1-[(3,4-dimethoxyphenyl)methyl]-2-[3-({5-[(3-{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

• ChemBase ID: 613
• Molecular Formular: C53H72N2O12++
• Molecular Mass: 929.14498
• Monoisotopic Mass: 928.50852575
• SMILES: O(c1cc2C([N+](CCc2cc1OC)(CCC(=O)OCCCCCOC(=O)CC[N+]1(C(c2c(CC1)cc(OC)c(OC)c2)Cc1cc(OC)c(OC)cc1)C)C)Cc1cc(OC)c(OC)cc1)C
• Canonical SMILES: COc1cc2c(cc1OC)CC[N+](C2Cc1ccc(c(c1)OC)OC)(C)CCC(=O)OCCCCCOC(=O)CC[N+]1(C)CCc2c(C1Cc1ccc(c(c1)OC)OC)cc(c(c2)OC)OC
• InChI: InChI=1S/C53H72N2O12/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/h14-17,30-35,42-43H,11-13,18-29H2,1-10H3/q+2
• InChIKey: YXSLJKQTIDHPOT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(3,4-dimethoxyphenyl)methyl]-2-[3-({5-[(3-{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
• IUPAC Traditional name: atracurium
• Synonyms: Atracurium; Atracurium besilate

Database IDs

• CAS Number: 64228-79-1
• PubChem SID: 160964076; 46504689
• PubChem CID: 47319
• CHEBI ID: 2914
• ATC CODE: M03AC04
• CHEMBL: 1360
• Chemspider ID: 43067
• DrugBank ID: DB00732
• Unique Ingredient Identifier: 40AX66P76P
• Wikipedia Title: Atracurium_besilate

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.016506
• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): -0.95903206
• LogD (pH = 7.4): -0.95903206
• Log P: -0.95903206
• Molar Refractivity: 280.6772 cm^3
• Polarizability: 100.60693 Å^3
• Polar Surface Area: 126.44 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.41
• LOG S: -7.63
• Solubility (Water): 2.32e-05 g/l

PROPERTIES

Physical Property

• Solubility: Miscible

Pharmacology Properties

• Admin Routes: IV
• Bioavailability: 100% (IV)
• Half Life: 17–21 minutes
• Metabolism: Hofmann elimination (retro-Michael addition) and ester hydrolysis by nonspecific esterases
• Protein Bound: 82%
• Legal Status: Worldwide: Prescription only medicine

DETAILS

DrugBank - DB00732

• Drug Groups: approved
• Description: A non-depolarizing neuromuscular blocking agent with short duration of action. Its lack of significant cardiovascular effects and its lack of dependence on good kidney function for elimination provide clinical advantage over alternate non-depolarizing neuromuscular blocking agents. [PubChem]
• Indication: For use, as an adjunct to general anesthesia, to facilitate endotracheal intubation and to provide skeletal muscle relaxation during surgery or mechanical ventilation.
• Pharmacology: Atracurium is a nondepolarizing skeletal muscle relaxant. Atracurium can be used most advantageously if muscle twitch response to peripheral nerve stimulation is monitored to assess degree of muscle relaxation. The duration of neuromuscular block produced by Atracurium is approximately one third to one half the duration of block by d-tubocurarine, metocurine, and pancuronium at initially equipotent doses. As with other nondepolarizing neuromuscular blockers, the time to onset of paralysis decreases and the duration of maximum effect increases with increasing doses of Atracurium. Repeated administration of maintenance doses of Atracurium has no cumulative effect on the duration of neuromuscular block if recovery is allowed to begin prior to repeat dosing. Moreover, the time needed to recover from repeat doses does not change with additional doses. Repeat doses can therefore be administered at relatively regular intervals with predictable results.
• Toxicity: Excessive doses can be expected to produce enhanced pharmacological effects. Overdosage may increase the risk of histamine release and cardiovascular effects, especially hypotension.
• Affected Organisms: Humans and other mammals
• Half Life: The elimination half-life is approximately 20 minutes.
• External Links: Wikipedia; RxList