[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
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[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
structure -
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CAS No:
16974-53-1
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Formula:
C35H60N2O4+2
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Chemical Name:
[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
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Synonyms:
Bromide, Pancuronium;Pancuronium;Pancuronium Bromide;Pancuronium Curamed;Pancuronium Organon;Pavulon;pancuronium;Pavulon;Pancuronium dibromide;UNII-J76UF062FS;pancuronium (cation);Bromure de pancuronium [INN-French];Bromuro de pancuronio [INN-Spanish];NA 97;CHEBI:7907;J76UF062FS;15500-66-0;16974-53-1;Poncuronium bromide;Pancuronium cation;NSC293162;Prestwick0_001034;Prestwick1_001034;Prestwick2_001034;Prestwick3_001034;Lopac0_000887;BSPBio_001247;Piperidinium, 1,1'-[(2.beta.,3.alpha.,5.alpha.,16.beta.,17.beta.)-3,17-bis(acetyloxy)androstane-2,16-diyl]bis[1-methyl-, dibromide;SPBio_003098;BPBio1_001372;CHEMBL185073;GTPL4001;DTXSID7048405;SCHEMBL13790650;HMS2089M07;ZINC4097383;CCG-204969;DB01337;3alpha,17beta-diacetoxy-2beta,16beta-bis(1-methylpiperidinium-1-yl)-5alpha-androstane;NCGC00023037-03;NCGC00023037-04;NCGC00023037-05;NCGC00023037-09;NCGC00023037-14;1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-4-(1-methylpiperidin-1-ium-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1-methylpiperidin-1-ium;AB00384328;C07551;AB00384328-09;AB00384328-10;AB00384328_11;Q424297;[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetoxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate;1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-13-(1-methylpiperidin-1-ium-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-4-yl]-1-methylpiperidin-1-ium
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CAS No:
Description
Solid
Pancuronium is a steroid ester in which a 5alpha-androstane skeleton is C-3alpha- and C-17beta-disubstituted with acetoxy groups and 2beta- and 16beta-disubstituted with 1-methylpiperidinium-1-yl groups. It is a non-depolarizing curare-mimetic muscle relaxant. It has a role as a muscle relaxant, a cholinergic antagonist and a nicotinic antagonist. It is a steroid ester and an acetate ester.|A bis-quaternary steroid that is a competitive nicotinic antagonist. As a neuromuscular blocking agent it is more potent than curare but has less effect on the circulatory system and on histamine release.|Pancuronium is a Nondepolarizing Neuromuscular Blocker. The physiologic effect of pancuronium is by means of Neuromuscular Nondepolarizing Blockade.|Pancuronium is a synthetic, long-acting bis-quaternary steroid and non-depolarizing neuromuscular blocking agent, with muscle relaxant activity. Pancuronium competitively binds to and blocks the nicotinic acetylcholine receptor at the neuromuscular junction, thereby preventing acetylcholine (ACh) binding and resulting in skeletal muscle relaxation and paralysis.|A bis-quaternary steroid that is a competitive nicotinic antagonist. As a neuromuscular blocking agent it is more potent than CURARE but has less effect on the circulatory system and on histamine release.
[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate Basic Attributes
572.9 g/mol
572.45530840 g/mol
239-532-5
J76UF062FS
DTXSID7048405
C61876
Crystals|WHITE POWDER
M - Musculo-skeletal system
Characteristics
52.6 Ų
215 °C|215°C
1 g sol in 30 parts chloroform, 1 part water (20 °C)|SOL IN ALCOHOL|Very soluble in water.|3.08e-06 g/L
Pancuronium bromide should be stored under refrigeration at 2-8 °C.
Odorless
Bitter
HYGROSCOPIC
Safety Information
SENSITIVE TO HEAT|... The manufacturer indicates that the drug is stable for 6 mos at room temperature.
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 58 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
FROM CLINICAL VIEWPOINT, MOST IMPORTANT PHARMACOLOGICAL INTERACTIONS OF THESE DRUGS ARE WITH CERTAIN GENERAL ANESTHETICS, CERTAIN ANTIBIOTICS, AND ANTI-CHOLINESTERASE COMPOUNDS. /NEUROMUSCULAR BLOCKING AGENTS/|...DIETHYL ETHERS, AS WELL AS PRIOR SUCCINYLCHOLINE, INTENSIFY & PROLONG ACTION /OF PANCURONIUM/.|ETHER EXERTS STABILIZING EFFECT ON POSTJUNCTIONAL MEMBRANE & THEREFORE, ACTS SYNERGISTICALLY WITH COMPETITIVE BLOCKING AGENTS. ... HALOTHANE, CYCLOPROPANE, FLUROXENE, METHOXYFLURANE, & ENFLURANE LIKEWISE ACT SYNERGISTICALLY WITH COMPETITIVE BLOCKING AGENTS, BUT TO LESSER EXTENT. /NEUROMUSCULAR COMPETITIVE BLOCKING AGENTS/|AMINOGLYCOSIDE ANTIBIOTICS PRODUCE NEUROMUSCULAR BLOCKADE BY INHIBITING ACETYLCHOLINE RELEASE FROM THE PREGANGLIONIC TERMINAL (THROUGH COMPETITION WITH CA(2+)) AND ... BY STABILIZING THE POSTJUNCTIONAL MEMBRANE. THE BLOCKADE IS ANTAGONIZED BY CALCIUM SALTS, BUT ONLY INCONSISTENTLY BY ANTICHOLINESTERASE AGENTS. THE TETRACYCLINE ANTIBIOTICS ALSO CAN PRODUCE NEUROMUSCULAR BLOCK, POSSIBLY BY CHELATION OF CALCIUM IONS. ADDITIONAL ANTIBIOTICS THAT HAVE NEUROMUSCULAR BLOCKING ACTION ... INCLUDE POLYMYXIN B, COLISTIN, CLINDAMYCIN, & LINCOMYCIN. /NEUROMUSCULAR BLOCKING AGENTS/|For more Interactions (Complete) data for PANCURONIUM BROMIDE (27 total), please visit the HSDB record page.
LD50 Rat oral 202 mg/kg|LD50 Rat ip 479 ug/kg|LD50 Rat sc 436 ug/kg|LD50 Rat iv 153 ug/kg|For more Non-Human Toxicity Values (Complete) data for PANCURONIUM BROMIDE (10 total), please visit the HSDB record page.
77 to 91%
Drug Information
Used as a muscle relaxant during anesthesia and surgical procedures.
Neuromuscular Nondepolarizing Agents; Nicotinic Antagonists|THE MAIN CLINICAL USE OF THE NEUROMUSCULAR BLOCKING AGENTS IS AS AN ADJUVANT IN SURGICAL ANESTHESIA TO OBTAIN RELAXATION OF SKELETAL MUSCLE, PARTICULARLY OF THE ABDOMINAL WALL ... MUSCLE RELAXATION IS ALSO OF VALUE IN VARIOUS ORTHOPEDIC PROCEDURES, SUCH AS THE CORRECTION OF DISLOCATIONS & THE ALIGNMENT OF FRACTURES. /NEUROMUSCULAR BLOCKING AGENTS/|...MAY BE USED MORE SAFELY IN PT WITH CARDIOVASCULAR DISEASE OR BRONCHIAL ASTHMA THAN ANY OTHER NEUROMUSCULAR BLOCKING DRUG. ...IT HAS ACTUALLY BEEN USED IN MGMNT OF STATUS ASTHMATICUS TO RELAX MUSCLES, THEREBY FACILITATING ARTIFICIAL RESPIRATION & DECR OXYGEN DEMAND. ... DURATION OF ACTION OF USUAL DOSE IS GENERALLY 30-60 MIN...|/NEUROMUSCULAR BLOCKING AGENTS/ HAVE BEEN USED TO FACILITATE LARYNGOSCOPY, BRONCHOSCOPY, & ESOPHAGOSCOPY, IN COMBINATION WITH A GENERAL ANESTHETIC AGENT. /NEUROMUSCULAR BLOCKING AGENTS/|For more Therapeutic Uses (Complete) data for PANCURONIUM BROMIDE (9 total), please visit the HSDB record page.
THE NEUROMUSCULAR BLOCKING AGENTS ARE POTENTIALLY HAZARDOUS DRUGS. CONSEQUENTLY, THEY SHOULD BE ADMINISTERED TO PATIENTS ONLY BY ANESTHESIOLOGISTS & OTHER CLINICIANS WHO HAVE HAD EXTENSIVE TRAINING IN THEIR USE & IN A SETTING WHERE FACILITIES FOR RESPIRATORY & CARDIOVASCULAR RESUSCITATION ARE IMMEDIATELY AT HAND. /NEUROMUSCULAR BLOCKING AGENTS/|...IT IS ADVISABLE TO USE DRUG CAUTIOUSLY IN PRESENCE OF RENAL OR LIVER DISEASES.|EFFECT OF SPECIFIC DOSE OF ... PANCURONIUM MAY /POSSIBLY/ BE REDUCED IN PT WITH HIGH PLASMA GLOBULIN LEVELS (EG THOSE WITH LIVER DISEASE).|GREAT CARE SHOULD BE TAKEN WHEN ADMIN MUSCLE RELAXANTS TO DEHYDRATED OR SEVERELY ILL PATIENTS. /NEUROMUSCULAR BLOCKING AGENTS/|For more Drug Warnings (Complete) data for PANCURONIUM BROMIDE (17 total), please visit the HSDB record page.
Pancuronium is a non-depolarising muscle relaxant similar to curare. It acts as a competitive acetylcholine antagonist on neuromuscular junctions, displacing acetylcholine (hence competitive) from its post-synaptic nicotinic acetylcholine receptors. It is, unlike suxamethonium, a non-depolarising agent, which means, that it causes no spontaneous depolarisations upon association with the nicotinic receptor in neuromuscular junction, thus producing no muscle fasciculations upon administration. Pancuronium has no hormonal activity. It exerts slight vagolytic activity (i.e. diminishing activity of the vagus nerve) and no ganglioplegic (i.e., blocking ganglions) activity.
Drugs that interrupt transmission at the skeletal neuromuscular junction without causing depolarization of the motor end plate. They prevent acetylcholine from triggering muscle contraction and are used as muscle relaxants during electroshock treatments, in convulsive states, and as anesthesia adjuvants. (See all compounds classified as Neuromuscular Nondepolarizing Agents.)|Drugs that bind to nicotinic cholinergic receptors (RECEPTORS, NICOTINIC) and block the actions of acetylcholine or cholinergic agonists. Nicotinic antagonists block synaptic transmission at autonomic ganglia, the skeletal neuromuscular junction, and at central nervous system nicotinic synapses. (See all compounds classified as Nicotinic Antagonists.)
241 to 280 mL/kg|Plasma cl=1.1–1.9 mL/minute/kg|BOTH LIVER & KIDNEYS ARE INVOLVED IN DEGRADATION & EXCRETION OF ... PANCURONIUM ...|AFTER IV INJECTION, EFFECTS...BECOME MAXIMAL IN LESS THAN 3 MIN IN ADULTS & 90 SEC IN CHILDREN. ... PLASMA HALF-LIFE IS PROBABLY SLIGHTLY LESS THAN 2 HR. PANCURONIUM IS MOSTLY EXCRETED UNCHANGED INTO URINE.|PLACENTAL TRANSFER OF...PANCURONIUM BROMIDE...OCCURS RAPIDLY AFTER ADMIN TO MOTHERS, BUT FETAL:MATERNAL DRUG CONCN RATIO ARE VERY LOW.|PLASMA LEVELS OF PANCURONIUM OBEYED TWO-COMPARTMENT KINETICS IN SEVEN PATIENTS ON IV INJECTION & THE BETA-PHASE HALF-TIME VARIED BETWEEN 90 AND 162 MIN. THE MEAN VOLUME OF THE CENTRAL COMPARTMENT WAS 100 ML/KG, WHILE THE OVERALL DISTRIBUTION VOLUME WAS 261 MG/KG. IN PATIENTS WITH CHRONIC RENAL FAILURE, THE PLASMA CLEARANCE...WAS SIGNIFICANTLY REDUCED, WHILE VOLUMES OF BOTH THE OVERALL & CENTRAL COMPARTMENTS WERE SIGNIFICANTLY INCREASED.|For more Absorption, Distribution and Excretion (Complete) data for PANCURONIUM BROMIDE (6 total), please visit the HSDB record page.
Hepatic.|IN CATS, 8 HR AFTER IV INJECTION OF PANCURONIUM BROMIDE, UNCHANGED PANCURONIUM BROMIDE IN URINE, BILE, & LIVER ACCOUNTED FOR 58% OF DOSE, 3-HYDROXY-DERIV FOR 14.5%, 17-HYDROXY-DERIV FOR 7% & 3,17-DIHYDROXY-DERIV FOR 4.5%.
1.5 to 2.7 hours.|PLASMA HALF-LIFE IS PROBABLY SLIGHTLY LESS THAN 2 HR.
Nondepolarizing neuromuscular blocking agents inhibit neuromuscular transmission by competing with acetylcholine for the cholinergic receptors of the motor end plate, thereby reducing the response of the end plate to acetylcholine. This type of neuromuscular block is usually antagonized by anticholinesterase agents.|LOW CONCN OF PANCURONIUM BROMIDE (5X10-8 G/ML OR LESS), HAD NO PRESYNAPTIC EFFECT ON MURINE PHRENIC NERVE-DIAPHRAGM PREPN. AT HIGH CONCN (5X10-7 G/ML), PANCURONIUM BROMIDE DEPRESSED QUANTAL RELEASE TO 26% OF CONTROL IN CUT-FIBER PREPN & 40% OF CONTROL IN HIGH-MAGNESIUM PREPN. POSTSYNAPTIC EFFECTS REVEALED DEPRESSION TO 16 & 22% OF CONTROL, RESPECTIVELY, AT A CONCN OF 5X10-7 G/ML. PANCURONIUM BROMIDE HAD NO EFFECT ON DIRECTLY ELICITED ACTION POTENTIALS & ELECTRIC MEMBRANE CONSTANTS. THUS, PRESYNAPTIC AS WELL AS POSTSYNAPTIC EFFECTS OF PANCURONIUM BROMIDE IN PARALYTIC DOSES ARE ESSENTIAL IN CONTRIBUTING TO THE TOTAL EFFICACY OF NEUROMUSCULAR DEPRESSION.|THE PHARMACODYNAMICS OF D-TUBOCURARINE (D-TC), PANCURONIUM BROMIDE, METOCURINE, & GALLAMINE WERE STUDIED IN RAT PHRENIC NERVE-HEMIDIAPHRAGM PREPN WITH VASCULAR PERFUSION AT 25, 31, & 37 °C. D-TC, METOCURINE, & GALLAMINE EACH DEMONSTRATED A NEAR 2-FOLD INCREASE IN ED50 AT 25 °C COMPARED WITH 37 °C. NO SUCH RELATIONSHIP WAS APPARENT WITH PANCURONIUM BROMIDE. SLOPES OF THE DOSE-RESPONSE CURVES WERE NOT INFLUENCED BY TEMP; HOWEVER, THE SLOPES FOR METOCURINE & D-TC WERE LOWER THAN THOSE FOR PANCURONIUM BROMIDE & GALLAMINE. THUS, IN THE RAT, PANCURONIUM BROMIDE RETAINS POTENCY AT HYPOTHERMIA, WHEREAS THE OTHER RELAXANTS DECREASE POTENCY. IN ADDITION, METOCURINE & D-TC EXHIBIT LESS STEEP DOSE-RESPONSE CURVES UNDER THESE EXPTL CONDITIONS.
Bromide, Pancuronium
[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-10,13-dimethyl-2,16-bis(1-methylpiperidin-1-ium-1-yl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate Use and Manufacturing
Prepared by reaction of 2alpha, 3alpha: 16alpha, 17alpha-diepoxy- 17beta-acetoxy-5alpha-androstane with piperidine, and subsequent alkylation with methyl bromide.
PANCURONIUM BROMIDE (PAVULON) IS AVAILABLE IN SOLN CONTAINING 1 OR 2 MG/ML.|Pancuronium bromide (Organon) is available in 2- and 5-ml ampuls containing 2 mg/ml of the drug. It is also available in 10-ml vials at a concentration of 1 mg/ml.
US PATENT 3,553,212.|... A precipitate may be formed if pancuronium bromide is mixed with barbiturates.
PANCURONIUM BROMIDE WAS DETERMINED QUANTITATIVELY IN AQ SOLN BY ION PAIR EXTRACTION. SEPARATE DETERMINATION OF PANCURONIUM BROMIDE & DEGRADATION PRODUCTS WAS POSSIBLE AFTER THIN LAYER CHROMATOGRAPHY. IN THE DIRECT METHOD, 0.1 MG PANCURONIUM BROMIDE WAS DETERMINED WITH A REPRODUCIBILITY OF +/- 1.0%.
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:572.9
XLogP3:6.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:572.45530840
Monoisotopic Mass:572.45530840
Topological Polar Surface Area:52.6
Heavy Atom Count:41
Formal Charge:2
Complexity:1000
Defined Atom Stereocenter Count:10
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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