(1S,16R)-9,10,21,25-tetramethoxy-15,15,30,30-tetramethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18(33),19,21,24(32),25,27(31),35-dodecaene-15,30-diium diiodide

• ChemBase ID: 299
• Molecular Formular: C40H48I2N2O6
• Molecular Mass: 906.62786
• Monoisotopic Mass: 906.16018327
• SMILES: [I-].[I-].O1c2c3[C@H]([N+](CCc3cc(OC)c2OC)(C)C)Cc2cc(Oc3cc4[C@@H]([N+](CCc4cc3OC)(C)C)Cc3ccc1cc3)c(OC)cc2
• Canonical SMILES: COc1ccc2cc1Oc1cc3c(cc1OC)CC[N+]([C@H]3Cc1ccc(Oc3c4[C@@H](C2)[N+](C)(C)CCc4cc(c3OC)OC)cc1)(C)C.[I-].[I-]
• InChI: InChI=1S/C40H48N2O6.2HI/c1-41(2)17-15-27-22-34(44-6)36-24-30(27)31(41)19-25-9-12-29(13-10-25)47-40-38-28(23-37(45-7)39(40)46-8)16-18-42(3,4)32(38)20-26-11-14-33(43-5)35(21-26)48-36;;/h9-14,21-24,31-32H,15-20H2,1-8H3;2*1H/q+2;;/p-2/t31-,32+;;/m0../s1
• InChIKey: DIGFQJFCDPKEPF-OIUSMDOTSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,16R)-9,10,21,25-tetramethoxy-15,15,30,30-tetramethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18(33),19,21,24(32),25,27(31),35-dodecaene-15,30-diium diiodide
• IUPAC Traditional name: (1S,16R)-9,10,21,25-tetramethoxy-15,15,30,30-tetramethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2^{3,6}.1^{8,12}.1^{18,22}.0^{27,31}.0^{16,34}]hexatriaconta-3,5,8,10,12(34),18(33),19,21,24(32),25,27(31),35-dodecaene-15,30-diium diiodide
• Brand Name: Metubine; Metubine iodide; Mutubine Iodide
• Synonyms: (+)-O,O'-Dimethylchondrocurarine Di-iodide; Dimethyl Tubocurarine Iodide; Dimethyltubocurarine Iodide; Dimetiltubocurarinio, ioduro de; Metocurini Iodidum; Metokuriinijodidi; Metokurinjodid; Trimethyltubocurarine Iodide; Metocurine Iodide

Database IDs

• CAS Number: 7601-55-0
• PubChem SID: 46507773; 160963762
• PubChem CID: 24244

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.994155
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.8464106
• LogD (pH = 7.4): -1.8464094
• Log P: -1.8464106
• Molar Refractivity: 211.9418 cm^3
• Polarizability: 73.147705 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.81
• LOG S: -6.87
• Solubility (Water): 1.23e-04 g/l

DETAILS

DrugBank - DB00416

• Drug Groups: approved
• Description: Metocurine iodide is a benzylisoquinolinium competitive nondepolarizing neuromuscular blocking agent. It is used as an anesthesia adjunct to induce skeletal muscle relaxation and to reduce the intensity of muscle contractions in convulsive therapy Metocurine iodide has a moderate risk of inducing histamine release and has some ganglion blocking activity. Metocurine iodide can be used most advantageously if muscle twitch response to peripheral nerve stimulation is monitored to assess degree of muscle relaxation.
• Indication: For use as an anesthesia adjunct to induce skeletal muscle relaxation and to reduce the intensity of muscle contractions in convulsive therapy.
• Pharmacology: Metocurine iodide is a benzylisoquinolinium competitive nondepolarizing neuromuscular blocking agent. Metocurine iodide has a moderate risk of inducing histamine release and has some ganglion blocking activity. Metocurine iodide can be used most advantageously if muscle twitch response to peripheral nerve stimulation is monitored to assess degree of muscle relaxation. As with other nondepolarizing neuromuscular blockers, the time to onset of paralysis decreases and the duration of maximum effect increases with increasing doses of metocurine iodide. Repeated administration of maintenance doses of metocurine iodide 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: 3 to 4 hours
• Protein Binding: 35% in plasma