File:Tetracycline_skeletal.svg · Wikimedia Commons · See Wikimedia Commons
tetracycline
Sign in to saveAlso known as Achromycin, Tetracyn, Cyclopar, PanmycI dont careiquamycin, (4S,4AS,5as,12as)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide, Tetracyclin, Tetracyclinum, Deschlorobiomycin
Tetracycline, sold under various brand names, is an antibiotic in the tetracyclines family of medications, used to treat a number of infections, including acne, cholera, brucellosis, plague, malaria, and syphilis. It is available in oral and topical formulations.
OverviewAI-generated
Tetracycline is a chemical compound with the formula C₂₂H₂₄N₂O₈. It has a mass of 444.1533 and a weight of 444.4. The substance has a charge of 0 and an xlogp value of -2. Its structure includes 6 hydrogen bond donors and 9 hydrogen bond acceptors, with a topological polar surface area of 182.
The compound is identified by the InChIKey NWXMGUDVXFXRIG-WESIUVDSSA-N. It is associated with a PubMed query count of 88203. Additionally, tetracycline is referenced by 966 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C22H24N2O8
- Molecular weight
- 444.4 g/mol
- IUPAC name
- (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide
- SMILES
- C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
- InChIKey
- NWXMGUDVXFXRIG-WESIUVDSSA-N
- XLogP
- -2
- Polar surface area
- 182 Ų
- H-bond donors
- 6
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Research
88,203 papers- Re-establishing the utility of tetracycline-class antibiotics for current challenges with antibiotic resistance.ReviewAnnals of medicine · 2022LaPlante KL, Dhand A, Wright K et al.DOI: 10.1080/07853890.2022.2085881
- Sarecycline (Seysara) - another oral tetracycline for acne.ReviewThe Medical letter on drugs and therapeutics · 2019
- Nanomaterial-modified electrochemical aptasensors for tetracycline detection: a review.ReviewThe Analyst · 2025Huo J, Guo R, Yin J et al.DOI: 10.1039/d5an00097a
- 45 years of tetracycline post exposure prophylaxis for STIs and the risk of tetracycline resistance: a systematic review and meta-analysis.BMC infectious diseases · 2024Vanbaelen T, Manoharan-Basil SS, Kenyon CDOI: 10.1186/s12879-024-09275-3
- Tetracycline inhibition and the cellular source of collagenase in gingival crevicular fluid in different periodontal diseases. A review article.ReviewJournal of periodontology · 1993Ingman T, Sorsa T, Suomalainen K et al.DOI: 10.1902/jop.1993.64.2.82
- A tetracycline-binding RNA aptamer.Bioorganic & medicinal chemistry · 2001Berens C, Thain A, Schroeder RDOI: 10.1016/s0968-0896(01)00063-3
- Bioflavonoid Baicalein Modulates Tetracycline Resistance by Inhibiting Efflux Pump in Staphylococcus aureus.Microbial drug resistance (Larchmont, N.Y.) · 2024Moulick S, Roy DNDOI: 10.1089/mdr.2024.0099
- Plasmid-determined resistance to tetracycline.ReviewMicrobios · 1981Sompolinsky D, Samra Z
via PubMed
Wikidata facts
- Mass
- 444.1533
- Has use
- medication
Show 6 more facts
- chemical formula
- C₂₂H₂₄N₂O₈
- World Health Organisation international non-proprietary name
- tetracycline
- isomeric SMILES
- C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O
- Commons category
- Tetracycline
- canonical SMILES
- CN(C)C1C(=O)C(C(N)=O)=C(O)C2(O)C(=O)C3=C(O)c4c(O)cccc4C(C)(O)C3CC12
- significant drug interaction
- isotretinoin
Sources (3)
via Wikidata · CC0
~11 min read
Encyclopedic overview
18 sectionsContents
- Medical uses
- Spectrum of activity
- Anti-eukaryote use
- Use as a biomarker
- Side effects
- Pharmacology
- Mechanism of action
- Mechanisms of resistance
- History
- Discovery
- Evidence in antiquity
- Society and culture
- Economics
- Brand names
- Media
- Research
- Genetic engineering
- References
Tetracycline, sold under various brand names, is an antibiotic in the tetracyclines family of medications, used to treat a number of infections, including acne, cholera, brucellosis, plague, malaria, and syphilis. It is available in oral and topical formulations.
Common side effects include vomiting, diarrhea, rash, and loss of appetite. Other side effects include poor tooth development if used by children less than eight years of age, kidney problems, and sunburning easily. Use during pregnancy may harm the baby. It works by inhibiting protein synthesis in bacteria.
Excerpted from Wikipedia’s “tetracycline” article, available under the CC BY-SA 4.0 licence.