LOMOFUNGIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H10N2O6
Molecular Weight	314.2497
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1=CC=C(O)C2=NC3=C(C=O)C(O)=CC(O)=C3N=C12

InChI

InChIKey=CRANETCJDDEINO-UHFFFAOYSA-N

InChI=1S/C15H10N2O6/c1-23-15(22)6-2-3-8(19)13-11(6)16-14-10(21)4-9(20)7(5-18)12(14)17-13/h2-5,19-21H,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4790624 | https://www.ncbi.nlm.nih.gov/pubmed/20959871 | https://www.ncbi.nlm.nih.gov/pubmed/24799433 | https://www.ncbi.nlm.nih.gov/pubmed/26141568

Lomofungin, a natural product compound first isolated from the soil-dwelling Gram-positive bacteria Streptomyces lomodensis. Lomofungin has a broad antibacterial and antifungal spectrum, being active against gram-positive and gram-negative bacteria, yeasts, and other fungi. It prevents RNA synthesis by a direct interaction with the bacterial DNA-dependent ribonucleic acid (RNA) polymerase and not with the template or substrate. Lomofungin was identified as an inhibitor of botulinum neurotoxin light chain protease and as a potential therapeutic for myotonic dystrophy type 1. Lomofungin inhibited HIV-1 replication in peripheral blood mononuclear cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Botulinum neurotoxin type A 3 Target ID: CHEMBL5192 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20959871	Inhibitor 8504	6.7 µM [Ki]
CUG(exp) RNA 1 Target ID: CUG(exp) RNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799433	Inhibitor 8504
Bacterial DNA-directed RNA polymerase 11 Target ID: CHEMBL2364672 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4790624	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Botulism 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20959871	Primary	Basic research	Unknown Approved Use Unknown
Myotonic dystrophy type 1 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799433	Primary	Basic research	Unknown Approved Use Unknown
HIV-1 infection 156 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26141568	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Lomofungin inhibition of allophanate hydrolase synthesis in Saccharomyces cerevisiae.	1975	1102915
Chelation of divalent cations by lomofungin: role in inhibition of nucleic acid synthesis.	1974-10-08	4215422
Lomofungine as an inhibitor of nucleic acid synthesis in Saccharomyces cerevisiae.	1974-09	4619013
Rapid and selective inhibition of the synthesis of high molecular weight RNA in yeast by lomofungin.	1973-07-27	4583093
Inhibition by lomofungin of nucleic acid and protein synthesis in Saccharomyces cerevisiae.	1973-06-01	4582157
Lomofungin, an inhibitor of ribonucleic acid synthesis in yeast protoplasts: its effect on enzyme formation.	1973-06	4790623
Lomofungin, an inhibitor of deoxyribonucleic acid-dependent ribonucleic acid polymerases.	1973-06	4790624
Lomofungin. I. Degradative studies of a new phenazine antibiotic.	1970-03-11	5414752
Mode of action of lomofungin.	1969-07	5803629
Lomofungin, a new antibiotic produced by Streptomyces lomondensis sp. n.	1969-05	5785961
Lomofungin, a new broad spectrum antibiotic. Isolation and characterization.	1969-03	5789900

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Lomofungin inhibited the growth of some yeasts and mycelial fungi at concentrations between 5 and 10 ug/ml. At such concentrations, there was no decrease in endogenous and exogenous oxygen consumption, and even 50 ug of antibiotic per ml caused only slight decreases. The permeation of the cell membrane was changed so that leakage of ninhydrin-positive substances was reduced, and the uptake of (14)C-labeled glucose, amino acids, uracil, and thymidine was decreased at concentrations as low as 4 ug/ml. Protein synthesis in whole cells of Saccharomyces cerevisiae was reduced 35% at 10 ug/ml.

Name

Type

Language

LOMOFUNGIN

Official Name

English

NSC-156939

Preferred Name

English

U-24,792

Code

English

U-24792

Code

English

NSC-106995

Code

English

Methyl 6-formyl-4,7,9-trihydroxy-1-phenazinecarboxylate

Systematic Name

English

1-PHENAZINECARBOXYLIC ACID, 6-FORMYL-4,7,9-TRIHYDROXY-, METHYL ESTER

Common Name

English

LOMOFUNGIN [USAN]

Common Name

English

Code System Code Type Description

CAS

26786-84-5