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Merck
CN

SML1897

NSC73306

≥98% (HPLC)

Synonym(s):

2-(1,2-Dihydro-2-oxo-3H-indol-3-ylidene)-N-(4-methoxyphenyl)hydrazinecarbothioamide, NSC 671054, NSC 73304

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About This Item

Empirical Formula (Hill Notation):
C16H14N4O2S
CAS Number:
79560-74-0
Molecular Weight:
326.37
UNSPSC Code:
12352202
NACRES:
NA.77

Key Documents

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SMILES string

S=C(N\N=C2\c3c(c(cc(c3)Cl)Cl)NC\2=O)Nc1ccc(cc1)OC

InChI

1S/C16H12Cl2N4O2S/c1-24-10-4-2-9(3-5-10)19-16(25)22-21-14-11-6-8(17)7-12(18)13(11)20-15(14)23/h2-7H,1H3,(H2,19,22,25)(H,20,21,23)

InChI key

HPXWWBMVIMFLLU-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

, yellow to light brown

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

NSC73306, a thiosemicarbazone, is a cell penetrant, cytotoxic agent that exhibits greater toxicity against cells expressing functional P-gp (P-glycoprotein) than against other cells.
NSC73306, a thiosemicarbazone, is a cell penetrant, cytotoxic agent that exhibits greater toxicity against cells expressing functional P-gp (P-glycoprotein) than against other cells. Irrespective of variations in cell line background, NSC73306 consistently demonstrated a Pgp-potentiated MDR-selective toxicity. It appears that NSC73306 is transported into the cell by copper transporter 1 (CTR1, SLC31A1). It is not P-gp inhibitor.

flash_point_c

Not applicable

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
027M4617V

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Joseph A Ludwig et al.
Cancer research, 66(9), 4808-4815 (2006-05-03)
ATP-binding cassette (ABC) proteins include the best known mediators of resistance to anticancer drugs. In particular, ABCB1 [MDR1/P-glycoprotein (P-gp)] extrudes many types of drugs from cancer cells, thereby conferring resistance to those agents. Attempts to overcome P-gp-mediated drug resistance using
Felipe S Pessoto et al.
Oxidative medicine and cellular longevity, 2015, 394367-394367 (2015-06-16)
A series of thiosemicarbazone (TSC) p-substituted acetophenone derivatives were synthesized and chemically characterized. The p-substituents appended to the phenyl group of the TSC structures were hydrogen, fluor, chlorine, methyl, and nitro, producing compounds named TSC-H, TSC-F, TSC-Cl, TSC-Me, and TSC-NO2
King Leung Fung et al.
Molecular pharmaceutics, 11(8), 2692-2702 (2014-05-08)
Acquired drug resistance in cancer continues to be a challenge in cancer therapy, in part due to overexpression of the drug efflux transporter P-glycoprotein (P-gp, MDR1, ABCB1). NSC73306 is a thiosemicarbazone compound that displays greater toxicity against cells expressing functional

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