Oxytetracycline

Oxytetracycline

Systematic (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
Clinical data
Pregnancy cat.	D: (United States) D: (Australia])
Legal status	Prescription only
Routes	Oral, Ophthalmic
Pharmacokinetic data
Half-life	6-8 hours
Excretion	Renal
Identifiers
CAS number	79-57-2 Y
ATC code	D06AA03 G01AA07 J01AA06 S01AA04 QG51AA01 QJ51AA06
PubChem	CID 5353856
DrugBank	APRD00019
ChemSpider	10482174 Y
UNII	SLF0D9077S Y
KEGG	D00205 Y
ChEBI	CHEBI:27701 N
ChEMBL	CHEMBL1517 Y
Chemical data
Formula	C22H24N2O9
Mol. mass	460.434 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1 Y Key:IWVCMVBTMGNXQD-PXOLEDIWSA-N Y
N(what is this?)  (verify)

Oxytetracycline was the second of the broad-spectrum tetracycline group of antibiotics to be discovered.

Oxytetracycline works by interfering with the ability of bacteria to produce proteins that are essential to them. 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.

Oxytetracycline is a broad spectrum antibiotic that 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 infection.

Oxytetracycline is still used to treat infections caused by chlamydia (e.g. the chest infection psittacosis, the eye infection trachoma, and the genital infection urethritis) and infections caused by mycoplasma organisms (e.g. pneumonia).

Oxytetracycline is used to treat acne, due to its activity against the bacteria on the skin that cause acne (Propionebacterium acnes). It is used to treat flare-ups of chronic bronchitis, due to its activity against the bacteria usually responsible, Haemophilus influenzae.

Oxytetracycline may also be used to treat other rarer infections, such as those caused by a group of micro-organisms called rickettsiae (e.g. Q fever). To make sure the bacteria causing an infection are susceptible to oxytetracycline your doctor may take a tissue sample, for example a swab from the infected area, or a urine or blood sample.

History

It was first found near Pfizer laboratories in a soil sample yielding the soil actinomycete, Streptomyces rimosus by Finlay et al. In 1950, a celebrated American 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 by Woodward 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.

Indications

Oxytetracycline, like other Tetracyclines, is used to treat many infections common and rare (see Tetracycline antibiotics group). 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 6–8 weeks at a time, but alternatives should be sought if no improvement occurs by 3 months.^[1]

It is sometimes used to treat Spirochaetal infection, 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 the use of Tetracyclines 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 Legionnaire's Disease as a substitute for a Macrolide or Quinolone.

Oxytetracycline is especially valuable in treating Non-Specific-Urethritis, LGV, Lyme disease, Brucellosis, Cholera, Plague, Typhus, Relapsing Fever, 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.

The standard dose is 250–500 mg six-hourly 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.

Veterinary indications

Oxytetracycline is used to control the outbreak of American Foulbrood and European Foulbrood in honeybees.

Oxytetracycline can also be used to correct breathing disorders in livestock. Oxytetracycline is administered in a powder or through an intramuscular injection. American livestock producers apply oxytetracycline to livestock feed to prevent diseases and infections in cattle and poultry. The antibiotic is partially absorbed in the gastrointestinal tract of the animal and the remaining is deposited in manure. Researchers at the Agricultural Research Service studied the breakdown of oxytetracycline in manure depending on various environmental conditions. They found that the breakdown of oxytetracycline slowed with increased saturation of the manure and concluded that this was a result of decreased oxygen levels. [1] This research helps producers understand the effects of oxytetracycline in animal feed on the environment, bacteria, and antimicrobial resistance.

Side effects

Side effects are mainly gastrointestinal and photosensitive allergic reactions common to the tetracycline antibiotics group.
Can also damage calcium rich organs such as teeth and bones although this is very rare, sometimes causes nasal cavities to erode, quite common, the BNF suggests that because of this Tetracyclines should not be used to treat pregnant or lactating women and children under 12 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.

Formulation

Tablets containing 250 mg Tablets of Oxytetracycline as the dihydrate

References

1. ^ British National Formulary 45 March 2003