Human Metabolome Database: Showing metabocard for Thiethylperazine (HMDB0014516)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

enzymes (3) Show 3 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2018-03-12 22:08:42 UTC

HMDB ID

HMDB0014516

Secondary Accession Numbers

HMDB14516

Metabolite Identification

Common Name

Thiethylperazine

Description

A 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

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

Synonyms

Value	Source
2-(ethylthio)-10-[3-(4-Methylpiperazin-1-yl)propyl]-10H-phenothiazine	ChEBI
3-ethylmercapto-10-(1'-Methylpiperazinyl-4'-propyl)phenothiazine	ChEBI
Ethylthioperazine	ChEBI
Thiethylperazinum	ChEBI
Tietilperazina	ChEBI
Theithylperazine	HMDB
Norzine	MeSH
Thiethlperazine novartis brand	MeSH
Novartis brand OF thiethlperazine	MeSH
Novartis brand OF thiethlperazine maleate	MeSH
Torecan	MeSH
Purdue frederick brand OF thiethlperazine	MeSH
Thiethylperazine maleate (2:1)	MeSH
Thiethylperazine malate	MeSH
Roxane brand OF thiethlperazine maleate	MeSH

Chemical Formula

C₂₂H₂₉N₃S₂

Average Molecular Weight

399.616

Monoisotopic Molecular Weight

399.180289323

IUPAC Name

2-(ethylsulfanyl)-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine

Traditional Name

thiethylperazine

CAS Registry Number

1420-55-9

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 Key

XCTYLCDETUVOIP-UHFFFAOYSA-N

Chemical 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

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:9544 )
N-methylpiperazine (CHEBI:9544 )

Ontology

Disposition

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	62 - 64 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0049 g/L	Not Available
LogP	5	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0049 g/L	ALOGPS
logP	5.12	ALOGPS
logP	4.66	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Basic)	8.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.72 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.56 m³·mol⁻¹	ChemAxon
Polarizability	46.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-8497000000-f74869de3204be504dbd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0000900000-66239882c220302aee87	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0400900000-67c33b4bb0599ec5f25e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-01ox-1920000000-8306550db4ba65e81586	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03kc-6960000000-91d197f5c5cc7ac38c4d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0229-9560000000-c669a4875fb62a347fb8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2215900000-ffc07dcb1f848c67b2b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ikc-9635300000-38c5898c5d89ce67fff5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btm-9811000000-ed022855ffaf130a53ba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00ds-1009000000-e8c4718debea1fbf8c96	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01zi-2196000000-47bccb0c653426fe5a15	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03e9-9110000000-d488161115936197120f	View in MoNA

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Taking drug identified by DrugBank entry DB00372	21059682	details
Urine	Expected but not Quantified		Not Available	Not Available	Taking drug identified by DrugBank entry DB00372	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00372

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5245

KEGG Compound ID

C07132

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thiethylperazine

METLIN ID

Not Available

PubChem Compound

5440

PDB ID

Not Available

ChEBI ID

9544

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Showing metabocard for Thiethylperazine (HMDB0014516)

Structure for HMDB0014516 (Thiethylperazine)

Enzymes

References

References

References