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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
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
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
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 UTC 2023
Edited
by admin
on Sat Dec 16 09:54:31 UTC 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 UTC 2023 , Edited by admin on Sat Dec 16 09:54:31 UTC 2023
PRIMARY
CAS
1361013-49-1
Created by admin on Sat Dec 16 09:54:31 UTC 2023 , Edited by admin on Sat Dec 16 09:54:31 UTC 2023
ALTERNATIVE
EPA CompTox
DTXSID601315222
Created by admin on Sat Dec 16 09:54:31 UTC 2023 , Edited by admin on Sat Dec 16 09:54:31 UTC 2023
PRIMARY
FDA UNII
7HSY5812F9
Created by admin on Sat Dec 16 09:54:31 UTC 2023 , Edited by admin on Sat Dec 16 09:54:31 UTC 2023
PRIMARY
PUBCHEM
54694061
Created by admin on Sat Dec 16 09:54:31 UTC 2023 , Edited by admin on Sat Dec 16 09:54:31 UTC 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