Cisatracurium besylateProduct ingredient for Cisatracurium

Name
Cisatracurium besylate
Drug Entry
Cisatracurium

Cisatracurium is a non-depolarising neuromuscular blocking agent of the benzylisoquinolinium class, available in its salt form, cisatracurium besylate.1,2 Cisatracurium has an intermediate duration of action and is one of the most commonly used neuromuscular blocking agents in intensive care.2,3. Cisatracurium acts on cholinergic receptors, blocking neuromuscular transmission. This action is antagonized by acetylcholinesterase inhibitors such as neostigmine.1,2 Cisatracurium is an R-cis-R-cis isomer of atracurium and has approximately 3 times its neuromuscular blocking potency.1 Compared to atracurium, cisatracurium produces a lower degree of histamine release.3

Accession Number
DBSALT002671  (DB13450)
Structure
Synonyms
Cisatracurium besilate / Cisatracurium dibenzenesulfonate
External IDs
51-W-89 / 51-W89 / 51W-89 / 51W89
UNII
80YS8O1MBS
CAS Number
96946-42-8
Weight
Average: 1243.479
Monoisotopic: 1242.50040521
Chemical Formula
C65H82N2O18S2
InChI Key
XXZSQOVSEBAPGS-DONVQRBFSA-L
InChI
InChI=1S/C53H72N2O12.2C6H6O3S/c1-54(22-18-38-32-48(62-7)50(64-9)34-40(38)42(54)28-36-14-16-44(58-3)46(30-36)60-5)24-20-52(56)66-26-12-11-13-27-67-53(57)21-25-55(2)23-19-39-33-49(63-8)51(65-10)35-41(39)43(55)29-37-15-17-45(59-4)47(31-37)61-6;2*7-10(8,9)6-4-2-1-3-5-6/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3;2*1-5H,(H,7,8,9)/q+2;;/p-2/t42-,43-,54-,55-;;/m1../s1
IUPAC Name
(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-2-(3-{[5-({3-[(1R,2R)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl]propanoyl}oxy)pentyl]oxy}-3-oxopropyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-2-ium dibenzenesulfonate
SMILES
[O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1.COC1=CC2=C(C=C1OC)[C@@H](CC1=CC(OC)=C(OC)C=C1)[N@@+](C)(CCC(=O)OCCCCCOC(=O)CC[N@@+]1(C)CCC3=C(C=C(OC)C(OC)=C3)[C@H]1CC1=CC(OC)=C(OC)C=C1)CC2
Human Metabolome Database
HMDB0014705
KEGG Drug
D00759
PubChem Compound
62887
PubChem Substance
347829301
ChemSpider
56614
ChEBI
3721
ChEMBL
CHEMBL1200641
PharmGKB
PA164744925
Wikipedia
Cisatracurium
Predicted Properties
PropertyValueSource
Water Solubility4.17e-05 mg/mLALOGPS
logP3.34ALOGPS
logP-0.96Chemaxon
logS-7.5ALOGPS
pKa (Strongest Acidic)19.02Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area126.44 Å2Chemaxon
Rotatable Bond Count28Chemaxon
Refractivity280.68 m3·mol-1Chemaxon
Polarizability105.56 Å3Chemaxon
Number of Rings8Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon