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Showing metabocard for Thiethylperazine (HMDB0014516)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-08-16 08:45:51 UTC
HMDB IDHMDB0014516
Secondary Accession Numbers
  • HMDB14516
Metabolite Identification
Common NameThiethylperazine
DescriptionA dopamine antagonist that is particularly useful in treating the nausea and vomiting associated with anesthesia, mildly emetic cancer chemotherapy agents, radiation therapy, and toxins. This piperazine phenothiazine does not prevent vertigo or motion sickness. (From AMA Drug Evaluations Annual, 1994, p457)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(ethylthio)-10-[3-(4-Methylpiperazin-1-yl)propyl]-10H-phenothiazineChEBI
3-ethylmercapto-10-(1'-Methylpiperazinyl-4'-propyl)phenothiazineChEBI
EthylthioperazineChEBI
ThiethylperazinumChEBI
TietilperazinaChEBI
TheithylperazineHMDB
NorzineMeSH
Thiethlperazine novartis brandMeSH
Novartis brand OF thiethlperazineMeSH
Novartis brand OF thiethlperazine maleateMeSH
TorecanMeSH
Purdue frederick brand OF thiethlperazineMeSH
Thiethylperazine maleate (2:1)MeSH
Thiethylperazine malateMeSH
Roxane brand OF thiethlperazine maleateMeSH
Chemical FormulaC22H29N3S2
Average Molecular Weight399.616
Monoisotopic Molecular Weight399.180289323
IUPAC Name2-(ethylsulfanyl)-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
Traditional Namethiethylperazine
CAS Registry Number1420-55-9
SMILES
CCSC1=CC2=C(SC3=CC=CC=C3N2CCCN2CCN(C)CC2)C=C1
InChI Identifier
InChI=1S/C22H29N3S2/c1-3-26-18-9-10-22-20(17-18)25(19-7-4-5-8-21(19)27-22)12-6-11-24-15-13-23(2)14-16-24/h4-5,7-10,17H,3,6,11-16H2,1-2H3
InChI KeyXCTYLCDETUVOIP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Thiophenol ether
  • Alkylarylthioether
  • N-alkylpiperazine
  • N-methylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Para-thiazine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Sulfenyl compound
  • Azacycle
  • Thioether
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-emetics
  • Antiemetics
  • Dopamine Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point62 - 64 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.87e-03 g/LNot Available
LogP5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0049 mg/mLALOGPS
logP5.12ALOGPS
logP4.66ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)8.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.72 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.56 m3·mol-1ChemAxon
Polarizability46.53 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0000900000-66239882c220302aee87View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0400900000-67c33b4bb0599ec5f25eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ox-1920000000-8306550db4ba65e81586View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03kc-6960000000-91d197f5c5cc7ac38c4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0229-9560000000-c669a4875fb62a347fb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00372 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00372 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00372
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5245
KEGG Compound IDC07132
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiethylperazine
NuGOwiki LinkHMDB0014516
METLIN IDNot Available
PubChem Compound5440
PDB IDNot Available
ChEBI ID9544
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Maurer H, Pfleger K: Identification of phenothiazine antihistamines and their metabolites in urine. Arch Toxicol. 1988;62(2-3):185-91. [PubMed:2904251 ]

Enzymes

Enzyme Details
1. D(2) dopamine receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
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. Briani C, Cagnin A, Chierichetti F, Tiberio M, Battistin L, Pizzolato G: Thiethylperazine-induced parkinsonism: in vivo demonstration of dopamine D2 receptors blockade. Eur J Neurol. 2004 Oct;11(10):709-10. [PubMed:15469457 ]
Enzyme Details
2. D(4) dopamine receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD4
Uniprot ID:
P21917
Molecular weight:
48359.9
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 ]
Enzyme Details
3. D(1A) dopamine receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8
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 ]