U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 8 / 10
E/Z Centers 2
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17722904 | https://goo.gl/8mllN4 | https://www.drugs.com/international/alcuronium-chloride.html

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

Curator's Comment: # F. Hoffmann-La Roche & Co., A.-G.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Alloferin

Approved Use

Indications. Alcuronium (Cl) is primarily indicated in conditions like Adjunct to anesthesia, Neuromuscular blockade.
PubMed

PubMed

TitleDatePubMed
Pharmacological characteristics and binding modes of caracurine V analogues and related compounds at the neuronal alpha7 nicotinic acetylcholine receptor.
2007 Sep 20
Patents

Patents

Sample Use Guides

Adult: Initially, 150-250 mcg/kg; additional doses of 30 mcg/kg may be given as needed.
Route of Administration: Intravenous
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
Created
by admin
on Fri Dec 15 16:13:57 GMT 2023
Edited
by admin
on Fri Dec 15 16:13:57 GMT 2023
Record UNII
490DW6501Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALCURONIUM CHLORIDE
EP   INN   JAN   MART.   USAN   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
ALCURONIUM DICHLORIDE [MI]
Common Name English
Alcuronium chloride [WHO-DD]
Common Name English
alcuronium chloride [INN]
Common Name English
RO-4-3816
Code English
TOXIFERINE I, 2,2',16,16'-TETRADEHYDRO-4,4'-DIDEMETHYL 16,16',17,17'-TETRAHYDRO-4,4'-DI-2-PROPENYL-, DICHLORIDE
Common Name English
ALCURONIUM CHLORIDE [USAN]
Common Name English
N,N'-DIALLYLNORTOXIFERINIUM DICHLORIDE
Common Name English
ALCURONIUM DICHLORIDE
MI   WHO-IP  
Common Name English
TOXIFERINE I, 4,4'-DIDEMETHYL-4,4'-DI-2-PROPENYL-, DICHLORIDE
Common Name English
ALLOFERIN
Brand Name English
RO 4-3816
Code English
ALCURONII CHLORIDUM [WHO-IP]
Common Name English
ALCURONIUM CHLORIDE [JAN]
Common Name English
ALCURONIUM DICHLORIDE [WHO-IP]
Common Name English
ALCURONIUM CHLORIDE [EP MONOGRAPH]
Common Name English
DIALLYLNORTOXIFERENE DICHLORIDE
Common Name English
ALCURONIUM CHLORIDE [WHO-IP]
Common Name English
ALCURONIUM CHLORIDE [MART.]
Common Name English
RO-43816
Code English
Classification Tree Code System Code
NCI_THESAURUS C66886
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID0045414
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
FDA UNII
490DW6501Y
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
NCI_THESAURUS
C79728
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
CAS
15180-03-7
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
RXCUI
66852
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY RxNorm
INN
2166
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
PUBCHEM
21158559
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ALCURONIUM CHLORIDE
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY Description: A white to yellow-white, crystalline powder. Solubility: Soluble in water and ethanol (~750 g/l) TS. Category: Muscle relaxant. Storage: Alcuronium chloride should be kept in a tightly closed container. Labelling: The designation Alcuronium chloride for parenteral use indicates that the substance complies with the additionalrequirements and may be used for parenteral administration. Expiry date. Additional information: CAUTION: Alcuronium chloride is highly toxic. It must be handled with care, avoiding contact with the skin and inhalation of airborne particles. It is hygroscopic. Requirement: Alcuronium chloride contains not less than 98.0% and not more than 101.0% of C44H50Cl2N4O2, calculated with reference to the anhydrous substance. Note: All tests must be carried out immediately after opening the container, and as rapidly as possible.
CHEBI
31185
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
ChEMBL
CHEMBL1180293
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
SMS_ID
100000087718
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
ECHA (EC/EINECS)
239-229-8
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
DRUG BANK
DBSALT002830
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
WIKIPEDIA
ALCURONIUM CHLORIDE
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
EVMPD
SUB05302MIG
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY
MERCK INDEX
m1484
Created by admin on Fri Dec 15 16:13:57 GMT 2023 , Edited by admin on Fri Dec 15 16:13:57 GMT 2023
PRIMARY Merck Index
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