Oxytetracycline

Overview

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

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. WP

Oxytetracycline is active against a wide variety of bacteria. However, some strains of bacteria have developed resistance to this antibiotic, which has reduced its effectiveness for treating some types of infections. WP

Oxytetracycline is used to treat infections caused by Chlamydia, such as psittacosis, trachoma, and urethritis, and infections caused by Mycoplasma organisms, such as pneumonia. WP

Oxytetracycline is used to treat acne, due to its activity against the bacteria on the skin that influence the development of acne (Cutibacterium acnes). It is used to treat flare-ups of chronic bronchitis, due to its activity against Haemophilus influenzae. Oxytetracycline may be used to treat other rarer infections, such as those caused by a group of microorganisms called rickettsiae (e.g., Rocky Mountain spotted fever). To make sure the bacteria causing an infection are susceptible to it, a tissue sample is usually taken; for example, a swab from the infected area or a urine or blood sample. WP⚠ Wikipedia itself has flagged this text: citation needed.

Oxytetracycline was patented in 1949 and came into commercial use in 1950. It is on the World Health Organization's List of Essential Medicines as an alternative to tetracycline.[1][2] WP

Uses, dosage and effects

Medical uses

Oxytetracycline, like other tetracyclines, is used to treat many infections, both common and rare. Its better absorption profile makes it preferable to tetracycline for moderately severe acne at a dosage of 250–500 mg four times a day for usually six to eight weeks at a time, but alternatives should be sought if no improvement occurs by three months.[3] WP

It is sometimes used to treat spirochaetal infections, clostridial wound infection, and anthrax in patients sensitive to penicillin. Oxytetracycline is used to treat infections of the respiratory and urinary tracts, skin, ear, eye and gonorrhoea, although its use for such purposes has declined in recent years due to large increases in bacterial resistance to this class of drugs. The drug is particularly useful when penicillins and/or macrolides cannot be used due to allergy. It may be used to treat Legionnaires' disease as a substitute for a macrolide or quinolones. WP

Oxytetracycline is especially valuable in treating nonspecific urethritis, Lyme disease, brucellosis, cholera, typhus, tularaemia, and infections caused by Chlamydia, Mycoplasma, and Rickettsia. Doxycycline is now preferred to oxytetracycline for many of these indications because it has improved pharmacologic features. WP⚠ Wikipedia itself has flagged this text: clarification needed.

The standard dose is 250 to 500 mg every six hours by mouth. In particularly severe infections, this dose may be increased accordingly. Occasionally, oxytetracycline is given by intramuscular injection or topically in the form of creams, ophthalmic ointments, or eye drops. WP

Risks and side effects

Side effects

Side effects are mainly gastrointestinal and photosensitive allergic reactions common to the tetracycline antibiotics group. It can damage calcium-rich organs, such as teeth and bones, although this is very rare. It sometimes causes nasal cavities to erode; because of this, tetracyclines should not be used to treat pregnant or lactating women and children under age twelve except in certain conditions where it has been approved by a specialist because there are no obvious substitutes. Candidiasis (thrush) is not uncommon following treatment with broad-spectrum antibiotics. WP⚠ Wikipedia itself has flagged this text: citation needed.

History

History

It was first found near Pfizer laboratories in a soil sample yielding the thennew actinomycete Streptomyces rimosus by Finlay et al. In 1950, a group at Pfizer led by Francis A. Hochstein, working in a loose collaboration with the Harvard organic chemist Robert B. Woodward, worked out the chemical structure of oxytetracycline, enabling Pfizer to mass-produce the drug under the trade name Terramycin. This discovery was a major advancement in tetracycline research and paved the way for the discovery of an oxytetracycline derivative, doxycycline, which is one of the most popularly used antibiotics today.[4][5][6] WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.

Chemistry

Formula

C22H24N2O9 PC

Molar mass (g/mol)

460.4 PC

IUPAC name (computed by PubChem)

(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 PC

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 PC

InChIKey

OWFJMIVZYSDULZ-PXOLEDIWSA-N PC

PubChem CID

54675779

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006
2. Other World Health Organization model list of essential medicines: 22nd list (2021). 2021
3. Other British National Formulary 45 March 2003
4. Other Finlay, A. C., and others: Terramycin, a New Antibiotic, Science 111: 85 (27 January 1950)
5. Journal / agency Melcher GW, Gibson CD, Rose HM, Kneeland Y. Terramycin in the treatment of pneumococcic and primary atypical pneumonia. Journal of the American Medical Association. August 1950. doi:10.1001/jama.1950.02910500005002 · PMID 15428258
6. Journal / agency Pickens LB, Tang Y. Oxytetracycline biosynthesis. The Journal of Biological Chemistry. September 2010. doi:10.1074/jbc.R110.130419 · PMID 20522541 · PMC2934616

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.