U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of STREPTONIGRIN

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

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
Record UNII
261Q3JB310
Record Status Validated (UNII)
Record Version