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Chemistry

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Also known as: 65-29-2, Flaxedil, Benzcurine iodide, Remyolan, Syncurarine, Benzkurin
Molecular Formula
C30H60I3N3O3
Molecular Weight
891.5  g/mol
InChI Key
REEUVFCVXKWOFE-UHFFFAOYSA-K
FDA UNII
Q3254X40X2

Gallamine Triethiodide
A synthetic nondepolarizing blocking drug. The actions of gallamine triethiodide are similar to those of TUBOCURARINE, but this agent blocks the cardiac vagus and may cause sinus tachycardia and, occasionally, hypertension and increased cardiac output. It should be used cautiously in patients at risk from increased heart rate but may be preferred for patients with bradycardia. (From AMA Drug Evaluations Annual, 1992, p198)
1 2D Structure

Gallamine Triethiodide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[2,3-bis[2-(triethylazaniumyl)ethoxy]phenoxy]ethyl-triethylazanium;triiodide
2.1.2 InChI
InChI=1S/C30H60N3O3.3HI/c1-10-31(11-2,12-3)22-25-34-28-20-19-21-29(35-26-23-32(13-4,14-5)15-6)30(28)36-27-24-33(16-7,17-8)18-9;;;/h19-21H,10-18,22-27H2,1-9H3;3*1H/q+3;;;/p-3
2.1.3 InChI Key
REEUVFCVXKWOFE-UHFFFAOYSA-K
2.1.4 Canonical SMILES
CC[N+](CC)(CC)CCOC1=C(C(=CC=C1)OCC[N+](CC)(CC)CC)OCC[N+](CC)(CC)CC.[I-].[I-].[I-]
2.2 Other Identifiers
2.2.1 UNII
Q3254X40X2
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Flaxedil

2. Gallamine

3. Gallamine Triethochloride

4. Gallamine Triethyl Iodide

5. Gallamonium Iodide

6. Iodide, Gallamine Triethyl

7. Iodide, Gallamonium

8. Triethiodide, Gallamine

9. Triethochloride, Gallamine

10. Triethyl Iodide, Gallamine

2.3.2 Depositor-Supplied Synonyms

1. 65-29-2

2. Flaxedil

3. Benzcurine Iodide

4. Remyolan

5. Syncurarine

6. Benzkurin

7. Pirolakson

8. Sincurarine

9. Gallaflex

10. Parexyl

11. Pyrolaxon

12. Relaxan

13. Retensin

14. Tricuran

15. Gallamin Triethiodide

16. Gallamone Triethiodide

17. Gallamine Iodide

18. Gallamini Triethiodidum

19. Miowas G

20. Gallamine-3eti

21. Fourneau 2559

22. Gallamine Triiodoethylate

23. Triiodoethylate De Gallamine

24. (v-phenenyltris(oxyethylene))tris(triethylammonium) Triiodide

25. Hl 8583

26. Rp 3697

27. F 2559

28. Gallamoni Jodidum

29. 2-[2,3-bis[2-(triethylazaniumyl)ethoxy]phenoxy]ethyl-triethylazanium;triiodide

30. Gallaminii Iodidum

31. (v-phenenyltris(oxyethylene))tris(triethylammoniumiodide)

32. (v-phenenyltris(oxyethylene))tris(triethylammonium Iodide)

33. Nsc-102690

34. Q3254x40x2

35. Dsstox_cid_3089

36. Gallaminum Triaethjodidum

37. Gallaminum Triaethoiodatum

38. 2,2',2''-(benzene-1,2,3-triyltris(oxy))tris(n,n,n-triethylethan-1-aminium) Iodide

39. Dsstox_rid_76870

40. Dsstox_gsid_23089

41. 3697 R.p.

42. Gallamine Triethiodide [inn]

43. Gallamina Triodoetilato

44. Gallamina Triodoetilato [dcit]

45. Triethiodure De Gallamine

46. 2,2',2''-(benzene-1,2,3-triyltris(oxy))tris(n,n,n-triethylethanaminium) Iodide

47. Gallamini Triethiodidum [inn-latin]

48. Flaxedil (tn)

49. Triiodoethylate De Gallamine [french]

50. Triethiodure De Gallamine [inn-french]

51. Triethioduro De Galamina [inn-spanish]

52. Hsdb 3229

53. Triethioduro De Galamina

54. Cas-65-29-2

55. Sr-01000075317

56. Ncgc00163245-01

57. Einecs 200-605-1

58. Nsc 102690

59. 1,2,3-tris(diethylaminoethoxy)benzene Triethiodide

60. 1,2,3-tris(2-diethylaminoethoxy)benzene Triethiodide

61. 1,2,3-tri(beta-diethylaminoethoxy)benzene Triethiodide

62. Gallamine Triethiodide (usp)

63. 1,2,3-tris(2-triethylammonium Ethoxy)benzene Triiodide

64. 1,2,3-tris(2-diethylaminoethoxy)benzene Tris(ethyliodide)

65. Pyrogallol 1,2,3-(diethylaminoethyl Ether) Trisethyl Iodide

66. Tri(beta-diethylaminoethoxy)-1,2,3-benzene Tri-iodoethylate

67. Triiodoethylate Of Tri(diethylaminoethyloxy)-1,2,3-benzene

68. Unii-q3254x40x2

69. Pyrogallol 1,2,3-(diethylaminoethyl Ether) Tris(ethyliodide)

70. Ammonium, (v-phenenyltris(oxyethylene))tris(triethyl-, Triiodide

71. Gallamine Triethiodide [usp:inn]

72. Triiodure De Tri(beta-triethylammoniumethoxy)-1,2,3 Benzene [french]

73. Tri(iodoethylate) De Tri (beta Diethylaminoethoxy)-1,2,3 Benzene [french]

74. Prestwick_237

75. 2,2',2''-(1,2,3-benzenetriyltris(oxy))tris(n,n,n-triethylethanaminium) Triiodide

76. Ethanaminium, 2,2',2''-(1,2,3-benzenetriyltris(oxy))tris(n,n,n-triethyl)-, Triiodide

77. Ethanaminium, 2,2',2''-(1,2,3-benzenetriyltris(oxy))tris(n,n,n-triethyl-, Triiodide

78. Triiodure De Tri(beta-triethylammoniumethoxy)-1,2,3 Benzene

79. Ammonium, (v-phenenyltris(oxyethylene)tris(triethyl-, Triiodide

80. Tri(iodoethylate) De Tri (beta Diethylaminoethoxy)-1,2,3 Benzene

81. 3.697 R.p.

82. G 8134

83. Ethanaminium, 2,2',2'-(1,2,3-benzenetriyltris(oxy))tris(n,n,n-triethyl)-, Triiodide

84. Chembl1200993

85. Dtxsid5023089

86. Hms502a12

87. Gallamine Triethiodide (flaxedil)

88. Hms1568o16

89. Hms2091h09

90. Hms2095o16

91. Hms3261n21

92. Hms3656g04

93. Hms3712o16

94. Hms3884b21

95. Gallamine Triethiodide [mi]

96. Hy-b0416

97. Tox21_112040

98. Tox21_500550

99. Ccg-40105

100. Gallamine Triethiodide [hsdb]

101. S2471

102. Gallamine Triethiodide [vandf]

103. Akos026749935

104. Gallamine Triethiodide [mart.]

105. Tox21_112040_1

106. Db00483

107. Gallamine Triethiodide [who-dd]

108. Gallamine Triethiodide [who-ip]

109. Lp00550

110. 2,2',2''-[benzene-1,2,3-triyltris(oxy)]tris(n,n,n-triethylethanaminium) Triiodide

111. Ncgc00015482-07

112. Ncgc00093937-01

113. Ncgc00261235-01

114. As-57694

115. Gallamine Triethiodide [orange Book]

116. Eu-0100550

117. Ft-0703297

118. G0554

119. Gallamine Triethiodide [usp Impurity]

120. Sw196544-3

121. Gallamini Triethiodidum [who-ip Latin]

122. C76041

123. D02292

124. Q3094785

125. Sr-01000075317-1

126. Sr-01000075317-3

127. Sr-01000075317-6

128. W-104798

129. Gallamine Triethiodide, European Pharmacopoeia (ep) Reference Standard

130. Gallamine Triethiodide, United States Pharmacopeia (usp) Reference Standard

131. (2-{2,3-bis[2-(triethylazaniumyl)ethoxy]phenoxy}ethyl)triethylazanium Triiodide

132. 6b,7a-dihydro-7h-cycloprop[a]acenaphthylene-7-carboxylicacidethylester

133. Gallamine Triethiodide, >=98% (tlc), Powder, Muscarinic Receptor Antagonist

134. Ethanaminium, 2,2',2''-(benzene-1,2,3-triyltris(oxy))tris(n,n,n-triethyl-, Triiodide

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 891.5 g/mol
Molecular Formula C30H60I3N3O3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count21
Exact Mass891.1769 g/mol
Monoisotopic Mass891.1769 g/mol
Topological Polar Surface Area27.7 Ų
Heavy Atom Count39
Formal Charge0
Complexity489
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count4
4 Drug and Medication Information
4.1 Therapeutic Uses

Neuromuscular Nondepolarizing Agents; Nicotinic Antagonists

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


A NEUROMUSCULAR BLOCKING DRUG SIMILAR IN ITS ACTIONS & USES TO TUBOCURARINE CHLORIDE. ...IN GENERAL, IT HAS VERY LITTLE ACTION ON AUTONOMIC GANGLIA, BUT IT USUALLY BLOCKS CARDIAC VAGUS... IT ALSO DOES NOT RELEASE HISTAMINE /IN LOW DOSES/.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 852


... IT HAS NO PERCEPTIBLE EFFECT ON NEWBORN INFANTS WHEN USUAL DOSES ARE GIVEN FOR CESAREAN SECTION & VAGINAL DELIVERY & TONE OF UTERUS IS NOT AFFECTED.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 337


...HAS BEEN REPORTED TO REDUCE OCULAR PRESSURE SLIGHTLY IN PT.

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 519


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


4.2 Drug Warning

THE NEUROMUSCULAR BLOCKING AGENTS ARE POTENTIALLY HAZARDOUS DRUGS. ... 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 SHOULD BE USED CAUTIOUSLY IF TACHYCARDIA PREEXISTS. .../SINCE IT/ IS ELIMINATED MAINLY BY RENAL EXCRETION...ITS ACTION MAY BE PROLONGED IF THERE IS RENAL DYSFUNCTION.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 863


... /IT SHOULD NOT/ BE USED IN PT WITH RENAL DISEASE.

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 338


CROSS SENSITIVITY BETWEEN ALCURONIUM & D-TUBOCURARINE OCCURS & SIMILAR SITUATION MAY EXIST FOR SUXAMETHONIUM & GALLAMINE.

PMID:7396189 FISHER MM; ANAESTH INTENSIVE CARE 8 (2): 211 (1980)


For more Drug Warnings (Complete) data for GALLAMINE TRIETHIODIDE (6 total), please visit the HSDB record page.


4.3 Drug Indication

For use as adjuncts to anesthesia to induce skeletal muscle relaxation and to facilitate the management of patients undergoing mechanical ventilation


5 Pharmacology and Biochemistry
5.1 Pharmacology

Gallamine Triethiodide is a nondepolarizing neuromuscular blocking drug (NDMRD) used as an adjunct to anesthesia to induce skeletal muscle relaxation. The actions of gallamine triethiodide are similar to those of tubocurarine, but this agent blocks the cardiac vagus and may cause sinus tachycardia and, occasionally, hypertension and increased cardiac output. Muscle groups differ in their sensitivity to these types of relaxants with ocular muscles (controlling eyelids) being most sensitive, followed by the muscles of the neck, jaw, limbs and then abdomen. The diaphragm is the least sensitive muscle to NDMRDs. Although the nondepolarizing neuromuscular blocking drugs do not have the same adverse effects as succinylcholine, their onset of action is slower. They also have a longer duration of action, making them more suitable for maintaining neuromuscular relaxation during major surgical procedures.


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 Absorption, Distribution and Excretion

STUDIES HAVE DEMONSTRATED THAT GALLAMINE IS EXCRETED IN DOG URINE AT RATE FASTER THAN OTHER MUSCLE RELAXANTS. .../IT/ DID NOT CROSS BLOOD-CEREBROSPINAL FLUID BARRIER. OTHER STUDIES...HAVE DETECTED GALLAMINE IN CEREBROSPINAL FLUID IN CONCN APPROACHING THOSE IN PLASMA DURING 1ST HR AFTER IV INJECTION. /GALLAMINE/

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


GALLAMINE IS ELIMINATED MAINLY BY RENAL EXCRETION...

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 863


... GALLAMINE CROSSES PLACENTAL BARRIER ...

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 4th ed. Chicago: American Medical Association, 1980., p. 337


TRACE AMT OF GALLAMINE APPEARS IN FETUS 3 MIN AFTER ADMIN. /GALLAMINE, FROM TABLE/

LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug Metabolism and Disposition. Baltimore: Williams and Wilkins, 1971., p. 101


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


5.4 Metabolism/Metabolites

.../GALLAMINE/ IS UNMETABOLIZED. /GALLAMINE/

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


5.5 Biological Half-Life

135 minutes /From table/

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 8-11


5.6 Mechanism of Action

It competes with acetylcholine (ACh) molecules and binds to muscarinic acetylcholine receptors on the post-synaptic membrane of the motor endplate. It acts by combining with the cholinergic receptor sites in muscle and competitively blocking the transmitter action of acetylcholine. It blocks the action of ACh and prevents activation of the muscle contraction process. It can also act on nicotinic presynaptic acetylcholine receptors which inhibits the release of ACh.


GALLAMINE TRIETHIODIDE...PRODUCES SKELETAL MUSCLE RELAXATION BY COMBINING WITH RECEPTOR SITE AT NEUROMUSCULAR JUNCTION & BLOCKING ACTION OF NEUROTRANSMITTER ACETYLCHOLINE.

Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 75


IN RAT PHRENIC NERVE-DIAPHRAGM GALLAMINE HAD NO SIGNIFICANT EFFECTS ON ELECTROGENIC PROPERTIES OF EXCITABLE MEMBRANES OF MOTOR NERVE TERMINALS & MUSCLE FIBERS; IT DEPRESSED RESPONSE OF POSTSYNAPTIC RECEPTORS TO ACTION OF ACETYLCHOLINE.

GALINDO A, KELLY PJ; MECHANISM OF ACTION OF GALLAMINE; ANESTH ANALG (CLEVELAND) 59(7) 484 (1980)


AT NEUROMUSCULAR JUNCTIONS IN MICE AND FROGS, FOLLOWING STEP CHANGES OF MEMBRANE POTENTIAL FROM -70 TO -130 MV, GALLAMINE (5 UMOL) IN THE PRESENCE OF ACETYLCHOLINE (3 UMOL) CAUSED AN INITIAL RAPID DECR IN CURRENT FOLLOWED BY OPENING OF CHANNELS AT A SLOWER RATE THAN WITH ACETYLCHOLINE ALONE. WHEN THE INTERNAL POTENTIAL WAS REDUCED TO -70 MV, THERE WAS A RAPID INCR IN CURRENT AT FIRST, FOLLOWED BY THE USUAL DECR WHICH WAS AGAIN SLOWER THAN NORMAL. THUS, GALLAMINE MAY PRODUCE A POTENTIAL-DEPENDENT BLOCK OF OPEN ION CHANNELS.

COLQUHOUN D, SHERIDAN RE; MODES OF ACTION OF GALLAMINE AT THE NEUROMUSCULAR JUNCTION; BR J PHARMACOL 66(1) 78 (1979)


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