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

Molecular Formula	C15H10N2O6
Molecular Weight	314.2497
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/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 8297	6.7 µM [Ki]
CUG(exp) RNA 1 Target ID: CUG(exp) RNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/24799433	Inhibitor 8297
Bacterial DNA-directed RNA polymerase 11 Target ID: CHEMBL2364672 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4790624	Inhibitor 8297

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 151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26141568	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Lomofungin, a new broad spectrum antibiotic. Isolation and characterization.	1969 Mar	5789900
Lomofungin, a new antibiotic produced by Streptomyces lomondensis sp. n.	1969 May	5785961
Lomofungin, an inhibitor of ribonucleic acid synthesis in yeast protoplasts: its effect on enzyme formation.	1973 Jun	4790623
Chelation of divalent cations by lomofungin: role in inhibition of nucleic acid synthesis.	1974 Oct 8	4215422
Lomofungin inhibition of allophanate hydrolase synthesis in Saccharomyces cerevisiae.	1975	1102915

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:16:57 GMT 2023` Edited by `admin` on `Fri Dec 15 15:16:57 GMT 2023`
Record UNII	Z6Z18X1Y4D
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

LOMOFUNGIN

Official 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

NSC-156939

Code

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