oxytetracycline

Also known as Hi-Tet, Microtet, Tetraplex, OXTC, Terramycin, Oxytetracycline amphoteric, Oxyterracin, Oxyterracine

Oxytetracycline is a broad-spectrum tetracycline antibiotic, the second of the group to be discovered.

Key facts

Drug.pregnancy_AU: D
Drug.verifiedrevid: 464196886
Drug.IUPAC_name: (4S,4aR,5S,5aR,6S,12aS)-4-(Dimethylamino)-3,5,6,10,11,12a-hexahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide
Drug.image: Oxytetracycline.svg
Drug.image_class: skin-invert-image
Drug.image2: Oxytetracycline-from-xtal-Mercury-3D-balls.png
Drug.image_class2: bg-transparent
Drug.tradename: Terramycin
Drug.legal_status: Rx-only
Drug.routes_of_administration: By mouth, topical (eye drop)
Drug.ATC_prefix: D06
Drug.ATC_suffix: AA03
Drug.ATC_supplemental: , , , , ,
Drug.elimination_half life: 6–8 hours
Drug.excretion: Kidney
Drug.CAS_number: 79-57-2
Drug.PubChem: 54675779
Drug.DrugBank: DB00595

via Wikipedia infobox

Chemical data

Formula: C22H24N2O9
Molecular weight: 460.4 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
SMILES: C[C@@]1([C@H]2[C@@H]([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)O
InChIKey: OWFJMIVZYSDULZ-PXOLEDIWSA-N
XLogP: -1.6
Polar surface area: 202 Å²
H-bond donors: 7
H-bond acceptors: 10
Formal charge: 0

via PubChem

Research

10,585 papers

Oxytetracycline.Journal of the American Pharmaceutical Association · 1975
Oxytetracycline.The Practitioner · 1956
OXYTETRACYCLINE (terramycin).Tubercle · 1955
[Oxytetracycline--mechanism of action and application in skin diseases].Wiadomosci lekarskie (Warsaw, Poland : 1960) · 2006
[Oxytetracycline].Therapie · 1958

via PubMed

Wikidata facts

Mass: 460.1482
Has use: medication

Show 7 more facts

chemical formula: C₂₂H₂₄N₂O₉
World Health Organisation international non-proprietary name: oxytetracycline
Commons category: Oxytetracycline
isomeric SMILES: C[C@]1(C2=CC=CC(=C2C(=O)C3=C([C@]4([C@@H]([C@H]([C@@H]31)O)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O
canonical SMILES: CC1(C2=CC=CC(=C2C(=O)C3=C(C4(C(C(C31)O)C(C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O
MCN code: 2941.30.20
significant drug interaction: isotretinoin

Sources (7)

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Encyclopedic overview

6 sections

Contents

Medical uses
Side effects
History
Biosynthesis
Veterinary indications
References

Oxytetracycline is a broad-spectrum tetracycline antibiotic, the second of the group to be discovered.

Oxytetracycline works by interfering with the ability of bacteria to produce essential proteins. Without these proteins, the bacteria cannot grow, multiply and increase in numbers. Oxytetracycline therefore stops the spread of the infection, and the remaining bacteria are killed by the immune system or eventually die.

Excerpted from Wikipedia’s “oxytetracycline” article, available under the CC BY-SA 4.0 licence.