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

Details

Stereochemistry ABSOLUTE
Molecular Formula C37H41N2O6
Molecular Weight 609.7312
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of TUBOCURARINE

SMILES

COC1=CC2=C3C=C1OC4=CC(C[C@@H]5C6=C(OC7=CC=C(C[C@@H]3N(C)CC2)C=C7)C(O)=C(OC)C=C6CC[N+]5(C)C)=CC=C4O

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

Molecular Formula C37H40N2O6
Molecular Weight 608.7233
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Influence of tetrahydro-aminacrine on muscle pains after suxamethonium.
1975 Jan 18
"Precurarization" using pancuronium.
1975 Jan-Feb
Effects of pretreatment with cisatracurium, rocuronium, and d-tubocurarine on succinylcholine-induced fasciculations and myalgia: a comparison with placebo.
1999 Dec
Structural features of the ligand-binding domain of the serotonin 5HT3 receptor.
1999 Feb 26
Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant.
1999 Feb 5
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
Effect of cholinergic agonists on resting membrane potential of earthworm body wall muscle cells.
2001 Apr
Giant multimodal heart motoneurons of Achatina fulica: a new cardioregulatory input in pulmonates.
2001 Aug
Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors.
2001 Aug
Cholinergic transmission via central synapses in the locust nervous system.
2001 Dec
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
Interaction of Drosophila acetylcholinesterases with D-tubocurarine: an explanation of the activation by an inhibitor.
2001 Feb 6
N-cholinergic facilitation of glutamate release from an individual retinotectal fiber in frog.
2001 Jul-Aug
Modulation by nitric oxide (NO) of the intensity of non-quantum mediator secretion in neuromuscular junctions in rats.
2001 Jul-Aug
Action mechanism of betahistine in the vestibular end organs.
2001 Jun
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
Mesangial proliferative glomerulonephritis with deposits of anti-nicotinic acetylcholine receptor antibody in a patient with myasthenia gravis.
2001 Sep
Stimulation of non-alpha7 nicotinic receptors partially protects dopaminergic neurons from 1-methyl-4-phenylpyridinium-induced toxicity in culture.
2002
Adenosine depresses a Ca(2+)-independent step in transmitter exocytosis at frog motor nerve terminals.
2002 Apr
Characterization of the interactions between volatile anesthetics and neuromuscular blockers at the muscle nicotinic acetylcholine receptor.
2002 Aug
[3H]Epibatidine binding to bovine adrenal medulla: evidence for alpha3beta4* nicotinic receptors.
2002 Jan 25
Characterization of [(125) I]epibatidine binding and nicotinic agonist-mediated (86) Rb(+) efflux in interpeduncular nucleus and inferior colliculus of beta2 null mutant mice.
2002 Jun
Properties of nicotinic receptors underlying Renshaw cell excitation by alpha-motor neurons in neonatal rat spinal cord.
2002 Jun
Acetylcholine increases intracellular Ca2+ in taste cells via activation of muscarinic receptors.
2002 Jun
Nicotine increases hepatic oxygen uptake in the isolated perfused rat liver by inhibiting glycolysis.
2002 Jun
The potency of new muscle relaxants on recombinant muscle-type acetylcholine receptors.
2002 Mar
Fm1-43 reveals membrane recycling in adult inner hair cells of the mammalian cochlea.
2002 May 15
Effect of glycine on synaptic transmission at the third order giant synapse of the squids Alloteuthis subulata and Loligo vulgaris.
2002 May 31
Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives.
2002 Nov
Orientation of d-tubocurarine in the muscle nicotinic acetylcholine receptor-binding site.
2002 Nov 1
Pharmacology of nicotinic receptors in preBötzinger complex that mediate modulation of respiratory pattern.
2002 Oct
Comparative fading responses induced by mivacurium, cisatracurium, and d-tubocurarine in the evoked muscular compound action potentials of the cat.
2003
Characterization of an apamin-sensitive potassium current in suprachiasmatic nucleus neurons.
2003
Blockade of neuronal facilitatory nicotinic receptors containing alpha 3 beta 2 subunits contribute to tetanic fade in the rat isolated diaphragm.
2003 Aug
A comparison of tubocurarine, rocuronium, and cisatracurium in the prevention and reduction of succinylcholine-induced muscle fasciculations.
2003 Feb
Nicotinic activation of reticulospinal cells involved in the control of swimming in lampreys.
2003 Jan
A novel class of ligand-gated ion channel is activated by Zn2+.
2003 Jan 10
Neuromuscular transmission of pectoral fin muscles of the goldfish Carassius auratus.
2003 Jul
Curariform antagonists bind in different orientations to acetylcholine-binding protein.
2003 Jun 20
Screening procedure for eight quaternary nitrogen muscle relaxants in blood by high-performance liquid chromatography-electrospray ionization mass spectrometry.
2003 Jun 5
Bisindole alkaloids from Strychnos guianensis are effective antagonists of nicotinic acetylcholine receptors in cultured human TE671 cells.
2003 Mar
D-tubocurarine reduces GABA responses in rat substantia nigra dopamine neurons.
2003 Mar
Task-dependent presynaptic inhibition.
2003 Mar 1
Nicotine modulates the expression of a diverse set of genes in the neuronal SH-SY5Y cell line.
2003 May 2
Monitoring neuronal calcium signalling using a new method for ratiometric confocal calcium imaging.
2003 Sep
GABAergic systems modulate nicotinic receptor-mediated seizures in mice.
2003 Sep
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:31:59 UTC 2023
Edited
by admin
on Wed Jul 05 22:31:59 UTC 2023
Record UNII
W9YXS298BM
Record Status Validated (UNII)
Record Version
  • Download
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 [WHO-DD]
Common Name English
TUBOCURARINE [HSDB]
Common Name English
TUBOCURARINE ION
Common Name English
D-TUBOCURARINE
Common Name English
(+)-TUBOCURARINE
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 Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
WHO-VATC QM03AA02
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
Code System Code Type Description
DAILYMED
W9YXS298BM
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
EVMPD
SUB15635MIG
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
PUBCHEM
6000
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
DRUG BANK
DB01199
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
HSDB
2152
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
RXCUI
10917
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY RxNorm
CAS
57-95-4
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
MESH
D014403
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
DRUG CENTRAL
2781
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
SMS_ID
100000077304
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
CHEBI
9774
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
IUPHAR
2294
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
FDA UNII
W9YXS298BM
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
WIKIPEDIA
Tubocurarine
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID0048393
Created by admin on Wed Jul 05 22:31:59 UTC 2023 , Edited by admin on Wed Jul 05 22:31:59 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
Related Record Type Details
ACTIVE MOIETY