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Identification
NameEthopropazine
Accession NumberDB00392  (APRD00729)
TypeSmall Molecule
GroupsApproved
DescriptionEthopropazine (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
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Parsitan 50mgTablet50 mgOralErfa Canada 2012 Inc1952-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DibutilBayer
ParkinTanabe
ParsidanNot Available
ParsidolNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ethopropazine hydrochloride
1094-08-2
Thumb
  • InChI Key: VXPCQISYVPFYRK-UHFFFAOYNA-N
  • Monoisotopic Mass: 348.142697207
  • Average Mass: 348.933
DBSALT000813
Categories
UNII7WI4P02YN1
CAS number522-00-9
WeightAverage: 312.472
Monoisotopic: 312.166019468
Chemical FormulaC19H24N2S
InChI KeyCDOZDBSBBXSXLB-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
IndicationFor use in the treatment of Parkinson's disease and also used to control severe reactions to certain medicines such as reserpine.
Structured Indications
PharmacodynamicsEthopropazine, 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 actionEthopropazine'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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Muscarinic acetylcholine receptor M1Proteinyes
antagonist
HumanP11229 details
Glutamate receptor ionotropic, NMDA 3AProteinyes
antagonist
HumanQ8TCU5 details
Muscarinic acetylcholine receptor M2Proteinunknown
antagonist
HumanP08172 details
Related Articles
AbsorptionWell-absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein binding93%
MetabolismNot Available
Route of eliminationNot Available
Half life1 to 2 hours
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine 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
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
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
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
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
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
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
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
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
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Gallamine Triethiodide.Approved
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
Hydroxyamphetamine hydrobromideHydroxyamphetamine hydrobromide 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
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
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
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
MethyclothiazideThe serum concentration of Methyclothiazide can be increased when it is combined with Ethopropazine.Approved
MetixeneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Metixene.Approved
MetolazoneThe serum concentration of Metolazone can be increased when it is combined with Ethopropazine.Approved
MianserinMianserin may increase the anticholinergic activities of Ethopropazine.Approved
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
N-butylscopolammonium bromideThe risk or severity of adverse effects can be increased when Ethopropazine is combined with N-butylscopolammonium bromide.Vet Approved
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
NormethadoneThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Normethadone.Approved, Illicit
NVA237The risk or severity of adverse effects can be increased when Ethopropazine is combined with NVA237.Investigational
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
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 Oxyphenonium is combined with Ethopropazine.Approved
PancuroniumThe risk or severity of adverse effects can be increased when Ethopropazine is combined with Pancuronium.Approved
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
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
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
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
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 Trospium is combined with Ethopropazine.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 InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesN04AA05
AHFS Codes
  • 12:08.04
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74 KB)
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Parke davis div warner lambert co
PackagersNot 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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point166-168Berg, 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.73 KB)
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Benzenoid
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
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 play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism (By similarity).
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
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 action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23