Human Metabolome Database: Showing metabocard for Tinidazole (HMDB0015047)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

enzymes (1) Show 1 protein

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2017-12-07 02:48:57 UTC

HMDB ID

HMDB0015047

Secondary Accession Numbers

HMDB15047

Metabolite Identification

Common Name

Tinidazole

Description

Tinidazole is only found in individuals that have used or taken this drug. It is a nitroimidazole antitrichomonal agent effective against Trichomonas vaginalis, Entamoeba histolytica, and Giardia lamblia infections. [PubChem]Tinidazole is a prodrug and antiprotozoal agent. The nitro group of tinidazole is reduced in Trichomonas by a ferredoxin-mediated electron transport system. The free nitro radical generated as a result of this reduction is believed to be responsible for the antiprotozoal activity. It is suggested that the toxic free radicals covalently bind to DNA, causing DNA damage and leading to cell death. The mechanism by which tinidazole exhibits activity against Giardia and Entamoeba species is not known, though it is probably similar.

Structure

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

Synonyms

Value	Source
Timidazole	ChEBI
Pierre fabre brand OF tinidazole	MeSH
Simplotan	MeSH
Teofarma brand OF tinidazole	MeSH
Farmasierra brand OF tinidazole	MeSH
Fasigyne	MeSH
Pfizer brand OF tinidazole	MeSH
Bioshik	MeSH
Fasigin	MeSH
Fasygin	MeSH
Tricolam	MeSH
Fasigyn	MeSH

Chemical Formula

C₈H₁₃N₃O₄S

Average Molecular Weight

247.272

Monoisotopic Molecular Weight

247.062676609

IUPAC Name

1-[2-(ethanesulfonyl)ethyl]-2-methyl-5-nitro-1H-imidazole

Traditional Name

tinidazole

CAS Registry Number

19387-91-8

SMILES

CCS(=O)(=O)CCN1C(C)=NC=C1[N+]([O-])=O

InChI Identifier

InChI=1S/C8H13N3O4S/c1-3-16(14,15)5-4-10-7(2)9-6-8(10)11(12)13/h6H,3-5H2,1-2H3

InChI Key

HJLSLZFTEKNLFI-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as nitroimidazoles. These are compounds containing an imidazole ring which bears a nitro group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Imidazoles

Direct Parent

Nitroimidazoles

Alternative Parents

Substituents

1,2,5-trisubstituted-imidazole
Nitroaromatic compound
Nitroimidazole
Trisubstituted imidazole
N-substituted imidazole
Sulfone
Heteroaromatic compound
Sulfonyl
C-nitro compound
Organic nitro compound
Organic oxoazanium
Azacycle
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

imidazoles (CHEBI:63627 )

Ontology

Disposition

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Drug

Household products:

Antimicrobial agent:

Antiprotozoal

Pharmaceutical industry:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	127 - 128 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.03 g/L	Not Available
LogP	0.7	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.03 g/L	ALOGPS
logP	-0.41	ALOGPS
logP	-0.58	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Basic)	3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.66 m³·mol⁻¹	ChemAxon
Polarizability	23.27 Å³	ChemAxon
Number of Rings	1	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	splash10-0fb9-9810000000-354c2d3adb67449ebc17	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-4910000000-8c46b903514b344ac47c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0290000000-6e567c97c2cf4ca3fd01	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0002-0390000000-28e470db2eb20392a17a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-4910000000-8c46b903514b344ac47c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-49cf52076ccfb3b25895	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0090000000-da3fd95a7532428a5726	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056v-9230000000-93e746c9cb99b3a385b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-43812f7131b453b9807f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9380000000-f2bc3f5e5a79df21ed11	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ftg-9210000000-7de9903c49d10753fac8	View in MoNA

Biological Properties

Cellular Locations

Cytoplasm
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 DB00911	21059682	details
Urine	Expected but not Quantified		Not Available	Not Available	Taking drug identified by DrugBank entry DB00911	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00911

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5279

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tinidazole

METLIN ID

Not Available

PubChem Compound

5479

PDB ID

Not Available

ChEBI ID

63627

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Fung HB, Doan TL: Tinidazole: a nitroimidazole antiprotozoal agent. Clin Ther. 2005 Dec;27(12):1859-84. [PubMed:16507373 ]
Lopez Nigro MM, Carballo MA: Genotoxicity and cell death induced by tinidazole (TNZ). Toxicol Lett. 2008 Jul 30;180(1):46-52. doi: 10.1016/j.toxlet.2008.05.017. Epub 2008 Jun 5. [PubMed:18582545 ]
MedlinePlus [Link]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Showing metabocard for Tinidazole (HMDB0015047)

Structure for HMDB0015047 (Tinidazole)

Enzymes

References