Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H27NO4 |
| Molecular Weight | 357.4434 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1OC)[C@H](CC3=CC(OC)=C(OC)C=C3)N(C)CC2
InChI
InChIKey=KGPAYJZAMGEDIQ-KRWDZBQOSA-N
InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1
| Molecular Formula | C21H27NO4 |
| Molecular Weight | 357.4434 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Laudanosine, a potentially epileptogenic metabolite of the neuromuscular relaxant atracurium besylate with potentially toxic effects. Laudanosine is a non-competitive and voltage-dependent inhibitor of alpha7, alpha4beta2 or alpha4beta4 nicotinic acetylcholine receptors, opioid mu 1 type receptors and possesses a low-affinity to the GABA receptors, but didn’t interact with the benzodiazepine or muscarinic receptors.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: gamma-aminobutyric acid (GABA) receptors |
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Target ID: CHEMBL1907589 |
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Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) |
2.7 µM [Ki] | ||
Target ID: CHEMBL1907591 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Concentration-effect relationship of cisatracurium at three different dose levels in the anesthetized patient. | 2001 Aug |
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| The pharmacokinetics of cisatracurium in patients with acute respiratory distress syndrome. | 2001 Aug |
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| Does ester hydrolysis change the in vitro degradation rate of cisatracurium and atracurium? | 2002 Apr |
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| Pharmacodynamics and atracurium and laudanosine concentrations during a fixed continuous infusion of atracurium in mechanically ventilated patients with acute respiratory distress syndrome. | 2002 Aug |
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| Cerebrospinal fluid concentrations of atracurium, laudanosine and vecuronium following clinical subarachnoid hemorrhage. | 2002 Nov |
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| Instability of pancuronium in postmortem blood and liver taken after a fatal intramuscular Pavulon injection. | 2004 Jul 16 |
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| The GC-MS detection and characterization of reticuline as a marker of opium use. | 2004 May 28 |
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| Synthesis and biological evaluation of N-methyl-laudanosine iodide analogues as potential SK channel blockers. | 2005 Feb 15 |
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| Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling. | 2008 Apr 25 |
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| [Absorption of papaverine, laudanosine and cepharanthine across human intestine by using human Caco-2 cells monolayers model]. | 2008 Feb |
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| Laudanosine has no effects on respiratory activity but induces non-respiratory excitement activity in isolated brainstem-spinal cord preparation of neonatal rats. | 2010 |
Sample Use Guides
In mice and rats: i.v. bolus doses of laudanosine 10-20 mg kg-1, caused convulsions and hind limb extensions
Route of Administration:
Intravenous
Laudanosine was almost ineffective at [3H]muscimol binding to high-affinity GABA receptors (IC50 = 100 microM). However, laudanosine displayed an inhibitory effect at the low-affinity GABA receptors labeled by [3H]bicuculline methochloride, with an IC50 value of 10 microM. At the opioid receptor subtype, laudanosine lowered radiolabeled opioid binding at the mu 1, mu 2, delta, kappa 1, and kappa 3 receptors with Ki values of 2.7, 13, 5.5, 21, and 24 microM, respectively.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:05:07 UTC 2023
by
admin
on
Fri Dec 15 18:05:07 UTC 2023
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| Record UNII |
DA7R5WVN48
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| Record Status |
Validated (UNII)
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| Record Version |
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2688-77-9
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300000043559
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73397
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35045
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DTXSID30878577
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m6706
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LAUDANOSINE
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DA7R5WVN48
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220-253-2
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C001522
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1699-51-0
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NON-SPECIFIC STEREOCHEMISTRY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE ACTIVE |
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