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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9463808
Curator's Comment: Tubocurarine does not penetrate the normal intact blood-brain barrier.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1907594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15203153 |
2.0 µM [IC50] | ||
Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23757208 |
9.2 µM [IC50] | ||
Target ID: Q15822 Gene ID: 1135.0 Gene Symbol: CHRNA2 Target Organism: Homo sapiens (Human) |
|||
Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18633030 |
24.0 nM [IC50] | ||
Target ID: CHEMBL1899 |
84.1 nM [Ki] | ||
27.0 µM [IC50] | |||
Target ID: CHEMBL4469 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10696100 |
17.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Diagnostic | TUBOCURARINE CHLORIDE Approved UseTubocurarine is indicated as a diagnostic aid for myasthenia gravis when the results of tests with neostigmine or edrophonium are inconclusive Launch Date1945 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.173 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7114542/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
117 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7114542/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
89 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7114542/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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 victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Ca2+-activated K+ channels in human leukemic Jurkat T cells. Molecular cloning, biochemical and functional characterization. | 2000 Dec 22 |
|
Increased sensitivity to depolarization and nondepolarizing neuromuscular blocking agents in young rat hemidiaphragms. | 2001 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 |
|
[Extrarenal effects of furosemide on normal and ischemic cerebral tissue in the rat]. | 2001 Mar 1-15 |
|
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 |
|
Stimulation of non-alpha7 nicotinic receptors partially protects dopaminergic neurons from 1-methyl-4-phenylpyridinium-induced toxicity in culture. | 2002 |
|
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 |
|
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 |
|
Effect of glycine on synaptic transmission at the third order giant synapse of the squids Alloteuthis subulata and Loligo vulgaris. | 2002 May 31 |
|
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 |
|
Comparative fading responses induced by mivacurium, cisatracurium, and d-tubocurarine in the evoked muscular compound action potentials of the cat. | 2003 |
|
Synthesis and biological evaluation of 16 beta-pyrrolidinosteroidal derivatives. | 2003 |
|
A novel class of ligand-gated ion channel is activated by Zn2+. | 2003 Jan 10 |
|
Curariform antagonists bind in different orientations to acetylcholine-binding protein. | 2003 Jun 20 |
|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/mmx/tubocurarine-chloride.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12429579
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
Edited
Fri Dec 15 14:59:55 GMT 2023
by
admin
on
Fri Dec 15 14:59:55 GMT 2023
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Record UNII |
W9YXS298BM
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
M03AA02
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WHO-VATC |
QM03AA02
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D014403
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Tubocurarine
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DTXSID0048393
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
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BINDER->LIGAND |
Related Record | Type | Details | ||
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ACTIVE MOIETY |