oxytetracycline   Click here for help

GtoPdb Ligand ID: 10919

Synonyms: E703 | NSC-9169 | Terramycin®
Approved drug PDB Ligand
oxytetracycline is an approved drug (FDA (1964), UK (2011))
Compound class: Synthetic organic
Comment: Oxytetracycline is a tetracycline class antibiotic. It has activity against Gram-positive and -negative bacteria, including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae, and Diplococcus pneumoniae.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 7
Rotatable bonds 2
Topological polar surface area 201.85
Molecular weight 460.15
XLogP -0.77
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1[C@@H](O)[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
Isomeric SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1[C@@H](O)[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
InChI 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/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1
InChI Key OWFJMIVZYSDULZ-PXOLEDIWSA-N
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Summary of Clinical Use Click here for help
Use in the US has been discontinued. In the UK, oxytetracycline monotherapy is indicated for respiratory tract infections, urinary tract infections, sexually transmitted diseases (Chlamydia and non-gonococcal urethritis caused by Ureaplasma urealyticum), ophthalmic infections, Rickettsial infections, plus others. It can be used as an alternative drug in the treatment of leptospirosis, gas-gangrene and tetanus. oxytetracycline is also available in fixed-dose combinations with anti-inflammatory agents- Terra-Cortril® (hydrocortisone + oxytetracycline), Trimovate® (clobetasone + nystatin + oxytetracycline).
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