STREPTONIGRIN

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC)C(O)=C(C=C1)C2=C(C)C(=NC(C3=NC4=C(C=C3)C(=O)C(OC)=C(N)C4=O)=C2N)C(O)=O

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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6353197 | https://www.ncbi.nlm.nih.gov/pubmed/5339036

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5532028	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6353197	Primary		Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5339036	Primary		Phase III 656	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM3930196	http://www.alfa-chemistry.com/search.aspx?q=ACM3930196
BOC Sciences	3930-19-6	http://www.bocsci.com/description.asp?cas=3930-19-6
MolPort	MolPort-003-939-340	https://www.molport.com/shop/molecule-link/MolPort-003-939-340
NCI Diversity	45383
NCI Diversity	83950
NCI Plated 2007	45383
NCI Plated 2007	83950
eMolecules	531613	https://orderbb.emolecules.com/search/#?query=531613

PubMed

Title	Date	PubMed
Biological properties of streptonigrin derivatives. II. Inhibition of reverse transcriptase activity.	1986 Feb	2420775
Comparative study on biological activities of heterocyclic quinones and streptonigrin.	1987 May	2440840
Bioactivation of quinones by DT-diaphorase, molecular, biochemical, and chemical studies.	1994	7620217
Role of NAD(P)H:quinone oxidoreductase (DT-diaphorase) in cytotoxicity and induction of DNA damage by streptonigrin.	1996 Mar 8	8615901
Modulation of the toxicity and macromolecular binding of benzene metabolites by NAD(P)H:Quinone oxidoreductase in transfected HL-60 cells.	1999 Jun	10368308
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	11751423
Antitumor antibiotic streptonigrin and its derivatives as inhibitors of nitric oxide-dependent activation of soluble guanylyl cyclase.	2004 Jan 12	14729099
Enhanced cytotoxicity of bioreductive antitumor agents with dimethyl fumarate in human glioblastoma cells.	2005 Feb	15655414
A fluopol-ABPP HTS assay to identify PAD inhibitors.	2010 Oct 14	20740228
Insights into the mechanism of streptonigrin-induced protein arginine deiminase inactivation.	2014 Feb 15	24440480

Patents

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: Other

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 `Fri Dec 15 15:08:13 GMT 2023` Edited by `admin` on `Fri Dec 15 15:08:13 GMT 2023`
Record UNII	261Q3JB310
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

STREPTONIGRIN

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

Rufocromomycin [WHO-DD]

Common Name

English

NIGRIN

Brand Name

English

ANTIBIOTIC PRODUCED BY STREPTOMYCES FLOCCULUS

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

Official Name

English

rufocromomycin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C259