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Tiazofurin

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Category Orthopoxvirus
CAS 60084-10-8
Description Tiazofurin is a synthetic nucleoside analogue with antineoplastic activity. Tiazofurin (TR) is anabolized intracellularly to an analogue of NAD, tiazole-4-carboxamide adenine dinucleotide (TAD), a potent inhibitor of IMP dehydrogenase (IMPDH); IMPDH is the rate-limiting enzyme for de novo purine synthesis. Inhibition of IMPDH results in reduced levels of guanylates, resulting in the inhibition tumor cell growth in vitro and in vivo.
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Product Information

Synonyms 2-b-D-Ribofuranosyl-4-thiazolecarboxamide; CI 909; NSC 286-193
IUPAC Name 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide
Molecular Weight 260.27
Molecular Formula C9H12N2O5S
Canonical SMILES C1=C(N=C(S1)C2C(C(C(O2)CO)O)O)C(=O)N
InChI InChI=1S/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/m1/s1
InChIKey FVRDYQYEVDDKCR-DBRKOABJSA-N
Boiling Point 641.3±55.0 °C at 760 mmHg
Flash Point 341.6±31.5 °C
Purity 97%
Density 1.6±0.1 g/cm3
Solubility Soluble in DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)
Appearance White to Off-White Solid
Application Antineoplastic Agents
Storage Store at -20°C
Complexity 305
Exact Mass 260.04669266
Index Of Refraction 1.675
PSA 154.14000
Target Nucleoside Antimetabolite/Analog; Orthopoxvirus
Vapor Pressure 0.0±2.0 mmHg at 25°C
XLogP3-AA -1.7

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