Tiazofurin
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Tiazofurin
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CAS No:
60084-10-8
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Formula:
C9H12N2O5S
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Chemical Name:
Tiazofurin
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Synonyms:
4-Thiazolecarboxamide,2-β-D-ribofuranosyl-;2-β-D-Ribofuranosyl-4-thiazolecarboxamide;2-β-D-Ribofuranosylthiazole-4-carboxamide;NSC 286193;Tiazofurin;Tiazofurine;Riboxamide;TCAR;NSC 286-193;CI 909
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CAS No:
Description
Tiazofurine is a C-glycosyl compound that is 1,3-thiazole-4-carboxamide in which the hydrogen at position 2 has been replaced by a beta-D-ribofuranosyl group. It is metabolised to thiazole-4-carboxamide adenine dinucleotide (TAD), a selective inhibitor of inosine monophosphate dehydrogenase (IMP dehydrogenase). It has a role as an EC 1.1.1.205 (IMP dehydrogenase) inhibitor, a prodrug and an antineoplastic agent. It is a C-glycosyl compound, a member of 1,3-thiazoles and a monocarboxylic acid amide. It derives from a beta-D-ribose.|Tiazofurine has potential clinical use in cancer treatment as it is a potential inhibitor of Inosine- 5’-monophosphate (IMP) dehydrogenase.|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. (NCI04)
Tiazofurin Basic Attributes
260.27 g/mol
260.27
ULJ82834RE
DTXSID00208827
C1254
L - Antineoplastic and immunomodulating agents
Safety Information
Bulk: The compound was stable through 30 days at 60 °C in the dark (HPLC). Solution: In water < 1% decomposition occurs through 24 hours (HPLC).
Drug Information
Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)
2-beta-D-ribofuranosylthiazole-4-carboxamide
Computed Properties
Molecular Weight:260.27
XLogP3:-1.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:3
Exact Mass:260.04669266
Monoisotopic Mass:260.04669266
Topological Polar Surface Area:154
Heavy Atom Count:17
Complexity:305
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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