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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24N2O9
Molecular Weight 460.434
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYTETRACYCLINE ANHYDROUS

SMILES

[H][C@@]12[C@@H](O)[C@@]3([H])C(C(=O)C4=C(O)C=CC=C4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C

InChI

InChIKey=IWVCMVBTMGNXQD-PXOLEDIWSA-N
InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H24N2O9
Molecular Weight 460.434
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Oxytetracycline, a tetracycline analog isolated from the actinomycete streptomyces rimosus, was the second of the broad-spectrum tetracycline group of antibiotics to be discovered The drug is used for the prophylaxis and local treatment of superficial ocular infections due to oxytetracycline- and polymyxin-sensitive organisms for animal use only. These infections include the following: Ocular infections due to streptococci, rickettsiae E. coli, and A. aerogenes (such as conjunctivitis, keratitis, pinkeye, corneal ulcer, and blepharitis in dogs); ocular infections due to secondary bacterial complications associated with distemper in dogs; and ocular infections due to bacterial inflammatory conditions which may occur secondary to other diseases in dogs. Allergic reactions may occasionally occur. Treatment should be discontinued if reactions are severe. If new infections due to nonsensitive bacteria or fungi appear during therapy, appropriate measures should be taken. Oxytetracycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Oxytetracycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TERRAMYCIN W/ POLYMYXIN B SULFATE

Cmax

ValueDoseCo-administeredAnalytePopulation
15 μg/mL
250 mg/kg bw single, oral
OXYTETRACYCLINE plasma
Oryctolagus cuniculus

AUC

ValueDoseCo-administeredAnalytePopulation
90.72 μg × h/mL
250 mg/kg bw single, oral
OXYTETRACYCLINE plasma
Oryctolagus cuniculus

T1/2

ValueDoseCo-administeredAnalytePopulation
2.46 h
250 mg/kg bw single, oral
OXYTETRACYCLINE plasma
Oryctolagus cuniculus

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
For Animal Use Only: topically to the eye 2–4 times daily.
Route of Administration: Other
In Vitro Use Guide
It was investigated the possible toxic mechanism of oxytetracycline (OTC) on the human red blood cells (hRBCs). The experimental results indicate that OTC can cause a decline in the function of the antioxidant defense system of hRBCs, resulting in oxidative stress. OTC can bring about morphological changes to hRBCs, and further leads to hemolysis, when the concentration of OTC is over 8×10(-5) M (about 164 µg/ml). At a low OTC concentration, below 4×10(-5) M (82 µg/ml), OTC can enhance the activity of ATP enzyme of hRBCs, known as hormesis. However, at a high concentration, above 4×10(-5) M (about 82 µg/ml), the ATP enzymatic activity was inhibited, affecting the function of hRBCs.
Substance Class Chemical
Record UNII
SLF0D9077S
Record Status Validated (UNII)
Record Version