Skip to Content
Merck
All Photos(1)

Key Documents

SML0568

Sigma-Aldrich

3-AP

≥98% (HPLC)

Synonym(s):

3-AP, 3-Aminopyridine-2-carboxaldehyde thiosemicarbazone, PAN-811

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C7H9N5S
CAS Number:
143621-35-6
Molecular Weight:
195.24
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 10 meq/mL, clear

storage temp.

2-8°C

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+

InChI key

XMYKNCNAZKMVQN-NYYWCZLTSA-N

Biochem/physiol Actions

3-Aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) is a ribonucleotide reductase inhibitor and iron chelator with anti-tumor activity.
3-aminopyridine carboxaldehyde thiosemicarbazone (3-AP) has a IC50 value of 0.3μM. It exhibits anti-proliferative activity in preclinical models of cancer, such as lung cancer. It also has an ability to increase the cytotoxicity, intracellular uptake and DNA incorporation of gemcitabine in vitro.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

5-Azacytidine ≥98% (HPLC)

Sigma-Aldrich

A2385

5-Azacytidine

5-Aza-2′-deoxycytidine ≥97%

Sigma-Aldrich

A3656

5-Aza-2′-deoxycytidine

Charles A Kunos et al.
Gynecologic oncology, 130(1), 75-80 (2013-04-23)
Cervical and vaginal cancers have virally-mediated or mutated defects in DNA damage repair responses, making these cancers sensible targets for ribonucleotide reductase inhibition during radiochemotherapy. We conducted a phase II study evaluating 3× weekly 2-hour intravenous 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, 25
C M Nutting et al.
Annals of oncology : official journal of the European Society for Medical Oncology, 20(7), 1275-1279 (2009-02-28)
Treatment options for recurrent or metastatic head and neck squamous cell carcinoma (HNSCC) are limited with response rates to cytotoxic chemotherapy of approximately 30% and median survival of 6 months. In a multicentre phase II study, 32 patients with recurrent
Patricia Quach et al.
Molecular pharmacology, 82(1), 105-114 (2012-04-18)
Thiosemicarbazones are a group of compounds that have received comprehensive investigation as anticancer agents. The antitumor activity of the thiosemicarbazone, 3-amino-2-pyridinecarboxaldehyde thiosemicarbazone (3-AP; triapine), has been extensively assessed in more than 20 phase I and II clinical trials. These studies
Charles Kunos et al.
Journal of translational medicine, 10, 79-79 (2012-05-01)
The potent ribonucleotide reductase (RNR) inhibitor 3-aminopyridine-2-carboxyaldehyde-thiosemicarbazone (3-AP) was tested as a chemosensitizer for restored cisplatin-mediated cytotoxicity in platinum-resistant ovarian cancer. Preclinical in vitro platinum-resistant ovarian cancer cell survival, RNR activity, and DNA damage assays were done after cisplatin or
Charles A Kunos et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 16(4), 1298-1306 (2010-02-11)
This study assessed the safety/tolerability, pharmacokinetics, and clinical activity of three times weekly i.v. 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) in combination with once-weekly i.v. cisplatin and daily pelvic radiation in patients with gynecologic malignancies. 3-AP is a novel small-molecule inhibitor
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service