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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 .ALPHA.-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-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

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Characterisation of the abiotic degradation pathways of oxytetracyclines in soil interstitial water using LC-MS-MS.
2003 Mar
Determination and fate of oxytetracycline and related compounds in oxytetracycline production wastewater and the receiving river.
2008 Jan
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 09:46:24 UTC 2023
Edited
by admin
on Sat Dec 16 09:46:24 UTC 2023
Record UNII
H4GV157YJQ
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Sat Dec 16 09:46:24 UTC 2023 , Edited by admin on Sat Dec 16 09:46:24 UTC 2023
PRIMARY
CAS
1361013-47-9
Created by admin on Sat Dec 16 09:46:24 UTC 2023 , Edited by admin on Sat Dec 16 09:46:24 UTC 2023
ALTERNATIVE
EPA CompTox
DTXSID40940158
Created by admin on Sat Dec 16 09:46:24 UTC 2023 , Edited by admin on Sat Dec 16 09:46:24 UTC 2023
PRIMARY
FDA UNII
H4GV157YJQ
Created by admin on Sat Dec 16 09:46:24 UTC 2023 , Edited by admin on Sat Dec 16 09:46:24 UTC 2023
PRIMARY
CAS
18695-01-7
Created by admin on Sat Dec 16 09:46:24 UTC 2023 , Edited by admin on Sat Dec 16 09:46:24 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