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Chemistry

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Also known as: Pancuronium dibromide, 15500-66-0, Pavulon, Mioblock, Org na 97, Pancuronium (dibromide)

Molecular Formula

C₃₅H₆₀Br₂N₂O₄

Molecular Weight

732.7 g/mol

InChI Key

NPIJXCQZLFKBMV-YTGGZNJNSA-L

FDA UNII

U9LY9Y75X2

A bis-quaternary steroid that is a competitive nicotinic antagonist. As a neuromuscular blocking agent it is more potent than CURARE but has less effect on the circulatory system and on histamine release.

1 2D Structure

Pancuronium Bromide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate;dibromide

2.1.2 InChI

InChI=1S/C35H60N2O4.2BrH/c1-24(38)40-32-21-26-13-14-27-28(35(26,4)23-31(32)37(6)19-11-8-12-20-37)15-16-34(3)29(27)22-30(33(34)41-25(2)39)36(5)17-9-7-10-18-36;;/h26-33H,7-23H2,1-6H3;2*1H/q+2;;/p-2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-;;/m0../s1

2.1.3 InChI Key

NPIJXCQZLFKBMV-YTGGZNJNSA-L

2.1.4 Canonical SMILES

CC(=O)OC1CC2CCC3C(C2(CC1[N+]4(CCCCC4)C)C)CCC5(C3CC(C5OC(=O)C)[N+]6(CCCCC6)C)C.[Br-].[Br-]

2.1.5 Isomeric SMILES

CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@@H]([C@]2(C[C@@H]1[N+]4(CCCCC4)C)C)CC[C@]5([C@H]3C[C@@H]([C@@H]5OC(=O)C)[N+]6(CCCCC6)C)C.[Br-].[Br-]

2.2 Other Identifiers

2.2.1 UNII

U9LY9Y75X2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bromide, Pancuronium

2. Pancuronium

3. Pancuronium Curamed

4. Pancuronium Organon

5. Pavulon

2.3.2 Depositor-Supplied Synonyms

1. Pancuronium Dibromide

2. 15500-66-0

3. Pavulon

4. Mioblock

5. Org Na 97

6. Pancuronium (dibromide)

7. Pancuronii Bromidum

8. Bromuro De Pancuronio

9. Bromure De Pancuronium

10. Bromurex

11. Org-na 97

12. Chebi:7908

13. Org-na-97

14. 3alpha,17beta-diacetoxy-2beta,16beta-dipiperidino-5alpha-androstane Dimethobromide

15. Na 97

16. 2beta,16beta-dipiperidino-5alpha-androstane-3alpha,17beta-diol Diacetate Dimethobromide

17. U9ly9y75x2

18. Bromure De Pancuronium [inn-french]

19. Bromuro De Pancuronio [inn-spanish]

20. 15500-66-0 (bromide)

21. Nsc-293162

22. 1,1'-((2s,3s,5s,8r,9s,10s,13s,14s,16s,17r)-3,17-diacetoxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthrene-2,16-diyl)bis(1-methylpiperidin-1-ium) Bromide

23. (2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)-2,16-bis(1-methylpiperidinium-1-yl)androstane Dibromide

24. 3alpha,17beta-diacetoxy-2beta,16beta-bis(1-methylpiperidinium-1-yl)-5alpha-androstane Dibromide

25. Hsdb 3244

26. Pancuronii Bromidum [inn-latin]

27. Einecs 239-532-5

28. Nsc 293162

29. Unii-u9ly9y75x2

30. Pavulon (tn)

31. Mfcd00079223

32. Ncgc00163232-01

33. Dsstox_cid_3415

34. Pancuronium Bromide [usan:usp:inn:ban:jan]

35. Cas-15500-66-0

36. 1,1'-(3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1-methylpiperidinium) Dibromide

37. 2beta,16beta-dipiperidino-5alpha-androstane-3alpha,17beta-dioldiacetatedimethobromide

38. 3-alpha,17-beta-diacetoxy-2-beta,16-beta-dipiperidino-5-alpha-androstane Dimethobromide

39. 5alpha-androstan-3alpha,17beta-diol, 2beta,16beta-dipipecolinio-, Dibromide, Diacetate

40. Dsstox_rid_77018

41. Dsstox_gsid_23415

42. Schembl41185

43. 1,1'-(3alpha,17beta-bis(acetyloxy)-5alpha-androstane-2beta,16beta-diyl)bis(1-methylpiperidinium) Dibromide

44. 1,1'-(3alpha,17beta-dihydroxy-5alpha-androstan-2beta,16beta-ylene)bis(1-methylpiperidinium) Dibromide Diacetate

45. Piperidinium, 1,1'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1-methyl-, Dibromide

46. Piperidinium, 1,1'-(2-beta,16-beta-(3-alpha,17-beta-dihydroxy-5-alpha-androstanylene))bis(1-methyl-, Dibromide, Diacetate

47. Piperidinium, 1,1'-(3alpha,17beta-dihydroxy-5alpha-androstan-2beta,16beta-ylene)bis(1-methyl-, Dibromide, Diacetate

48. Chembl1200757

49. Pancuronium Bromide [mi]

50. Pancuronium Bromide [inn]

51. Pancuronium Bromide [jan]

52. Hms1571o09

53. Hms2098o09

54. Hms3262b16

55. Hms3715o09

56. Hms3884p21

57. Pancuronium Bromide [hsdb]

58. Pancuronium Bromide [usan]

59. Pancuronium Bromide [vandf]

60. Hy-b0429

61. Pancuronium Bromide [mart.]

62. Tox21_112033

63. Tox21_500887

64. Bdbm50248016

65. Pancuronium Bromide [usp-rs]

66. Pancuronium Bromide [who-dd]

67. S2497

68. Akos037515715

69. Pancuronium Bromide (jp17/usp/inn)

70. Ccg-221034

71. Ccg-222191

72. Lp00887

73. Ncgc00261572-01

74. Pancuronium Bromide [orange Book]

75. Bs-15969

76. Pancuronium Bromide [ep Monograph]

77. Piperidinium, 1,1'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1-methyl)-, Dibromide

78. Pancuronium Bromide [usp Monograph]

79. Eu-0100887

80. D00492

81. P 1918

82. A809594

83. Sr-01000000127

84. Sr-01000076059

85. Q-101015

86. Sr-01000000127-3

87. Sr-01000076059-1

88. Q27107612

89. Pancuronium Bromide, European Pharmacopoeia (ep) Reference Standard

90. Pancuronium Bromide, United States Pharmacopeia (usp) Reference Standard

91. Vecuronium Bromide Impurity, Pancuronium Bromide- [usp Impurity]

92. Pancuronium Bromide For System Suitability, European Pharmacopoeia (ep) Reference Standard

93. [(2s,3s,5s,8r,9s,10s,13s,14s,16s,17r)-17-acetyloxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl] Acetate;bromide

94. [(2s,3s,5s,8r,9s,10s,13s,14s,16s,17r)-17-acetyloxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl] Acetate;dibromide

95. [17-acetoxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl] Acetate Dibromide

96. 1,1'-((2s,3s,5s,8r,9s,10s,13s,14s,16s,17r)-3,17-diacetoxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthrene-2,16-diyl)bis(1-methylpiperidin-1-ium) Bromi

97. 1,1'-([2beta,3alpha,5alpha,16beta,17beta]-3,17-bis[acetyloxy]androstane-2,16-diyl)bis(1-methylpiperidinium) Dibromide

98. 1,1'-(3.alpha.,17.beta.-dihydroxy-5.alpha.-androstan-2.beta.,16.beta.-ylene)bis(1-methylpiperidinium)dibromide Diacetate

99. 1,1'-(3alpha,17beta-dihydroxy-2beta,5alpha-androstan-2beta,16beta-ylene) Bis[1-methylpiperidinium] Diacetate Dibromide

100. 2.beta.,16.beta.-dipiperidino-5.alpha.-androstane-3.alpha.,17.beta.-diol Diacetate Dimethobromide

101. Piperidinium, 1,1'-((2.beta.,3.alpha.,5.alpha.,16.beta.,17.beta.)-3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1-methyl)-, Dibromide

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₅H₆₀Br₂N₂O₄
Molecular Weight	732.7 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	732.28993 g/mol
Monoisotopic Mass	730.29198 g/mol
Topological Polar Surface Area	52.6 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	1000
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	3

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Pancuronium bromide
Drug Label	Pancuronium Bromide is a nondepolarizing neuromuscular blocking agent chemically designated as the aminosteroid 2, 16 - dipiperidino-5-androstane-3, 17- diol diacetate dimethobromide, C35H60Br2N2O4. It is a fine white odorless powder which...
Active Ingredient	Pancuronium bromide
Dosage Form	Injectable
Route	Injection
Strength	2mg/ml; 1mg/ml
Market Status	Prescription
Company	Hospira; Teva Pharms Usa

2 of 2
Drug Name	Pancuronium bromide
Drug Label	Pancuronium Bromide is a nondepolarizing neuromuscular blocking agent chemically designated as the aminosteroid 2, 16 - dipiperidino-5-androstane-3, 17- diol diacetate dimethobromide, C35H60Br2N2O4. It is a fine white odorless powder which...
Active Ingredient	Pancuronium bromide
Dosage Form	Injectable
Route	Injection
Strength	2mg/ml; 1mg/ml
Market Status	Prescription
Company	Hospira; Teva Pharms Usa

4.2 Therapeutic Uses

Neuromuscular Nondepolarizing Agents; Nicotinic Antagonists

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

THE MAIN CLINICAL USE OF THE NEUROMUSCULAR BLOCKING AGENTS IS AS AN ADJUVANT IN SURGICAL ANESTHESIA TO OBTAIN RELAXATION OF SKELETAL MUSCLE, PARTICULARLY OF THE ABDOMINAL WALL ... MUSCLE RELAXATION IS ALSO OF VALUE IN VARIOUS ORTHOPEDIC PROCEDURES, SUCH AS THE CORRECTION OF DISLOCATIONS & THE ALIGNMENT OF FRACTURES. /NEUROMUSCULAR BLOCKING AGENTS/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 189

...MAY BE USED MORE SAFELY IN PT WITH CARDIOVASCULAR DISEASE OR BRONCHIAL ASTHMA THAN ANY OTHER NEUROMUSCULAR BLOCKING DRUG. ...IT HAS ACTUALLY BEEN USED IN MGMNT OF STATUS ASTHMATICUS TO RELAX MUSCLES, THEREBY FACILITATING ARTIFICIAL RESPIRATION & DECR OXYGEN DEMAND. ... DURATION OF ACTION OF USUAL DOSE IS GENERALLY 30-60 MIN...

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 864

/NEUROMUSCULAR BLOCKING AGENTS/ HAVE BEEN USED TO FACILITATE LARYNGOSCOPY, BRONCHOSCOPY, & ESOPHAGOSCOPY, IN COMBINATION WITH A GENERAL ANESTHETIC AGENT. /NEUROMUSCULAR BLOCKING AGENTS/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 190

For more Therapeutic Uses (Complete) data for PANCURONIUM BROMIDE (9 total), please visit the HSDB record page.

4.3 Drug Warning

THE NEUROMUSCULAR BLOCKING AGENTS ARE POTENTIALLY HAZARDOUS DRUGS. CONSEQUENTLY, THEY SHOULD BE ADMINISTERED TO PATIENTS ONLY BY ANESTHESIOLOGISTS & OTHER CLINICIANS WHO HAVE HAD EXTENSIVE TRAINING IN THEIR USE & IN A SETTING WHERE FACILITIES FOR RESPIRATORY & CARDIOVASCULAR RESUSCITATION ARE IMMEDIATELY AT HAND. /NEUROMUSCULAR BLOCKING AGENTS/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 190

...IT IS ADVISABLE TO USE DRUG CAUTIOUSLY IN PRESENCE OF RENAL OR LIVER DISEASES.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 864

EFFECT OF SPECIFIC DOSE OF ... PANCURONIUM MAY /POSSIBLY/ BE REDUCED IN PT WITH HIGH PLASMA GLOBULIN LEVELS (EG THOSE WITH LIVER DISEASE).

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 310

GREAT CARE SHOULD BE TAKEN WHEN ADMIN MUSCLE RELAXANTS TO DEHYDRATED OR SEVERELY ILL PATIENTS. /NEUROMUSCULAR BLOCKING AGENTS/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 188

For more Drug Warnings (Complete) data for PANCURONIUM BROMIDE (17 total), please visit the HSDB record page.

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.)

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

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

5.3 Absorption, Distribution and Excretion

BOTH LIVER & KIDNEYS ARE INVOLVED IN DEGRADATION & EXCRETION OF ... PANCURONIUM ...

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 310

AFTER IV INJECTION, EFFECTS...BECOME MAXIMAL IN LESS THAN 3 MIN IN ADULTS & 90 SEC IN CHILDREN. ... PLASMA HALF-LIFE IS PROBABLY SLIGHTLY LESS THAN 2 HR. PANCURONIUM IS MOSTLY EXCRETED UNCHANGED INTO URINE.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 864

PLACENTAL TRANSFER OF...PANCURONIUM BROMIDE...OCCURS RAPIDLY AFTER ADMIN TO MOTHERS, BUT FETAL:MATERNAL DRUG CONCN RATIO ARE VERY LOW.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 156

PLASMA LEVELS OF PANCURONIUM OBEYED TWO-COMPARTMENT KINETICS IN SEVEN PATIENTS ON IV INJECTION & THE BETA-PHASE HALF-TIME VARIED BETWEEN 90 AND 162 MIN. THE MEAN VOLUME OF THE CENTRAL COMPARTMENT WAS 100 ML/KG, WHILE THE OVERALL DISTRIBUTION VOLUME WAS 261 MG/KG. IN PATIENTS WITH CHRONIC RENAL FAILURE, THE PLASMA CLEARANCE...WAS SIGNIFICANTLY REDUCED, WHILE VOLUMES OF BOTH THE OVERALL & CENTRAL COMPARTMENTS WERE SIGNIFICANTLY INCREASED.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 57

For more Absorption, Distribution and Excretion (Complete) data for PANCURONIUM BROMIDE (6 total), please visit the HSDB record page.

5.4 Metabolism/Metabolites

IN CATS, 8 HR AFTER IV INJECTION OF PANCURONIUM BROMIDE, UNCHANGED PANCURONIUM BROMIDE IN URINE, BILE, & LIVER ACCOUNTED FOR 58% OF DOSE, 3-HYDROXY-DERIV FOR 14.5%, 17-HYDROXY-DERIV FOR 7% & 3,17-DIHYDROXY-DERIV FOR 4.5%.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 273

5.5 Biological Half-Life

PLASMA HALF-LIFE IS PROBABLY SLIGHTLY LESS THAN 2 HR.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 864

5.6 Mechanism of Action

LOW CONCN OF PANCURONIUM BROMIDE (5X10-8 G/ML OR LESS), HAD NO PRESYNAPTIC EFFECT ON MURINE PHRENIC NERVE-DIAPHRAGM PREPN. AT HIGH CONCN (5X10-7 G/ML), PANCURONIUM BROMIDE DEPRESSED QUANTAL RELEASE TO 26% OF CONTROL IN CUT-FIBER PREPN & 40% OF CONTROL IN HIGH-MAGNESIUM PREPN. POSTSYNAPTIC EFFECTS REVEALED DEPRESSION TO 16 & 22% OF CONTROL, RESPECTIVELY, AT A CONCN OF 5X10-7 G/ML. PANCURONIUM BROMIDE HAD NO EFFECT ON DIRECTLY ELICITED ACTION POTENTIALS & ELECTRIC MEMBRANE CONSTANTS. THUS, PRESYNAPTIC AS WELL AS POSTSYNAPTIC EFFECTS OF PANCURONIUM BROMIDE IN PARALYTIC DOSES ARE ESSENTIAL IN CONTRIBUTING TO THE TOTAL EFFICACY OF NEUROMUSCULAR DEPRESSION.

SU PC ET AL; PRE- AND POSTSYNAPTIC EFFECTS OF PANCURONIUM AT THE NEUROMUSCULAR JUNCTION OF THE MOUSE; ANESTHESIOLOGY 50(3) 199 (1979)

THE PHARMACODYNAMICS OF D-TUBOCURARINE (D-TC), PANCURONIUM BROMIDE, METOCURINE, & GALLAMINE WERE STUDIED IN RAT PHRENIC NERVE-HEMIDIAPHRAGM PREPN WITH VASCULAR PERFUSION AT 25, 31, & 37 C. D-TC, METOCURINE, & GALLAMINE EACH DEMONSTRATED A NEAR 2-FOLD INCREASE IN ED50 AT 25 C COMPARED WITH 37 C. NO SUCH RELATIONSHIP WAS APPARENT WITH PANCURONIUM BROMIDE. SLOPES OF THE DOSE-RESPONSE CURVES WERE NOT INFLUENCED BY TEMP; HOWEVER, THE SLOPES FOR METOCURINE & D-TC WERE LOWER THAN THOSE FOR PANCURONIUM BROMIDE & GALLAMINE. THUS, IN THE RAT, PANCURONIUM BROMIDE RETAINS POTENCY AT HYPOTHERMIA, WHEREAS THE OTHER RELAXANTS DECREASE POTENCY. IN ADDITION, METOCURINE & D-TC EXHIBIT LESS STEEP DOSE-RESPONSE CURVES UNDER THESE EXPTL CONDITIONS.

HORROW JC, BARTKOWSKI RR; PANCURONIUM, UNLIKE OTHER NONDEPOLARIZING RELAXANTS, RETAINS POTENCY AT HYPOTHERMIA; ANESTHESIOLOGY 58(4) 357 (1983)

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