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

1945
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
[Effects of non-depolarizing muscle relaxants on the duration of mivacurium].
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
Differential effects of chronic drug treatment on alpha3* and alpha7 nicotinic receptor binding sites, in hippocampal neurones and SH-SY5Y cells.
2001 Aug
Peripheral site ligands accelerate inhibition of acetylcholinesterase by neutral organophosphates.
2001 Dec
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
Action mechanism of betahistine in the vestibular end organs.
2001 Jun
[Extrarenal effects of furosemide on normal and ischemic cerebral tissue in the rat].
2001 Mar 1-15
[Cholinergic regulation of the sea urchin embryonic and larval development].
2001 Nov
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
Evaluation of the cholinomimetic actions of trimethylsulfonium, a compound present in the midgut gland of the sea hare Aplysia brasiliana (Gastropoda, Opisthobranchia).
2002 Apr
The nature of the acetylcholine and 5-hydroxytryptamine receptors in buccal smooth muscle of the pest slug Deroceras reticulatum.
2002 Apr
Characterization of the interactions between volatile anesthetics and neuromuscular blockers at the muscle nicotinic acetylcholine receptor.
2002 Aug
Mapping the agonist binding site of the nicotinic acetylcholine receptor by cysteine scanning mutagenesis: antagonist footprint and secondary structure prediction.
2002 Feb
Acceleration of Drosophila melanogaster acetylcholinesterase methanesulfonylation: peripheral ligand D-tubocurarine enhances the affinity for small methanesulfonylfluoride.
2002 Feb 20
Biochemical and pharmacological characterization of the venom of the black scorpion Heterometrus spinifer.
2002 Jan 1
Modulation by nicotine of the ionic currents in guinea pig ventricular cardiomyocytes. Relatively higher sensitivity to IKr and IKl.
2002 Jul
New evidence for a presynaptic action of prednisolone at neuromuscular junctions.
2002 Jul
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
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
Sex difference in urethral response to electrical stimulation of efferent nerves in the pudendal sensory branch of rats.
2002 Oct
Pharmacology of nicotinic receptors in preBötzinger complex that mediate modulation of respiratory pattern.
2002 Oct
Interaction of d-tubocurarine analogs with mutant 5-HT(3) receptors.
2002 Sep
Nicotinic alpha 7 receptor clusters on hippocampal GABAergic neurons: regulation by synaptic activity and neurotrophins.
2002 Sep 15
Characterization of an apamin-sensitive potassium current in suprachiasmatic nucleus neurons.
2003
Synthesis and biological evaluation of 16 beta-pyrrolidinosteroidal derivatives.
2003
Blockade of neuronal facilitatory nicotinic receptors containing alpha 3 beta 2 subunits contribute to tetanic fade in the rat isolated diaphragm.
2003 Aug
Curariform antagonists bind in different orientations to the nicotinic receptor ligand binding domain.
2003 Aug 22
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
4-Aminopyridine inhibits the neuromuscular effects of nitric oxide and 8-Br-cGMP.
2003 Jul
Neuromuscular transmission of pectoral fin muscles of the goldfish Carassius auratus.
2003 Jul
Neuromuscular effects of candoxin, a novel toxin from the venom of the Malayan krait (Bungarus candidus).
2003 Jun
Dopaminergic excitation of the goat carotid body is mediated by the serotonin type 3 receptor subtype.
2003 Jun 12
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.
2003 Jun 12
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
Chronic intraperitoneal endotoxin treatment in rats induces resistance to d-tubocurarine, but does not produce up-regulation of acetylcholine receptors.
2003 Mar
Bisindole alkaloids from Strychnos guianensis are effective antagonists of nicotinic acetylcholine receptors in cultured human TE671 cells.
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
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 Fri Dec 15 14:59:55 GMT 2023
Edited
by admin
on Fri Dec 15 14:59:55 GMT 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 Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
WHO-VATC QM03AA02
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
Code System Code Type Description
DAILYMED
W9YXS298BM
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
EVMPD
SUB15635MIG
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
PUBCHEM
6000
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
DRUG BANK
DB01199
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
HSDB
2152
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
RXCUI
10917
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY RxNorm
CAS
57-95-4
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
MESH
D014403
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
DRUG CENTRAL
2781
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
SMS_ID
100000077304
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
CHEBI
9774
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
IUPHAR
2294
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
FDA UNII
W9YXS298BM
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
WIKIPEDIA
Tubocurarine
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID0048393
Created by admin on Fri Dec 15 14:59:55 GMT 2023 , Edited by admin on Fri Dec 15 14:59:55 GMT 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
Related Record Type Details
ACTIVE MOIETY