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Details

Stereochemistry ACHIRAL
Molecular Formula C25H22N4O8
Molecular Weight 506.4642
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of STREPTONIGRIN

SMILES

COC1=CC=C(C(O)=C1OC)C2=C(N)C(=NC(C(O)=O)=C2C)C3=CC=C4C(=O)C(OC)=C(N)C(=O)C4=N3

InChI

InChIKey=PVYJZLYGTZKPJE-UHFFFAOYSA-N
InChI=1S/C25H22N4O8/c1-9-14(10-6-8-13(35-2)23(36-3)20(10)30)15(26)19(29-17(9)25(33)34)12-7-5-11-18(28-12)22(32)16(27)24(37-4)21(11)31/h5-8,30H,26-27H2,1-4H3,(H,33,34)

HIDE SMILES / InChI

Molecular Formula C25H22N4O8
Molecular Weight 506.4642
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Streptonigrin is an antibiotic produced by Streptomyces flocculus. Streptonigrin exhibits activity as a broad spectrum antibiotic against both Gram-positive and Gram-negative bacteria. Streptonigrin shows antitumor activity against sarcomas, carcinomas, leukemias and lymphomas in vivo and in vitro. Due to its high toxicity, streptonigrin has not recieved widespread clinical use.

CNS Activity

Originator

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
PMID

PMID

TitleDatePMID
Biological properties of streptonigrin derivatives. II. Inhibition of reverse transcriptase activity.
1986 Feb
Comparative study on biological activities of heterocyclic quinones and streptonigrin.
1987 May
Bioactivation of quinones by DT-diaphorase, molecular, biochemical, and chemical studies.
1994
Role of NAD(P)H:quinone oxidoreductase (DT-diaphorase) in cytotoxicity and induction of DNA damage by streptonigrin.
1996 Mar 8
Modulation of the toxicity and macromolecular binding of benzene metabolites by NAD(P)H:Quinone oxidoreductase in transfected HL-60 cells.
1999 Jun
The Chinese hamster FANCG/XRCC9 mutant NM3 fails to express the monoubiquitinated form of the FANCD2 protein, is hypersensitive to a range of DNA damaging agents and exhibits a normal level of spontaneous sister chromatid exchange.
2001 Dec
Antitumor antibiotic streptonigrin and its derivatives as inhibitors of nitric oxide-dependent activation of soluble guanylyl cyclase.
2004 Jan 12
Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells.
2005 Feb
A fluopol-ABPP HTS assay to identify PAD inhibitors.
2010 Oct 14
Insights into the mechanism of streptonigrin-induced protein arginine deiminase inactivation.
2014 Feb 15
Patent

Sample Use Guides

In Vivo Use Guide
In clinical trials, streptonigrin was administered by intravenous infusion (daily dose 7 ug/kg), or orally in the form of 0.2 mg capsule.
Route of Administration: intravenous; oral
In Vitro Use Guide
Exposure to 1-10 ug/ml streptonigrin results in an induction of phage production in lysogenic S. typhimurium LT7 cells.
Substance Class Chemical
Created
by admin
on Tue Mar 06 17:15:53 UTC 2018
Edited
by admin
on Tue Mar 06 17:15:53 UTC 2018
Record UNII
261Q3JB310
Record Status Validated (UNII)
Record Version
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Name Type Language
STREPTONIGRIN
MI   USAN  
USAN  
Official Name English
NSC-83950
Code English
STREPTONIGRIN [MI]
Common Name English
2-PYRIDINECARBOXYLIC ACID, 5-AMINO-6-(7-AMINO-5,8-DIHYDRO-6-METHOXY-5,8-DIOXO-2-QUINOLINYL)-4-(2-HYDROXY-3,4-DIMETHOXYPHENYL)-3-METHYL-
Common Name English
NSC-45383
Code English
STREPTONIGRIN [USAN]
Common Name English
NIGRIN
Brand Name English
ANTIBIOTIC PRODUCED BY STREPTOMYCES FLOCCULUS
Common Name English
RUFOCROMOMYCIN [WHO-DD]
Common Name English
5-AMINO-6-(7-AMINO-5,8-DIHYDRO-6-METHOXY-5,8-DIOXO-2-QUINOLYL)-4-(2-HYDROXY-3,4-DIMETHOXYPHENYL)-3-METHYLPICOLINIC ACID
Systematic Name English
RUFOCROMOMYCIN
INN   WHO-DD  
INN  
Official Name English
RUFOCROMOMYCIN [INN]
Common Name English
Code System Code Type Description
NCI_THESAURUS
C844
Created by admin on Tue Mar 06 17:15:53 UTC 2018 , Edited by admin on Tue Mar 06 17:15:53 UTC 2018
PRIMARY
INN
1261
Created by admin on Tue Mar 06 17:15:53 UTC 2018 , Edited by admin on Tue Mar 06 17:15:53 UTC 2018
PRIMARY
ChEMBL
CHEMBL11417
Created by admin on Tue Mar 06 17:15:53 UTC 2018 , Edited by admin on Tue Mar 06 17:15:53 UTC 2018
PRIMARY
CAS
3930-19-6
Created by admin on Tue Mar 06 17:15:53 UTC 2018 , Edited by admin on Tue Mar 06 17:15:53 UTC 2018
PRIMARY
MERCK INDEX
M10227
Created by admin on Tue Mar 06 17:15:53 UTC 2018 , Edited by admin on Tue Mar 06 17:15:53 UTC 2018
PRIMARY Merck Index
ECHA (EC/EINECS)
223-501-8
Created by admin on Tue Mar 06 17:15:53 UTC 2018 , Edited by admin on Tue Mar 06 17:15:53 UTC 2018
PRIMARY
EVMPD
SUB20556
Created by admin on Tue Mar 06 17:15:53 UTC 2018 , Edited by admin on Tue Mar 06 17:15:53 UTC 2018
PRIMARY
MESH
D013308
Created by admin on Tue Mar 06 17:15:53 UTC 2018 , Edited by admin on Tue Mar 06 17:15:53 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY