Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H22N2O9.Ca |
| Molecular Weight | 498.496 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Ca++].[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=QJHKFWPAQRFQBG-IFLJXUKPSA-L
InChI=1S/C22H24N2O9.Ca/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);/q;+2/p-2/t12-,13-,14+,17+,21-,22+;/m1./s1
| Molecular Formula | Ca |
| Molecular Weight | 40.078 |
| Charge | 2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C22H22N2O9 |
| Molecular Weight | 458.4181 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363135 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | TERRAMYCIN W/ POLYMYXIN B SULFATE Approved UseTerramycin Ophthalmic Ointment with Polymyxin B Sulfate is indicated for the prophylaxis and local treatment of superficial ocular infections due to oxytetracycline- and polymyxin-sensitive organisms, including infections due to streptococci, rickettsiae, E. coli, and A. aerogenes, such as conjunctivitis, keratitis, pink eye, corneal ulcer, blepharitis in dogs, cats, cattle, sheep, and horses; ocular infections due to secondary bacterial complications of distemper in dogs, and bacterial inflammatory conditions which may occur secondary to other infectious diseases in the above species. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31185241/ |
250 mg/kg bw single, oral dose: 250 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
OXYTETRACYCLINE plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
90.72 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31185241/ |
250 mg/kg bw single, oral dose: 250 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
OXYTETRACYCLINE plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31185241/ |
250 mg/kg bw single, oral dose: 250 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
OXYTETRACYCLINE plasma | Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
Other AEs: Nausea, Diarrhoea... Other AEs: Nausea (grade 1-2, 15 patients) Sources: Diarrhoea (grade 1-2, 13 patients) Rash (grade 1-2, 1 patient) Lassitude (grade 1-2, 1 patient) Nausea (grade 3, 10 patients) Diarrhoea (grade 3, 5 patients) Nausea (grade 4, 1 patient) Diarrhoea (grade 4, 1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Lassitude | grade 1-2, 1 patient | 250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
| Rash | grade 1-2, 1 patient | 250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
| Diarrhoea | grade 1-2, 13 patients | 250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
| Nausea | grade 1-2, 15 patients | 250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
| Nausea | grade 3, 10 patients | 250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
| Diarrhoea | grade 3, 5 patients | 250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
| Diarrhoea | grade 4, 1 patient | 250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
| Nausea | grade 4, 1 patient | 250 mg 4 times / day steady, oral Recommended Dose: 250 mg, 4 times / day Route: oral Route: steady Dose: 250 mg, 4 times / day Sources: |
unhealthy, adult n = 369 Health Status: unhealthy Condition: cough and cold Age Group: adult Sex: unknown Population Size: 369 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening for new compounds with antiherpes activity. | 1984 Oct |
|
| Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
|
| Oxytetracycline-induced nephrotoxicosis in dogs after intravenous administration for experimental bone labeling. | 1996 Oct |
|
| Identification of HIV-1 integrase inhibitors via three-dimensional database searching using ASV and HIV-1 integrases as targets. | 2000 Oct |
|
| Human organic anion transporters mediate the transport of tetracycline. | 2002 Jan |
|
| In vitro effects of oxytetracycline on matrix metalloproteinase-1 mRNA expression and on collagen gel contraction by cultured myofibroblasts obtained from the accessory ligament of foals. | 2004 Apr |
|
| Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010 Jul |
|
| Impact of isoflupredone acetate treatment on clinical signs and weight gain in weanling heifers with experimentally induced Mannheimia haemolytica bronchopneumonia. | 2011 Dec |
|
| Environmental impact on vascular development predicted by high-throughput screening. | 2011 Nov |
Patents
Sample Use Guides
For Animal Use Only: topically to the eye 2–4 times daily.
Route of Administration:
Other
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
Created
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Edited
Sat Dec 16 09:10:51 GMT 2023
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Sat Dec 16 09:10:51 GMT 2023
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| Record UNII |
M90SJ24J2X
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| Record Status |
Validated (UNII)
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| Record Version |
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