AZAERYTHROMYCIN A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C37H70N2O12
Molecular Weight	734.9579
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@](C)(O)C[C@@H](C)CN[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]2C

InChI

InChIKey=HRKNNHYKWGYTEN-HOQMJRDDSA-N

InChI=1S/C37H70N2O12/c1-14-26-37(10,45)30(41)23(6)38-18-19(2)16-35(8,44)32(51-34-28(40)25(39(11)12)15-20(3)47-34)21(4)29(22(5)33(43)49-26)50-27-17-36(9,46-13)31(42)24(7)48-27/h19-32,34,38,40-42,44-45H,14-18H2,1-13H3/t19-,20-,21+,22-,23-,24+,25+,26-,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C37H70N2O12
Molecular Weight	734.9579
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	18 / 18
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.scbt.com/scbt/product/9-deoxo-9a-aza-9a-homo-erythromycin-a-desmethyl-azithromycin-76801-85-9

Azaerythromycin A is a novel intermediate of Azithromycin which acts as an antibiotic. Azithromycin binds to the 50S subunit of the bacterial ribosome, and thus inhibits translation of mRNA.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial 70S ribosome 179 Target ID: CHEMBL2363135 Sources: https://www.medchemexpress.com/Azathramycin.html \| https://www.ncbi.nlm.nih.gov/pubmed/21428405	Inhibitor 8297
Toxoplasma gondii 10 Target ID: CHEMBL612888 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21428405	Inhibitor 8297		65.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Toxoplasmosis 12 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21428405	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Quantitative thin-layer chromatographic method of analysis of azithromycin in pure and capsule forms.	2003 Jan	12597590
Chemistry and biology of macrolide antiparasitic agents.	2011 Apr 28	21428405
Stress degradation studies on azithromycin and development of a validated stability-indicating TLC-densitometric method with HPLC/electrospray ionization-MS analysis of degradation products.	2012 Sep-Oct	23175975
Factors Influencing the HPLC Determination for Related Substances of Azithromycin.	2016 Feb	26324196

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Azaerythromycin A inhibited Toxoplasma gondii with IC50 65 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:50:08 UTC 2023` Edited by `admin` on `Sat Dec 16 05:50:08 UTC 2023`
Record UNII	4LSP9FJT5B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZAERYTHROMYCIN A

Common Name

English

AZATHRAMYCIN

Common Name

English

AZAERYTHROMYCIN A [USP-RS]

Common Name

English

9-DEOXO-9A-AZA-9A-HOMOERYTHROMYCIN A

Common Name

English

6-DEMETHYLAZITHROMYCIN

Common Name

English

AZITHROMYCIN IMPURITY A [EP IMPURITY]

Common Name

English

Code System Code Type Description

PUBCHEM

9810601