NYSTATIN A1

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C47H75NO17
Molecular Weight	926.0949
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@@]([H])(O[C@@H]3O[C@H](C)[C@@H](O)[C@H](N)[C@@H]3O)\C=C\C=C\C=C\C=C\CC\C=C\C=C\[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]1C(O)=O)O2

InChI

InChIKey=VQOXZBDYSJBXMA-NQTDYLQESA-N

InChI=1S/C47H75NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33+,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C47H75NO17
Molecular Weight	926.0949
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	19 / 19
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB00646
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/14781786 | https://www.ncbi.nlm.nih.gov/pubmed/25082221 | https://www.ncbi.nlm.nih.gov/pubmed/27379602

Nystatin A1 is the one of the first member of important class of a macrocyclic polyene and poly-ol antibiotics isolated from Streptomyces noursei in 1950. Nystatin A1 binds to ergosterol, a major component of the fungal cell membrane. When present in sufficient concentrations, it forms pores in the membrane that lead to K+ leakage, acidification, and death of the fungus. Nystatin A1 is major component of Nystatin an important antifungal antibiotic, which for over half a century has been broadly used in medicine for the treatment of topical fungal infections caused by a broad spectrum of fungal pathogens comprising yeast-like and filamentous species.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Ergosterol 7 Target ID: CHEMBL2364028 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24924305	Binding Agent 1064		570.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Antimicrobial activity of Calotropis procera Ait. (Asclepiadaceae) and isolation of four flavonoid glycosides as the active constituents.	2013 Jul	23417281
Anthelmintic and antimicrobial activity of methanolic and aqueous extracts of Euphorbia helioscopia L.	2013 Mar	23065392
Otomycosis in the north of Iran: common pathogens and resistance to antifungal agents.	2014 May	23595615

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The minimal inhibitory concentration (MIC) was determined for C. albicans . Nystatin A1previously prepared in DMSO were diluted in the RPMI-1640 medium to give final concentration ranges of 0.03125–16 mkg/ml . Nystatin A1 MICs was from 0.5 mkg/ml for Candida albicans ATCC 10231.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:59:26 UTC 2023` Edited by `admin` on `Fri Dec 15 15:59:26 UTC 2023`
Record UNII	W1LX4T91WI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NYSTATIN A1

Common Name

English

NYSTATIN A1 [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C514