydroxy-10,13-dimethyl-2-morpholin-4-yl-16-(1-prop-2-enylpyrrolidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl] Acetate;bromide

11. Pyrrolidinium, 1-[(2beta,3alpha,5alpha,16beta,17beta)-17-(acetyloxy)-3-hydroxy-2-(4-morpholinyl)androstan-16-yl]-1-(2-propenyl)-, Bromide

12. Rocuronium Hydrobromide

13. 1-[17b-(acetyloxy)-3a-hydroxy-2b-(4-morpholinyl)-5a-androstan-16b-yl]-1-(2-propenyl)pyrrolidinium Bromide

14. Pyrrolidinium, 1-((2beta,3alpha,5alpha,16beta,17beta)-17-(acetyloxy)-3-hydroxy-2-(4-morpholinyl)androstan-16-yl)-1-(2-propenyl)-, Bromide

15. Ncgc00167433-01

16. Unii-i65mw4ofhz

17. Org9426

18. Eslax

19. Rocuroniumbromide

20. Zemuron (tn)

21. Mfcd00867768

22. Rocuronium Bromide [usan:usp:inn:ban]

23. Rocuronium Bromide - Ep

24. Dsstox_cid_3566

25. Org 9426 (bromide)

26. Dsstox_rid_77083

27. Dsstox_gsid_23566

28. Schembl41320

29. (+)-rocuronium Bromide

30. Rocuronium Bromide [mi]

31. Chembl1200648

32. Dtxsid7023566

33. Rocuronium Bromide [inn]

34. Rocuronium Bromide [jan]

35. Rocuronium Bromide [usan]

36. Hms3884o13

37. Rocuronium Bromide [vandf]

38. Rocuronium Bromide [mart.]

39. Rocuronium Bromide (jan/usp/inn)

40. Rocuronium Bromide [usp-rs]

41. Rocuronium Bromide [who-dd]

42. Tox21_112437

43. Bdbm50248153

44. S1397

45. Akos025149635

46. Ac-2004

47. Ccg-270222

48. Cs-1467

49. Rocuronium Bromide [orange Book]

50. Rocuronium Bromide [ep Monograph]

51. 1-((2s,3s,5s,8r,9s,10s,13s,14s,16s,17r)-17-acetoxy-3-hydroxy-10,13-dimethyl-2-morpholinohexadecahydro-1h-cyclopenta[a]phenanthren-16-yl)-1-allylpyrrolidin-1-ium Bromide

52. 111ge014

53. As-13323

54. Br177300

55. Hy-17440

56. Rocuronium Bromide [usp Monograph]

57. Bcp0726000028

58. Cas-119302-91-9

59. R0099

60. D00765

61. Q-101010

62. Q27108171

63. Rocuronium Bromide, >=98% (perchloric Acid Titration)

64. Rocuronium Bromide, European Pharmacopoeia (ep) Reference Standard

65. Rocuronium Bromide, United States Pharmacopeia (usp) Reference Standard

66. Rocuronium For Peak Identification, European Pharmacopoeia (ep) Reference Standard

67. (2beta,3alpha,5alpha,16beta,17beta)-17-(acetyloxy)-3-hydroxy-2-morpholin-4-yl-16-(1-prop-2-en-1-ylpyrrolidinium-1-yl)androstane Bromide

68. 1-((2s,3s,8r,9s,10s,13s,14s,16s,17r)-17-acetoxy-3-hydroxy-10,13-dimethyl-2-morpholinohexadecahydro-1h-cyclopenta[a]phenanthren-16-yl)-1-allylpyrrolidinium Bromide

69. 1-[(2beta,3alpha,5alpha,16beta,17beta)-17-acetyloxy-3-hydroxy-2-(4-morpholinyl)-androstan-16-yl]-1(2-propenyl)pyrrolidinium Bromide

70. 1-[17beta-acetyloxy-3alpha-hydroxy-2beta-(4-morpholinyl)-5alpha-androstan-16beta-yl]-1-(2-propenyl)pyrrolidinium Bromide

71. 1-allyl-1-(3.alpha.,17.beta.-dihydroxy-2.beta.-morpholino-5.alpha.-androstan-16.beta.-yl)pyrrolidinium Bromide, 17-acetate

72. 17beta-(acetyloxy)-3alpha-hydroxy-2beta-(morpholin-4-yl)-16beta-[1-(prop-2-en-1-yl)pyrrolidinium-1-yl]-5alpha-androstane

73. 17beta-acetoxy-16beta-(1-allylpyrrolidinium-1-yl)-3alpha-hydroxy-2beta-(morpholin-4-yl)-5alphaandrostane

74. Pyrrolidinium, 1-((2.beta.,3.alpha.,5.alpha.,16.beta.,17.beta.)-17-(acetyloxy)-3-hydroxy-2-(4-morpholinyl)androstan-16-yl)-1-(2-propenyl)-, Bromide

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₅₃BrN₂O₄
Molecular Weight	609.7 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	608.31887 g/mol
Monoisotopic Mass	608.31887 g/mol
Topological Polar Surface Area	59 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	898
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Rocuronium bromide
PubMed Health	Rocuronium (Injection)
Drug Classes	Musculoskeletal Agent
Drug Label	Rocuronium bromide injection is a nondepolarizing neuromuscular blocking agent with a rapid to intermediate onset depending on dose and intermediate duration. Rocuronium bromide USP is chemically designated as 1-[17-(acetyloxy)-3-hydroxy-2-(4-m...
Active Ingredient	Rocuronium bromide
Dosage Form	Injectable
Route	Injection
Strength	50mg/5ml (10mg/ml); 100mg/10ml (10mg/ml)
Market Status	Prescription
Company	Sagent Strides; Hospira; Sandoz; Teva Pharms; Fresenius Kabi Usa; Tamarang; Mylan Institutional

2 of 4
Drug Name	Zemuron
Drug Label	ZEMURON (rocuronium bromide) injection is a nondepolarizing neuromuscular blocking agent with a rapid to intermediate onset depending on dose and intermediate duration. Rocuronium bromide is chemically designated as 1-[17-(acetyloxy)-3-hydroxy-2...
Active Ingredient	Rocuronium bromide
Dosage Form	Injectable
Route	Injection
Strength	50mg/5ml (10mg/ml); 100mg/10ml (10mg/ml)
Market Status	Prescription
Company	Organon Usa

3 of 4
Drug Name	Rocuronium bromide
PubMed Health	Rocuronium (Injection)
Drug Classes	Musculoskeletal Agent
Drug Label	Rocuronium bromide injection is a nondepolarizing neuromuscular blocking agent with a rapid to intermediate onset depending on dose and intermediate duration. Rocuronium bromide USP is chemically designated as 1-[17-(acetyloxy)-3-hydroxy-2-(4-m...
Active Ingredient	Rocuronium bromide
Dosage Form	Injectable
Route	Injection
Strength	50mg/5ml (10mg/ml); 100mg/10ml (10mg/ml)
Market Status	Prescription
Company	Sagent Strides; Hospira; Sandoz; Teva Pharms; Fresenius Kabi Usa; Tamarang; Mylan Institutional

4 of 4
Drug Name	Zemuron
Drug Label	ZEMURON (rocuronium bromide) injection is a nondepolarizing neuromuscular blocking agent with a rapid to intermediate onset depending on dose and intermediate duration. Rocuronium bromide is chemically designated as 1-[17-(acetyloxy)-3-hydroxy-2...
Active Ingredient	Rocuronium bromide
Dosage Form	Injectable
Route	Injection
Strength	50mg/5ml (10mg/ml); 100mg/10ml (10mg/ml)
Market Status	Prescription
Company	Organon Usa

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

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

5.3 ATC Code

M - Musculo-skeletal system

M03 - Muscle relaxants

M03A - Muscle relaxants, peripherally acting agents

M03AC - Other quaternary ammonium compounds

M03AC09 - Rocuronium bromide