Oxytetracycline
S01A - Antiinfectives
ATC S01AA04
Small molecule
approved 1964
Oral
Parenteral
Topical
Natural product
🧬 Cross-allergy: Tetracyclines
JFDA label: TERRACORTRIL E/E SUSP
Mechanism of Action
Inhibitor of Bacterial 70S ribosome — Bacterial 70S ribosome inhibitor
| Target | Action | Gene / class |
|---|---|---|
| Bacterial 70S ribosome efficacy | INHIBITOR |
Indications
Approved
- Bacterial Infections — bacterial disease
- Eye Infections — eye infection
- Infections — infection
Off-label
- Acne Vulgaris
Pregnancy & Lactation
Lactation
Contraindicated
Hale L5
Although the manufacturer recommends avoiding breastfeeding during administration of oxytetracycline, short-term use of oxytetracycline is probably acceptable in nursing mothers.
LactMed: monitor the infant.
Chemistry & Properties
| Formula | C22H24N2O9 |
|---|---|
| Molecular weight | 460.44 g/mol |
| IUPAC name | (4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide |
| CAS | 79-57-2 |
| PubChem CID | 54675779 |
| InChIKey | IWVCMVBTMGNXQD-PXOLEDIWSA-N |
| logP | -1.24 (XLogP -1.6) |
| Polar surface area | 201.85 Ų |
| H-bond acceptors / donors | 10 / 7 |
| Drug-likeness (QED) | 0.26 |
| Lipinski violations | 1 |
SMILES
CN(C)[C@@H]1C(O)=C(C(N)=O)C(=O)[C@@]2(O)C(O)=C3C(=O)c4c(O)cccc4[C@@](C)(O)[C@H]3[C@H](O)[C@@H]12Biology & Pharmacokinetics
Pharmacokinetics
| BBB penetrant | No |
|---|
Transporters
BCRP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)OAT1 (Inhibitor)OAT2 (Inhibitor)OAT3 (Inhibitor)OAT4 (Inhibitor)OATP1B1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)OAT2 (Substrate)OAT3 (Substrate)OAT4 (Substrate)P-gp (Substrate)
Drug–drug interactions (100+, DDInter)
| Interacting drug | Severity | Management |
|---|---|---|
| Acitretin | major | |
| Isotretinoin | major | |
| Lomitapide | major | |
| Mipomersen | major | |
| Pexidartinib | major | |
| Tretinoin | major | |
| Typhoid vaccine (live) | major | |
| Vibrio cholerae CVD 103-HgR strain live antigen (live) | major | |
| Vitamin A | major | |
| Activated charcoal | moderate | |
| Aluminum hydroxide | moderate | |
| Aminolevulinic acid (topical) | moderate | |
| Aminophylline | moderate | |
| Amoxicillin | moderate | |
| Ampicillin | moderate | |
| Asparaginase Erwinia chrysanthemi | moderate | |
| Asparaginase Escherichia coli | moderate | |
| Atracurium | moderate | |
| Balsalazide | moderate | |
| Bedaquiline | moderate | |
| Benzylpenicillin | moderate | |
| Benzylpenicillin (potassium) | moderate | |
| Benzylpenicillin (sodium) | moderate | |
| Bismuth subgallate | moderate | |
| Bismuth subsalicylate | moderate | |
| Calaspargase pegol | moderate | |
| Calcium Phosphate | moderate | |
| Calcium acetate | moderate | |
| Calcium carbonate | moderate | |
| Calcium chloride | moderate | |
| Calcium citrate | moderate | |
| Calcium glubionate anhydrous | moderate | |
| Calcium glucoheptonate | moderate | |
| Calcium gluconate | moderate | |
| Calcium lactate | moderate | |
| Carbenicillin | moderate | |
| Cisatracurium | moderate | |
| Collagenase clostridium histolyticum | moderate | |
| Dicloxacillin | moderate | |
| Digoxin | moderate |
Showing 40 of 100+.
Registered Products (2)
| Brand | Form / strength | Pack | Agent | Citizen (JOD) |
|---|---|---|---|---|
| TERRACORTRIL E/E OINTMENT | Ointment 10 mg, 5 mg, 10000 IU | 3.5 g tube | Sabbagh Drug Store | 1.320 |
| TERRACORTRIL E/E SUSP | Suspension 5.7 mg, 11.400 IU, 17 mg | 5 ml | Sabbagh Drug Store | 1.350 |