Laudexium metilsulfate

Laudexium metilsulfate is a neuromuscular blocking drug or skeletal muscle relaxant in the category of non-depolarizing neuromuscular-blocking drugs, used adjunctively in surgical anesthesia to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.

Laudexium metilsulfate
Clinical data
Other namesLaudolissin
Routes of
administration		IV
Legal status
Legal status
  • discontinued from clinical use
Pharmacokinetic data
Bioavailability100% (IV)
Identifiers
IUPAC name
  • 1-[(3,4-Dimethoxyphenyl)methyl]-2-[10-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium-2-yl]decyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinolin-2-ium methyl sulfate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC54H80N2O16S2
Molar mass1077.35 g·mol−1
3D model (JSmol)
SMILES
  • C[N+]1(CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC)CCCCCCCCCC[N+]4(CCC5=CC(=C(C=C5C4CC6=CC(=C(C=C6)OC)OC)OC)OC)C.COS(=O)(=O)[O-].COS(=O)(=O)[O-]
InChI
  • InChI=1S/C52H74N2O8.2CH4O4S/c1-53(27-23-39-33-49(59-7)51(61-9)35-41(39)43(53)29-37-19-21-45(55-3)47(31-37)57-5)25-17-15-13-11-12-14-16-18-26-54(2)28-24-40-34-50(60-8)52(62-10)36-42(40)44(54)30-38-20-22-46(56-4)48(32-38)58-6;2*1-5-6(2,3)4/h19-22,31-36,43-44H,11-18,23-30H2,1-10H3;2*1H3,(H,2,3,4)/q+2;;/p-2 N
  • Key:LADQAYSLFLCKOD-UHFFFAOYSA-L N
 NY (what is this?)  (verify)

Laudexium[1] is no longer used in clinical practice, though it was introduced clinically in the early 1950s. It has about half the potency, a slower onset of action and a duration of action much longer than that of d-tubocurarine.[2] As with all clinically established (as well as experimental agents) with a non-depolarizing mechanism of action, its pharmacological action can be antagonized by anticholinesterases.

The displacement of laudexium from clinical use was assured owing to recurrent reports of significant post-operative re-curarization.[3]

References
  1. Taylor EP (1952). "Synthetic neuromuscular blocking agents. Part II. Bis(quaternary ammonium salts) derived from laudanosine". J Chem Soc: 142–145. doi:10.1039/JR9520000142.
  2. Hunter AR (February 1955). "The action of laudexium in man and experimental animals" (PDF). British Journal of Anaesthesia. 27 (2): 73–9. doi:10.1093/bja/27.2.73. PMID 13230365.
  3. Collier HO, Macauley B (September 1952). "The pharmacological properties of "laudolissin" a long-acting curarizing agent". British Journal of Pharmacology and Chemotherapy. 7 (3): 398–408. doi:10.1111/j.1476-5381.1952.tb00707.x. PMC 1509112. PMID 12978243.
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