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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014536
Secondary Accession Numbers
  • HMDB14536
Metabolite Identification
Common NameEthopropazine
DescriptionEthopropazine is only found in individuals that have used or taken this drug.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.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.
Structure
Data?1582753190
Synonyms
ValueSource
10-(2-Diethylaminopropyl)phenothiazineChEBI
10-[2-(Diethylamino)-1-propyl]phenothiazineChEBI
10-[2-(Diethylamino)-2-methylethyl]phenothiazineChEBI
10-[2-(Diethylamino)propyl]phenothiazineChEBI
2-Diethylamino-1-propyl-N-dibenzoparathiazineChEBI
EthopropazineChEBI
N,N-Diethyl-1-(10H-phenothiazin-10-yl)-2-propanamineChEBI
N,N-Diethyl-alpha-methyl-10H-phenothiazine-10-ethanamineChEBI
ProfenaminaChEBI
ProfenaminumChEBI
N,N-Diethyl-a-methyl-10H-phenothiazine-10-ethanamineGenerator
N,N-Diethyl-α-methyl-10H-phenothiazine-10-ethanamineGenerator
AethopropropazinHMDB
AthapropazineHMDB
AthopropazinHMDB
EthapropazineHMDB
EthopromazineHMDB
EtopropezinaHMDB
FempropazineHMDB
FenpropazinaHMDB
IsopthazineHMDB
IsotazinHMDB
IsothazineHMDB
IsothiazineHMDB
PhenopropazineHMDB
PhenoprozineHMDB
ProdierazineHMDB
ProfenamineHMDB
Profenamine monohydrochlorideHMDB
ProphenamineHMDB
ProphenaminumHMDB
LysivaneMeSH, HMDB
Profenamine hydrochlorideMeSH, HMDB
ParsitanMeSH, HMDB
ParsidolMeSH, HMDB
Ethopropazine hydrochlorideMeSH, HMDB
Chemical FormulaC19H24N2S
Average Molecular Weight312.472
Monoisotopic Molecular Weight312.166019468
IUPAC Namediethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]amine
Traditional Nameethopropazine
CAS Registry Number1094-08-2
SMILES
CCN(CC)C(C)CN1C2=CC=CC=C2SC2=CC=CC=C12
InChI Identifier
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
InChI KeyCDOZDBSBBXSXLB-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Para-thiazine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point64.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0052 g/LNot Available
LogP5.2Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available168.494http://allccs.zhulab.cn/database/detail?ID=AllCCS00000971
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0052 g/LALOGPS
logP5.75ALOGPS
logP5ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)9.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98 m³·mol⁻¹ChemAxon
Polarizability36.34 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.84331661259
DarkChem[M-H]-174.64831661259
DeepCCS[M-2H]-197.89430932474
DeepCCS[M+Na]+173.45930932474
AllCCS[M+H]+174.432859911
AllCCS[M+H-H2O]+171.332859911
AllCCS[M+NH4]+177.332859911
AllCCS[M+Na]+178.132859911
AllCCS[M-H]-176.632859911
AllCCS[M+Na-2H]-176.132859911
AllCCS[M+HCOO]-175.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EthopropazineCCN(CC)C(C)CN1C2=CC=CC=C2SC2=CC=CC=C123485.0Standard polar33892256
EthopropazineCCN(CC)C(C)CN1C2=CC=CC=C2SC2=CC=CC=C122397.7Standard non polar33892256
EthopropazineCCN(CC)C(C)CN1C2=CC=CC=C2SC2=CC=CC=C122368.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethopropazine EI-B (Non-derivatized)splash10-0udi-1900000000-add857d98ef29f21b7b82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethopropazine EI-B (Non-derivatized)splash10-0udi-1900000000-31728da531ce58ffd47f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethopropazine CI-B (Non-derivatized)splash10-0w29-2971000000-c72e808a24ef57c33eef2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethopropazine EI-B (Non-derivatized)splash10-0udi-1900000000-add857d98ef29f21b7b82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethopropazine EI-B (Non-derivatized)splash10-0udi-1900000000-31728da531ce58ffd47f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethopropazine CI-B (Non-derivatized)splash10-0w29-2971000000-c72e808a24ef57c33eef2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethopropazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gvk-7490000000-bef89aa8a01a6818d5f12017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethopropazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethopropazine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 10V, Positive-QTOFsplash10-03di-0319000000-f9eb1eae4d3106ba96c72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 20V, Positive-QTOFsplash10-01ox-4691000000-b059098487f2f1ec08b62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 40V, Positive-QTOFsplash10-00g0-9320000000-f93dea7e53c94e4914782017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 10V, Negative-QTOFsplash10-03di-0019000000-7846101ba71705bb04ba2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 20V, Negative-QTOFsplash10-0w2a-1894000000-569e9e8bdedcdfec95b12017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 40V, Negative-QTOFsplash10-0002-3910000000-fc9170b8a01d37752f472017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 10V, Negative-QTOFsplash10-03di-0009000000-b6c288bc9cf2d6b362aa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 20V, Negative-QTOFsplash10-03dl-0397000000-5a47475c5ac3ec27012e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 40V, Negative-QTOFsplash10-03dj-0791000000-dfe945bb0f61305362522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 10V, Positive-QTOFsplash10-03di-0519000000-1c833ce963042958cab82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 20V, Positive-QTOFsplash10-03di-9734000000-4b1eac12a1b36ee582482021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethopropazine 40V, Positive-QTOFsplash10-0002-3920000000-35b6cacc575ddd14297b2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00392 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00392 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00392
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3174
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthopropazine
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID313639
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
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
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 ]
General function:
Involved in ionotropic glutamate receptor activity
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
Gene Name:
GRIN3A
Uniprot ID:
Q8TCU5
Molecular weight:
125464.1
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
51420.4
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
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 ]