Identification

Name
Trimethaphan
Accession Number
DB01116  (APRD00044)
Type
Small Molecule
Groups
Approved
Description

A 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
Product Ingredients
IngredientUNIICASInChI Key
Trimethaphan camsylate8W556014K968-91-7HALWUDBBYKMYPW-STOWLHSFSA-M
International/Other Brands
Arfonad
Categories
UNII
6G8X656T45
CAS number
7187-66-8
Weight
Average: 365.512
Monoisotopic: 365.168759122
Chemical Formula
C22H25N2OS
InChI Key
CHQOEHPMXSHGCL-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

Indication

For the controlled reduction of blood pressure during surgery and in the treatment of hypertensive emergencies.

Structured Indications
Not Available
Pharmacodynamics

Trimethaphan 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 action

Trimethaphan 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.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-10
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not 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
AlcuroniumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Alcuronium.Experimental
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
AlphaprodineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Alphaprodine.Illicit
AlprenololTrimethaphan may increase the hypotensive activities of Alprenolol.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
AmlodipineTrimethaphan may increase the hypotensive activities of Amlodipine.Approved
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Trimethaphan.Approved
AtenololTrimethaphan may increase the hypotensive activities of Atenolol.Approved
AtracuriumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Atracurium.Experimental
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
BenazeprilTrimethaphan may increase the hypotensive activities of Benazepril.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
BetaxololTrimethaphan may increase the hypotensive activities of Betaxolol.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
BietaserpineTrimethaphan may increase the hypotensive activities of Bietaserpine.Experimental
BimatoprostTrimethaphan may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BiperidenThe risk or severity of adverse effects can be increased when Biperiden is combined with Trimethaphan.Approved
BisoprololTrimethaphan may increase the hypotensive activities of Bisoprolol.Approved
BornaprineThe risk or severity of adverse effects can be increased when Bornaprine is combined with Trimethaphan.Experimental
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
BQ-123Trimethaphan may increase the hypotensive activities of BQ-123.Investigational
BretyliumTrimethaphan may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Trimethaphan.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Trimethaphan.Experimental
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
CadralazineTrimethaphan may increase the hypotensive activities of Cadralazine.Experimental
CafedrineTrimethaphan may increase the hypotensive activities of Cafedrine.Investigational
CandesartanTrimethaphan may increase the hypotensive activities of Candesartan.Approved
CandoxatrilTrimethaphan may increase the hypotensive activities of Candoxatril.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
CarteololTrimethaphan may increase the hypotensive activities of Carteolol.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
CicletanineTrimethaphan may increase the hypotensive activities of Cicletanine.Investigational
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
CloranololTrimethaphan may increase the hypotensive activities of Cloranolol.Experimental
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
CryptenamineTrimethaphan may increase the hypotensive activities of Cryptenamine.Approved
CyclopenthiazideThe serum concentration of Cyclopenthiazide can be increased when it is combined with Trimethaphan.Experimental
CyclopentolateThe risk or severity of adverse effects can be increased when Cyclopentolate is combined with Trimethaphan.Approved
CyclothiazideTrimethaphan may increase the hypotensive activities of Cyclothiazide.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
DelaprilTrimethaphan may increase the hypotensive activities of Delapril.Experimental
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 Dexetimide is combined with Trimethaphan.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
diethylnorspermineTrimethaphan may increase the hypotensive activities of diethylnorspermine.Investigational
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
DiltiazemTrimethaphan may increase the hypotensive activities of Diltiazem.Approved
DiphenoxylateThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Diphenoxylate.Approved, Illicit
DistigmineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Distigmine.Experimental
DonepezilThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Donepezil.Approved
DorzolamideTrimethaphan may increase the hypotensive activities of Dorzolamide.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
EmeproniumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Emepronium.Experimental
EnalaprilTrimethaphan may increase the hypotensive activities of Enalapril.Approved, Vet Approved
EnalaprilatTrimethaphan may increase the hypotensive activities of Enalaprilat.Approved
EndralazineTrimethaphan may increase the hypotensive activities of Endralazine.Experimental
EpanololTrimethaphan may increase the hypotensive activities of Epanolol.Experimental
EpoprostenolTrimethaphan may increase the hypotensive activities of Epoprostenol.Approved
EprosartanTrimethaphan may increase the hypotensive activities of Eprosartan.Approved
EtanautineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Etanautine.Experimental
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
EtybenzatropineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Etybenzatropine.Experimental
FelodipineTrimethaphan may increase the hypotensive activities of Felodipine.Approved, Investigational
FenoldopamTrimethaphan may increase the hypotensive activities of Fenoldopam.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
Ferulic acidTrimethaphan may increase the hypotensive activities of Ferulic acid.Experimental
FesoterodineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Fesoterodine.Approved
FosinoprilTrimethaphan may increase the hypotensive activities of Fosinopril.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
GallamineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Gallamine.Experimental
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
GuanabenzTrimethaphan may increase the hypotensive activities of Guanabenz.Approved
GuanadrelTrimethaphan may increase the hypotensive activities of Guanadrel.Approved
GuanazodineTrimethaphan may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineTrimethaphan may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Trimethaphan.Approved, Investigational
GuanoclorTrimethaphan may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzTrimethaphan may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanTrimethaphan may increase the hypotensive activities of Guanoxan.Experimental
HarmalineHarmaline may increase the hypotensive activities of Trimethaphan.Experimental
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.Experimental
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
IpidacrineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Ipidacrine.Experimental
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
IrbesartanTrimethaphan may increase the hypotensive activities of Irbesartan.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
IsradipineTrimethaphan may increase the hypotensive activities of Isradipine.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
LabetalolTrimethaphan may increase the hypotensive activities of Labetalol.Approved
LacidipineTrimethaphan may increase the hypotensive activities of Lacidipine.Approved
LatanoprostTrimethaphan may increase the hypotensive activities of Latanoprost.Approved, Investigational
LercanidipineTrimethaphan may increase the hypotensive activities of Lercanidipine.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
LinsidomineTrimethaphan may increase the hypotensive activities of Linsidomine.Experimental
LisinoprilTrimethaphan may increase the hypotensive activities of Lisinopril.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
LosartanTrimethaphan may increase the hypotensive activities of Losartan.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
MazaticolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Mazaticol.Experimental
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
MeptazinolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Meptazinol.Experimental
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
MethoserpidineTrimethaphan may increase the hypotensive activities of Methoserpidine.Experimental
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Trimethaphan.Approved
Methyl salicylateThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Methyl salicylate.Approved, Vet Approved
MethyldopaTrimethaphan may increase the hypotensive activities of Methyldopa.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
MetoclopramideThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Metoclopramide.Approved, Investigational
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Trimethaphan.Approved
MetoprololTrimethaphan may increase the hypotensive activities of Metoprolol.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
MirodenafilMirodenafil may increase the antihypertensive activities of Trimethaphan.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Trimethaphan.Approved
MoexiprilTrimethaphan may increase the hypotensive activities of Moexipril.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
MuzolimineTrimethaphan may increase the hypotensive activities of Muzolimine.Experimental
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
NicardipineTrimethaphan may increase the hypotensive activities of Nicardipine.Approved
NicomorphineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Nicomorphine.Experimental
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
NimodipineTrimethaphan may increase the hypotensive activities of Nimodipine.Approved
NisoldipineTrimethaphan may increase the hypotensive activities of Nisoldipine.Approved
NitrendipineTrimethaphan may increase the hypotensive activities of Nitrendipine.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
ObinutuzumabTrimethaphan may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Trimethaphan.Withdrawn
OlmesartanTrimethaphan may increase the hypotensive activities of Olmesartan.Approved, Investigational
OmapatrilatTrimethaphan may increase the hypotensive activities of Omapatrilat.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 Orphenadrine is combined with Trimethaphan.Approved
OtiloniumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Otilonium.Experimental
OxitropiumThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Oxitropium.Investigational
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
ParaoxonThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Paraoxon.Experimental
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
PerindoprilTrimethaphan may increase the hypotensive activities of Perindopril.Approved
PethidineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Pethidine.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Phenazocine.Experimental
PhenelzinePhenelzine may increase the hypotensive activities of Trimethaphan.Approved
PhenglutarimideThe risk or severity of adverse effects can be increased when Phenglutarimide is combined with Trimethaphan.Experimental
PheniprazinePheniprazine may increase the hypotensive activities of Trimethaphan.Withdrawn
PhenoperidineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Phenoperidine.Experimental
PhenoxybenzamineTrimethaphan may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Trimethaphan.Withdrawn
PhentolamineTrimethaphan may increase the hypotensive activities of Phentolamine.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
PindololTrimethaphan may increase the hypotensive activities of Pindolol.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
PropranololTrimethaphan may increase the hypotensive activities of Propranolol.Approved, Investigational
PyridostigmineThe therapeutic efficacy of Trimethaphan can be decreased when used in combination with Pyridostigmine.Approved
QuinaprilTrimethaphan may increase the hypotensive activities of Quinapril.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
RamiprilTrimethaphan may increase the hypotensive activities of Ramipril.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
RemikirenTrimethaphan may increase the hypotensive activities of Remikiren.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, Vet 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
TalinololTrimethaphan may increase the hypotensive activities of Talinolol.Investigational
TapentadolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Tapentadol.Approved
TelmisartanTrimethaphan may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilTrimethaphan may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerlipressinTrimethaphan may increase the hypotensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatineTrimethaphan may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TheodrenalineTrimethaphan may increase the hypotensive activities of Theodrenaline.Investigational
TiboloneTrimethaphan may increase the hypotensive activities of Tibolone.Approved
TicrynafenTrimethaphan may increase the hypotensive activities of Ticrynafen.Withdrawn
TilidineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Tilidine.Experimental
TimololTrimethaphan may increase the hypotensive activities of Timolol.Approved
TiotropiumTrimethaphan may increase the anticholinergic activities of Tiotropium.Approved
TolazolineTrimethaphan may increase the hypotensive activities of Tolazoline.Approved, Vet Approved
TolonidineTrimethaphan may increase the hypotensive activities of Tolonidine.Experimental
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
TorasemideTrimethaphan may increase the hypotensive activities of Torasemide.Approved
TramadolThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Tramadol.Approved, Investigational
TrandolaprilTrimethaphan may increase the hypotensive activities of Trandolapril.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Trimethaphan.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Trimethaphan.Approved
TravoprostTrimethaphan may increase the hypotensive activities of Travoprost.Approved
TreprostinilTrimethaphan may increase the hypotensive activities of Treprostinil.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
TropatepineThe risk or severity of adverse effects can be increased when Trimethaphan is combined with Tropatepine.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
UrapidilTrimethaphan may increase the hypotensive activities of Urapidil.Investigational
ValsartanTrimethaphan may increase the hypotensive activities of Valsartan.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
VincamineTrimethaphan may increase the hypotensive activities of Vincamine.Experimental
VinpocetineTrimethaphan may increase the hypotensive activities of Vinpocetine.Investigational
XipamideTrimethaphan may increase the hypotensive activities of Xipamide.Experimental
XylometazolineTrimethaphan may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Trimethaphan.Approved, Vet Approved
ZofenoprilTrimethaphan may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB15248
KEGG Compound
C07174
PubChem Compound
23576
PubChem Substance
46508994
ChemSpider
22044
BindingDB
82545
ChEBI
9728
ChEMBL
CHEMBL1201329
Therapeutic Targets Database
DAP001143
PharmGKB
PA451784
Wikipedia
Trimethaphan
ATC Codes
C02BA01 — Trimetaphan
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableBMI >30 kg/m2 / Hypertensive1
1CompletedNot AvailableEndothelial Dysfunction1
1CompletedDiagnosticBMI >30 kg/m2 / Hypertensive / Progressive autonomic failure / Shy-Drager Syndrome1
1RecruitingNot AvailableHypertensive1
1RecruitingBasic ScienceInsulin Resistance1
1RecruitingBasic ScienceIdiopathic orthostatic hypotension / Multiple System Atrophy (MSA) / Supine Hypertension1
1RecruitingOtherHypertension,Essential / Hypertensive1
Not AvailableCompletedNot AvailableBMI >30 kg/m21
Not AvailableCompletedNot AvailableHypertensive / Progressive autonomic failure1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Thienoimidazolidines
Sub Class
Not Available
Direct Parent
Thienoimidazolidines
Alternative Parents
Imidazolidinones / Benzene and substituted derivatives / Thiophenes / Thiolanes / Ureas / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
show 2 more
Substituents
Thienoimidazolidine / Monocyclic benzene moiety / Imidazolidinone / Benzenoid / Imidazolidine / Thiolane / Thiophene / Carbonic acid derivative / Urea / Azacycle
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfonium compound (CHEBI:9728)

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 i...
Gene Name
CHRNA10
Uniprot ID
Q9GZZ6
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-10
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
Uniprot Name
Cholinesterase
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]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:53