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Pancuronium bromide

CAS No.
15500-66-0
Chemical Name:
Pancuronium bromide
Synonyms
diacetate;pancuronium;pavulon;acetic acid [17-acetyloxy-10,13-dimethyl-2,16-bis(1-methyl-1-piperidin-1-iumyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] ester dibromide;na97;orgna97;Miobloc;mioblock;Org-NE 35;thobromide
CBNumber:
CB7167065
Molecular Formula:
C35H60Br2N2O4
Molecular Weight:
732.67
MDL Number:
MFCD00079223
MOL File:
15500-66-0.mol
MSDS File:
SDS

Pancuronium bromide Properties

Melting point 215°
Boiling point ~100°C
Density ~1, mp: 0°C
storage temp. 2-8°C
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
Odor Odorless
Merck 13,7077
BRN 4226892
CAS DataBase Reference 15500-66-0(CAS DataBase Reference)
FDA UNII U9LY9Y75X2
ATC code M03AC01

Pharmacokinetic data

Protein binding 80-90%
Excreted unchanged in urine 40-60%
Volume of distribution 0.15-0.38(L/kg)
Biological half-life 2 / 4.3-8.2

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P301+P310
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
Toxicity LD50 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 price More Price(33)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich BP276 Pancuronium bromide British Pharmacopoeia (BP) Reference Standard 15500-66-0 25MG $262 2022-05-15 Buy
Sigma-Aldrich 5.05226 Pancuronium Dibromide - CAS 15500-66-0 - Calbiochem 15500-66-0 10MG $75.6 2022-05-15 Buy
Sigma-Aldrich 1494217 Pancuronium bromide United States Pharmacopeia (USP) Reference Standard 15500-66-0 500mg $720 2022-05-15 Buy
Cayman Chemical 23778 Pancuronium (bromide) ≥95% 15500-66-0 5mg $25 2021-12-16 Buy
Cayman Chemical 23778 Pancuronium (bromide) ≥95% 15500-66-0 10mg $45 2021-12-16 Buy
Product number Packaging Price Buy
BP276 25MG $262 Buy
5.05226 10MG $75.6 Buy
1494217 500mg $720 Buy
23778 5mg $25 Buy
23778 10mg $45 Buy

Pancuronium bromide Chemical Properties,Uses,Production

Description

Pancuronium bromide, a bisquaternary amine and the first steroid N MBA used clinically, was developed by Savege and Hewitt and marketed in 1964. The intubating dose is 0.1mgkg–1, which takes 3-4min to reach its maximum effect. The clinical duration of action of the drug is long, especially in the presence of potent inhalational agents or renal dysfunction, as 60% of a dose of the drug is excreted unchanged through the kidneys. I t is also deacetylated in the liver; some of the metabolites have neuromuscular blocking properties.
Pancuronium does not stimulate histamine release; however, it has direct vagolytic and sympathomimetic effects which may cause tachycardia and hypertension. It slightly inhibits plasma cholinesterase and therefore potentiates any drug metabolised by this enzyme, such as suxamethonium and mivacurium.

Chemical Properties

Light Beige Solid

Originator

Pavulon,Organon-Teknika ,UK,1968

Uses

Pancuronium is a steroid compound that does not possess hormonal activity. It is used in anesthesiology as a myorelaxant, causing prolonged muscle relaxation during surgical interventions of the thoracic and abdominal cavities, in proctology, ophthalmology, orthopedic practice, and in heart surgeries. A synonym of this drug is pavulon.

Uses

A potent steroidal neuromuscular blocking agent; muscle relaxant.

Uses

progestinantineoplastic

Uses

Pancuronium Bromide has been used as an analgesic in various experiments.

Definition

ChEBI: A bromide salt consisting of two bromide ions and one pancuronium dication.

Manufacturing Process

A 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 name

Pavulon (Organon).

Therapeutic Function

Muscle relaxant

Biological Functions

Pancuronium 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 Description

Although 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 Activity

Nicotine (neuromuscular) antagonist. Skeletal muscle relaxant.

Biochem/physiol Actions

Aminosteroidal neuromuscular blocking agent; skeletal muscle relaxant

Pharmacology

Pancuronium bromide, a bisquaternary amine and the first steroid NMBA used clinically, was developed by Savege and Hewi and marketed in 1964. The intubating dose is 0.1 mg kg–1, which takes 3–4min to reach its maximum effect. The clinical duration of action of the drug is long, especially in the presence of potent inhalational agents or renal dysfunction, as 60% of a dose of the drug is excreted unchanged through the kidneys. I t is also deacetylated in the liver; some of the metabolites have neuromuscular blocking properties.
Pancuronium does not stimulate histamine release; however, it has direct vagolytic and sympathomimetic effects which may cause tachycardia and hypertension. It slightly inhibits plasma cholinesterase and therefore potentiates any drug metabolised by this enzyme, such as suxamethonium and mivacurium.

Clinical Use

As 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 Profile

A 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

Safety Profile

A deadly poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and Brí.

Chemical Synthesis

Pancuronium, 1,1-(3α,17β-diacetoxy-5α-androstan-2β,16β-ylene)-bis- (1-methylpiperidinium) dibromide (15.1.8), is synthesized from 3,17-bis-(acetoxy)-2,16- 5α-androstane. Oxidation with 3-chloroperbenzoic acid gives the bis-epoxy compound (15.1.5), the reaction of which with piperidine and subsequent hydrolysis gives an aminoketone (15.1.6). The keto group of the resulting compound (15.1.6) is reduced by sodium borohydride to hydroxyl group, giving the bis-aminoalcohol (15.1.7), subsequent acetylation of which by acetic anhydride and alkylation of both nitrogen atoms by methylbromide give the desired pancuronium (15.1.8).

Veterinary Drugs and Treatments

Pancuronium is indicated as an adjunct to general anesthesia to produce muscle relaxation during surgical procedures or m

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced muscle relaxant effect.
Anti-arrhythmics: procainamide enhances muscle relaxant effect.
Antibacterials: effect enhanced by aminoglycosides, clindamycin, polymyxins and piperacillin.
Antiepileptics: muscle relaxant effects antagonised by carbamazepine; effects reduced by long-term use of fosphenytoin and phenytoin but might be increased by acute use.
Botulinum toxin: neuromuscular block enhanced (risk of toxicity).

Metabolism

A small proportion of pancuronium is metabolised in the liver to metabolites with weak neuromuscular blocking activity.
It is largely excreted in urine as unchanged drug and metabolites; a small amount is excreted in bile.

Purification Methods

The 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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View Lastest Price from Pancuronium bromide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2022-02-23 Pancuronium bromide;Pavulon
15500-66-0
US $1.00 / Kg/Bag 1Kg/Bag 99.79% HPLC 5000tons/year Wuhan Dujiang Industrial Co., Ltd.
2022-02-10 Pancuronium bromide
15500-66-0
US $25.00 / KG 1KG 0.99 50000kg/month XINGTAI XINGJIU NEW MATERIAL TECHNOLOGY CO., LTD
2021-12-01 Pancuronium bromide
15500-66-0
US $1.00 / KG 1KG 99% 50 ton Hebei Crovell Biotech Co Ltd
  • Pancuronium bromide
    15500-66-0
  • US $25.00 / KG
  • 0.99
  • XINGTAI XINGJIU NEW MATERIAL TECHNOLOGY CO., LTD
1,1’-(3alpha,17beta-dihydroxy-5alpha-androstan-2beta,16beta-ylene)bis[1-methyl 1,1’-[3alpha,17beta-bis(acetyloxy)-5alpha-androstane-2beta,16beta-diyl]bis[1-m 16-diyl)bis(1-methyl-ostane-dibromide 2beta,16beta-dipiperidino-5alpha-androstane-3alpha,17beta-dioldiacetatedimetho 3-alpha,17-beta-diacetoxy-2-beta,16-beta-dipiperidino-5-alpha-androstanedime 3-alpha,17-beta-diacetoxy-2-beta,16-beta-dipiperidino-5-alpha-androstanedimeth 3alpha,17beta-diacetoxy-2beta,16beta-dipiperidino-5alpha-androstanedimethobrom 5alpha-androstan-3alpha,17beta-diol,2beta,16beta-dipipecolinio-,dibromide, 5alpha-androstan-3alpha,17beta-diol,2beta,16beta-dipipecolinio-,dibromide,di ethylpiperidinium]dibromide mioblock na97 orgna97 piperidinium,1,1’-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)andr piperidinium,1,1’-(3alpha,17beta-dihydroxy-5alpha-androstan-2beta,16beta-ylen piperidinium]dibromidediacetate thobromide ylene))bis(1-methyl,dibromide,diacetate ylene))bis(1-methyl-,dibromide,diacetate 1,1’-[(2β,3α,5α,16β,17β)-3,17-Bis(acetoxy)androstane-2,16-diyl]bis[1-methyl-piperidinium]dibmmide Mioblock:Pavulon Piperidinium, 1,1'-[(2b,3a,5a,16b,17b)-3,17-bis(acetyloxy)androstane-2,16-diyl]bis[1-methyl-, dibromide 1,1'-(3alpha,17beta-Bis(acetyloxy)-5alpha-androstane-2beta,16beta-diyl)bis(1-methylpiperidinium) dibromide PancuroniuM (Pavulon) 1,1'-(3α,17β-Dihydroxy-5α-androstan-2β,16β-ylene)bis[1-MethylpiperidiniuM] DibroMide Diacetate 2β,16β-Dipiperidino-5α-androstane-3α,17β-diol Diacetate DiMethobroMide 1,1'-[(2β,3α,5α,16β,17β)-3,17-Bis(acetyloxy)androstane-2,16-diyl]bis[1-methylpiperidinium] 1,1'-[3α,17β-Bis(acetoxy)-5α-androstane-2β,16β-diyl]bis[1-methylpiperidinium] 1,1'-[3α,17β-Bis(acetyloxy)-5α-androstane-2β,16β-diyl]bis(1-methylpiperidinium) 1,1'-[3α,17β-Bis(acetyloxy)-5α-androstane-2β,16β-diyl]bis[1-methylpiperidin-1-ium] Miobloc 1,1'-(3α,17β-Dihydroxy-2β,5α-androstan-2β,16β-ylene)bis[1-methylpiperidinium]diacetatedibromide Pancuronium Bromide (200 mg) 1,1'-((2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3,17-Diacetoxy-10,13-dimethylhexadecahydro-1H-cyclo 1,1'-(3A,17B-DIHYDROXY-2B,5A-ANDROSTAN-2B,16B-YLENE) BIS[1-METHYLPIPERIDINIUM] DIACETATE DIBROMIDE 1,1'-[(2b,3a,5a,16b,17b)-3,17-bis(acetyloxy)androstane-2,16-diyl]bis(1-methylpiperidinium) dibromide 1,1'-[(2BETA,3ALPHA,5ALPHA,16BETA,17BETA)-3,17-BIS(ACETYLOXY)ANDROSTANE-2,16-DIYL]BIS[1-METHYLPIPERIDINIUM]DIBROMIDE 2-beta,16-beta-bis(1-methylpiperidinio)androstane-3-alpha,17-beta-diol 3-alpha,17-beta-di(acetate) dibromide PANCURONIUM BROMIDE PANCURONIUM DIBROMIDE 1,1'-[(2β,3α,5α,16β,17β)-3,17-bis(acetyloxy)androstane-2,16-diyl]bis(1-methylpiperidinium) dibromide 1,1'-(3a,17b-Dihydroxy-5a-androstan-2b,16b-ylene)bis[1-methylpiperidinium] dibromide diacetate 2b,16b-Dipiperidino-5a-androstane-3a,17b-diol diacetate dimethobromide 5a-Androstane-3a,17b-diol, 2b,16b-bis(1-methylpiperidinio)-, dibromide, diacetate (8CI) NSC 293162 Org-NE 35 Piperidinium, 1,1'-(3a,17b-dihydroxy-5a-androstan-2b,16b-ylene)bis[1-methyl-, dibromide, diacetate (8CI) Piperidinium, 1,1'-[(2b,3a,5a,16b,17b)-3,17-bis(acetyloxy)androstane-2,16-diyl]bis[1-methyl-, dibromide (9CI) Pancuronium bromide (Injectable Grade) 1,1’-(3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1-methylpiperidinium)dibro Vecuronium Bromide EP Impurity B Resveratrol 3,4&rsquo Vecuronium Bromide Impurity 2(Vecuronium Bromide EP Impurity B) Pancuronium Dibromide - CAS 15500-66-0 - Calbiochem Vecuronium EP Impurity B Pancuronium bromide CRS Pancuronium bromide for system suitability CRS Pancuronium bromide USP/EP/BP