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Triapine

Triapine structure

CAS No:
143621-35-6
Formula:
C7H9N5S
Chemical Name:
Triapine
Synonyms:
Hydrazinecarbothioamide,2-[(3-amino-2-pyridinyl)methylene]-;2-[(3-Amino-2-pyridinyl)methylene]hydrazinecarbothioamide;3-Aminopyridine-2-carboxaldehyde thiosemicarbazone;NSC 663249;Triapine;OCX 191;Pan 811;3-AP;OCX 0191;[(3-Aminopyridin-2-yl)methylideneamino]thiourea;236392-56-6
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

Triapine is a novel inhibitor of the M2 subunit of ribonucleotide reductase (RR), and is a potent radiosensitizer.

Triapine Basic Attributes

Molecular Weight：

195.24

Exact Mass：

195.24

HScode：

2933990090

Characteristics

PSA：

125.95000

XLogP3：

1.52370

Appearance：

white to light brown

Density：

1.46±0.1 g/cm3(Predicted)

Boiling Point：

436.0±55.0 °C(Predicted)

Flash Point：

217.5±31.5 °C

Refractive Index：

1.720

Water Solubility：

DMSO: soluble10Meq/mL, clear

Storage Conditions：

2-8°C

Toxicity：

LDLo ivn-rat: 20 mg/kg IJTOFN 19,85,2000

Safety Information

Transport codes：

UN 2811 6.1 / PGIII

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

Marks：

Precautionary statement(s)：

P261-P301 + P310-P305 + P351 + P338

Hazard Statements：

H301-H315-H319-H335

GHS Classification：

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

3-aminopyridine-2-carboxaldehyde thiosemicarbazone

Triapine Use and Manufacturing

Ribonucleotide reductase, the rate-limiting enzyme for de novo DNA synthesis, is an excellent target for chemotherapy. Its increased activity in cancer cells is associated with malignant transformation and proliferation. 3-AP is a ribonucleotide reductase inhibitor and iron chelator with antitumor activity. At 5 μM it can enhance DU145, U251, and PSN1 tumor cell radiosensitivity in vitro, inhibiting DNA synthesis and repair. It destroys the tyrosine free radical in the R2/p53R2 subunits of ribonucleotide reductase by forming a redox active complex with iron, thus producing reactive oxygen species. Furthermore, 3-AP has been shown to activate an endoplasmic reticulum stress pathway, leading to the unfolded protein response and apoptosis.[Cayman Chemical]

Computed Properties

Molecular Weight:195.25
XLogP3:-0.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:195.05786648
Monoisotopic Mass:195.05786648
Topological Polar Surface Area:121
Heavy Atom Count:13
Complexity:205
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of Triapine

HANGZHOU LEAP CHEM CO., LTD. Contact Supplier

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3-aminopyridine-2-carboxaldehyde thiosemicarbazone

CAS No.: 143621-35-6

Content: 99.00%

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