.BETA.-APO-OXYTETRACYCLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H22N2O8
Molecular Weight	442.4187
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)[C@H]1[C@H]([C@H]2OC(=O)C3=C(O)C4=C(C=CC=C4O)C(C)=C23)[C@@H](O)C(=O)C(C(N)=O)=C1O

InChI

InChIKey=DRKMHDAKULCOKQ-VPZFNDQJSA-N

InChI=1S/C22H22N2O8/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)20(32-22(12)31)13-15(24(2)3)17(27)14(21(23)30)19(29)18(13)28/h4-6,13,15,18,20,25-28H,1-3H3,(H2,23,30)/t13-,15-,18+,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H22N2O8
Molecular Weight	442.4187
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25892782 | https://www.ncbi.nlm.nih.gov/pubmed/19932817

beta-apo-Oxytetracycline is the degradation product of Oxytetracycline. It exhibits greater toxicity compared with the parent compound. The toxic effects of beta-apo-Oxytetracycline treatment could damage liver and kidney tissues of rats, as well as lead to the degeneration and necrosis in the hepatocytes.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
The degradation of oxytetracycline during thermal treatments of chicken and pig meat and the toxic effects of degradation products of oxytetracycline on rats.	2015-05	25892782
A liquid chromatography-tandem mass spectrometry confirmatory assay for the simultaneous determination of several tetracyclines in milk considering keto-enol tautomerism and epimerization phenomena.	2009-12-10	19932817
Determination and fate of oxytetracycline and related compounds in oxytetracycline production wastewater and the receiving river.	2008-01	18092864
C(18) columns for the simultaneous determination of oxytetracycline and its related substances by reversed-phase high performance liquid chromatography and UV detection.	2007-01-17	16989968
Tetracycline residues and tetracycline resistance genes in groundwater impacted by swine production facilities.	2006	17127527
Quantitative analysis of oxytetracycline and its impurities by LC-MS-MS.	2004-02-04	15013146
Susceptibility of Escherichia coli and Enterococcus faecium isolated from pigs and broiler chickens to tetracycline degradation products and distribution of tetracycline resistance determinants in E. coli from food animals.	2003-08-29	12860079
Characterisation of the abiotic degradation pathways of oxytetracyclines in soil interstitial water using LC-MS-MS.	2003-03	12586164
Determination of oxytetracycline and its degradation products by high-performance liquid chromatography-tandem mass spectrometry in manure-containing anaerobic test systems.	2003-01-05	12450520
Application of reversed-phase liquid chromatography and prepacked C18 cartridges for the analysis of oxytetracycline and related compounds.	1996-03-03	8704932
[Study of the mechanism of action of minocycline and of certain other tetracycline group compounds].	1976-03	776077

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 10 mg/kg body weight/day, 90 days

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:54:14 GMT 2025` Edited by `admin` on `Mon Mar 31 22:54:14 GMT 2025`
Record UNII	7HSY5812F9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

.BETA.-APO-5-OXYTETRACYCLINE

Preferred Name

English

.BETA.-APO-OXYTETRACYCLINE

Common Name

English

.BETA.-APOOXYTETRACYCLINE

Common Name

English

OXYTETRACYCLINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]

Common Name

English

(3S,4S,5R)-4-((1R)-4,5-DIHYDROXY-9-METHYL-3-OXO-1,3-DIHYDRONAPHTHO(2,3-C)FURAN-1-YL)-3-(DIMETHYLAMINO)-2,5-DIHYDROXY-6-OXOCYCLOHEX-1-ENECARBOXAMIDE

Systematic Name

English

APOOXYTETRACYCLINE, .BETA.

Common Name

English

1-CYCLOHEXENE-1-CARBOXAMIDE, 4-((1R)-1,3-DIHYDRO-4,5-DIHYDROXY-9-METHYL-3-OXONAPHTHO(2,3-C)FURAN-1-YL)-3-(DIMETHYLAMINO)-2,5-DIHYDROXY-6-OXO-, (3S,4S,5R)-

Systematic Name

English

.BETA.-APOTERRAMYCIN

Common Name

English

Code System Code Type Description

CAS

18751-99-0