.ALPHA.-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 of .ALPHA.-APO-OXYTETRACYCLINE

Structure Search

SMILES

[H][C@@]1(OC(=O)C2=C(O)C3=C(O)C=CC=C3C(C)=C12)[C@]4([H])[C@H](O)C(=O)C(C(N)=O)=C(O)[C@H]4N(C)C

InChI

InChIKey=DRKMHDAKULCOKQ-MLZJRGSSSA-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

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

alpha-apo-Oxytetracycline is the degradation product of Oxytetracycline. It exhibits greater toxicity compared with the parent compound. No significant differences in body weight were observed between rats in the control group and those in the group treated with alpha-apo-Oxytetracycline. No differences in hematological analyses were observed between rats in the control group and those in the group treated with alpha-apo-Oxytetracycline.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Application of reversed-phase liquid chromatography and prepacked C18 cartridges for the analysis of oxytetracycline and related compounds.	1996 Mar 3	8704932
Determination of oxytetracycline and its degradation products by high-performance liquid chromatography-tandem mass spectrometry in manure-containing anaerobic test systems.	2003 Jan 5	12450520
Characterisation of the abiotic degradation pathways of oxytetracyclines in soil interstitial water using LC-MS-MS.	2003 Mar	12586164
Quantitative analysis of oxytetracycline and its impurities by LC-MS-MS.	2004 Feb 4	15013146
C(18) columns for the simultaneous determination of oxytetracycline and its related substances by reversed-phase high performance liquid chromatography and UV detection.	2007 Jan 17	16989968
Determination and fate of oxytetracycline and related compounds in oxytetracycline production wastewater and the receiving river.	2008 Jan	18092864
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 Dec 10	19932817
The degradation of oxytetracycline during thermal treatments of chicken and pig meat and the toxic effects of degradation products of oxytetracycline on rats.	2015 May	25892782

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

Name

Type

Language

.ALPHA.-APO-OXYTETRACYCLINE

Common Name

English

.ALPHA.-APOTERRAMYCIN

Common Name

English

OXYTETRACYCLINE HYDROCHLORIDE IMPURITY D [EP IMPURITY]

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,5S)-

Systematic Name

English

.ALPHA.-APOOXYTETRACYCLINE

Common Name

English

APOOXYTETRACYCLINE, .ALPHA.

Common Name

English

(3S,4S,5S)-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

Code System Code Type Description

PUBCHEM

76971536