Trimethaphan - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)Enzymes (1)

Targets (1)Enzymes (1)Biointeractions (1)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Thimethaphan

Trimetaphan

Trimetaphanum

Trimethaphan

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Trimethaphan camsylate	8W556014K9	68-91-7	HALWUDBBYKMYPW-STOWLHSFSA-M	Details

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Arfonad	Not Available

Brand mixtures

Not Available

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Neuronal acetylcholine receptor subunit alpha-10	Protein	yes	antagonist	Human	Q9GZZ6	details

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

Drug	Interaction	Drug group
1,10-Phenanthroline	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with 1,10-Phenanthroline.	Experimental
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Trimethaphan.	Experimental
Acebutolol	Trimethaphan may increase the hypotensive activities of Acebutolol.	Approved
Aclidinium	Aclidinium may increase the anticholinergic activities of Trimethaphan.	Approved
Alfentanil	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Alfentanil.	Approved, Illicit
Alfuzosin	Alfuzosin may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Aliskiren	Trimethaphan may increase the hypotensive activities of Aliskiren.	Approved, Investigational
Alphacetylmethadol	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Alphacetylmethadol.	Experimental, Illicit
Alprenolol	Alprenolol may increase the hypotensive activities of Trimethaphan.	Approved, Withdrawn
Ambenonium	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Ambenonium.	Approved
Ambrisentan	Trimethaphan may increase the hypotensive activities of Ambrisentan.	Approved, Investigational
Amifostine	Trimethaphan may increase the hypotensive activities of Amifostine.	Approved, Investigational
Amlodipine	Amlodipine may increase the hypotensive activities of Trimethaphan.	Approved
Anisotropine Methylbromide	The risk or severity of adverse effects can be increased when Anisotropine Methylbromide is combined with Trimethaphan.	Approved
Atenolol	Atenolol may increase the hypotensive activities of Trimethaphan.	Approved
Atracurium besylate	The risk or severity of adverse effects can be increased when Atracurium besylate is combined with Trimethaphan.	Approved
Atropine	The risk or severity of adverse effects can be increased when Atropine is combined with Trimethaphan.	Approved, Vet Approved
Benactyzine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Benactyzine.	Withdrawn
Benazepril	Benazepril may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Bendroflumethiazide	The serum concentration of Bendroflumethiazide can be increased when it is combined with Trimethaphan.	Approved
Benmoxin	Benmoxin may increase the hypotensive activities of Trimethaphan.	Withdrawn
Benzatropine	The risk or severity of adverse effects can be increased when Benzatropine is combined with Trimethaphan.	Approved
Bepridil	Trimethaphan may increase the hypotensive activities of Bepridil.	Approved, Withdrawn
Betaxolol	Betaxolol may increase the hypotensive activities of Trimethaphan.	Approved
Bethanidine	Bethanidine may increase the hypotensive activities of Trimethaphan.	Approved
Bezitramide	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Bezitramide.	Experimental, Illicit, Withdrawn
Bimatoprost	Bimatoprost may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Biperiden	The risk or severity of adverse effects can be increased when Biperiden is combined with Trimethaphan.	Approved
Bisoprolol	Bisoprolol may increase the hypotensive activities of Trimethaphan.	Approved
Bosentan	Bosentan may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Botulinum Toxin Type A	Trimethaphan may increase the anticholinergic activities of Botulinum Toxin Type A.	Approved, Investigational
Botulinum Toxin Type B	Trimethaphan may increase the anticholinergic activities of Botulinum Toxin Type B.	Approved
Bretylium	Trimethaphan may increase the hypotensive activities of Bretylium.	Approved
Brimonidine	Brimonidine may increase the hypotensive activities of Trimethaphan.	Approved
Brimonidine	Brimonidine may increase the antihypertensive activities of Trimethaphan.	Approved
Bupranolol	Trimethaphan may increase the hypotensive activities of Bupranolol.	Approved
Buprenorphine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Buprenorphine.	Approved, Illicit, Investigational, Vet Approved
Butorphanol	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Butorphanol.	Approved, Illicit, Vet Approved
Candesartan	Candesartan may increase the hypotensive activities of Trimethaphan.	Approved
Candoxatril	Candoxatril may increase the hypotensive activities of Trimethaphan.	Experimental
Captopril	Trimethaphan may increase the hypotensive activities of Captopril.	Approved
Carfentanil	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Carfentanil.	Illicit, Vet Approved
Caroxazone	Caroxazone may increase the hypotensive activities of Trimethaphan.	Withdrawn
Carteolol	Carteolol may increase the hypotensive activities of Trimethaphan.	Approved
Carvedilol	Trimethaphan may increase the hypotensive activities of Carvedilol.	Approved, Investigational
Celiprolol	Trimethaphan may increase the hypotensive activities of Celiprolol.	Approved, Investigational
Chlorothiazide	The serum concentration of Chlorothiazide can be increased when it is combined with Trimethaphan.	Approved, Vet Approved
Chlorphenoxamine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Chlorphenoxamine.	Withdrawn
Chlorthalidone	The serum concentration of Chlorthalidone can be increased when it is combined with Trimethaphan.	Approved
Cilazapril	Trimethaphan may increase the hypotensive activities of Cilazapril.	Approved
Cimetropium	Trimethaphan may increase the anticholinergic activities of Cimetropium.	Experimental
Clonidine	Clonidine may increase the hypotensive activities of Trimethaphan.	Approved
Codeine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Codeine.	Approved, Illicit
Cryptenamine	Cryptenamine may increase the hypotensive activities of Trimethaphan.	Approved
Cyclopentolate	The risk or severity of adverse effects can be increased when Cyclopentolate is combined with Trimethaphan.	Approved
Cyclothiazide	Cyclothiazide may increase the hypotensive activities of Trimethaphan.	Approved
Darifenacin	The risk or severity of adverse effects can be increased when Darifenacin is combined with Trimethaphan.	Approved, Investigational
Debrisoquin	Trimethaphan may increase the hypotensive activities of Debrisoquin.	Approved
Decamethonium	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Decamethonium.	Approved
Demecarium	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Demecarium.	Approved
Deserpidine	Trimethaphan may increase the hypotensive activities of Deserpidine.	Approved
Desloratadine	The risk or severity of adverse effects can be increased when Desloratadine is combined with Trimethaphan.	Approved, Investigational
Dexetimide	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Dexetimide.	Withdrawn
Dextromoramide	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Dextromoramide.	Experimental, Illicit
Dextropropoxyphene	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Dextropropoxyphene.	Approved, Illicit, Withdrawn
Dezocine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Dezocine.	Approved
Diazoxide	Diazoxide may increase the hypotensive activities of Trimethaphan.	Approved
Dicyclomine	The risk or severity of adverse effects can be increased when Dicyclomine is combined with Trimethaphan.	Approved
Dihydralazine	Trimethaphan may increase the hypotensive activities of Dihydralazine.	Investigational
Dihydrocodeine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Dihydrocodeine.	Approved, Illicit
Dihydroetorphine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Dihydroetorphine.	Experimental, Illicit
Dihydromorphine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Dihydromorphine.	Experimental, Illicit
Diltiazem	Diltiazem may increase the hypotensive activities of Trimethaphan.	Approved
Diphenoxylate	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Diphenoxylate.	Approved, Illicit
Donepezil	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Donepezil.	Approved
Dorzolamide	Dorzolamide may increase the hypotensive activities of Trimethaphan.	Approved
Doxazosin	Doxazosin may increase the hypotensive activities of Trimethaphan.	Approved
Dronabinol	Trimethaphan may increase the tachycardic activities of Dronabinol.	Approved, Illicit
Echothiophate	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Echothiophate.	Approved
Edrophonium	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Edrophonium.	Approved
Efonidipine	Trimethaphan may increase the hypotensive activities of Efonidipine.	Approved
Eluxadoline	Trimethaphan may increase the constipating activities of Eluxadoline.	Approved
Enalapril	Enalapril may increase the hypotensive activities of Trimethaphan.	Approved, Vet Approved
Enalaprilat	Trimethaphan may increase the hypotensive activities of Enalaprilat.	Approved
Epoprostenol	Trimethaphan may increase the hypotensive activities of Epoprostenol.	Approved
Eprosartan	Eprosartan may increase the hypotensive activities of Trimethaphan.	Approved
Ethopropazine	The risk or severity of adverse effects can be increased when Ethopropazine is combined with Trimethaphan.	Approved
Ethylmorphine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Ethylmorphine.	Approved, Illicit
Etorphine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Etorphine.	Illicit, Vet Approved
Felodipine	Felodipine may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Fenoldopam	Fenoldopam may increase the hypotensive activities of Trimethaphan.	Approved
Fentanyl	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Fentanyl.	Approved, Illicit, Investigational, Vet Approved
Fesoterodine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Fesoterodine.	Approved
Fosinopril	Fosinopril may increase the hypotensive activities of Trimethaphan.	Approved
Furazolidone	Furazolidone may increase the hypotensive activities of Trimethaphan.	Approved, Vet Approved
Galantamine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Galantamine.	Approved
Gallamine Triethiodide	The risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Trimethaphan.	Approved
Ginkgo biloba	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Ginkgo biloba.	Approved, Nutraceutical
Glucagon recombinant	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Glucagon recombinant.	Approved
Glycopyrronium	Trimethaphan may increase the anticholinergic activities of Glycopyrronium.	Approved, Investigational, Vet Approved
Guanabenz	Guanabenz may increase the hypotensive activities of Trimethaphan.	Approved
Guanadrel	Guanadrel may increase the hypotensive activities of Trimethaphan.	Approved
Guanethidine	Trimethaphan may increase the hypotensive activities of Guanethidine.	Approved
Guanfacine	Guanfacine may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Heroin	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Heroin.	Approved, Illicit
Hexamethonium	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Hexamethonium.	Experimental
Huperzine A	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Huperzine A.	Investigational
Hydracarbazine	Hydracarbazine may increase the hypotensive activities of Trimethaphan.	Experimental
Hydralazine	Trimethaphan may increase the hypotensive activities of Hydralazine.	Approved
Hydrochlorothiazide	The serum concentration of Hydrochlorothiazide can be increased when it is combined with Trimethaphan.	Approved, Vet Approved
Hydrocodone	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Hydrocodone.	Approved, Illicit
Hydroflumethiazide	The serum concentration of Hydroflumethiazide can be increased when it is combined with Trimethaphan.	Approved
Hydromorphone	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Hydromorphone.	Approved, Illicit
Hyoscyamine	The risk or severity of adverse effects can be increased when Hyoscyamine is combined with Trimethaphan.	Approved
Iloprost	Iloprost may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Imidapril	Trimethaphan may increase the hypotensive activities of Imidapril.	Investigational
Indapamide	The serum concentration of Indapamide can be increased when it is combined with Trimethaphan.	Approved
Indenolol	Trimethaphan may increase the hypotensive activities of Indenolol.	Withdrawn
Indoramin	Trimethaphan may increase the hypotensive activities of Indoramin.	Withdrawn
Ipratropium bromide	The risk or severity of adverse effects can be increased when Ipratropium bromide is combined with Trimethaphan.	Approved
Iproclozide	Iproclozide may increase the hypotensive activities of Trimethaphan.	Withdrawn
Iproniazid	Iproniazid may increase the hypotensive activities of Trimethaphan.	Withdrawn
Irbesartan	Irbesartan may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Isocarboxazid	Isocarboxazid may increase the hypotensive activities of Trimethaphan.	Approved
Isoflurophate	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Isoflurophate.	Approved, Withdrawn
Isradipine	Isradipine may increase the hypotensive activities of Trimethaphan.	Approved
Itopride	The therapeutic efficacy of Itopride can be decreased when used in combination with Trimethaphan.	Investigational
Ketanserin	Trimethaphan may increase the hypotensive activities of Ketanserin.	Investigational
Ketobemidone	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Ketobemidone.	Approved
Labetalol	Labetalol may increase the hypotensive activities of Trimethaphan.	Approved
Lacidipine	Trimethaphan may increase the hypotensive activities of Lacidipine.	Approved
Latanoprost	Latanoprost may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Lercanidipine	Lercanidipine may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Levomethadyl Acetate	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Levomethadyl Acetate.	Approved
Levorphanol	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Levorphanol.	Approved
Lisinopril	Lisinopril may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Lofentanil	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Lofentanil.	Illicit
Lofexidine	Trimethaphan may increase the hypotensive activities of Lofexidine.	Approved, Investigational
Losartan	Losartan may increase the hypotensive activities of Trimethaphan.	Approved
Macitentan	Trimethaphan may increase the hypotensive activities of Macitentan.	Approved
Malathion	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Malathion.	Approved, Investigational
Manidipine	Trimethaphan may increase the hypotensive activities of Manidipine.	Approved
Mebanazine	Mebanazine may increase the hypotensive activities of Trimethaphan.	Withdrawn
Mecamylamine	The risk or severity of adverse effects can be increased when Mecamylamine is combined with Trimethaphan.	Approved
Mefloquine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Mefloquine.	Approved
Memantine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Memantine.	Approved, Investigational
Methadone	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Methadone.	Approved
Methadyl Acetate	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Methadyl Acetate.	Approved, Illicit
Methanesulfonyl Fluoride	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Methanesulfonyl Fluoride.	Investigational
Methantheline	The risk or severity of adverse effects can be increased when Methantheline is combined with Trimethaphan.	Approved
Methyclothiazide	The serum concentration of Methyclothiazide can be increased when it is combined with Trimethaphan.	Approved
Methyldopa	Methyldopa may increase the hypotensive activities of Trimethaphan.	Approved
Methylene blue	Methylene blue may increase the hypotensive activities of Trimethaphan.	Investigational
Methylphenidate	Methylphenidate may decrease the antihypertensive activities of Trimethaphan.	Approved, Investigational
Metipranolol	Trimethaphan may increase the hypotensive activities of Metipranolol.	Approved
Metixene	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Metixene.	Approved
Metolazone	The serum concentration of Metolazone can be increased when it is combined with Trimethaphan.	Approved
Metoprolol	Metoprolol may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Metyrosine	Trimethaphan may increase the hypotensive activities of Metyrosine.	Approved
Mianserin	Mianserin may increase the anticholinergic activities of Trimethaphan.	Approved
Mibefradil	Trimethaphan may increase the hypotensive activities of Mibefradil.	Withdrawn
Minaprine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Minaprine.	Approved
Minoxidil	Minoxidil may increase the hypotensive activities of Trimethaphan.	Approved
Mirabegron	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Mirabegron.	Approved
Moclobemide	Moclobemide may increase the hypotensive activities of Trimethaphan.	Approved
Moexipril	Moexipril may increase the hypotensive activities of Trimethaphan.	Approved
Molsidomine	Molsidomine may increase the hypotensive activities of Trimethaphan.	Approved
Morphine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Morphine.	Approved, Investigational
Moxonidine	Trimethaphan may increase the hypotensive activities of Moxonidine.	Approved
Nabilone	Trimethaphan may increase the tachycardic activities of Nabilone.	Approved, Investigational
Nadolol	Trimethaphan may increase the hypotensive activities of Nadolol.	Approved
Naftopidil	Trimethaphan may increase the hypotensive activities of Naftopidil.	Investigational
Nalbuphine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Nalbuphine.	Approved
Nebivolol	Trimethaphan may increase the hypotensive activities of Nebivolol.	Approved, Investigational
Neostigmine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Neostigmine.	Approved, Vet Approved
Nialamide	Nialamide may increase the hypotensive activities of Trimethaphan.	Withdrawn
Nicardipine	Nicardipine may increase the hypotensive activities of Trimethaphan.	Approved
Nicorandil	Trimethaphan may increase the hypotensive activities of Nicorandil.	Approved
Niguldipine	Trimethaphan may increase the hypotensive activities of Niguldipine.	Experimental
Nilvadipine	Trimethaphan may increase the hypotensive activities of Nilvadipine.	Approved
Nimodipine	Nimodipine may increase the hypotensive activities of Trimethaphan.	Approved
Nisoldipine	Nisoldipine may increase the hypotensive activities of Trimethaphan.	Approved
Nitrendipine	Nitrendipine may increase the hypotensive activities of Trimethaphan.	Approved
Nitroprusside	Nitroprusside may increase the hypotensive activities of Trimethaphan.	Approved
Normethadone	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Normethadone.	Approved, Illicit
Obinutuzumab	Trimethaphan may increase the hypotensive activities of Obinutuzumab.	Approved
Octamoxin	Octamoxin may increase the hypotensive activities of Trimethaphan.	Withdrawn
Olmesartan	Olmesartan may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Omapatrilat	Omapatrilat may increase the hypotensive activities of Trimethaphan.	Investigational
Opium	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Opium.	Approved, Illicit
Orphenadrine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Orphenadrine.	Approved
Oxprenolol	Trimethaphan may increase the hypotensive activities of Oxprenolol.	Approved
Oxybutynin	The risk or severity of adverse effects can be increased when Oxybutynin is combined with Trimethaphan.	Approved, Investigational
Oxycodone	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Oxycodone.	Approved, Illicit, Investigational
Oxymorphone	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Oxymorphone.	Approved, Investigational, Vet Approved
Oxyphenonium	The risk or severity of adverse effects can be increased when Oxyphenonium is combined with Trimethaphan.	Approved
Pancuronium	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Pancuronium.	Approved
Pargyline	Pargyline may increase the hypotensive activities of Trimethaphan.	Approved
Penbutolol	Trimethaphan may increase the hypotensive activities of Penbutolol.	Approved, Investigational
Pentazocine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Pentazocine.	Approved, Vet Approved
Pentolinium	The risk or severity of adverse effects can be increased when Pentolinium is combined with Trimethaphan.	Approved
Pentoxifylline	Pentoxifylline may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Perindopril	Perindopril may increase the hypotensive activities of Trimethaphan.	Approved
Pethidine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Pethidine.	Approved
Phenelzine	Phenelzine may increase the hypotensive activities of Trimethaphan.	Approved
Pheniprazine	Pheniprazine may increase the hypotensive activities of Trimethaphan.	Withdrawn
Phenoxybenzamine	Phenoxybenzamine may increase the hypotensive activities of Trimethaphan.	Approved
Phenoxypropazine	Phenoxypropazine may increase the hypotensive activities of Trimethaphan.	Withdrawn
Phentolamine	Phentolamine may increase the hypotensive activities of Trimethaphan.	Approved
Physostigmine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Physostigmine.	Approved
Pindolol	Pindolol may increase the hypotensive activities of Trimethaphan.	Approved
Pipecuronium	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Pipecuronium.	Approved
Pirenzepine	The risk or severity of adverse effects can be increased when Pirenzepine is combined with Trimethaphan.	Approved
Piritramide	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Piritramide.	Investigational
Pirlindole	Pirlindole may increase the hypotensive activities of Trimethaphan.	Approved
Pivhydrazine	Pivhydrazine may increase the hypotensive activities of Trimethaphan.	Withdrawn
Polythiazide	The serum concentration of Polythiazide can be increased when it is combined with Trimethaphan.	Approved
Potassium Chloride	Trimethaphan may increase the ulcerogenic activities of Potassium Chloride.	Approved, Withdrawn
Pramlintide	Pramlintide may increase the anticholinergic activities of Trimethaphan.	Approved, Investigational
Prazosin	Prazosin may increase the hypotensive activities of Trimethaphan.	Approved
Procyclidine	The risk or severity of adverse effects can be increased when Procyclidine is combined with Trimethaphan.	Approved
Propantheline	The risk or severity of adverse effects can be increased when Propantheline is combined with Trimethaphan.	Approved
Propiverine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Propiverine.	Investigational
Propranolol	Propranolol may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Pyridostigmine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Pyridostigmine.	Approved
Quinapril	Quinapril may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Quinethazone	The serum concentration of Quinethazone can be increased when it is combined with Trimethaphan.	Approved
Quinidine	The risk or severity of adverse effects can be increased when Quinidine is combined with Trimethaphan.	Approved
Quinine	Quinine may increase the hypotensive activities of Trimethaphan.	Approved
Ramipril	Ramipril may increase the hypotensive activities of Trimethaphan.	Approved
Ramosetron	Trimethaphan may increase the constipating activities of Ramosetron.	Approved
Rasagiline	Rasagiline may increase the hypotensive activities of Trimethaphan.	Approved
Remifentanil	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Remifentanil.	Approved
Remikiren	Remikiren may increase the hypotensive activities of Trimethaphan.	Approved
Rescinnamine	Trimethaphan may increase the hypotensive activities of Rescinnamine.	Approved
Reserpine	Reserpine may increase the hypotensive activities of Trimethaphan.	Approved
Rilmenidine	Trimethaphan may increase the hypotensive activities of Rilmenidine.	Investigational
Riociguat	Trimethaphan may increase the hypotensive activities of Riociguat.	Approved
Rituximab	Trimethaphan may increase the hypotensive activities of Rituximab.	Approved
Rivastigmine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Rivastigmine.	Approved, Investigational
Safrazine	Safrazine may increase the hypotensive activities of Trimethaphan.	Withdrawn
Saprisartan	Trimethaphan may increase the hypotensive activities of Saprisartan.	Experimental
Scopolamine	The risk or severity of adverse effects can be increased when Scopolamine is combined with Trimethaphan.	Approved
Scopolamine butylbromide	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Scopolamine butylbromide.	Approved, Vet Approved
Secretin	The therapeutic efficacy of Secretin can be decreased when used in combination with Trimethaphan.	Approved, Investigational
Selegiline	Selegiline may increase the hypotensive activities of Trimethaphan.	Approved, Investigational, Vet Approved
Selexipag	Trimethaphan may increase the hypotensive activities of Selexipag.	Approved
Sildenafil	Sildenafil may increase the antihypertensive activities of Trimethaphan.	Approved, Investigational
Sitaxentan	Trimethaphan may increase the hypotensive activities of Sitaxentan.	Approved, Investigational, Withdrawn
Solifenacin	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Solifenacin.	Approved
Spirapril	Trimethaphan may increase the hypotensive activities of Spirapril.	Approved
Sufentanil	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Sufentanil.	Approved, Investigational
Sulpiride	The therapeutic efficacy of Sulpiride can be decreased when used in combination with Trimethaphan.	Approved
Tacrine	The therapeutic efficacy of Trimethaphan can be decreased when used in combination with Tacrine.	Withdrawn
Tadalafil	Tadalafil may increase the antihypertensive activities of Trimethaphan.	Approved, Investigational
Tapentadol	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Tapentadol.	Approved
Telmisartan	Telmisartan may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Temocapril	Trimethaphan may increase the hypotensive activities of Temocapril.	Experimental, Investigational
Terlipressin	Trimethaphan may increase the hypotensive activities of Terlipressin.	Approved, Investigational
Tibolone	Trimethaphan may increase the hypotensive activities of Tibolone.	Approved
Ticrynafen	Trimethaphan may increase the hypotensive activities of Ticrynafen.	Withdrawn
Timolol	Timolol may increase the hypotensive activities of Trimethaphan.	Approved
Tiotropium	Trimethaphan may increase the anticholinergic activities of Tiotropium.	Approved
Tolazoline	Tolazoline may increase the hypotensive activities of Trimethaphan.	Approved, Vet Approved
Toloxatone	Toloxatone may increase the hypotensive activities of Trimethaphan.	Approved
Tolterodine	The risk or severity of adverse effects can be increased when Tolterodine is combined with Trimethaphan.	Approved, Investigational
Topiramate	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Topiramate.	Approved
Torasemide	Torasemide may increase the hypotensive activities of Trimethaphan.	Approved
Tramadol	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Tramadol.	Approved, Investigational
Trandolapril	Trandolapril may increase the hypotensive activities of Trimethaphan.	Approved
Trans-2-Phenylcyclopropylamine	Trans-2-Phenylcyclopropylamine may increase the hypotensive activities of Trimethaphan.	Experimental
Tranylcypromine	Tranylcypromine may increase the hypotensive activities of Trimethaphan.	Approved
Travoprost	Travoprost may increase the hypotensive activities of Trimethaphan.	Approved
Treprostinil	Treprostinil may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Trichlormethiazide	The serum concentration of Trichlormethiazide can be increased when it is combined with Trimethaphan.	Approved, Vet Approved
Trihexyphenidyl	The risk or severity of adverse effects can be increased when Trihexyphenidyl is combined with Trimethaphan.	Approved
Trimazosin	Trimethaphan may increase the hypotensive activities of Trimazosin.	Experimental
Tropicamide	The risk or severity of adverse effects can be increased when Tropicamide is combined with Trimethaphan.	Approved
Trospium	The risk or severity of adverse effects can be increased when Trospium is combined with Trimethaphan.	Approved
Tubocurarine	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Tubocurarine.	Approved
Udenafil	Udenafil may increase the antihypertensive activities of Trimethaphan.	Approved, Investigational
Umeclidinium	Umeclidinium may increase the anticholinergic activities of Trimethaphan.	Approved
Unoprostone	Trimethaphan may increase the hypotensive activities of Unoprostone.	Approved
Valsartan	Valsartan may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Vardenafil	Vardenafil may increase the antihypertensive activities of Trimethaphan.	Approved
Vecuronium	The risk or severity of adverse effects can be increased when Trimethaphan is combined with Vecuronium.	Approved
Vinpocetine	Trimethaphan may increase the hypotensive activities of Vinpocetine.	Investigational
Xylometazoline	Trimethaphan may increase the hypotensive activities of Xylometazoline.	Approved
Yohimbine	Yohimbine may decrease the antihypertensive activities of Trimethaphan.	Approved, Vet Approved

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	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

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	BMI >30 kg/m2 / Hypertensive	1
1	Completed	Not Available	Endothelial Dysfunction	1
1	Completed	Diagnostic	BMI >30 kg/m2 / Hypertensive / Progressive autonomic failure / Shy-Drager Syndrome	1
1	Recruiting	Not Available	Hypertension,Essential / Hypertensive	1
1	Recruiting	Not Available	Hypertensive	1
1	Recruiting	Basic Science	Insulin Resistance	1
1	Recruiting	Basic Science	Idiopathic orthostatic hypotension / Multiple System Atrophy (MSA) / Supine Hypertension	1
Not Available	Completed	Not Available	BMI >30 kg/m2	1
Not Available	Completed	Not Available	Hypertensive / Progressive autonomic failure	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
logP	3.473	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00665 mg/mL	ALOGPS
logP	4.4	ALOGPS
logP	2.32	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.43 m³·mol^-1	ChemAxon
Polarizability	40.13 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9641
Blood Brain Barrier	+	0.9897
Caco-2 permeable	-	0.5053
P-glycoprotein substrate	Substrate	0.6942
P-glycoprotein inhibitor I	Inhibitor	0.6012
P-glycoprotein inhibitor II	Non-inhibitor	0.6356
Renal organic cation transporter	Inhibitor	0.6812
CYP450 2C9 substrate	Non-substrate	0.7161
CYP450 2D6 substrate	Non-substrate	0.6162
CYP450 3A4 substrate	Non-substrate	0.5152
CYP450 1A2 substrate	Non-inhibitor	0.5223
CYP450 2C9 inhibitor	Inhibitor	0.5
CYP450 2D6 inhibitor	Inhibitor	0.5134
CYP450 2C19 inhibitor	Inhibitor	0.7361
CYP450 3A4 inhibitor	Non-inhibitor	0.8947
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.847
Ames test	Non AMES toxic	0.6511
Carcinogenicity	Non-carcinogens	0.9545
Biodegradation	Not ready biodegradable	0.9606
Rat acute toxicity	2.3658 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.597
hERG inhibition (predictor II)	Inhibitor	0.7575

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities 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

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Thienoimidazolidines

Direct Parent

Thienoimidazolidines

Alternative Parents

Imidazolidinones / Benzene and substituted derivatives / Thiophenes / Thiolanes / Ureas / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives

Substituents

Thienoimidazolidine / Monocyclic benzene moiety / Imidazolidinone / Benzenoid / Imidazolidine / Thiolane / Thiophene / Urea / Azacycle / Carbonyl group

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonium compound (CHEBI:9728 )

Targets

Details

1. Neuronal acetylcholine receptor subunit alpha-10

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

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 ]
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 ]
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 ]
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

Details

1. Cholinesterase

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

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 July 18, 2017 16:56

Get DrugBank to go!

Structure for DB01116 (Trimethaphan)

Targets

References

Enzymes

References