Tubocurarine
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Basic Info
| Common Name | Tubocurarine(F04809) |
| 2D Structure | |
| Description | Tubocurarine is only found in individuals that have used or taken this drug. It is a neuromuscular blocker and active ingredient in curare; plant based alkaloid of Menispermaceae. [PubChem]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. |
| FRCD ID | F04809 |
| CAS Number | 6989-98-6 |
| PubChem CID | 6000 |
| Formula | C37H41N2O6+ |
| IUPAC Name | None |
| InChI Key | JFJZZMVDLULRGK-URLMMPGGSA-O |
| InChI | 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 |
| Canonical SMILES | CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C6C(CC7=CC(=C(C=C7)O)O3)[N+](CCC6=CC(=C5O)OC)(C)C)OC |
| Isomeric SMILES | CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C6[C@@H](CC7=CC(=C(C=C7)O)O3)[N+](CCC6=CC(=C5O)OC)(C)C)OC |
| Wikipedia | Tubocurarine |
| Synonyms |
tubocurarine
d-Tubocurarine
Tubocurarin
(+)-Tubocurarine
Tubocurarine chloride
Tubocurarinum
Delacurarine
Tubarine
Isoquinoline alkaloid
Jexin
|
| Classifies |
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Ethers |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Diarylethers |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Diaryl ether - Tetrahydroisoquinoline - Anisole - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Aralkylamine - Benzenoid - Tetraalkylammonium salt - Quaternary ammonium salt - Tertiary amine - Tertiary aliphatic amine - Oxacycle - Azacycle - Organoheterocyclic compound - Amine - Organic nitrogen compound - Organonitrogen compound - Hydrocarbon derivative - Organopnictogen compound - Organic salt - Organic cation - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 609.743 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 2 |
| Complexity | 990 |
| Monoisotopic Mass | 609.296 |
| Exact Mass | 609.296 |
| XLogP | 6 |
| Formal Charge | 1 |
| Heavy Atom Count | 45 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Interaction of lipopolysaccharide endotoxin produced from Escherichia coli with D-tubocurarine at the nicotinic2 receptor and adenosine 3':5' cyclic monophosphate during physiological contraction in skeletal muscle. | Food Chem Toxicol | 1996 Jan | 8603799 |
| A comparison of the regional ontogenesis of nicotine- and muscarine-like binding sites in mouse brain. | Int J Dev Neurosci | 1983 | 24875947 |
| Reconstitution of a partially purified endplate acetylcholine receptor preparation in lipid bilayer membranes. | Biochem Biophys Res Commun | 1973 Sep 18 | 4796477 |
| Histamine liberators and melanophores of Rana tigrina. | J Pharm Pharmacol | 1967 Jan | 4382178 |
Targets
- General Function:
- Serine hydrolase activity
- Specific Function:
- Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
- Gene Name:
- ACHE
- Uniprot ID:
- P22303
- Molecular Weight:
- 67795.525 Da
References
- Radic Z, Taylor P: The influence of peripheral site ligands on the reaction of symmetric and chiral organophosphates with wildtype and mutant acetylcholinesterases. Chem Biol Interact. 1999 May 14;119-120:111-7. [10421444 ]
- General Function:
- Voltage-gated potassium channel activity
- Specific Function:
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel.
- Gene Name:
- HTR3A
- Uniprot ID:
- P46098
- Molecular Weight:
- 55279.835 Da
References
- Hefft S, Hulo S, Bertrand D, Muller D: Synaptic transmission at nicotinic acetylcholine receptors in rat hippocampal organotypic cultures and slices. J Physiol. 1999 Mar 15;515 ( Pt 3):769-76. [10066903 ]
- General Function:
- Ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA1
- Uniprot ID:
- P02708
- Molecular Weight:
- 54545.235 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNB1
- Uniprot ID:
- P11230
- Molecular Weight:
- 56697.9 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Acetylcholine-activated cation-selective channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRND
- Uniprot ID:
- Q07001
- Molecular Weight:
- 58894.55 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Cation transmembrane transporter activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNE
- Uniprot ID:
- Q04844
- Molecular Weight:
- 54696.54 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNG
- Uniprot ID:
- P07510
- Molecular Weight:
- 57882.8 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Drug transmembrane transporter activity
- Specific Function:
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acyclovir, and ganciclovir. Responsible for the secretion of cationic drugs across the brush border membranes.
- Gene Name:
- SLC47A2
- Uniprot ID:
- Q86VL8
- Molecular Weight:
- 65083.915 Da
References
- Wittwer MB, Zur AA, Khuri N, Kido Y, Kosaka A, Zhang X, Morrissey KM, Sali A, Huang Y, Giacomini KM: Discovery of potent, selective multidrug and toxin extrusion transporter 1 (MATE1, SLC47A1) inhibitors through prescription drug profiling and computational modeling. J Med Chem. 2013 Feb 14;56(3):781-95. doi: 10.1021/jm301302s. Epub 2013 Jan 22. [23241029 ]
- General Function:
- Drug binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA2
- Uniprot ID:
- Q15822
- Molecular Weight:
- 59764.82 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA3
- Uniprot ID:
- P32297
- Molecular Weight:
- 57479.54 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
- Gene Name:
- CHRNA4
- Uniprot ID:
- P43681
- Molecular Weight:
- 69956.47 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA5
- Uniprot ID:
- P30532
- Molecular Weight:
- 53053.965 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Acetylcholine-activated cation-selective channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNA6
- Uniprot ID:
- Q15825
- Molecular Weight:
- 56897.745 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Calcium channel activity
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasma membrane (PubMed:11752216, PubMed:25282151). The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane (PubMed:11752216, PubMed:25282151). In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion (PubMed:11021840).
- Gene Name:
- CHRNA9
- Uniprot ID:
- Q9UGM1
- Molecular Weight:
- 54806.63 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodiun ions.
- Gene Name:
- CHRNB2
- Uniprot ID:
- P17787
- Molecular Weight:
- 57018.575 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Drug binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNB3
- Uniprot ID:
- Q05901
- Molecular Weight:
- 52728.215 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Ligand-gated ion channel activity
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name:
- CHRNB4
- Uniprot ID:
- P30926
- Molecular Weight:
- 56378.985 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare
- General Function:
- Quaternary ammonium group transmembrane transporter activity
- Specific Function:
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity.
- Gene Name:
- SLC22A2
- Uniprot ID:
- O15244
- Molecular Weight:
- 62579.99 Da
References
- Wittwer MB, Zur AA, Khuri N, Kido Y, Kosaka A, Zhang X, Morrissey KM, Sali A, Huang Y, Giacomini KM: Discovery of potent, selective multidrug and toxin extrusion transporter 1 (MATE1, SLC47A1) inhibitors through prescription drug profiling and computational modeling. J Med Chem. 2013 Feb 14;56(3):781-95. doi: 10.1021/jm301302s. Epub 2013 Jan 22. [23241029 ]
- General Function:
- Toxic substance binding
- Specific Function:
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
- Gene Name:
- CHRNA7
- Uniprot ID:
- P36544
- Molecular Weight:
- 56448.925 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Briggs CA, McKenna DG, Monteggia LM, Touma E, Roch JM, Arneric SP, Gopalakrishnan M, Sullivan JP: Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant. Eur J Pharmacol. 1999 Feb 5;366(2-3):301-8. [10082212 ]
- General Function:
- Monovalent cation:proton antiporter activity
- Specific Function:
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acyclovir, ganciclovir and also the zwitterionic cephalosporin, cephalexin and cephradin. Seems to also play a role in the uptake of oxaliplatin (a new platinum anticancer agent). Able to transport paraquat (PQ or N,N-dimethyl-4-4'-bipiridinium); a widely used herbicid. Responsible for the secretion of cationic drugs across the brush border membranes.
- Gene Name:
- SLC47A1
- Uniprot ID:
- Q96FL8
- Molecular Weight:
- 61921.585 Da
References
- Wittwer MB, Zur AA, Khuri N, Kido Y, Kosaka A, Zhang X, Morrissey KM, Sali A, Huang Y, Giacomini KM: Discovery of potent, selective multidrug and toxin extrusion transporter 1 (MATE1, SLC47A1) inhibitors through prescription drug profiling and computational modeling. J Med Chem. 2013 Feb 14;56(3):781-95. doi: 10.1021/jm301302s. Epub 2013 Jan 22. [23241029 ]
- General Function:
- Receptor binding
- Specific Function:
- Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
- Gene Name:
- CHRNA10
- Uniprot ID:
- Q9GZZ6
- Molecular Weight:
- 49704.295 Da
- Mechanism of Action:
- Curare is a non-depolarizing muscle relaxant that acts as a competitive antagonist at the nicotinic acetylcholine receptors.
References
- Wikipedia. Curare. Last Updated 9 June 2009. : http://en.wikipedia.org/wiki/Curare