6,7,8-trimethoxy-2-methyl-2-(3-{[4-oxo-4-(3-{6,7,8-trimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl}propoxy)butanoyl]oxy}propyl)-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium

• ChemBase ID: 1006
• Molecular Formular: C56H78N2O16++
• Molecular Mass: 1035.22232
• Monoisotopic Mass: 1034.53513443
• SMILES: O(c1c2C([N+](CCc2cc(OC)c1OC)(CCCOC(=O)CCC(=O)OCCC[N+]1(C(c2c(CC1)cc(OC)c(OC)c2OC)Cc1cc(OC)c(OC)c(OC)c1)C)C)Cc1cc(OC)c(OC)c(OC)c1)C
• Canonical SMILES: COc1c(OC)cc2c(c1OC)C(Cc1cc(OC)c(c(c1)OC)OC)[N+](CC2)(C)CCCOC(=O)CCC(=O)OCCC[N+]1(C)CCc2c(C1Cc1cc(OC)c(c(c1)OC)OC)c(OC)c(c(c2)OC)OC
• InChI: InChI=1S/C56H78N2O16/c1-57(23-19-37-33-45(65-7)53(69-11)55(71-13)49(37)39(57)27-35-29-41(61-3)51(67-9)42(30-35)62-4)21-15-25-73-47(59)17-18-48(60)74-26-16-22-58(2)24-20-38-34-46(66-8)54(70-12)56(72-14)50(38)40(58)28-36-31-43(63-5)52(68-10)44(32-36)64-6/h29-34,39-40H,15-28H2,1-14H3/q+2
• InChIKey: GBLRQXKSCRCLBZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,7,8-trimethoxy-2-methyl-2-(3-{[4-oxo-4-(3-{6,7,8-trimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium-2-yl}propoxy)butanoyl]oxy}propyl)-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-ium
• IUPAC Traditional name: doxacurii chloridum
• Brand Name: Nuromax
• Synonyms: Doxacurium chloride; Doxacurium

Database IDs

• CAS Number: 106819-53-8
• PubChem SID: 46506733; 160964469
• PubChem CID: 60169

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.405167
• H Acceptors: 14
• H Donor: 0
• LogD (pH = 5.5): -2.4916887
• LogD (pH = 7.4): -2.4916887
• Log P: -2.4916887
• Molar Refractivity: 302.1498 cm^3
• Polarizability: 108.90727 Å^3
• Polar Surface Area: 163.36 Å^2
• Rotatable Bonds: 29
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.44
• LOG S: -7.09
• Solubility (Water): 9.02e-05 g/l

DETAILS

DrugBank - DB01334

Drug information: approved

DrugBank - DB01135

• Drug Groups: approved
• Description: Doxacurium chloride is a long-acting, nondepolarizing skeletal muscle relaxant for intravenous administration.
• Indication: Used to provide skeletal muscle relaxation as an adjunct to general anesthesia, for endotracheal intubation or to facilitate mechanical ventilation.
• Pharmacology: Doxacurium chloride is a long-acting, nondepolarizing skeletal muscle relaxant. The neuromuscular block produced by doxacurium chloride may be antagonized by anticholinesterase agents. As with other nondepolarizing neuromuscular blocking agents, the more profound the neuromuscular block at reversal, the longer the time and the greater the dose of anticholinesterase required for recovery of neuromuscular function. Doxacurium chloride is approximately 2.5 to 3 times more potent than pancuronium and 10 to 12 times more potent than metocurine.
• Toxicity: Overdosage with neuromuscular blocking agents may result in neuromuscular block beyond the time needed for surgery and anesthesia.
• Affected Organisms: Humans and other mammals
• Biotransformation: In vivo data from humans suggest that doxacurium chloride is not metabolized and that the major elimination pathway is excretion of unchanged drug in urine and bile.
• Half Life: 99 minutes in normal healthy adults.
• Protein Binding: Approximately 30%.
• Elimination: In vivo data from humans suggest that NUROMAX is not metabolized and that the major elimination pathway is excretion of unchanged drug in urine and bile.
• Distribution: * 0.11-0.43 L/kg [Healthy Young Adult Patients]; * 0.17-0.55 L/kg [Kidney Transplant Patients]; * 0.17-0.35 L/kg [Liver Transplant Patients]
• Clearance: * 2.66 mL/min/kg [Healthy Young Adult Patients]; * 1.23 mL/min/kg [Kidney Transplant Patients]; * 2.3 mL/min/kg [Liver Transplant Patients]; * 1.75 +/- 0.16 mL/min/kg [Elderly patients (70-83 yrs)]; * 2.54 +/- 0.24 mL/min/kg [younger patients (19-39 yrs)]
• References: Martinez EA, Wooldridge AA, Hartsfield SM, Mealey KL: Neuromuscular effects of doxacurium chloride in isoflurane-anesthetized dogs. Vet Surg. 1998 May-Jun;27(3):279-83. [Pubmed]
• External Links: Wikipedia; RxList

REFERENCES

• Martinez EA, Wooldridge AA, Hartsfield SM, Mealey KL: Neuromuscular effects of doxacurium chloride in isoflurane-anesthetized dogs. Vet Surg. 1998 May-Jun;27(3):279-83. Pubmed