Identification

Name
Ethopropazine
Accession Number
DB00392  (APRD00729)
Type
Small Molecule
Groups
Approved
Description

Ethopropazine (also known as profenamine hydrochloride) is a medication derived from phenothiazine. It is primarily used as an antidyskinetic to treat parkinsonism. It is sold under the trade names Parsidol in the United States and Parsidan in Canada.

Structure
Thumb
Synonyms
  • 10-(2-Diethylaminopropyl)phenothiazine
  • 10-[2-(Diethylamino)-1-propyl]phenothiazine
  • 10-[2-(Diethylamino)-2-methylethyl]phenothiazine
  • 10-[2-(Diethylamino)propyl]phenothiazine
  • 2-Diethylamino-1-propyl-N-dibenzoparathiazine
  • Ethopropazine
  • N,N-Diethyl-1-(10H-phenothiazin-10-yl)-2-propanamine
  • N,N-Diethyl-alpha-methyl-10H-phenothiazine-10-ethanamine
  • Profenamina
  • Profenamine
  • Profenaminum
Product Ingredients
IngredientUNIICASInChI Key
Ethopropazine hydrochlorideO00T1I1VRN1094-08-2VXPCQISYVPFYRK-UHFFFAOYNA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Parsitan 50mgTablet50 mgOralErfa Canada 2012 Inc1952-12-31Not applicableCanada
International/Other Brands
Dibutil (Bayer) / Parkin (Tanabe) / Parsidan / Parsidol
Categories
UNII
7WI4P02YN1
CAS number
522-00-9
Weight
Average: 312.472
Monoisotopic: 312.166019468
Chemical Formula
C19H24N2S
InChI Key
CDOZDBSBBXSXLB-UHFFFAOYSA-N
InChI
InChI=1S/C19H24N2S/c1-4-20(5-2)15(3)14-21-16-10-6-8-12-18(16)22-19-13-9-7-11-17(19)21/h6-13,15H,4-5,14H2,1-3H3
IUPAC Name
diethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
SMILES
CCN(CC)C(C)CN1C2=CC=CC=C2SC2=CC=CC=C12

Pharmacology

Indication

For use in the treatment of Parkinson's disease and also used to control severe reactions to certain medicines such as reserpine.

Structured Indications
Pharmacodynamics

Ethopropazine, a phenothiazine and antidyskinetic, is used in the treatment of Parkinson's disease. By improving muscle control and reducing stiffness, this drug permits more normal movements of the body as the disease symptoms are reduced. It is also used to control severe reactions to certain medicines such as reserpine, phenothiazines, chlorprothixene, thiothixene, loxapine, and haloperidol. Unlike other NMDA antagonists, ethopropazine — because of its anticholinergic action — is largely devoid of neurotoxic side effects. Ethopropazine also has a slight antihistaminic and local anesthetic effect.

Mechanism of action

Ethopropazine's antiparkinson action can be attributed to its anticholinergic properties. Ethopropazine partially blocks central (striatal) cholinergic receptors, thereby helping to balance cholinergic and dopaminergic activity in the basal ganglia; salivation may be decreased, and smooth muscle may be relaxed. Drug-induced extrapyramidal symptoms and those due to parkinsonism may be relieved, but tardive dyskinesia is not alleviated and may be aggravated by anticholinergic effects. Ethopropazine's local anesthetic effect is due to its antagonism of the NMDA glutamate receptor. Glutamate is recognized as an important transmitter in nociceptive pathways, and the N-methyl-D-aspartate (NMDA) subtype of the glutamate receptor, in particular, has been implicated in the mediation of neuropathic pain. Excessive release of glutamate at NMDA receptors on dorsal horn neurons of the spinal cord results in hyperactivation and hypersensitivity of these receptors (perceived as hyperalgesia), thought to be an integral feature of neuropathic pain.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
AGlutamate receptor ionotropic, NMDA 3A
antagonist
Human
UMuscarinic acetylcholine receptor M2
antagonist
Human
Absorption

Well-absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

93%

Metabolism
Not Available
Route of elimination
Not Available
Half life

1 to 2 hours

Clearance
Not Available
Toxicity

Symptoms of overdose include severe clumsiness or unsteadiness, severe drowsiness, severe dryness of mouth, nose, or throat, fast heartbeat, shortness of breath or troubled breathing, and warmth, dryness, and flushing of skin.

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 Ethopropazine can be decreased when used in combination with 1,10-Phenanthroline.Experimental
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Ethopropazine.Experimental, Illicit
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Ethopropazine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Ethopropazine.Experimental, Illicit
AclidiniumAclidinium may increase the anticholinergic activities of Ethopropazine.Approved
AlcuroniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Alcuronium.Experimental
AlfentanilThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Alfentanil.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Alphacetylmethadol.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Alphaprodine.Illicit
AmbenoniumThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Ambenonium.Approved
AmphetamineAmphetamine may decrease the sedative activities of Ethopropazine.Approved, Illicit
Anisotropine MethylbromideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Anisotropine Methylbromide.Approved
AtracuriumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Atracurium.Experimental
Atracurium besylateThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Atracurium besylate.Approved
AtropineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Atropine.Approved, Vet Approved
BenactyzineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Benactyzine.Withdrawn
BendroflumethiazideThe serum concentration of Bendroflumethiazide can be increased when it is combined with Ethopropazine.Approved
BenzatropineThe risk or severity of adverse effects can be increased when Benzatropine is combined with Ethopropazine.Approved
BenzphetamineBenzphetamine may decrease the sedative activities of Ethopropazine.Approved, Illicit
Benzylpenicilloyl PolylysineEthopropazine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Ethopropazine.Approved
BezitramideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Bezitramide.Experimental, Illicit, Withdrawn
BiperidenThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Biperiden.Approved
BornaprineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Bornaprine.Experimental
Botulinum Toxin Type AEthopropazine may increase the anticholinergic activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BEthopropazine may increase the anticholinergic activities of Botulinum Toxin Type B.Approved
BuprenorphineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Butorphanol.Approved, Illicit, Vet Approved
CarfentanilThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Carfentanil.Illicit, Vet Approved
ChlorothiazideThe serum concentration of Chlorothiazide can be increased when it is combined with Ethopropazine.Approved, Vet Approved
ChlorphenoxamineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Chlorphenoxamine.Withdrawn
ChlorphentermineChlorphentermine may decrease the sedative activities of Ethopropazine.Illicit, Withdrawn
ChlorthalidoneThe serum concentration of Chlorthalidone can be increased when it is combined with Ethopropazine.Approved
CimetropiumEthopropazine may increase the anticholinergic activities of Cimetropium.Experimental
CodeineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Codeine.Approved, Illicit
CoumaphosThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Coumaphos.Vet Approved
CyclopenthiazideThe serum concentration of Cyclopenthiazide can be increased when it is combined with Ethopropazine.Experimental
CyclopentolateThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Cyclopentolate.Approved
DarifenacinThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Darifenacin.Approved, Investigational
DecamethoniumThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Decamethonium.Approved
DemecariumThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Demecarium.Approved
DesloratadineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Desloratadine.Approved, Investigational
DexetimideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Dexetimide.Withdrawn
DextroamphetamineDextroamphetamine may decrease the sedative activities of Ethopropazine.Approved, Illicit
DextromoramideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Dextromoramide.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Dextropropoxyphene.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Dezocine.Approved
DichlorvosThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Dichlorvos.Vet Approved
DicyclomineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Dicyclomine.Approved
DiethylpropionDiethylpropion may decrease the sedative activities of Ethopropazine.Approved, Illicit
DihydrocodeineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Dihydrocodeine.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Dihydroetorphine.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Dihydromorphine.Experimental, Illicit
DiphenoxylateThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Diphenoxylate.Approved, Illicit
DistigmineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Distigmine.Experimental
DonepezilThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Donepezil.Approved
DPDPEThe risk or severity of adverse effects can be increased when Ethopropazine is combined with DPDPE.Investigational
DronabinolEthopropazine may increase the tachycardic activities of Dronabinol.Approved, Illicit
EchothiophateThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Echothiophate.Approved
EdrophoniumThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Edrophonium.Approved
EluxadolineEthopropazine may increase the constipating activities of Eluxadoline.Approved
EmeproniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Emepronium.Experimental
EtanautineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Etanautine.Experimental
EthylmorphineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Ethylmorphine.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Etorphine.Illicit, Vet Approved
EtybenzatropineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Etybenzatropine.Experimental
FentanylThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FenthionThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Fenthion.Vet Approved
FesoterodineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Fesoterodine.Approved
GalantamineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Galantamine.Approved
GallamineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Gallamine.Experimental
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Gallamine Triethiodide.Approved
GepefrineGepefrine may decrease the sedative activities of Ethopropazine.Experimental
Ginkgo bilobaThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Ginkgo biloba.Approved, Nutraceutical
Glucagon recombinantThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Glucagon recombinant.Approved
GlycopyrroniumEthopropazine may increase the anticholinergic activities of Glycopyrronium.Approved, Investigational, Vet Approved
HeroinThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Heroin.Approved, Illicit
HexamethoniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Hexamethonium.Experimental
HomatropineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Homatropine.Approved
Huperzine AThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Huperzine A.Investigational
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Ethopropazine.Approved, Investigational
HydrochlorothiazideThe serum concentration of Hydrochlorothiazide can be increased when it is combined with Ethopropazine.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Hydrocodone.Approved, Illicit
HydroflumethiazideThe serum concentration of Hydroflumethiazide can be increased when it is combined with Ethopropazine.Approved
HydromorphoneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Hydromorphone.Approved, Illicit
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Ethopropazine.Approved
HyoscyamineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Hyoscyamine.Approved
IndapamideThe serum concentration of Indapamide can be increased when it is combined with Ethopropazine.Approved
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Ethopropazine.Approved
IpidacrineThe therapeutic efficacy of Ethopropazine 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 Ethopropazine.Approved
IsoflurophateThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Isoflurophate.Approved, Withdrawn
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Ethopropazine.Investigational
KetobemidoneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Ketobemidone.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Levomethadyl Acetate.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Levorphanol.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Ethopropazine.Approved, Investigational
LofentanilThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Lofentanil.Illicit
MalathionThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Malathion.Approved, Investigational
MazaticolThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Mazaticol.Experimental
MecamylamineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Mecamylamine.Approved
MefloquineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Mefloquine.Approved
MemantineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Memantine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Ethopropazine.Investigational
MephentermineMephentermine may decrease the sedative activities of Ethopropazine.Approved
MeptazinolThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Meptazinol.Experimental
MethadoneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Methadone.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Methadyl Acetate.Approved, Illicit
MethamphetamineMethamphetamine may decrease the sedative activities of Ethopropazine.Approved, Illicit
Methanesulfonyl FluorideThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Methanesulfonyl Fluoride.Investigational
MethanthelineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Methantheline.Approved
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Ethopropazine.Experimental
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Ethopropazine.Approved
Methyl salicylateThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Methyl salicylate.Approved, Vet Approved
MetixeneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Metixene.Approved
MetoclopramideThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Metoclopramide.Approved, Investigational
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Ethopropazine.Approved
MianserinMianserin may increase the anticholinergic activities of Ethopropazine.Approved
Midomafetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Ethopropazine.Experimental, Illicit
MinaprineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Minaprine.Approved
MirabegronThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Mirabegron.Approved
MMDAMMDA may decrease the sedative activities of Ethopropazine.Experimental, Illicit
MorphineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Morphine.Approved, Investigational
NabiloneEthopropazine may increase the tachycardic activities of Nabilone.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Nalbuphine.Approved
NeostigmineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Neostigmine.Approved, Vet Approved
NicomorphineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Nicomorphine.Experimental
NormethadoneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Normethadone.Approved, Illicit
OpiumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Opium.Approved, Illicit
OrphenadrineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Orphenadrine.Approved
OtiloniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Otilonium.Experimental
OxitropiumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Oxitropium.Investigational
OxybutyninThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Oxybutynin.Approved, Investigational
OxycodoneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Oxycodone.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Oxymorphone.Approved, Investigational, Vet Approved
OxyphenoniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Oxyphenonium.Approved
PancuroniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Pancuronium.Approved
ParaoxonThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Paraoxon.Experimental
PentazocineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Pentazocine.Approved, Vet Approved
PentoliniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Pentolinium.Approved
PethidineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Pethidine.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Phenazocine.Experimental
PhenglutarimideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Phenglutarimide.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Phenoperidine.Experimental
PhenterminePhentermine may decrease the sedative activities of Ethopropazine.Approved, Illicit
PhysostigmineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Physostigmine.Approved
PipecuroniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Pipecuronium.Approved
PirenzepineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Pirenzepine.Approved
PiritramideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Piritramide.Investigational
PolythiazideThe serum concentration of Polythiazide can be increased when it is combined with Ethopropazine.Approved
Potassium ChlorideEthopropazine may increase the ulcerogenic activities of Potassium Chloride.Approved, Withdrawn
PramlintidePramlintide may increase the anticholinergic activities of Ethopropazine.Approved, Investigational
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Ethopropazine.Approved
PropanthelineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Propantheline.Approved
PropiverineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Propiverine.Investigational
PseudoephedrinePseudoephedrine may decrease the sedative activities of Ethopropazine.Approved
PyridostigmineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Pyridostigmine.Approved
QuinethazoneThe serum concentration of Quinethazone can be increased when it is combined with Ethopropazine.Approved
QuinidineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Quinidine.Approved
RamosetronEthopropazine may increase the constipating activities of Ramosetron.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Remifentanil.Approved
RitobegronRitobegron may decrease the sedative activities of Ethopropazine.Investigational
RivastigmineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Rivastigmine.Approved, Investigational
ScopolamineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Scopolamine.Approved
Scopolamine butylbromideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Scopolamine butylbromide.Approved, Vet Approved
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Ethopropazine.Approved, Investigational
SolifenacinThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Solifenacin.Approved
SufentanilThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Sufentanil.Approved, Investigational
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Ethopropazine.Approved
TacrineThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Tacrine.Withdrawn
TapentadolThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Tapentadol.Approved
TilidineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Tilidine.Experimental
TiotropiumEthopropazine may increase the anticholinergic activities of Tiotropium.Approved
TolterodineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Tolterodine.Approved, Investigational
TopiramateThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Topiramate.Approved
TramadolThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Tramadol.Approved, Investigational
TrichlorfonThe therapeutic efficacy of Ethopropazine can be decreased when used in combination with Trichlorfon.Vet Approved
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Ethopropazine.Approved, Vet Approved
TrihexyphenidylThe risk or severity of adverse effects can be increased when Trihexyphenidyl is combined with Ethopropazine.Approved
TrimethaphanThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Trimethaphan.Approved
TropatepineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Tropatepine.Experimental
TropicamideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Tropicamide.Approved
TrospiumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Trospium.Approved
TubocurarineThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Tubocurarine.Approved
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Ethopropazine.Approved
VecuroniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Vecuronium.Approved
Food Interactions
Not Available

References

Synthesis Reference

Berg, S.S. and Ashley, J.N.; U.S. Patent 2,607,773; August 19,1952; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.

General References
Not Available
External Links
Human Metabolome Database
HMDB14536
KEGG Drug
D01118
PubChem Compound
3290
PubChem Substance
46507375
ChemSpider
3174
BindingDB
8958
ChEBI
313639
ChEMBL
CHEMBL1206
Therapeutic Targets Database
DAP001119
PharmGKB
PA449531
Wikipedia
Ethopropazine
ATC Codes
N04AA05 — Profenamine
AHFS Codes
  • 12:08.04
PDB Entries
Not Available
FDA label
Not Available
MSDS
Download (74 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableActive Not RecruitingNot AvailableDYT 1 Dystonia / Primary Cervical Dystonia1

Pharmacoeconomics

Manufacturers
  • Parke davis div warner lambert co
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral50 mg
Prices
Unit descriptionCostUnit
Parsitan 50 mg Tablet0.23USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)166-168Berg, S.S. and Ashley, J.N.; U.S. Patent 2,607,773; August 19,1952; assigned to Societe des Usines Chimiques Rhone-Poulenc, France.
water solubility0.693 mg/LNot Available
logP5.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00524 mg/mLALOGPS
logP5.75ALOGPS
logP5ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)9.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98 m3·mol-1ChemAxon
Polarizability36.34 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9898
Blood Brain Barrier+0.9915
Caco-2 permeable+0.766
P-glycoprotein substrateSubstrate0.8802
P-glycoprotein inhibitor IInhibitor0.8555
P-glycoprotein inhibitor IINon-inhibitor0.8161
Renal organic cation transporterNon-inhibitor0.5524
CYP450 2C9 substrateNon-substrate0.815
CYP450 2D6 substrateSubstrate0.7193
CYP450 3A4 substrateNon-substrate0.5838
CYP450 1A2 substrateInhibitor0.9108
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.885
CYP450 3A4 inhibitorNon-inhibitor0.8035
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6592
Ames testNon AMES toxic0.798
CarcinogenicityNon-carcinogens0.8551
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4696 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9544
hERG inhibition (predictor II)Inhibitor0.8448
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.73 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-1900000000-add857d98ef29f21b7b8
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-1900000000-31728da531ce58ffd47f
GC-MS Spectrum - CI-BGC-MSsplash10-0w29-2971000000-c72e808a24ef57c33eef
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
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Phenothiazines
Direct Parent
Phenothiazines
Alternative Parents
Alkyldiarylamines / Diarylthioethers / Benzenoids / 1,4-thiazines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenothiazine / Alkyldiarylamine / Diarylthioether / Aryl thioether / Tertiary aliphatic/aromatic amine / Para-thiazine / Benzenoid / Tertiary amine / Tertiary aliphatic amine / Thioether
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines, tertiary amino compound (CHEBI:313639)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. 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]
  2. Burke RE: The relative selectivity of anticholinergic drugs for the M1 and M2 muscarinic receptor subtypes. Mov Disord. 1986;1(2):135-44. [PubMed:2904117]
  3. Katayama S, Ishizaki F, Yamamura Y, Khoriyama T, Kito S: Effects of anticholinergic antiparkinsonian drugs on binding of muscarinic receptor subtypes in rat brain. Res Commun Chem Pathol Pharmacol. 1990 Sep;69(3):261-70. [PubMed:2236897]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein phosphatase 2a binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 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. Jevtovic-Todorovic V, Meyenburg AP, Olney JW, Wozniak DF: Anti-parkinsonian agents procyclidine and ethopropazine alleviate thermal hyperalgesia in neuropathic rats. Neuropharmacology. 2003 May;44(6):739-48. [PubMed:12681372]
  4. Reynolds IJ, Miller RJ: [3H]MK801 binding to the N-methyl-D-aspartate receptor reveals drug interactions with the zinc and magnesium binding sites. J Pharmacol Exp Ther. 1988 Dec;247(3):1025-31. [PubMed:2849655]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Burke RE: The relative selectivity of anticholinergic drugs for the M1 and M2 muscarinic receptor subtypes. Mov Disord. 1986;1(2):135-44. [PubMed:2904117]
  2. Katayama S, Ishizaki F, Yamamura Y, Khoriyama T, Kito S: Effects of anticholinergic antiparkinsonian drugs on binding of muscarinic receptor subtypes in rat brain. Res Commun Chem Pathol Pharmacol. 1990 Sep;69(3):261-70. [PubMed:2236897]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. Reiner E, Bosak A, Simeon-Rudolf V: Activity of cholinesterases in human whole blood measured with acetylthiocholine as substrate and ethopropazine as selective inhibitor of plasma butyrylcholinesterase. Arh Hig Rada Toksikol. 2004 Apr;55(1):1-4. [PubMed:15137175]
  2. Sinko G, Kovarik Z, Reiner E, Simeon-Rudolf V, Stojan J: Mechanism of stereoselective interaction between butyrylcholinesterase and ethopropazine enantiomers. Biochimie. 2011 Oct;93(10):1797-807. doi: 10.1016/j.biochi.2011.06.023. Epub 2011 Jun 29. [PubMed:21740955]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:36