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Substance Name: Tubocurarine
RN: 57-95-4
UNII: W9YXS298BM
InChIKey: JFJZZMVDLULRGK-URLMMPGGSA-O

Note

  • A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.

Molecular Formula

  • C37-H41-N2-O6

Molecular Weight

  • 609.739
 

Classification Codes

  • Cholinergic Agents
  • Cholinergic Antagonists
  • Drug / Therapeutic Agent
  • Natural Product
  • Neuromuscular Agents
  • Neuromuscular Blocking Agents
  • Neuromuscular Nondepolarizing Agents
  • Neurotransmitter Agents
  • Nicotinic Antagonists
  • Peripheral Nervous System Agents
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Names and Synonyms

Name of Substance

  • Tubocurarine

MeSH Heading

  • Tubocurarine

Synonyms

  • (+)-Tubocurarine
  • 13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido(3',2':14,15)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolinium, 2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-, (13aR-(13aR*,25aS*))-
  • D-Tubocurarine
  • HSDB 2152
  • Tubocurarin
  • Tubocurarine
  • Tubocurarinum
  • UNII-W9YXS298BM

Systematic Names

  • 13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido(3',2':14,15)(1,11)dioxacycloeicosino(2,3,4-ij)isoquinolinium, 2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-, (13aR,25aS)-
  • Tubocuraranium, 7',12'-dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyl-
  • Tubocurarine, (+)-

Registry Numbers

CAS Registry Number

  • 57-95-4

FDA UNII

  • W9YXS298BM

Other Registry Numbers

  • 1370-17-8
  • 30519-12-1
  • 31498-75-6
  • 3671-75-8
  • 548-18-5

System Generated Number

  • 0000057954

Structure Descriptors

InChI

1S/C37H40N2O6/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41)/p+1/t28-,29+/m0/s1

InChIKey

JFJZZMVDLULRGK-URLMMPGGSA-O

Smiles

c12c3c(c(OC)cc2CC[N+]([C@@H]1Cc1cc(Oc2cc4[C@H](Cc5ccc(O3)cc5)[N@@](CCc4cc2OC)C)c(O)cc1)(C)C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 intravenous 700ug/kg (0.7mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 122, Pg. 152, 1959.
dog LD50 intravenous 500ug/kg (0.5mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 80, Pg. 172, 1949.
dog LDLo intramuscular 250ug/kg (0.25mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 10, Pg. 638, 1958.
mouse LD50 intraperitoneal 410ug/kg (0.41mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 308, 1965.
mouse LD50 intravenous 130ug/kg (0.13mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 130, 1965.
mouse LD50 subcutaneous 525ug/kg (0.525mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 85, Pg. 603, 1954.
mouse LD50 unreported 450ug/kg (0.45mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" Pharmaceutical Chemistry Journal Vol. 2, Pg. 117, 1968.
rabbit LD50 intravenous 20ug/kg (0.02mg/kg)   Rendiconti Istituto Superiore di Sanita Vol. 13, Pg. 339, 1950.
rabbit LD50 subcutaneous 500ug/kg (0.5mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 631, 1948.
rat LD50 intraperitoneal 220ug/kg (0.22mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ATAXIA

CARDIAC: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 92, Pg. 454, 1948.
rat LDLo intramuscular 500ug/kg (0.5mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacy and Pharmacology. Vol. 10, Pg. 638, 1958.