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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 .BETA.-APO-OXYTETRACYCLINE

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-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 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[Study of the mechanism of action of minocycline and of certain other tetracycline group compounds].
1976 Mar
Application of reversed-phase liquid chromatography and prepacked C18 cartridges for the analysis of oxytetracycline and related compounds.
1996 Mar 3
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 Aug 29
Determination of oxytetracycline and its degradation products by high-performance liquid chromatography-tandem mass spectrometry in manure-containing anaerobic test systems.
2003 Jan 5
Characterisation of the abiotic degradation pathways of oxytetracyclines in soil interstitial water using LC-MS-MS.
2003 Mar
Quantitative analysis of oxytetracycline and its impurities by LC-MS-MS.
2004 Feb 4
Tetracycline residues and tetracycline resistance genes in groundwater impacted by swine production facilities.
2006
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
Determination and fate of oxytetracycline and related compounds in oxytetracycline production wastewater and the receiving river.
2008 Jan
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
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
Patents

Patents

Sample Use Guides

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 Sat Dec 16 09:54:31 GMT 2023
Edited
by admin
on Sat Dec 16 09:54:31 GMT 2023
Record UNII
7HSY5812F9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.BETA.-APO-OXYTETRACYCLINE
Common Name English
.BETA.-APOOXYTETRACYCLINE
Common Name English
OXYTETRACYCLINE HYDROCHLORIDE IMPURITY E [EP IMPURITY]
Common Name English
.BETA.-APO-5-OXYTETRACYCLINE
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
Created by admin on Sat Dec 16 09:54:31 GMT 2023 , Edited by admin on Sat Dec 16 09:54:31 GMT 2023
PRIMARY
CAS
1361013-49-1
Created by admin on Sat Dec 16 09:54:31 GMT 2023 , Edited by admin on Sat Dec 16 09:54:31 GMT 2023
ALTERNATIVE
EPA CompTox
DTXSID601315222
Created by admin on Sat Dec 16 09:54:31 GMT 2023 , Edited by admin on Sat Dec 16 09:54:31 GMT 2023
PRIMARY
FDA UNII
7HSY5812F9
Created by admin on Sat Dec 16 09:54:31 GMT 2023 , Edited by admin on Sat Dec 16 09:54:31 GMT 2023
PRIMARY
PUBCHEM
54694061
Created by admin on Sat Dec 16 09:54:31 GMT 2023 , Edited by admin on Sat Dec 16 09:54:31 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
total of impurities D, E and F (eluting between the latter two): not more than the area of the peak due to impurity E in the chromatogram obtained with reference solution (g) (2.0 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP