CHEBI:27902 - tetracycline

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ChEBI Name tetracycline
ChEBI ID CHEBI:27902
Definition A broad-spectrum polyketide antibiotic produced by the Streptomyces genus of actinobacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:45729, CHEBI:9474, CHEBI:26894
Supplier Information ChemicalBook:CB6153810, eMolecules:35862322, eMolecules:532008, ZINC000084441937
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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. Tetracycline was patented in 1953 and was approved for prescription use in 1954. It is on the World Health Organization's List of Essential Medicines. Tetracycline is available as a generic medication. Tetracycline was originally made from bacteria of the genus Streptomyces.
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Formula C22H24N2O8
Net Charge 0
Average Mass 444.43460
Monoisotopic Mass 444.15327
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/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1
InChIKey OFVLGDICTFRJMM-WESIUVDSSA-N
SMILES [H][C@@]12C[C@@]3([H])C(C(=O)c4c(O)cccc4[C@@]3(C)O)=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial drug
A drug used to treat or prevent bacterial infections.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
protein synthesis inhibitor
A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via tetracyclines )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
antiprotozoal drug
Any antimicrobial drug which is used to treat or prevent protozoal infections.
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ChEBI Ontology
Outgoing tetracycline (CHEBI:27902) has role Escherichia coli metabolite (CHEBI:76971)
tetracycline (CHEBI:27902) has role antibacterial drug (CHEBI:36047)
tetracycline (CHEBI:27902) has role antimicrobial agent (CHEBI:33281)
tetracycline (CHEBI:27902) has role antiprotozoal drug (CHEBI:35820)
tetracycline (CHEBI:27902) has role protein synthesis inhibitor (CHEBI:48001)
tetracycline (CHEBI:27902) is a tertiary α-hydroxy ketone (CHEBI:139592)
tetracycline (CHEBI:27902) is a tetracyclines (CHEBI:26895)
tetracycline (CHEBI:27902) is tautomer of tetracycline zwitterion (CHEBI:77932)
Incoming 11a-hydroxytetracycline (CHEBI:134017) has functional parent tetracycline (CHEBI:27902)
tetracycline zwitterion (CHEBI:77932) is tautomer of tetracycline (CHEBI:27902)
IUPAC Name
(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide
INNs Sources
tetracycline ChemIDplus
tetracyclinum ChemIDplus
Synonyms Sources
(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 ChemIDplus
Abramycin ChemIDplus
Achromycin ChEBI
Anhydrotetracycline DrugBank
Deschlorobiomycin ChemIDplus
Liquamycin ChemIDplus
Tetracyclin ChEBI
Tetracycline KEGG COMPOUND
TETRACYCLINE PDBeChem
tétracycline ChEBI
Tetrazyklin ChEBI
Tsiklomitsin ChemIDplus
Manual Xrefs Databases
1739 VSDB
2611 DrugCentral
C06570 KEGG COMPOUND
CPD0-1414 MetaCyc
D00201 KEGG DRUG
DB00759 DrugBank
TAC PDBeChem
Tetracycline Wikipedia
US2699054 Patent
US2712517 Patent
US2886595 Patent
US3005023 Patent
US3019173 Patent
US3301899 Patent
View more database links
Registry Numbers Types Sources
1103368 Gmelin Registry Number Gmelin
2230417 Reaxys Registry Number Reaxys
60-54-8 CAS Registry Number ChemIDplus
Citations
Cronan JE (2016)
pBR322 vectors having tetracycline-dependent replication.
Plasmid 84-85, 20-26 [PubMed:26876942]
[show Abstract]
Huang X, Zhang X, Feng F, Xu X (2016)
Biodegradation of tetracycline by the yeast strain Trichosporon mycotoxinivorans XPY-10.
Preparative biochemistry & biotechnology 46, 15-22 [PubMed:25286144]
[show Abstract]
Antony B, Thomas S, Chandrashekar SC, Kumar MS, Kumar V (2009)
Osteomyelitis of the mandible due to Aggregatibacter (Actinobacillus) actinomycetemcomitans.
Indian journal of pathology & microbiology 52, 115-116 [PubMed:19136803]
[show Abstract]
Aleksandrov A, Simonson T (2008)
Binding of tetracyclines to elongation factor Tu, the Tet repressor, and the ribosome: a molecular dynamics simulation study.
Biochemistry 47, 13594-13603 [PubMed:19032078]
[show Abstract]
Farombi EO, Ugwuezunmba MC, Ezenwadu TT, Oyeyemi MO, Ekor M (2008)
Tetracycline-induced reproductive toxicity in male rats: effects of vitamin C and N-acetylcysteine.
Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 60, 77-85 [PubMed:18406588]
[show Abstract]
Adişen E, Kaymak Y, Gurer MA, Durukan E (2008)
Topical tetracycline in the treatment of acne vulgaris.
Journal of drugs in dermatology : JDD 7, 953-955 [PubMed:19112759]
[show Abstract]
Kulik EM, Lenkeit K, Chenaux S, Meyer J (2008)
Antimicrobial susceptibility of periodontopathogenic bacteria.
The Journal of antimicrobial chemotherapy 61, 1087-1091 [PubMed:18326855]
[show Abstract]
Charlat S, Davies N, Roderick GK, Hurst GD (2007)
Disrupting the timing of Wolbachia-induced male-killing.
Biology letters 3, 154-156 [PubMed:17251127]
[show Abstract]
Cham G, Pan JC, Lim F, Earnest A, Gopalakrishnakone P (2006)
Effects of topical heparin, antivenom, tetracycline and dexamethasone treatment in corneal injury resulting from the venom of the black spitting cobra (Naja sumatrana), in a rabbit model.
Clinical toxicology (Philadelphia, Pa.) 44, 287-292 [PubMed:16749547]
[show Abstract]
Nublat C, Braud C, Garreau H, Vert M (2006)
Ammonium bicarbonate as porogen to make tetracycline-loaded porous bioresorbable membranes for dental guided tissue regeneration: failure due to tetracycline instability.
Journal of biomaterials science. Polymer edition 17, 1333-1346 [PubMed:17260506]
[show Abstract]
Sapadin AN, Fleischmajer R (2006)
Tetracyclines: nonantibiotic properties and their clinical implications.
Journal of the American Academy of Dermatology 54, 258-265 [PubMed:16443056]
[show Abstract]
de Jong CE, Jonsson N, Field H, Smith C, Crichton EG, Phillips N, Johnston SD (2005)
Collection, seminal characteristics and chilled storage of spermatozoa from three species of free-range flying fox (Pteropus spp.).
Theriogenology 64, 1072-1089 [PubMed:15913752]
[show Abstract]
Domingues ZR, Cortés ME, Gomes TA, Diniz HF, Freitas CS, Gomes JB, Faria AM, Sinisterra RD (2004)
Bioactive glass as a drug delivery system of tetracycline and tetracycline associated with beta-cyclodextrin.
Biomaterials 25, 327-333 [PubMed:14585720]
[show Abstract]
Zou MX, Xia ZD, Liang XH (2003)
[Antibiotic susceptibility of Neisseria gonorrhoeae epidemic strains in Changsha].
Hunan yi ke da xue xue bao = Hunan yike daxue xuebao = Bulletin of Hunan Medical University 28, 53-55 [PubMed:12934399]
[show Abstract]
Simkovicová M, Hanzen J, Milosovic P, Lisalová M (2001)
[Coagulase negative staphylococci isolated on blood cultures].
Epidemiologie, mikrobiologie, imunologie : casopis Spolecnosti pro epidemiologii a mikrobiologii Ceske lekarske spolecnosti J.E. Purkyne 50, 117-120 [PubMed:11550419]
[show Abstract]
Orrett FA, Shurland SM (2001)
Susceptibility patterns and serotypes of non-typhoidal salmonella in Trinidad.
Saudi medical journal 22, 852-855 [PubMed:11744940]
[show Abstract]
Bondi M, Messi P, Guerrieri E, Bitonte F (2000)
Virulence profiles and other biological characters in water isolated Aeromonas hydrophila.
The new microbiologica 23, 347-356 [PubMed:11061623]
[show Abstract]
Varga JM, Kalchschmid G, Klein GF, Fritsch P (1991)
Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody.
Molecular immunology 28, 641-654 [PubMed:1650428]
[show Abstract]
Wilkins TD, Smith LD (1974)
Chemotherapy of an experimental Fusobacterium (Sphaerophorus) necrophorum infection in mice.
Antimicrobial agents and chemotherapy 5, 658-662 [PubMed:15825421]
[show Abstract]
Last Modified
19 September 2018