Pyrazofurin

Modify Date: 2024-01-02 14:19:07

Pyrazofurin structure	Common Name	Pyrazofurin
	CAS Number	30868-30-5	Molecular Weight	259.21600
	Density	1.786g/cm3	Boiling Point	584.397ºC at 760 mmHg
	Molecular Formula	C₉H₁₃N₃O₆	Melting Point	N/A
	MSDS	N/A	Flash Point	307.232ºC

Use of Pyrazofurin

Pyrazofurin, a pyrimidine nucleoside analogue with antineoplastic activity, inhibits cell proliferation and DNA synthesis in cells by inhibiting uridine 5'-phosphate (UMP) synthase[1]. Pyrazofurin is an active, sensitive orotate-phosphoribosyltransferase inhibitor with IC50s between 0.06-0.37 µM in the three squamous cell carcinoma (SCC) cell lines Hep-2, HNSCC-14B and HNSCC-14C[2].

Name	5-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-3-carboxamide
Synonym	More Synonyms

Description	Pyrazofurin, a pyrimidine nucleoside analogue with antineoplastic activity, inhibits cell proliferation and DNA synthesis in cells by inhibiting uridine 5'-phosphate (UMP) synthase[1]. Pyrazofurin is an active, sensitive orotate-phosphoribosyltransferase inhibitor with IC50s between 0.06-0.37 µM in the three squamous cell carcinoma (SCC) cell lines Hep-2, HNSCC-14B and HNSCC-14C[2].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis
References	[1]. Ringer DP, et al. Alteration in de novo pyrimidine biosynthesis during uridine reversal of pyrazofurin-inhibited DNA synthesis. Neuropsychopharmacology. J Biochem Toxicol. 1991 Spring;6(1):19-27. [2]. Peters GJ, et al. Antipyrimidine effects of five different pyrimidine de novo synthesis inhibitors in three head and neck cancer cell lines. Nucleosides Nucleotides Nucleic Acids. 2018;37(6):329-339.

Description

Related Catalog

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

References

[1]. Ringer DP, et al. Alteration in de novo pyrimidine biosynthesis during uridine reversal of pyrazofurin-inhibited DNA synthesis. Neuropsychopharmacology. J Biochem Toxicol. 1991 Spring;6(1):19-27.

[2]. Peters GJ, et al. Antipyrimidine effects of five different pyrimidine de novo synthesis inhibitors in three head and neck cancer cell lines. Nucleosides Nucleotides Nucleic Acids. 2018;37(6):329-339.

Density	1.786g/cm3
Boiling Point	584.397ºC at 760 mmHg
Molecular Formula	C₉H₁₃N₃O₆
Molecular Weight	259.21600
Flash Point	307.232ºC
Exact Mass	259.08000
PSA	161.92000
Index of Refraction	1.718
Storage condition	-20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ6360000

CHEMICAL NAME :: 1H-Pyrazole-5-carboxamide, 4-hydroxy-3-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 30868-30-5

LAST UPDATED :: 199112

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C9-H13-N3-O6

MOLECULAR WEIGHT :: 259.25

WISWESSER LINE NOTATION :: T5OTJ B1Q CQ DQ E- CT5MNJ DQ EVZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 108 mg/kg/5D

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 48 mg/kg/5D

TOXIC EFFECTS :: Gastrointestinal - other changes Blood - changes in bone marrow (not otherwise specified)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 84 mg/kg/5D

TOXIC EFFECTS :: Blood - changes in bone marrow (not otherwise specified) Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 108 mg/kg/5D

TOXIC EFFECTS :: Gastrointestinal - other changes Blood - changes in bone marrow (not otherwise specified)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human

DOSE/DURATION :: 144 mg/kg/5D

TOXIC EFFECTS :: Gastrointestinal - other changes Blood - changes in bone marrow (not otherwise specified) Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 70 mg/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - dehydration

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - guinea pig Lymphocyte

DOSE/DURATION :: 10 umol/L

REFERENCE :: JBTOEB Journal of Biochemical Toxicology. (VCH Publishers, Inc., 220 E. 23rd St., Suite 909, New York, NY USA 10010) V.1- 1986- Volume(issue)/page/year: 6,19,1991

Precursor 10
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DownStream 0