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Identification
NameTrimethaphan
Accession NumberDB01116  (APRD00044)
TypeSmall Molecule
GroupsApproved
DescriptionA nicotinic antagonist that has been used as a ganglionic blocker in hypertension, as an adjunct to anesthesia, and to induce hypotension during surgery. [PubChem]
Structure
Thumb
Synonyms
Thimethaphan
Trimetaphan
Trimetaphanum
Trimethaphan
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ArfonadNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Trimethaphan camsylate
ThumbNot applicableDBSALT001381
Categories
UNII6G8X656T45
CAS number7187-66-8
WeightAverage: 365.512
Monoisotopic: 365.168759122
Chemical FormulaC22H25N2OS
InChI KeyCHQOEHPMXSHGCL-UHFFFAOYSA-N
InChI
InChI=1S/C22H25N2OS/c25-22-23(14-17-8-3-1-4-9-17)19-16-26-13-7-12-20(26)21(19)24(22)15-18-10-5-2-6-11-18/h1-6,8-11,19-21H,7,12-16H2/q+1
IUPAC Name
3,5-dibenzyl-4-oxo-8λ⁴-thia-3,5-diazatricyclo[6.3.0.0²,⁶]undecan-8-ylium
SMILES
O=C1N(CC2=CC=CC=C2)C2C[S+]3CCCC3C2N1CC1=CC=CC=C1
Pharmacology
IndicationFor the controlled reduction of blood pressure during surgery and in the treatment of hypertensive emergencies.
Structured Indications Not Available
PharmacodynamicsTrimethaphan is indicated for production of controlled hypotension during surgery to reduce bleeding into the surgical field and also for rapid reduction of blood pressure in the treatment of hypertensive emergencies, especially in patients with acute dissecting aneurysm, and in the emergency treatment of pulmonary edema in patients with pulmonary hypertension associated with systemic hypertension.
Mechanism of actionTrimethaphan is a ganglionic blocking agent prevents stimulation of postsynaptic receptors by competing with acetylcholine for these receptor sites. Additional effects may include direct peripheral vasodilation and release of histamine. Trimethaphan's hypotensive effect is due to reduction in sympathetic tone and vasodilation, and is primarily postural.
TargetKindPharmacological actionActionsOrganismUniProt ID
Neuronal acetylcholine receptor subunit alpha-10Proteinyes
antagonist
HumanQ9GZZ6 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with 1,10-Phenanthroline.Experimental
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Trimethaphan.Experimental
AcebutololTrimethaphan may increase the hypotensive activities of Acebutolol.Approved
AclidiniumAclidinium may increase the anticholinergic activities of Trimethaphan.Approved
AlfentanilThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Alfentanil.Approved, Illicit
AlfuzosinAlfuzosin may increase the hypotensive activities of Trimethaphan.Approved, Investigational
AliskirenTrimethaphan may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Alphacetylmethadol.Experimental, Illicit
AlprenololAlprenolol may increase the hypotensive activities of Trimethaphan.Approved, Withdrawn
AmbenoniumThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Ambenonium.Approved
AmbrisentanTrimethaphan may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostineTrimethaphan may increase the hypotensive activities of Amifostine.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Trimethaphan.Approved
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Trimethaphan.Approved
AtenololAtenolol may increase the hypotensive activities of Trimethaphan.Approved
Atracurium besylateThe risk or severity of adverse effects can be increased when Atracurium besylate is combined with Trimethaphan.Approved
AtropineThe risk or severity of adverse effects can be increased when Atropine is combined with Trimethaphan.Approved, Vet Approved
BenactyzineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Benactyzine.Withdrawn
BenazeprilBenazepril may increase the hypotensive activities of Trimethaphan.Approved, Investigational
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Trimethaphan.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Trimethaphan.Withdrawn
BenzatropineThe risk or severity of adverse effects can be increased when Benzatropine is combined with Trimethaphan.Approved
BepridilTrimethaphan may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Trimethaphan.Approved
BethanidineBethanidine may increase the hypotensive activities of Trimethaphan.Approved
BezitramideThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Bezitramide.Experimental, Illicit, Withdrawn
BimatoprostBimatoprost may increase the hypotensive activities of Trimethaphan.Approved, Investigational
BiperidenThe risk or severity of adverse effects can be increased when Biperiden is combined with Trimethaphan.Approved
BisoprololBisoprolol may increase the hypotensive activities of Trimethaphan.Approved
BosentanBosentan may increase the hypotensive activities of Trimethaphan.Approved, Investigational
Botulinum Toxin Type ATrimethaphan may increase the anticholinergic activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BTrimethaphan may increase the anticholinergic activities of Botulinum Toxin Type B.Approved
BretyliumTrimethaphan may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the hypotensive activities of Trimethaphan.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Trimethaphan.Approved
BupranololTrimethaphan may increase the hypotensive activities of Bupranolol.Approved
BuprenorphineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Butorphanol.Approved, Illicit, Vet Approved
CandesartanCandesartan may increase the hypotensive activities of Trimethaphan.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Trimethaphan.Experimental
CaptoprilTrimethaphan may increase the hypotensive activities of Captopril.Approved
CarfentanilThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Carfentanil.Illicit, Vet Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Trimethaphan.Withdrawn
CarteololCarteolol may increase the hypotensive activities of Trimethaphan.Approved
CarvedilolTrimethaphan may increase the hypotensive activities of Carvedilol.Approved, Investigational
CeliprololTrimethaphan may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Trimethaphan.Approved, Vet Approved
ChlorphenoxamineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Chlorphenoxamine.Withdrawn
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Trimethaphan.Approved
CilazaprilTrimethaphan may increase the hypotensive activities of Cilazapril.Approved
CimetropiumTrimethaphan may increase the anticholinergic activities of Cimetropium.Experimental
ClonidineClonidine may increase the hypotensive activities of Trimethaphan.Approved
CodeineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Codeine.Approved, Illicit
CoumaphosThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Coumaphos.Vet Approved
CryptenamineCryptenamine may increase the hypotensive activities of Trimethaphan.Approved
CyclopentolateThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Trimethaphan.Approved
CyclothiazideCyclothiazide may increase the hypotensive activities of Trimethaphan.Approved
DarifenacinThe risk or severity of adverse effects can be increased when Darifenacin is combined with Trimethaphan.Approved, Investigational
DebrisoquinTrimethaphan may increase the hypotensive activities of Debrisoquin.Approved
DecamethoniumThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Decamethonium.Approved
DemecariumThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Demecarium.Approved
DeserpidineTrimethaphan may increase the hypotensive activities of Deserpidine.Approved
DesloratadineThe risk or severity of adverse effects can be increased when Desloratadine is combined with Trimethaphan.Approved, Investigational
DexetimideThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Dexetimide.Withdrawn
DextromoramideThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Dextromoramide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Dextropropoxyphene.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Dezocine.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Trimethaphan.Approved
DichlorvosThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Dichlorvos.Vet Approved
DicyclomineThe risk or severity of adverse effects can be increased when Dicyclomine is combined with Trimethaphan.Approved
DihydralazineTrimethaphan may increase the hypotensive activities of Dihydralazine.Investigational
DihydrocodeineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Dihydrocodeine.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Dihydroetorphine.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Dihydromorphine.Experimental, Illicit
DiltiazemDiltiazem may increase the hypotensive activities of Trimethaphan.Approved
DiphenoxylateThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Diphenoxylate.Approved, Illicit
DonepezilThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Donepezil.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Trimethaphan.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Trimethaphan.Approved
DPDPEThe risk or severity of adverse effects can be increased when Trimethaphan is combined with DPDPE.Investigational
DronabinolTrimethaphan may increase the tachycardic activities of Dronabinol.Approved, Illicit
EchothiophateThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Echothiophate.Approved
EdrophoniumThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Edrophonium.Approved
EfonidipineTrimethaphan may increase the hypotensive activities of Efonidipine.Approved
EluxadolineTrimethaphan may increase the constipating activities of Eluxadoline.Approved
EnalaprilEnalapril may increase the hypotensive activities of Trimethaphan.Approved, Vet Approved
EnalaprilatTrimethaphan may increase the hypotensive activities of Enalaprilat.Approved
EpoprostenolTrimethaphan may increase the hypotensive activities of Epoprostenol.Approved
EprosartanEprosartan may increase the hypotensive activities of Trimethaphan.Approved
EthopropazineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Trimethaphan.Approved
EthylmorphineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Ethylmorphine.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Etorphine.Illicit, Vet Approved
FelodipineFelodipine may increase the hypotensive activities of Trimethaphan.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Trimethaphan.Approved
FentanylThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FenthionThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Fenthion.Vet Approved
FesoterodineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Fesoterodine.Approved
FosinoprilFosinopril may increase the hypotensive activities of Trimethaphan.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Trimethaphan.Approved, Vet Approved
GalantamineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Galantamine.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Trimethaphan.Approved
Ginkgo bilobaThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Ginkgo biloba.Approved, Nutraceutical
Glucagon recombinantThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Glucagon recombinant.Approved
GlycopyrroniumTrimethaphan may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Trimethaphan.Approved
GuanadrelGuanadrel may increase the hypotensive activities of Trimethaphan.Approved
GuanethidineTrimethaphan may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Trimethaphan.Approved, Investigational
HeroinThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Heroin.Approved, Illicit
HexamethoniumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Hexamethonium.Experimental
HomatropineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Homatropine.Approved
Huperzine AThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Huperzine A.Investigational
HydracarbazineHydracarbazine may increase the hypotensive activities of Trimethaphan.Approved
HydralazineTrimethaphan may increase the hypotensive activities of Hydralazine.Approved
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Trimethaphan.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Hydrocodone.Approved, Illicit
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Trimethaphan.Approved
HydromorphoneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Hydromorphone.Approved, Illicit
HyoscyamineThe risk or severity of adverse effects can be increased when Hyoscyamine is combined with Trimethaphan.Approved
IloprostIloprost may increase the hypotensive activities of Trimethaphan.Approved, Investigational
ImidaprilTrimethaphan may increase the hypotensive activities of Imidapril.Investigational
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Trimethaphan.Approved
IndenololTrimethaphan may increase the hypotensive activities of Indenolol.Withdrawn
IndoraminTrimethaphan may increase the hypotensive activities of Indoramin.Withdrawn
Ipratropium bromideThe risk or severity of adverse effects can be increased when Ipratropium bromide is combined with Trimethaphan.Approved
IproclozideIproclozide may increase the hypotensive activities of Trimethaphan.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Trimethaphan.Withdrawn
IrbesartanIrbesartan may increase the hypotensive activities of Trimethaphan.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Trimethaphan.Approved
IsoflurophateThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Isoflurophate.Approved, Withdrawn
IsradipineIsradipine may increase the hypotensive activities of Trimethaphan.Approved
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Trimethaphan.Investigational
KetanserinTrimethaphan may increase the hypotensive activities of Ketanserin.Investigational
KetobemidoneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Ketobemidone.Approved
LabetalolLabetalol may increase the hypotensive activities of Trimethaphan.Approved
LacidipineTrimethaphan may increase the hypotensive activities of Lacidipine.Approved
LatanoprostLatanoprost may increase the hypotensive activities of Trimethaphan.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Trimethaphan.Approved, Investigational
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Levomethadyl Acetate.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Levorphanol.Approved
LisinoprilLisinopril may increase the hypotensive activities of Trimethaphan.Approved, Investigational
LofentanilThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Lofentanil.Illicit
LofexidineTrimethaphan may increase the hypotensive activities of Lofexidine.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Trimethaphan.Approved
MacitentanTrimethaphan may increase the hypotensive activities of Macitentan.Approved
MalathionThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Malathion.Approved, Investigational
ManidipineTrimethaphan may increase the hypotensive activities of Manidipine.Approved
MebanazineMebanazine may increase the hypotensive activities of Trimethaphan.Withdrawn
MecamylamineThe risk or severity of adverse effects can be increased when Mecamylamine is combined with Trimethaphan.Approved
MefloquineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Mefloquine.Approved
MemantineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Memantine.Approved, Investigational
MethadoneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Methadone.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Methadyl Acetate.Approved, Illicit
Methanesulfonyl FluorideThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Methanesulfonyl Fluoride.Investigational
MethanthelineThe risk or severity of adverse effects can be increased when Methantheline is combined with Trimethaphan.Approved
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Trimethaphan.Approved
MethyldopaMethyldopa may increase the hypotensive activities of Trimethaphan.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Trimethaphan.Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Trimethaphan.Approved, Investigational
MetipranololTrimethaphan may increase the hypotensive activities of Metipranolol.Approved
MetixeneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Metixene.Approved
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Trimethaphan.Approved
MetoprololMetoprolol may increase the hypotensive activities of Trimethaphan.Approved, Investigational
MetyrosineTrimethaphan may increase the hypotensive activities of Metyrosine.Approved
MianserinMianserin may increase the anticholinergic activities of Trimethaphan.Approved
MibefradilTrimethaphan may increase the hypotensive activities of Mibefradil.Withdrawn
MinaprineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Minaprine.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Trimethaphan.Approved
MirabegronThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Mirabegron.Approved
MoclobemideMoclobemide may increase the hypotensive activities of Trimethaphan.Approved
MoexiprilMoexipril may increase the hypotensive activities of Trimethaphan.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Trimethaphan.Approved
MorphineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Morphine.Approved, Investigational
MoxonidineTrimethaphan may increase the hypotensive activities of Moxonidine.Approved
N-butylscopolammonium bromideThe risk or severity of adverse effects can be increased when Trimethaphan is combined with N-butylscopolammonium bromide.Vet Approved
NabiloneTrimethaphan may increase the tachycardic activities of Nabilone.Approved, Investigational
NadololTrimethaphan may increase the hypotensive activities of Nadolol.Approved
NaftopidilTrimethaphan may increase the hypotensive activities of Naftopidil.Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Nalbuphine.Approved
NebivololTrimethaphan may increase the hypotensive activities of Nebivolol.Approved, Investigational
NeostigmineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Neostigmine.Approved, Vet Approved
NialamideNialamide may increase the hypotensive activities of Trimethaphan.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Trimethaphan.Approved
NicorandilTrimethaphan may increase the hypotensive activities of Nicorandil.Approved
NiguldipineTrimethaphan may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineTrimethaphan may increase the hypotensive activities of Nilvadipine.Approved
NimodipineNimodipine may increase the hypotensive activities of Trimethaphan.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Trimethaphan.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Trimethaphan.Approved
NitroprussideNitroprusside may increase the hypotensive activities of Trimethaphan.Approved
NormethadoneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Normethadone.Approved, Illicit
NVA237The risk or severity of adverse effects can be increased when Trimethaphan is combined with NVA237.Investigational
ObinutuzumabTrimethaphan may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Trimethaphan.Withdrawn
OlmesartanOlmesartan may increase the hypotensive activities of Trimethaphan.Approved, Investigational
OmapatrilatOmapatrilat may increase the hypotensive activities of Trimethaphan.Investigational
OpiumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Opium.Approved, Illicit
OrphenadrineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Orphenadrine.Approved
OxprenololTrimethaphan may increase the hypotensive activities of Oxprenolol.Approved
OxybutyninThe risk or severity of adverse effects can be increased when Oxybutynin is combined with Trimethaphan.Approved, Investigational
OxycodoneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Oxycodone.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Oxymorphone.Approved, Investigational, Vet Approved
OxyphenoniumThe risk or severity of adverse effects can be increased when Oxyphenonium is combined with Trimethaphan.Approved
PancuroniumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Pancuronium.Approved
PargylinePargyline may increase the hypotensive activities of Trimethaphan.Approved
PenbutololTrimethaphan may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentazocineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Pentazocine.Approved, Vet Approved
PentoliniumThe risk or severity of adverse effects can be increased when Pentolinium is combined with Trimethaphan.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Trimethaphan.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Trimethaphan.Approved
PethidineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Pethidine.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Trimethaphan.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Trimethaphan.Withdrawn
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Trimethaphan.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Trimethaphan.Withdrawn
PhentolaminePhentolamine may increase the hypotensive activities of Trimethaphan.Approved
PhysostigmineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Physostigmine.Approved
PinacidilTrimethaphan may increase the hypotensive activities of Pinacidil.Withdrawn
PindololPindolol may increase the hypotensive activities of Trimethaphan.Approved
PipecuroniumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Pipecuronium.Approved
PirenzepineThe risk or severity of adverse effects can be increased when Pirenzepine is combined with Trimethaphan.Approved
PiritramideThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Piritramide.Investigational
PirlindolePirlindole may increase the hypotensive activities of Trimethaphan.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Trimethaphan.Withdrawn
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with Trimethaphan.Approved
Potassium ChlorideTrimethaphan may increase the ulcerogenic activities of Potassium Chloride.Approved, Withdrawn
PramlintidePramlintide may increase the anticholinergic activities of Trimethaphan.Approved, Investigational
PrazosinPrazosin may increase the hypotensive activities of Trimethaphan.Approved
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Trimethaphan.Approved
PropanthelineThe risk or severity of adverse effects can be increased when Propantheline is combined with Trimethaphan.Approved
PropiverineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Propiverine.Investigational
PropranololPropranolol may increase the hypotensive activities of Trimethaphan.Approved, Investigational
PyridostigmineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Pyridostigmine.Approved
QuinaprilQuinapril may increase the hypotensive activities of Trimethaphan.Approved, Investigational
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Trimethaphan.Approved
QuinidineThe risk or severity of adverse effects can be increased when Quinidine is combined with Trimethaphan.Approved
QuinineQuinine may increase the hypotensive activities of Trimethaphan.Approved
RamiprilRamipril may increase the hypotensive activities of Trimethaphan.Approved
RamosetronTrimethaphan may increase the constipating activities of Ramosetron.Approved
RasagilineRasagiline may increase the hypotensive activities of Trimethaphan.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Remifentanil.Approved
RemikirenRemikiren may increase the hypotensive activities of Trimethaphan.Approved
RescinnamineTrimethaphan may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Trimethaphan.Approved
RilmenidineTrimethaphan may increase the hypotensive activities of Rilmenidine.Investigational
RiociguatTrimethaphan may increase the hypotensive activities of Riociguat.Approved
RituximabTrimethaphan may increase the hypotensive activities of Rituximab.Approved
RivastigmineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Rivastigmine.Approved, Investigational
SafrazineSafrazine may increase the hypotensive activities of Trimethaphan.Withdrawn
SaprisartanTrimethaphan may increase the hypotensive activities of Saprisartan.Experimental
ScopolamineThe risk or severity of adverse effects can be increased when Scopolamine is combined with Trimethaphan.Approved
Scopolamine butylbromideThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Scopolamine butylbromide.Approved
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Trimethaphan.Approved, Investigational
SelegilineSelegiline may increase the hypotensive activities of Trimethaphan.Approved, Investigational, Vet Approved
SelexipagTrimethaphan may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Trimethaphan.Approved, Investigational
SitaxentanTrimethaphan may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SolifenacinThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Solifenacin.Approved
SpiraprilTrimethaphan may increase the hypotensive activities of Spirapril.Approved
SufentanilThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Sufentanil.Approved, Investigational
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Trimethaphan.Approved
TacrineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Tacrine.Withdrawn
TadalafilTadalafil may increase the antihypertensive activities of Trimethaphan.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Tapentadol.Approved
TelmisartanTelmisartan may increase the hypotensive activities of Trimethaphan.Approved, Investigational
TemocaprilTrimethaphan may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerlipressinTrimethaphan may increase the hypotensive activities of Terlipressin.Approved, Investigational
TiboloneTrimethaphan may increase the hypotensive activities of Tibolone.Approved
TicrynafenTrimethaphan may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Trimethaphan.Approved
TiotropiumTrimethaphan may increase the anticholinergic activities of Tiotropium.Approved
TolazolineTolazoline may increase the hypotensive activities of Trimethaphan.Approved, Vet Approved
ToloxatoneToloxatone may increase the hypotensive activities of Trimethaphan.Approved
TolterodineThe risk or severity of adverse effects can be increased when Tolterodine is combined with Trimethaphan.Approved, Investigational
TopiramateThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Topiramate.Approved
TorasemideTorasemide may increase the hypotensive activities of Trimethaphan.Approved
TramadolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Tramadol.Approved, Investigational
TrandolaprilTrandolapril may increase the hypotensive activities of Trimethaphan.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Trimethaphan.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Trimethaphan.Approved
TravoprostTravoprost may increase the hypotensive activities of Trimethaphan.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Trimethaphan.Approved, Investigational
TrichlorfonThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Trichlorfon.Vet Approved
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Trimethaphan.Approved, Vet Approved
TrihexyphenidylThe risk or severity of adverse effects can be increased when Trihexyphenidyl is combined with Trimethaphan.Approved
TrimazosinTrimethaphan may increase the hypotensive activities of Trimazosin.Experimental
TropicamideThe risk or severity of adverse effects can be increased when Tropicamide is combined with Trimethaphan.Approved
TrospiumThe risk or severity of adverse effects can be increased when Trospium is combined with Trimethaphan.Approved
TubocurarineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Tubocurarine.Approved
UdenafilUdenafil may increase the antihypertensive activities of Trimethaphan.Approved, Investigational
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Trimethaphan.Approved
UnoprostoneTrimethaphan may increase the hypotensive activities of Unoprostone.Approved
ValsartanValsartan may increase the hypotensive activities of Trimethaphan.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Trimethaphan.Approved
VecuroniumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Vecuronium.Approved
VinpocetineTrimethaphan may increase the hypotensive activities of Vinpocetine.Investigational
XylometazolineTrimethaphan may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Trimethaphan.Approved, Vet Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC02BA01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9641
Blood Brain Barrier+0.9897
Caco-2 permeable-0.5053
P-glycoprotein substrateSubstrate0.6942
P-glycoprotein inhibitor IInhibitor0.6012
P-glycoprotein inhibitor IINon-inhibitor0.6356
Renal organic cation transporterInhibitor0.6812
CYP450 2C9 substrateNon-substrate0.7161
CYP450 2D6 substrateNon-substrate0.6162
CYP450 3A4 substrateNon-substrate0.5152
CYP450 1A2 substrateNon-inhibitor0.5223
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorInhibitor0.5134
CYP450 2C19 inhibitorInhibitor0.7361
CYP450 3A4 inhibitorNon-inhibitor0.8947
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.847
Ames testNon AMES toxic0.6511
CarcinogenicityNon-carcinogens0.9545
BiodegradationNot ready biodegradable0.9606
Rat acute toxicity2.3658 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.597
hERG inhibition (predictor II)Inhibitor0.7575
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP3.473Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00665 mg/mLALOGPS
logP4.4ALOGPS
logP2.32ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.43 m3·mol-1ChemAxon
Polarizability40.13 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thienoimidazolidines. These are heterocyclic compounds containing a thiophene ring fused to an imidazolidine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Imidazolidine is 5-membered saturated ring of three carbon atoms, and two nitrogen centers at the 1- and 3-positions.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThienoimidazolidines
Sub ClassNot Available
Direct ParentThienoimidazolidines
Alternative Parents
Substituents
  • Thienoimidazolidine
  • Phenylmethylamine
  • Benzylamine
  • Benzenoid
  • Imidazolidinone
  • Monocyclic benzene moiety
  • Thiophene
  • Imidazolidine
  • Urea
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Receptor binding
Specific Function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes t...
Gene Name:
CHRNA10
Uniprot ID:
Q9GZZ6
Molecular Weight:
49704.295 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Kurenny DE, Selyanko AA, Derkach VA, Gmiro VE, Skok VI: Mechanism of long-lasting block of ganglion nicotinic receptors by mono-ammonium compounds with long aliphatic chain. J Auton Nerv Syst. 1994 Aug;48(3):231-40. [PubMed:7963258 ]
  4. Loiacono R, Stephenson J, Stevenson J, Mitchelson F: Multiple binding sites for nicotine receptor antagonists in inhibiting [3H](-)-nicotine binding in rat cortex. Neuropharmacology. 1993 Sep;32(9):847-53. [PubMed:8232788 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Identical protein binding
Specific Function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular Weight:
68417.575 Da
References
  1. Nakamura K, Koide M, Imanaga T, Ogasawara H, Takahashi M, Yoshikawa M: Prolonged neuromuscular blockade following trimetaphan infusion. A case report and in vitro study of cholinesterase inhibition. Anaesthesia. 1980 Dec;35(12):1202-7. [PubMed:7457791 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23