tetracycline   Click here for help

GtoPdb Ligand ID: 10927

Synonyms: achromycin | Ala-Tet® | Brodspec® | NSC-108579 | Panmycin® | Sumycin® | TCN
Approved drug
tetracycline is an approved drug (FDA (1953), UK (2001))
Compound class: Synthetic organic
Comment: Tetracycline is a long-used oral antibacterial. It has broad spectrum activity against aerobic and anaerobic bacteria, both Gram-negative and Gram-positive. Pseudomonas aeruginosa and Proteus spp. have natural resistance to tetracyclines. Acquired resistance to tetracycline is now commonplace.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 2
Topological polar surface area 181.62
Molecular weight 444.15
XLogP 0.26
No. Lipinski's rules broken 1
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Canonical SMILES CN([C@@H]1C(=O)C(=C([C@@]2([C@H]1C[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]1C[C@H]1C(=C(O)c3c([C@@]1(C)O)cccc3O)C2=O)O)O)C(=O)N)C
InChI InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,29,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1953), UK (2001))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Prodrug rolitetracycline
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
298 tetracycline
Synonyms Click here for help
achromycin | Ala-Tet® | Brodspec® | NSC-108579 | Panmycin® | Sumycin® | TCN
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Tetracycline
Other databases
BindingDB Ligand 50237605
CAS Registry No. 60-54-8 (source: WHO INN record)
ChEMBL Ligand ChEMBL1440
DrugBank Ligand DB00759
GtoPdb PubChem SID 405560368
PubChem CID 54675776
Search Google for chemical match using the InChIKey NWXMGUDVXFXRIG-WESIUVDSSA-N
Search Google for chemicals with the same backbone NWXMGUDVXFXRIG
Search PubMed clinical trials tetracycline
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Search PubMed titles/abstracts tetracycline
UniChem Compound Search for chemical match using the InChIKey NWXMGUDVXFXRIG-WESIUVDSSA-N
UniChem Connectivity Search for chemical match using the InChIKey NWXMGUDVXFXRIG-WESIUVDSSA-N