Quaternary Ammonium Compounds

Derivatives of ammonium compounds, NH4+ Y-, in which all four of the hydrogens bonded to nitrogen have been replaced with hydrocarbyl groups. These are distinguished from IMINES which are RN=CR2.
DrugDrug NameDrug Indication
DB13705DecamethoxineNot Available
DB01718CetrimoniumNot Available
DB00122CholineFor nutritional supplementation, also for treating dietary shortage or imbalance
DB00202SuccinylcholineUsed in surgical procedures where a rapid onset and brief duration of muscle relaxation is needed (includes intubation, endoscopies, and ECT)
DB00219OxyphenoniumFor the treatment of visceral spasms
DB00411CarbamoylcholinePrimarily used in the treatment of glaucoma, but is also used during ophthalmic surgery.
DB00416Metocurine IodideFor use as an anesthesia adjunct to induce skeletal muscle relaxation and to reduce the intensity of muscle contractions in convulsive therapy.
DB00483Gallamine triethiodideFor use as adjuncts to anesthesia to induce skeletal muscle relaxation and to facilitate the management of patients undergoing mechanical ventilation
DB00583LevocarnitineFor treatment of primary systemic carnitine deficiency, a genetic impairment of normal biosynthesis or utilization of levocarnitine from dietary sources, or for the treatment of secondary carnitine deficiency resulting from an inborn error of metabolism such as glutaric aciduria II, methyl malonic aciduria, propionic acidemia, and medium chain fatty acylCoA dehydrogenase deficiency. Used therapeutically to stimulate gastric and pancreatic secretions and in the treatment of hyperlipoproteinemias. Parenteral levocarnitine is indicated for the prevention and treatment of carnitine deficiency in patients with end-stage renal disease.
DB00782PropanthelineFor the treatment of enuresis. It has also been used for hyperhidrosis, and cramps or spasms of the stomach, intestines or bladder.
DB00941HexafluroniumUsed as an adjunct with succinylcholine (or suxamethonium chloride) to prolong muscle relaxation and to prevent succinylcholine-induced muscle fasciculations.
DB00986GlycopyrroniumFor use as a preoperative antimuscarinic to reduce salivary, tracheobronchial, and pharyngeal secretions, to reduce the volume and free acidity of gastric secretions and to block cardiac vagal inhibitory reflexes during induction of anesthesia and intubation. Also used to treat chronic obstructive pulmonary disease (COPD).
DB01010EdrophoniumFor the differential diagnosis of myasthenia gravis and as an adjunct in the evaluation of treatment requirements in this disease. It may also be used for evaluating emergency treatment in myasthenic crises.
DB01019BethanecholFor the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.
DB01122AmbenoniumAmbenonium is used to treat muscle weakness due to muscle disease (myasthenia gravis).
DB01158BretyliumFor use in the prophylaxis and therapy of ventricular fibrillation. Also used in the treatment of life-threatening ventricular arrhythmias, such as ventricular tachycardia, that have failed to respond to adequate doses of a first-line antiarrhythmic agent, such as lidocaine.
DB01199TubocurarineUsed as a diagnosis agent for myasthenia gravis, and also to facilitate the intubation after induction of anesthesia in surgical procedure
DB01245DecamethoniumFor use as a skeletal muscle relaxant
DB01303OxtriphyllineUsed to treat the symptoms of asthma, bronchitis, COPD, and emphysema.
DB01336MetocurineMetocurine is a muscle relaxant.
DB01400NeostigmineNeostigmine is used for the symptomatic treatment of myasthenia gravis by improving muscle tone.
DB01401Choline magnesium trisalicylateCholine magnesium trisalicylate is used to reduce pain and inflammation caused by conditions such as arthritis. This medication is also used to treat fever in adults.
DB02261Platelet Activating FactorNot Available
DB03945N,N,N-Trimethyl-2-(phosphonooxy)ethanaminiumNot Available
DB04250ButyrylthiocholineNot Available
DB05398C31GInvestigated for use/treatment in contraception, HIV infection, and prevention of stdis.
DB06641PerifosineInvestigated for use/treatment in solid tumors, multiple myeloma, leukemia (unspecified), lung cancer, and brain cancer.
DB06709MethacholineIt is most commonly used for diagnosing bronchial hyperreactivity, using the bronchial challenge test.
DB06756Glycine betaineBetaine is indicated for the treatment of homocystinuria to decrease elevated homocysteine blood levels. Included within the category of homocystinuria are deficiencies or defects in: 1. cystathionine beta-synthase (CBS), 2. 5,10-methylenetetrahydrofolate reductase (MTHFR), 3. cobalamin cofactor metabolism (cbl).
DB08837TetraethylammoniumTetraethylammonium is an experimental drug with no approved indication.
DB08842AcetylcarnitineAcetylcarnitine is not approved for any indication in the United states and Canada, but it is approved and indicated in Italy for cerebrovascular disorders, mental function disorders, peripheral nerve disorders, diabetic neuropathy, and nutritional supplementation; Portugal for mental function disorders; Argentina for cerebral vasculopathy, nutritional supplementation, and peripheral neuropathy; Chile for dementia; Philippines for cerebrovascular disorders and mental function disorders; Australia for nutritional supplementation; and India for nutritional supplementation to increase sperm count. Acetylcarnitine also has several potential therapeutic indications for which it is still being investigated: in Norway, acetylcarnitine is in a phase IV trial for prophylactic treatment of migraines; in Italy acetylcarnitine is in a phase II trial for use in patients with type 2 Diabetes Mellitus, a phase III trial for alleviating fatigue in patients with chronic hepatitis C, and for use in patients with Minimal Hepatic Encephalopathy; in the United States acetylcarnitine is in a phase II trial for the neurodegenerative disorder Progressive Supranuclear Palsy, a phase II and III trial for reducing peripheral neuropathy in cancer patients as an adjunct to chemotherapy, a phase I and II trial for treating patients in septic shock, a phase II trial for bipolar depression, a phase II trial to reduce oxidative stress in patients with Sickle Cell disease, a phase I and II trial for chronic fatigue syndrome, and a study for preventing nerve damage in HIV patients; in China acetylcarnitine is in a phase III trial for reducing peripheral neuropathy in cancer patients as an adjunct to chemotherapy; in the United Kingdom acetylcarnitine is being investigated for preventing nerve damage in HIV patients; and in Israel acetylcarnitine is being studied for the treatment of male infertility.
DB08960HexamethoniumNot Available
DB09031MiltefosineFor the treatment of mucosal (caused by Leishmania braziliensis), cutaneous (caused by L. braziliensis, L. guyanensis, and L. panamensis), and visceral leishmaniasis (caused by L. donovani). In comparing Leishmania drug susceptibility, it has been found that L. donovani is the most susceptible to miltefosine while L. major is the least susceptible. Off-label use includes treatment of free-living amebae (FLA) infections (unlabeled use; CDC, 2013).
DB09300ButylscopolamineUsed to treat abdmoninal cramping and pain [FDA Label].
DB11105BenzalkoniumWhen used as an active ingredient in products like antibacterial, antiseptic, or disinfectant soaps, topical sanitizers, or cleaning agents, benzalkonium is primarily implemented in its salt form, benzalkonium chloride, where it may often be the only active ingredient present and indicated for the primary purpose of topical washing to decrease bacteria on skin [L1806]. Conversely, when implemented as an excipient ingredient in a variety of multidose aqueous nose, eye, or ear products, benzalkonium chloride is being used as the antimicrobial preservative of choice to facilitate effective bactericidal and fungicidal actions to help minimize the growth of unwanted organisms in the multidose containers [FDA Label].
DB11125BenzethoniumIndicated as an antiseptic agent. No therapeutic indications for clinical use.
DB11183Light green SF yellowishNot Available
DB11350Cocamidopropyl betaineNot Available
DB13282BenzododeciniumNot Available
DB13505EmeproniumNot Available
DB13565BenzoxoniumNot Available
DB13584GallamineNot Available
DB13648AlcuroniumNot Available
DB14006Choline salicylateThe oral gel is indicated for the relief of pain and discomfort of common mouth ulcers, cold sores, denture sore spots, infant teething and mouth ulcers, and sore spots due to orthodontic devices in children [L2135].
DB11073CetylpyridiniumTypically employed as the cetylpyridinium chloride salt, this compound is commonly used as an active ingredient in various over-the-counter mouthwashes, toothpastes, lozenges, and mouth sprays where it is generally indicated for antiseptic actions, gingivitis and plaque prevention, as well as action or prevention against some other oropharyngeal bacterial infections [A24813, L2754, L2755].
DB12624OctenidineNot Available
DB12153CiticolineNot Available
DB04221DidecyldimethylammoniumNot Available
DB00940MethanthelineFor the treatment of peptic ulcer disease, irritable bowel syndrome, pancreatitis, gastritis, biliary dyskinesia, pylorosplasm, and reflex neurogenic bladder in children.
DrugDrug NameTargetType
DB01718CetrimoniumCyclopropane mycolic acid synthase MmaA2target
DB01718CetrimoniumCyclopropane mycolic acid synthase 1target
DB00122CholineCholine-phosphate cytidylyltransferase Btarget
DB00122CholineAcetylcholinesterasetarget
DB00122CholineCholine-phosphate cytidylyltransferase Atarget
DB00122CholinePhospholipase D2target
DB00122CholineCholinesterasetarget
DB00122CholinePhospholipase D1target
DB00122CholinePhosphoethanolamine/phosphocholine phosphatasetarget
DB00122CholineSolute carrier family 22 member 2transporter
DB00122CholineSolute carrier family 22 member 1transporter
DB00122CholineSolute carrier family 22 member 3transporter
DB00122CholineSolute carrier family 22 member 5transporter
DB00122CholineSolute carrier family 22 member 4transporter
DB00122CholineCholine/ethanolaminephosphotransferase 1enzyme
DB00122CholineCholine transporter-like protein 1transporter
DB00122CholineCholine transporter-like protein 4transporter
DB00122CholineCholine transporter-like protein 2transporter
DB00122CholineCholine transporter-like protein 3transporter
DB00122CholineCholine/ethanolamine kinaseenzyme
DB00122CholineCholine O-acetyltransferaseenzyme
DB00122CholineCholine kinase alphaenzyme
DB00122CholineCholine dehydrogenase, mitochondrialenzyme
DB00122CholineHigh affinity choline transporter 1transporter
DB00122CholineNeuronal acetylcholine receptor subunit alpha-7target
DB00202SuccinylcholineMuscarinic acetylcholine receptor M1target
DB00202SuccinylcholineCholinesteraseenzyme
DB00202SuccinylcholineMuscarinic acetylcholine receptor M2target
DB00202SuccinylcholineMuscarinic acetylcholine receptor M3target
DB00202SuccinylcholineAlpha-7 nicotinic cholinergic receptor subunittarget
DB00202SuccinylcholineNeuronal acetylcholine receptor subunit alpha-10target
DB00219OxyphenoniumMuscarinic acetylcholine receptor M1target
DB00411CarbamoylcholineMuscarinic acetylcholine receptor M1target
DB00411CarbamoylcholineMuscarinic acetylcholine receptor M2target
DB00411CarbamoylcholineNeuronal acetylcholine receptor subunit alpha-2target
DB00411CarbamoylcholineCytosolic phospholipase A2enzyme
DB00411CarbamoylcholineAcetylcholinesterasetarget
DB00411CarbamoylcholineMuscarinic acetylcholine receptor M3target
DB00411CarbamoylcholineMuscarinic acetylcholine receptor M4target
DB00416Metocurine IodideNeuronal acetylcholine receptor subunit alpha-2target
DB00483Gallamine triethiodideNeuronal acetylcholine receptor subunit alpha-2target
DB00483Gallamine triethiodideMuscarinic acetylcholine receptor M2target
DB00483Gallamine triethiodideAcetylcholinesterasetarget
DB00483Gallamine triethiodideMuscarinic acetylcholine receptor M1target
DB00483Gallamine triethiodideMuscarinic acetylcholine receptor M5target
DB00583LevocarnitineCarnitine O-palmitoyltransferase 1, liver isoformtarget
DB00583LevocarnitineSolute carrier family 22 member 4target
DB00583LevocarnitineSolute carrier family 22 member 5target
DB00583LevocarnitineCarnitine O-acetyltransferasetarget
DB00583LevocarnitineMitochondrial carnitine/acylcarnitine carrier protein CACLtarget
DB00583LevocarnitineMitochondrial carnitine/acylcarnitine carrier proteintarget
DB00583LevocarnitinePeroxisomal carnitine O-octanoyltransferasetarget
DB00583LevocarnitineCarnitine O-palmitoyltransferase 2, mitochondrialtarget
DB00583LevocarnitineSolute carrier family 22 member 4transporter
DB00583LevocarnitineSolute carrier organic anion transporter family member 1B1transporter
DB00583LevocarnitineSolute carrier family 22 member 5transporter
DB00583LevocarnitineSolute carrier family 22 member 16transporter
DB00583LevocarnitineSolute carrier family 22 member 8transporter
DB00583LevocarnitineXanthine dehydrogenase/oxidasetarget
DB00583LevocarnitineLiver carboxylesterase 1target
DB00583LevocarnitineMyeloperoxidasetarget
DB00782PropanthelineMuscarinic acetylcholine receptor M1target
DB00941HexafluroniumCholinesterasetarget
DB00986GlycopyrroniumMuscarinic acetylcholine receptor M1target
DB00986GlycopyrroniumMuscarinic acetylcholine receptor M3target
DB00986GlycopyrroniumMuscarinic acetylcholine receptor M2target
DB01010EdrophoniumAcetylcholinesterasetarget
DB01010EdrophoniumCholinesterasetarget
DB01019BethanecholMuscarinic acetylcholine receptor M2target
DB01019BethanecholMuscarinic acetylcholine receptor M1target
DB01019BethanecholMuscarinic acetylcholine receptor M3target
DB01019BethanecholMuscarinic acetylcholine receptor M4target
DB01122AmbenoniumAcetylcholinesterasetarget
DB01122AmbenoniumCholinesteraseenzyme
DB01158BretyliumSodium/potassium-transporting ATPase subunit alpha-1target
DB01199TubocurarineNeuronal acetylcholine receptor subunit alpha-2target
DB01199TubocurarineAcetylcholinesterasetarget
DB01199Tubocurarine5-hydroxytryptamine receptor 3Atarget
DB01199TubocurarineSolute carrier family 22 member 1transporter
DB01199TubocurarineSolute carrier family 22 member 2transporter
DB01199TubocurarineNeuronal acetylcholine receptor subunit alpha-7target
DB01199TubocurarineCholinesteraseenzyme
DB01245DecamethoniumNeuronal acetylcholine receptor subunit alpha-2target
DB01245DecamethoniumAcetylcholinesterasetarget
DB01245DecamethoniumCholinesteraseenzyme
DB01245DecamethoniumNeuronal acetylcholine receptor subunit alpha-4target
DB01245DecamethoniumNeuronal acetylcholine receptor subunit beta-2target
DB01303OxtriphyllinecGMP-inhibited 3',5'-cyclic phosphodiesterase Atarget
DB01303OxtriphyllinecAMP-specific 3',5'-cyclic phosphodiesterase 4Atarget
DB01303OxtriphyllineAdenosine receptor A2atarget
DB01303OxtriphyllineAdenosine receptor A1target
DB01303OxtriphyllineCytochrome P450 1A2enzyme
DB01303OxtriphyllineSolute carrier family 22 member 7transporter
DB01303OxtriphyllineHistone deacetylase 2target
DB01336MetocurineNeuronal acetylcholine receptor subunit alpha-2target
DB01336MetocurineMuscarinic acetylcholine receptor M2target
DB01400NeostigmineAcetylcholinesterasetarget
DB01400NeostigmineCholinesteraseenzyme
DB01401Choline magnesium trisalicylateProstaglandin G/H synthase 1target
DB01401Choline magnesium trisalicylateProstaglandin G/H synthase 2target
DB02261Platelet Activating FactorGanglioside GM2 activatortarget
DB02261Platelet Activating FactorMultidrug resistance protein 1transporter
DB02261Platelet Activating FactorPlatelet-activating factor receptortarget
DB03945N,N,N-Trimethyl-2-(phosphonooxy)ethanaminiumC-reactive proteintarget
DB03945N,N,N-Trimethyl-2-(phosphonooxy)ethanaminiumEpididymal sperm-binding protein 1target
DB03945N,N,N-Trimethyl-2-(phosphonooxy)ethanaminiumGamma-hemolysin component Btarget
DB04250ButyrylthiocholineCholinesterasetarget
DB04250ButyrylthiocholineCholinesteraseenzyme
DB05398C31GGag-Pol polyproteintarget
DB05398C31GCD9 antigentarget
DB06641PerifosineRAC-alpha serine/threonine-protein kinasetarget
DB06641PerifosineMitogen-activated protein kinase 1target
DB06641PerifosineProtein kinase C alpha typetarget
DB06709MethacholineMuscarinic acetylcholine receptor M3target
DB06756Glycine betaineCholinesteraseenzyme
DB06756Glycine betaineProline dehydrogenase 1, mitochondrialenzyme
DB06756Glycine betaineApoptosis regulator Bcl-2target
DB08837TetraethylammoniumSolute carrier family 22 member 1transporter
DB08837TetraethylammoniumSolute carrier family 22 member 2transporter
DB08837TetraethylammoniumSolute carrier family 22 member 3transporter
DB08837TetraethylammoniumSolute carrier family 22 member 4transporter
DB08837TetraethylammoniumSolute carrier family 22 member 5transporter
DB08837TetraethylammoniumSolute carrier family 22 member 8transporter
DB08837TetraethylammoniumpH-gated potassium channel KcsAtarget
DB08837TetraethylammoniumNeuronal acetylcholine receptor subunit alpha-9target
DB08837TetraethylammoniumCalcium-activated potassium channel subunit alpha-1target
DB08837TetraethylammoniumPotassium voltage-gated channel subfamily A member 1target
DB08837TetraethylammoniumMultidrug and toxin extrusion protein 1transporter
DB08842AcetylcarnitineSolute carrier family 22 member 5transporter
DB08842AcetylcarnitineSolute carrier family 22 member 21transporter
DB08960HexamethoniumNeuronal acetylcholine receptor subunit alpha-2target
DB09031MiltefosinePhospholipase D1enzyme
DB09031MiltefosineMultidrug resistance protein 1target
DB09300ButylscopolamineMuscarinic acetylcholine receptor M3target
DB09300ButylscopolamineMuscarinic acetylcholine receptor M2target
DB14006Choline salicylateCholine-phosphate cytidylyltransferase Btarget
DB14006Choline salicylateAcetylcholinesterasetarget
DB14006Choline salicylateCholine-phosphate cytidylyltransferase Atarget
DB14006Choline salicylatePhospholipase D2target
DB14006Choline salicylateCholinesterasetarget
DB14006Choline salicylatePhospholipase D1target
DB14006Choline salicylatePhosphoethanolamine/phosphocholine phosphatasetarget
DB14006Choline salicylateSolute carrier family 22 member 2transporter
DB14006Choline salicylateSolute carrier family 22 member 1transporter
DB14006Choline salicylateSolute carrier family 22 member 3transporter
DB14006Choline salicylateSolute carrier family 22 member 5transporter
DB14006Choline salicylateSolute carrier family 22 member 4transporter
DB14006Choline salicylateCholine/ethanolaminephosphotransferase 1enzyme
DB14006Choline salicylateCholine transporter-like protein 1transporter
DB14006Choline salicylateCholine transporter-like protein 4transporter
DB14006Choline salicylateCholine transporter-like protein 2transporter
DB14006Choline salicylateCholine transporter-like protein 3transporter
DB14006Choline salicylateCholine/ethanolamine kinaseenzyme
DB14006Choline salicylateCholine O-acetyltransferaseenzyme
DB14006Choline salicylateCholine kinase alphaenzyme
DB14006Choline salicylateCholine dehydrogenase, mitochondrialenzyme
DB14006Choline salicylateHigh affinity choline transporter 1transporter
DB14006Choline salicylateNeuronal acetylcholine receptor subunit alpha-7target
DB12153CiticolineLicC proteintarget
DB04221DidecyldimethylammoniumCyclopropane mycolic acid synthase 2target
DB00940MethanthelineMuscarinic acetylcholine receptor M1target
DB00940MethanthelineHistamine H2 receptortarget