Tubocurarine chloride pentahydrateProduct ingredient for Tubocurarine
- Name
- Tubocurarine chloride pentahydrate
- Drug Entry
- Tubocurarine
Tubocurarine is a non-depolarizing neuromuscular blocking agent and the first identified curare alkaloid.1 Curare is one of the names used to describe plant-derived poisons used by indigenous South Americans to coat the tips of hunting arrows and darts, which were typically derived from plants of the genera Chondrodendron and Strychnos.1 Tubocurarine is a benzylisoquinoline derivative and shares this structural backbone with a number of plant-derived alkaloids, including morphine and papaverine.2 It was first isolated by Harold King in 1935 and was used clinically to induce neuromuscular blockade during surgeries, particularly those involving the abdomen.4 Tubocurarine's clinical use was limited by its relatively long duration of action (30-60 minutes)4 and a number of significant side effects.6 Safer and more pharmacokinetically favorable non-depolarizing neuromuscular blockers, such as rocuronium, have largely replaced the use of tubocurarine in the clinical setting.6
- Accession Number
- DBSALT000238
- Structure
Structure for Tubocurarine chloride pentahydrate (DBSALT000238)
- Synonyms
- (+)-tubocurarine chloride hydrochloride pentahydrate / (+)-tubocurarine chloride hydrochloride, pentahydrate / Tubocurarine chloride / Tubocurarine chloride hydrochloride hydrate
- UNII
- 900961Z8VR
- CAS Number
- 6989-98-6
- Weight
- Average: 771.73
Monoisotopic: 770.2948159 - Chemical Formula
- C37H52Cl2N2O11
- InChI Key
- WMIZITXEJNQAQK-GGDSLZADSA-N
- InChI
- InChI=1S/C37H40N2O6.2ClH.5H2O/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33;;;;;;;/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41);2*1H;5*1H2/t28-,29+;;;;;;;/m0......./s1
- IUPAC Name
- (1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8,10,12(34),18,20,22(33),24(32),25,27(31),35-dodecaen-15-ium pentahydrate hydrochloride chloride
- SMILES
- O.O.O.O.O.Cl.[Cl-].[H][C@]12CC3=CC=C(OC4=C(O)C(OC)=CC5=C4[C@@]([H])(CC4=CC=C(O)C(OC6=CC1=C(CCN2C)C=C6OC)=C4)[N+](C)(C)CC5)C=C3
- External Links
- PubChem Compound
- 64645
- ChemSpider
- 21902
- ChEMBL
- CHEMBL3989821
- Predicted Properties
Property Value Source Water Solubility 0.000323 mg/mL ALOGPS logP 3.12 ALOGPS logP 3.25 Chemaxon logS -6.3 ALOGPS pKa (Strongest Acidic) 8.53 Chemaxon pKa (Strongest Basic) 7.96 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 80.62 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 187.06 m3·mol-1 Chemaxon Polarizability 66.88 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon