Trimedoxime bromide

Chemical compound

None

Legal statusLegal status

Experimental; in military use

Pharmacokinetic dataElimination half-life2 hours (mean)Identifiers

IUPAC name

1,1′-propane-1,3-diylbis{4-[(E)-(hydroxyimino)methyl]pyridinium} dibromide

CAS Number

56-97-3

PubChem CID

5359236

ChemSpider

4514238

UNII

ED0GXI9825

ECHA InfoCard100.000.276

Chemical and physical dataFormulaC₁₅H₁₈Br₂N₄O₂Molar mass446.143 g·mol⁻¹

Trimedoxime bromide (INN), also known as dipyroxime or TMB-4, is an oxime used in the treatment of organophosphate poisoning^[1] It is chemically related to asoxime, pralidoxime, and obidoxime.^[2]

References

^ Dhuguru J, Zviagin E, Skouta R (January 2022). "FDA-Approved Oximes and Their Significance in Medicinal Chemistry". Pharmaceuticals. 15 (1). Basel, Switzerland: 66. doi:10.3390/ph15010066. PMC 8779982. PMID 35056123.
^ Gupta R, Parmar M (2022). "Pralidoxime". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 32644334.

Antidotes (V03AB)

Nervous
system

Alcohol intoxication	Metadoxine Thiamine
Barbiturate overdose	Bemegride Ethamivan
Benzodiazepine overdose	Cyprodenate Flumazenil
GHB overdose	Physostigmine SCH-50911
Nerve agent / Organophosphate poisoning	Atropine^# Biperiden Diazepam^# Oximes Obidoxime Pralidoxime see also: Cholinesterase
Opioid overdose	Diprenorphine Doxapram Nalmefene Nalorphine Naloxone^# Naltrexone
Reversal of neuromuscular blockade	Sugammadex

Circulatory
system

Beta blocker	Glucagon
Digoxin toxicity	Digoxin immune fab
Anticoagulants	against direct Xa inhibitors (Andexanet alfa) against heparin (Protamine^#)

Other

Arsenic poisoning	Dimercaprol^# Succimer
Cyanide poisoning	4-Dimethylaminophenol Hydroxocobalamin nitrite Amyl nitrite Sodium nitrite^# Sodium thiosulfate^#
Hydrofluoric acid	Calcium gluconate^#
Methanol / Ethylene glycol poisoning	Primary alcohols: Ethanol Fomepizole
Paracetamol toxicity (Acetaminophen)	Acetylcysteine^# Glutathione Methionine^#
Toxic metals (cadmium lead mercury thallium)	Dimercaprol^# Edetates Prussian blue^#
Other	iodine-131 Potassium iodide Methylthioninium chloride^# oxidizing agent Potassium permanganate Prednisolone/promethazine

Emetic

Copper sulfate
Ipecacuanha
- Syrup of ipecac

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Acetylcholine metabolism and transport modulators

Enzyme
(modulators)

ChATTooltip Choline acetyltransferase	Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate
AChETooltip Acetylcholinesterase	Inhibitors: Reversible: Carbamates: Aldicarb Aminocarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Carbosulfan Chlorbufam Chloropropham Dimetilan Ethienocarb Ethiofencarb Fenobucarb Formetanate Formparanate Methiocarb Methomyl Metolcarb Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Promecarb Propamocarb Propham Propoxur Thiodicarb Thiofanox; Stigmines: Distigmine Eptastigmine Ganstigmine Neostigmine +glycopyrronium bromide Phenserine Physostigmine Pyridostigmine Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Caffeine Donepezil EA-3990 EA-4056 Edrophonium Galantamine Huperzine A Huprine W Huprine X Huprine Y Ipidacrine Itopride Ladostigil Minaprine Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) T-1123 T-1152 T-1194 TL-599 TL-1238 Tacrine Zanapezil Irreversible: Organophosphates: 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Acephate Armine Azinphos-ethyl Azinphos-methyl BAY-29952 Bensulide Cadusafos Carbophenothion Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Crotylsarin Cyanophos Cyclosarin (GF) Demephion Demeton Demeton-S-methyl Dialifor Diazinon Dichlorvos Dicrotophos Dicyclohexyl phosphorofluoridate Diisopropylphosphate Diisopropyl fluorophosphate Dimefox Dimethoate Dimethyl 4-(methylthio)phenyl phosphate Dioxathion Disulfoton EA-2012 EA-2054 EA-2098 EA-2192 EA-2613 EA-3148 EA-4352 Echothiophate Ethylsarin (GE) Endothion EPN Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fluorotabun Fonofos Formothion Fosthiazate GD-42 GH GT-45 GV Guanitoxin Hexaethyl tetraphosphate (HETP) Isofluorophate Isoxathion Leptophos Malaoxon Malathion Mazidox Methamidophos Methidathion Methyl phenkapton Methylfluorophosphonylcholine (MFPCh) Metrifonate Mevinphos Mipafox Monocrotophos MSPI Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosfolan Phosmet Phosphamidon Phoxim Pirimiphos-methyl Profenofos Prothoate R-16661 Ro 3-0340 Ro 3-0346 Ro 3-0347 Ro 3-0351 Ro 3-0352 Ro 3-0397 Ro 3-0411 Ro 3-0412 Ro 3-0417 Ro 3-0419 Ro 3-0422 Ro 3-0433 Ronnel Sarin (GB) Schradan Soman (GD) Sulfotep (TEDP) Tabun (GA) Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tetraethyl pyrophosphate (TEPP) Triazofos Tribufos Trichlorfon Trichloronate Tricresyl phosphate VE VG VM VP VS VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Methanesulfonyl fluoride Unsorted: α-Pinene α-Viniferin Affinine Affinisine Arisugacin A Bulbocapnine Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol Ungeremine Ungiminorine Dimethylcarbamoyl fluoride BW284C51 TMTFA 3152 CT Reactivators: Asoxime chloride Methoxime Obidoxime Pralidoxime Trimedoxime bromide
BChETooltip Butyrylcholinesterase	Inhibitors: Affinine Affinisine Conodurine Cymserine Ladostigil Profenamine (ethopropazine) Rivastigmine Tacrine ZINC-12613047 Many of the other AChE inhibitors listed above

Transporter
(modulators)

CHTTooltip Choline transporter	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam
VAChTTooltip Vesicular acetylcholine transporter	Inhibitors: Vesamicol

Release
(modulators)

Inhibitors	SNAP-25Tooltip Synaptosomal-associated protein 25 inactivators: Botulinum toxin (A, C, E) VAMPTooltip Vesicle-associated membrane protein inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)
Enhancers	LPHNTooltip Latrophilin agonists: α-Latrotoxin Others: Atracotoxins (e.g., robustoxin, versutoxin) Crotoxin