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Details

Stereochemistry ABSOLUTE
Molecular Formula C44H50N4O2.2Cl
Molecular Weight 737.799
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of ALCURONIUM CHLORIDE

SMILES

[Cl-].[Cl-].[H][C@]12C[C@]3([H])C4=CN5C6=CC=CC=C6[C@]78CC[N@@+]9(CC=C)C\C(=C\CO)[C@]([H])(C[C@@]79[H])C(=CN%10C%11=CC=CC=C%11[C@@]1(CC[N@@+]2(CC=C)C\C3=C\CO)[C@]4%10[H])[C@]58[H]

InChI

InChIKey=CPYGBGOXCJJJGC-GKLGUMFISA-L
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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C44H48N4O2
Molecular Weight 664.8775
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 8 / 10
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Alcuronium (diallylnortoxiferine) is a semi-synthetic substance prepared from C-toxiferine I a bis-quaternary alkaloid obtained from Strychnos toxifera. Alcuronium is a neuromuscular blocking (NMB) agent, alternatively referred to as a skeletal muscle relaxant. Alcuronium is used for endotracheal intubation and to produce muscle relaxation in general anesthesia during surgical procedures. The pharmacological action of alcuronium is readily reversed by neostigmine, and it produced little histamine release. The major disadvantage of alcuronium is that it elicits a vagolytic effect produced by a selective atropine-like blockade of cardiac muscarinic receptors.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.1 µM [IC50]
18.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Alloferin

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Adult: Initially, 150-250 mcg/kg; additional doses of 30 mcg/kg may be given as needed.
Route of Administration: Intravenous
In Vitro Use Guide
Left atria were mounted in organ baths containing 20 ml of oxygenated Tyrode’s solution. The preparations were preloaded with 5 millinewton and electrically stimulated via platinum contact electrodes at 3 Hz with rectangular pulses of 5-ms duration. The voltage was 1.5-fold over the threshold of excitation amounting to about 2 V. Contraction force (CF) was recorded isometrically. After an equilibration period of 60 min, a cumulative concentration/effect curve for the negative inotropic action of the agonist under study was recorded. Each agonist concentration was applied for 10 min, a period sufficient to obtain equilibrium effects. Contraction force was expressed as the percentage of the value found at the end of the equilibration period. The agonist was removed from the organ bath over a period of 30 min by replacing the Tyrode’s solution with fresh solution every 10 min. Thereafter, the preparation was preincubated with the Alcuronium for 60 min before another agonist concentration/effect curve was measured in the presence of the Alcuronium. Contraction force was expressed as the percentage of the value at the end of the preincubation period with the Alcuronium. The agonist was washed out using Tyrode’s solution still containing the Alcuronium in the concentration as before. After 30 min of washout, the concentration of the Alcuronium was increased, and, after a preincubation phase of 60 min, another concentration/effect curve of the agonist was measured.
Substance Class Chemical
Record UNII
490DW6501Y
Record Status Validated (UNII)
Record Version