triapine (CHEBI:231347)

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ChEBI Name	triapine

ChEBI ID	CHEBI:231347

Definition	A thiosemicarbazone resulting from the formal condensation of the formyl group of 3-aminopicolinaldehyde with the non-thioacylated amino group of hydrazinecarbothioamide. It is a ribonucleotide reductase inhibitor that exhibits anti-cancer properties.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Delphine Zhou

Supplier Information

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Formula

C7H9N5S

Net Charge

Average Mass

195.240

Monoisotopic Mass

195.05787

InChI

InChI=1S/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)

InChIKey

XMYKNCNAZKMVQN-UHFFFAOYSA-N

SMILES

[H]C(=NNC(N)=S)C1=C(N)C=CC=N1

Roles Classification
Chemical Role(s):	iron chelator Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor An EC 1.17.* (oxidoreductase acting on CH or CH2) inhibitor that inhibits the action of ribonucleoside-diphosphate reductase (EC 1.17.4.1). apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. neuroprotective agent Any compound that can be used for the treatment of neurodegenerative disorders. radiosensitizing agent A drug that makes increases the sensitivity of tumour cells to radiation therapy.

ChEBI Ontology
Outgoing	triapine (CHEBI:231347) has functional parent 3-aminopicolinaldehyde (CHEBI:231207) triapine (CHEBI:231347) has role antineoplastic agent (CHEBI:35610) triapine (CHEBI:231347) has role apoptosis inducer (CHEBI:68495) triapine (CHEBI:231347) has role EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor (CHEBI:74213) triapine (CHEBI:231347) has role iron chelator (CHEBI:38157) triapine (CHEBI:231347) has role neuroprotective agent (CHEBI:63726) triapine (CHEBI:231347) has role radiosensitizing agent (CHEBI:132992) triapine (CHEBI:231347) is a aminopyridine (CHEBI:38207) triapine (CHEBI:231347) is a thiosemicarbazone (CHEBI:156467)

IUPAC Name

2-[(3-aminopyridin-2-yl)methylidene]hydrazinecarbothioamide

Synonyms	Sources
2-[(3-amino-2-pyridinyl)methylene]-hydrazinecarbothioamide	ChEBI
2-[(3-amino-2-pyridinyl)methylene]hydrazinecarbothioamide	ChEBI
2-[(3-aminopyridin-2-yl)methylidene]hydrazine-1-carbothioamide	IUPAC
3-aminopyridine-2-carboxaldehyde thiosemicarbazone	ChEBI
3-AP	SUBMITTER
3AP	ChEBI
[(3-aminopyridin-2-yl)methylideneamino]thiourea	ChEBI
OCX 0191	ChEBI
OCX 191	SUBMITTER
OCX-0191	ChEBI
PAN 811	ChEBI
PAN-811	ChEBI
PAN811	ChEBI

Manual Xrefs	Databases
3-Aminopyridine-2-carboxaldehyde_thiosemicarbazone	Wikipedia
DB11940	DrugBank
View more database links

Last Modified

31 May 2024