Alcuronium chloride

Alcuronium chloride

Systematic (IUPAC) name
4,4'-Didemethyl-4,4'-di-propenyltoxiferin-1-dichloride
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Metabolism	not metabolized
Excretion	70-90% unchanged in urine 1.3ml/kg/min t1/2 2- 4 hours
Identifiers
CAS number	23214-96-2 N
ATC code	M03AA01
PubChem	CID 5311001
IUPHAR ligand	341
ChemSpider	20118193 Y
UNII	490DW6501Y N
ChEBI	CHEBI:31185 Y
Chemical data
Formula	C44H50N4O2+2
Mol. mass	666.894 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C44H50N4O2.2ClH/c1-3-17-47-19-15-43-35-9-5-7-11-37(35)45-26-34-32-24-40-44(16-20-48(40,18-4-2)28-30(32)14-22-50)36-10-6-8-12-38(36)46(42(34)44)25-33(41(43)45)31(23-39(43)47)29(27-47)13-21-49;;/h3-14,25-26,31-32,39-42,49-50H,1-2,15-24,27-28H2;2*1H/q+2;;/p-2/b29-13-,30-14-,33-25-,34-26-;;/t31-,32-,39-,40-,41-,42-,43+,44+,47-,48-;;/m0../s1 Y Key:CPYGBGOXCJJJGC-GKLGUMFISA-L Y
N (what is this?)  (verify)

Alcuronium is a peripherally acting muscle relaxant in the curare alkaloid family. It is a semi-synthetic substance derived from toxiferine.

Effects

• Cardiovascular system - histamine release and blockage of the sympathetic ganglia including adrenal medulla could cause Hypotension
• Respiratory - apnea due to phrenic blockage but bronchoconstriction can occur from the histamine release
• Central nervous system - no effect on intraoccular pressure
• Autonomic ganglion blockade can cause decrease in gut motility

Special points

• Duration of action prolonger in states of low potassium, calcium and protein, also in states of high magnesium and acidosis.
• Pharmaceutically incompatible with thiopentone
• Infusion can cause fixed dilated pupils

References

• Zahn K, Eckstein N, Tränkle C, Sadée W, Mohr K (2002). "Allosteric modulation of muscarinic receptor signaling: alcuronium-induced conversion of pilocarpine from an agonist into an antagonist.". J Pharmacol Exp Ther 301 (2): 720–8. doi:10.1124/jpet.301.2.720. PMID 11961078. 
• Maass A, Mohr K (1996). "Opposite effects of alcuronium on agonist and on antagonist binding to muscarinic receptors.". Eur J Pharmacol 305 (1-3): 231–4. doi:10.1016/0014-2999(96)00240-3. PMID 8813558. 
• Jakubík J, Tucek S (1994). "Protection by alcuronium of muscarinic receptors against chemical inactivation and location of the allosteric binding site for alcuronium.". J Neurochem 63 (5): 1932–40. doi:10.1046/j.1471-4159.1994.63051932.x. PMID 7931349. 
• Proska J, Tucek S (1994). "Mechanisms of steric and cooperative actions of alcuronium on cardiac muscarinic acetylcholine receptors.". Mol Pharmacol 45 (4): 709–17. PMID 8183250.