U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H41N2O6
Molecular Weight 609.7326
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of TUBOCURARINE

SMILES

CN1CCc2cc(c3cc2[C@]1([H])Cc4ccc(cc4)Oc5c6c(CC[N+](C)(C)[C@]6([H])Cc7ccc(c(c7)O3)O)cc(c5O)OC)OC

InChI

InChIKey=JFJZZMVDLULRGK-URLMMPGGSA-O
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

HIDE SMILES / InChI
Tubocurarine, a naturally occurring alkaloid, is used to treat smoking withdrawl syndrom. Tubocurarine, the chief alkaloid in tobacco products, binds stereo-selectively to nicotinic-cholinergic receptors at the autonomic ganglia, in the adrenal medulla, at neuromuscular junctions, and in the brain. Two types of central nervous system effects are believed to be the basis of Tubocurarine's positively reinforcing properties. A stimulating effect is exerted mainly in the cortex via the locus ceruleus and a reward effect is exerted in the limbic system. At low doses the stimulant effects predominate while at high doses the reward effects predominate. Intermittent intravenous administration of Tubocurarine activates neurohormonal pathways, releasing acetylcholine, norepinephrine, dopamine, serotonin, vasopressin, beta-endorphin, growth hormone, and ACTH. Tubocurarine competes with acetylcholine for post-synaptic nicotinic NM receptors and blocks them.

CNS Activity

Curator's Comment:: Tubocurarine does not penetrate the normal intact blood-brain barrier.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
TUBOCURARINE CHLORIDE

Approved Use

Tubocurarine is indicated as a diagnostic aid for myasthenia gravis when the results of tests with neostigmine or edrophonium are inconclusive

Launch Date

-7.8459837E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.173 μg/mL
16 μg/kg/min other, intravenous
dose: 16 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TUBOCURARINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
117 μg × min/mL
16 μg/kg/min other, intravenous
dose: 16 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TUBOCURARINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
89 min
16 μg/kg/min other, intravenous
dose: 16 μg/kg/min
route of administration: Intravenous
experiment type: OTHER
co-administered:
TUBOCURARINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely [IC50 >100 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
yes [IC50 133 uM]
yes [IC50 133 uM]
yes [IC50 133 uM]
yes [IC50 55.5 uM]
yes [IC50 62.4 uM]
yes [IC50 9.4 uM]
yes [IC50 9.6 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victimTox targets
PubMed

PubMed

TitleDatePubMed
"Precurarization" using pancuronium.
1975 Jan-Feb
Ketamine-pancuronium-narcotic technic for cardiovascular surgery in infants--a comparative study.
1975 Nov-Dec
Inducible, heterologous expression of human alpha7-nicotinic acetylcholine receptors in a native nicotinic receptor-null human clonal line.
1999 Apr 17
Effects of pretreatment with cisatracurium, rocuronium, and d-tubocurarine on succinylcholine-induced fasciculations and myalgia: a comparison with placebo.
1999 Dec
Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant.
1999 Feb 5
The influence of peripheral site ligands on the reaction of symmetric and chiral organophosphates with wildtype and mutant acetylcholinesterases.
1999 May 14
Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.
2000 Aug
Ca2+-activated K+ channels in human leukemic Jurkat T cells. Molecular cloning, biochemical and functional characterization.
2000 Dec 22
Nondepolarizing neuromuscular blockers inhibit the serotonin-type 3A receptor expressed in Xenopus oocytes.
2000 Feb
Pharmacological characterization of small-conductance Ca(2+)-activated K(+) channels stably expressed in HEK 293 cells.
2000 Mar
Betahistine produces post-synaptic inhibition of the excitability of the primary afferent neurons in the vestibular endorgans.
2001
Effect of cholinergic agonists on resting membrane potential of earthworm body wall muscle cells.
2001 Apr
Antagonism by hemoglobin of effects induced by L-arginine in neuromuscular preparations from rats.
2001 Apr
Giant multimodal heart motoneurons of Achatina fulica: a new cardioregulatory input in pulmonates.
2001 Aug
Characterization of vagal input to the rat esophageal muscle.
2001 Aug 13
Involvement of nicotinic acetylcholine receptors in suppression of antimicrobial activity and cytokine responses of alveolar macrophages to Legionella pneumophila infection by nicotine.
2001 Dec 1
Acetylcholine-evoked calcium increases in Deiters' cells of the guinea pig cochlea suggest alpha9-like receptors.
2001 Feb 1
Interaction of Drosophila acetylcholinesterases with D-tubocurarine: an explanation of the activation by an inhibitor.
2001 Feb 6
Complex intracellular messenger pathways regulate one type of neuronal alpha-bungarotoxin-resistant nicotinic acetylcholine receptors expressed in insect neurosecretory cells (dorsal unpaired median neurons).
2001 Jul
The initial mode of action of copper on the cardiac physiology of the blue mussel, Mytilus edulis.
2001 Mar
[Cholinergic regulation of the sea urchin embryonic and larval development].
2001 Nov
Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors.
2001 Nov 2
The kinetics of inhibition of nicotinic acetylcholine receptors by (+)-tubocurarine and pancuronium.
2001 Oct
Ongoing nicotinic and non-nicotinic inputs to inhibitory neurons in the mouse colon.
2001 Oct
Mesangial proliferative glomerulonephritis with deposits of anti-nicotinic acetylcholine receptor antibody in a patient with myasthenia gravis.
2001 Sep
Characterisation of [(125)I]-apamin binding sites in rat brain membranes with HE293 cells transfected with SK channel subtypes.
2001 Sep
Electrophysiological analysis of synaptic transmission in central neurons of Drosophila larvae.
2002 Aug
Mechanism of nicotine-evoked release of 3H-noradrenaline in human cerebral cortex slices.
2002 Dec
Mapping the agonist binding site of the nicotinic acetylcholine receptor by cysteine scanning mutagenesis: antagonist footprint and secondary structure prediction.
2002 Feb
Activity- and target-dependent regulation of large-conductance Ca2+-activated K+ channels in developing chick lumbar motoneurons.
2002 Jan 1
Biochemical and pharmacological characterization of the venom of the black scorpion Heterometrus spinifer.
2002 Jan 1
Activation of embryonic red and white muscle fibers during fictive swimming in the developing zebrafish.
2002 Mar
Fm1-43 reveals membrane recycling in adult inner hair cells of the mammalian cochlea.
2002 May 15
Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives.
2002 Nov
Nicotinic receptors regulate the release of glycine onto lamina X neurones of the rat spinal cord.
2002 Nov
Orientation of d-tubocurarine in the muscle nicotinic acetylcholine receptor-binding site.
2002 Nov 1
Sex difference in urethral response to electrical stimulation of efferent nerves in the pudendal sensory branch of rats.
2002 Oct
Effects of nicotine exposure on T cell development in fetal thymus organ culture: arrest of T cell maturation.
2002 Sep 15
Task-dependent presynaptic inhibition.
2003 Mar 1
Patents

Patents

Sample Use Guides

Diagnostic aid (myasthenia gravis) Intravenous, 4 to 33 mcg (0.004 to 0.033 mg) per kg of body weight. Note: It is recommended that the test be terminated within two to three minutes by intravenous injection of 1.5 mg of neostigmine, since the marked exaggeration of myasthenia gravis symptoms may result in prolonged respiratory paralysis.
Route of Administration: Intravenous
D-tubocurarine (30 uM), but not alpha-bungarotoxin (alpha-BTX, 0.1 uM), attenuated the nicotine (NIC) (100 uM)-evoked release of 3H-NA.
Name Type Language
TUBOCURARINE
HSDB   VANDF   WHO-DD  
Common Name English
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)-
Common Name English
TUBOCURARINE [HSDB]
Common Name English
TUBOCURARINE ION
Common Name English
D-TUBOCURARINE
Common Name English
(+)-TUBOCURARINE
Common Name English
TUBOCURARINE [WHO-DD]
Common Name English
TUBOCURARINE CATION
Common Name English
TUBOCURARANIUM, 7',12'-DIHYDROXY-6,6'-DIMETHOXY-2,2',2'-TRIMETHYL-
Common Name English
TUBOCURARINE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC M03AA02
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
WHO-VATC QM03AA02
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
Code System Code Type Description
EVMPD
SUB15635MIG
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
PUBCHEM
6000
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
DRUG BANK
DB01199
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
HSDB
2152
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
RXCUI
10917
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY RxNorm
CAS
57-95-4
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
MESH
D014403
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
DRUG CENTRAL
2781
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
IUPHAR
2294
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
FDA UNII
W9YXS298BM
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
WIKIPEDIA
Tubocurarine
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY
EPA CompTox
57-95-4
Created by admin on Sat Jun 26 10:31:41 UTC 2021 , Edited by admin on Sat Jun 26 10:31:41 UTC 2021
PRIMARY