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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

Molecular Formula C37H40N2O6
Molecular Weight 608.7247
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
Comparison of gallamine with d-tubocurarine effects on fasciculations after succinylcholine.
1975 Jan-Feb
Structural features of the ligand-binding domain of the serotonin 5HT3 receptor.
1999 Feb 26
Chick optic lobe contains a developmentally regulated alpha2alpha5beta2 nicotinic receptor subtype.
2000 Aug
Cloning, expression, and characterization of ferret 5-HT(3) receptor subunit.
2000 Jul 7
[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
Giant multimodal heart motoneurons of Achatina fulica: a new cardioregulatory input in pulmonates.
2001 Aug
Differential effects of chronic drug treatment on alpha3* and alpha7 nicotinic receptor binding sites, in hippocampal neurones and SH-SY5Y cells.
2001 Aug
Cholinergic transmission via central synapses in the locust nervous system.
2001 Dec
Modulation by nitric oxide (NO) of the intensity of non-quantum mediator secretion in neuromuscular junctions in rats.
2001 Jul-Aug
Pharmacological characterisation of the human small conductance calcium-activated potassium channel hSK3 reveals sensitivity to tricyclic antidepressants and antipsychotic phenothiazines.
2001 May
Ongoing nicotinic and non-nicotinic inputs to inhibitory neurons in the mouse colon.
2001 Oct
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
Electrophysiological analysis of synaptic transmission in central neurons of Drosophila larvae.
2002 Aug
Impairment of synaptic vesicle exocytosis and recycling during neuromuscular weakness produced in mice by 2,4-dithiobiuret.
2002 Dec
Modulation by nicotine of the ionic currents in guinea pig ventricular cardiomyocytes. Relatively higher sensitivity to IKr and IKl.
2002 Jul
Acetylcholine increases intracellular Ca2+ in taste cells via activation of muscarinic receptors.
2002 Jun
Activation of embryonic red and white muscle fibers during fictive swimming in the developing zebrafish.
2002 Mar
Characterization of an apamin-sensitive small-conductance Ca(2+)-activated K(+) channel in porcine coronary artery endothelium: relevance to EDHF.
2002 Mar
The potency of new muscle relaxants on recombinant muscle-type acetylcholine receptors.
2002 Mar
Neuromuscular action of Bothrops lanceolatus (Fer de lance) venom and a caseinolytic fraction.
2002 Sep
Nicotinic alpha 7 receptor clusters on hippocampal GABAergic neurons: regulation by synaptic activity and neurotrophins.
2002 Sep 15
Curariform antagonists bind in different orientations to the nicotinic receptor ligand binding domain.
2003 Aug 22
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
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
Nicotine modulates the expression of a diverse set of genes in the neuronal SH-SY5Y cell line.
2003 May 2
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 Sat Jun 26 10:31:41 UTC 2021
Edited
by admin
on Sat Jun 26 10:31:41 UTC 2021
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 [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
Related Record Type Details
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
BINDER->LIGAND
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ACTIVE MOIETY