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Triapine

CAT: 0013-GTR19163225-03Size: 1 gDry Ice: NoHazardous: No
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Description
Triapine (3-AP, PAN-811, OCX191, NSC 663249) is a potent ribonucleotide reductase inhibitor with broad spectrum antitumor activity.Ovarian Cancer Phase 2 Clinical (In Vitro) :3-AP (Triapine) is a potent derivative of α-heterocyclic carboxaldehyde thiosemicarbazone (HCT) that inhibits hRRM2 and p53R2 isoforms of the M2 subunit. 3-AP (Triapine) is thought to inhibit ribonucleotide reductase through its preformed iron chelate, rather than directly by removing iron from the active site. In cells containing less topoisomerase IIα fewer DNA strand breaks will be produced, and thus topoisomerase II poisons will be less inhibitory in the K/VP.5 cell line. The IC50s for Dp44mT growth inhibition are 48±9 nM and 60±12 nM, for K562 and K/VP.5 cells, respectively. The IC50s for 3-AP growth inhibition are 476±39 nM and 661±69 nM for K562 and K/VP.5 cells, respectively. PKIH and DpT Fe chelators show high antiproliferative activity against a range of tumor cell lines. Dp44mT shows the greatest antitumor efficacy with an IC50 that ranged from 0.005 to 0.4 μM. The average IC50 of Dp44mT over 28 cell types is 0.03±0.01 μM, which is significantly lower than that of 3-AP (Triapine; average IC50: 1.41±0.37 μM) . (In Vivo) :3-AP (Triapine) causes a significant increase (1.7-fold) in splenic weight when expressed as a percentage of total body weight (1.02±0.06%; n=25) compared with control mice (0.6±0.03%; n=27) . In the long-term group, a significant increase in heart weight is observed after Dp44mT (0.4 mg/kg per day) (0.8±0.06%; n=4) compared with control mice (0.5±0.01%; n=6) . A significant decrease in the expression of Ndrg1, TfR1, and VEGF1 in the liver is noted for Dp44mT- and 3-AP (12 mg/kg per day) -treated animals. The decreased expression could be related to the increased liver Fe in both Dp44mT- and 3-AP-treated mice.
CAS Number
143621-35-6
Product Name Alternative
3-AP | PAN-811 | OCX191 | NSC663249
Purity
>98% (HPLC)
Solubility
DMSO: ≥ 47 mg/mL
Smiles
NC1=CC=CN=C1/C=N/NC (N) =S
Molecular Formula
C7H9N5S
Molecular Weight
195.2449
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
Hydrazinecarbothioamide, 2-[ (3-amino-2-pyridinyl) methylene]-

Chemical Information

Triapine

Triapine is 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. It has a role as a radiosensitizing agent, an antineoplastic agent, an iron chelator, a neuroprotective agent, an apoptosis inducer and an EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor. It is a thiosemicarbazone and an aminopyridine. It is functionally related to a 3-aminopicolinaldehyde.

CAS Number143621-35-6
PubChem CID9571836
IUPAC Name[(E)-(3-amino-2-pyridinyl)methylideneamino]thiourea
Molecular FormulaC7H9N5S
Molecular Weight195.25
XLogP-0.2
Topological Polar Surface Area121
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Heavy Atom Count13
Formal Charge0
Complexity205
SMILES
C1=CC(=C(N=C1)/C=N/NC(=S)N)N
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)/b11-4+
InChIKey
XMYKNCNAZKMVQN-NYYWCZLTSA-N
Chemical Structure
2D Structure
2D structure of Triapine
CAS: 143621-35-6
CID: 9571836
Formula: C7H9N5S
MW: 195.25
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight195.25
XLogP3-0.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass195.05786648
Monoisotopic Mass195.05786648
Topological Polar Surface Area121 Ų
Heavy Atom Count13
Formal Charge0
Complexity205
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

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B3209-5.1Triapine
HY-10082RTriapine (Standard)
A14306-10Triapine 10mg
HY-10082BTriapine (hydrochloride)
A14306-50Triapine 50mg
HY-10082S1Triapine-d3
T87564-01Triapine hydrochloride
A14306-25Triapine 25mg
S7470-25mgTriapine (3-AP)

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