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Pancuronium bromide

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Pancuronium bromide Basic information
Pancuronium bromide Chemical Properties
  • Melting point:215°
  • Boiling point:~100°C
  • Density ~1, mp: 0°C
  • storage temp. Desiccate at RT
  • solubility Very soluble or freely soluble in water, very soluble in methylene chloride, freely soluble in ethanol (96 per cent).
  • form Off-white solid
  • color Clear, colorless solution
  • color Cystals
  • OdorOdorless
  • Merck 13,7077
  • BRN 4226892
  • CAS DataBase Reference15500-66-0(CAS DataBase Reference)
Safety Information
  • Hazard Codes Xn
  • Risk Statements 22
  • RIDADR UN 2811 6.1/PG 3
  • WGK Germany 3
  • RTECS TN4930000
  • 10-21-33
  • HazardClass 6.1(b)
  • PackingGroup III
  • HS Code 2933399090
  • Hazardous Substances Data15500-66-0(Hazardous Substances Data)
  • ToxicityLD50 in mice (mg/kg): 0.047 i.v.; 0.152 i.p.; 0.167 s.c.; 21.9 orally; in rats, rabbits: 0.153, 0.016 i.v. (Buckett, 1968)
Pancuronium bromide Usage And Synthesis
  • Chemical PropertiesLight Beige Solid
  • OriginatorPavulon,Organon-Teknika ,UK,1968
  • UsesA potent steroidal neuromuscular blocking agent; muscle relaxant.
  • Usesprogestinantineoplastic
  • DefinitionChEBI: A bromide salt consisting of two bromide ions and one pancuronium dication.
  • Manufacturing ProcessA solution of 2α,3α,16α,17α-diepoxy-17β-acetoxy-5α-androstane (25 grams), prepared from 3,17-diacetoxy-5α-androstane-2,16-diene (Chem. Abs. 1960, 54, 8908) by treatment with m-chlor-perbenzoic acid, in piperidine (120 ml) and water (40 ml) was boiled under reflux for 5 days, the solution was concentrated and the product precipitated by the addition of water. The solid was collected, dissolved in dilute hydrochloric acid, filtered to give a clear solution and precipitated by the addition of sodium hydroxide solution. Crystallization from acetone gave 2β,16β-bis-piperidino-5α-androstan-3α-ol17-one (18.9 grams), MP 179-185°C.
    A solution of sodium borohydride (8 grams) in water (16 ml) was added to a stirred solution of 2β,16β-bis-piperidino-5α-androstan-3α-ol-17-one (17 grams) in tetrahydrofuran (70 ml) and methanol (30 ml) and the solution stirred at room temperature for 16 hours. The product was precipitated by the addition of water, filtered off, dried, and crystallized from acetone to give the diol (14.9 grams).
    A solution of the piperidino-diol (9 grams) in acetic anhydride (18 ml) was heated at 90°C for 1 hour, the solution cooled, excess acetic anhydride destroyed by the careful addition of water, and the resulting solution carefully made alkaline with 2 N caustic soda solution to precipitate a solid product. The solid was dried, extracted with n-hexane and the solution filtered free of insoluble material before percolation down a column (4 x 1'' diameter) of alumina. Elution with n-hexane gave a fraction (4.2 grams) which was crystallized twice from ether to give the diacetate, MP 176°-180°C.
    Methyl bromide (17 grams) was added to a solution of the bispiperidinodiacetate (4 grams) in methylene chloride (10 ml) and the resulting solution allowed to stand at room temperature for 4 days. The solution was evaporated to dryness, the residue triturated with ether, and filtered to give the bis-methobromide (5.2 grams), MP 206°C. Recrystallization from acetonemethylene chloride gave material MP 214°-217°C.
  • brand namePavulon (Organon).
  • Therapeutic Function Muscle relaxant
  • Biological FunctionsPancuronium bromide (Pavulon) is a synthetic bisquaternary agent containing a steroid nucleus (amino steroid), as denoted by the -curonium suffix. It is five times as potent as d-tubocurarine. Unlike d-tubocurarine, it does not release histamine or block ganglionic transmission. Like d-tubocurarine, it has a moderately long onset (2.9 minutes) and duration of action (110 minutes). Pancuronium and its metabolite are eliminated in the urine.
  • General DescriptionAlthough pancuronium bromide,2 ,16 -dipiperidino-5 -androstane-3 ,17 -diol diacetatedimethobromide (Pavulon), is a synthetic product, it isbased on the naturally occurring alkaloid malouetine, found inarrow poisons used by primitive Africans. Pancuronium bromideacts on the nicotinic receptor and in the ion channel,inhibiting normal ion fluxes.
    This blocking agent is soluble in water and is marketed inconcentrations of 1 or 2 mg/mL for intravenous administration.It is a typical nondepolarizing blocker, with a potencyapproximately 5 times that of (+)-tubocurarine chloride anda duration of action approximately equal to the latter. Studiesindicate that it has little or no histamine-releasing potential organglion-blocking activity and that it has little effect on thecirculatory system, except for causing a slight rise in thepulse rate. As one might expect, ACh, anticholinesterases,and potassium ion competitively antagonize it, whereas itsaction is increased by inhalation anesthetics such as ether,halothane, enflurane, and methoxyflurane. The latter enhancementin activity is especially important to the anesthetistbecause the drug is frequently administered as anadjunct to the anesthetic procedure to relax the skeletal muscle.Perhaps the most frequent adverse reaction to this agentis occasional prolongation of the neuromuscular block beyondthe usual time course, a situation that can usually becontrolled with neostigmine or by manual or mechanical ventilation, since respiratory difficulty is a prominent manifestationof the prolonged blocking action.
  • Biological ActivityNicotine (neuromuscular) antagonist. Skeletal muscle relaxant.
  • Clinical UseAs indicated, the principal use of pancuronium bromideis as an adjunct to anesthesia, to induce relaxation of skeletalmuscle, but it is also used to facilitate the managementof patients undergoing mechanical ventilation. Only experiencedclinicians equipped with facilities for applyingartificial respiration should administer it, and the dosageshould be adjusted and controlled carefully.
  • Safety ProfileA deadly poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and Brí.
  • Safety ProfileA human poison by intravenous route. Poison experimentally by intravenous, subcutaneous, and intraperitoneal routes. Human systemic effects by intravenous route: chronic pulmonary edema, hemorrhage. Experimental reproductive effects. When heated to decom
  • Veterinary Drugs and TreatmentsPancuronium is indicated as an adjunct to general anesthesia to produce muscle relaxation during surgical procedures or m
  • Purification MethodsThe bromide forms odourless crystals with a bitter taste which are purified through acid-washed Al2O3 and eluted with isoPrOH/EtOAc (3:1) to remove impurities (e.g. the monomethobromide) and eluted with isoPrOH to give the pure dibromide which is recrystallised from CH2Cl2/Me2CO or isoPrOH/Me2CO. It is soluble in H2O (10%) and CHCl3 (3.3%) at 20o. It is a non-depolarising muscle relaxant. [Buckett et al. J Med Chem 16 1116 1973.]
Pancuronium bromide Preparation Products And Raw materials
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