Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C9H13N3O6 |
| Molecular Weight | 259.216 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=C(O)C(=NN1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
InChI
InChIKey=XESARGFCSKSFID-FLLFQEBCSA-N
InChI=1S/C9H13N3O6/c10-9(17)4-6(15)3(11-12-4)8-7(16)5(14)2(1-13)18-8/h2,5,7-8,13-16H,1H2,(H2,10,17)(H,11,12)/t2-,5-,7-,8+/m1/s1
| Molecular Formula | C9H13N3O6 |
| Molecular Weight | 259.216 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Pyrazofurin (PF) (3,β-D-ribofuranosyl, 4-hydroxyprazole-5-carboxamide) is a C-nucleoside antibiotic, one in which the ribose joins the base-ring carbon instead of a base-ring nitrogen. Pyrazofurin potently inhibits orotidine 5'-monophosphate (OMP) decarboxylase, thereby interfering with de novo synthesis of uridine nucleotides and resulting in cytotoxicity. This agent also causes a rapid depletion of the pyrimidine deoxynucleotide pool, thereby inhibiting DNA synthesis and cell replication. PF was isolated from fermentation filtrate of Strepomyces candidus. This compound was initially found to have inhibitory activity against the vaccinia, herpes simplex, rhino and measles viruses in vitro and the vaccinia virus in vivo. More recently the antiviral spectrum has been extended to include the polio, Coxsackie, Sindbis and vesicular stomatitis viruses.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 5.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of severe acute respiratory syndrome-associated coronavirus (SARSCoV) by calpain inhibitors and beta-D-N4-hydroxycytidine. | 2004-01 |
|
| Glycyrrhizin, an active component of liquorice roots, and replication of SARS-associated coronavirus. | 2003-06-14 |
|
| Identification of active antiviral compounds against a New York isolate of West Nile virus. | 2002-07 |
|
| Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. | 2001-04 |
|
| Antiviral and immunomodulating inhibitors of experimentally-induced Punta Toro virus infections. | 1994-10 |
|
| Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro. | 1990-10-01 |
|
| Comparative activities of several nucleoside analogs against duck hepatitis B virus in vitro. | 1990-07 |
|
| Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro. | 1989-09 |
|
| Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. | 1989-02 |
|
| Inhibitory effects of antiviral compounds on respiratory syncytial virus replication in vitro. | 1987-08 |
|
| Selective inhibitory effect of (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine and 2'-nor-cyclic GMP on adenovirus replication in vitro. | 1987-02 |
|
| Comparative inhibitory effects of suramin and other selected compounds on the infectivity and replication of human T-cell lymphotropic virus (HTLV-III)/lymphadenopathy-associated virus (LAV). | 1986-03-15 |
|
| Synthesis and biological activity of certain nucleoside and nucleotide derivatives of pyrazofurin. | 1986-02 |
|
| Comparative efficacy of broad-spectrum antiviral agents as inhibitors of rotavirus replication in vitro. | 1986-01 |
|
| Screening for new compounds with antiherpes activity. | 1984-10 |
|
| Rat hepatomas: chemotherapy with lycurim and pyrazofurin. | 1982-04 |
|
| Design, synthesis, and broad spectrum antiviral activity of 1- -D-ribofuranosyl-1,2,4-triazole-3-carboxamide and related nucleosides. | 1972-11 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/157807
Pyrazofurin was administered to 21 patients with solid tumors at a dose of 200 mg/m2 iv weekly, because this dose had been shown to be well-tolerated and pharmacologic effects of a single dose at this level persisted for up to 7 days.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2713848
Measurement of levels of pyrimidine and purine intermediates in cultured mouse L1210 leukemia cells has shown that 25 uM pyrazofurin induces an 8-fold accumulation of OMP and large accumulations of intermediates proximal to the blockade with abrupt decreases in uridine and cytidine nucleotides.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:52:40 GMT 2025
by
admin
on
Mon Mar 31 17:52:40 GMT 2025
|
| Record UNII |
4B15044GQZ
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C1557
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
||
|
NCI_THESAURUS |
C2170
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
30868-30-5
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
SUB09897MIG
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
143095
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
135413551
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
90284
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
100000081640
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
3579
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
CHEMBL2105330
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
DTXSID901028098
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
4B15044GQZ
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
Pyrazofurin
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
C1208
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY | |||
|
C002997
Created by
admin on Mon Mar 31 17:52:40 GMT 2025 , Edited by admin on Mon Mar 31 17:52:40 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |