tetracycline

Definition

Tetracyclines are medicines that kill certain infection-causing microorganisms.

Description

Tetracyclines are available only with a physician's prescription. They are sold in capsule, tablet, liquid, and injectable forms. Some commonly used medicines in this group are tetracycline (Achromycin V, Sumycin) and doxycycline (Doryx, Vibramycin).

— Nancy Ross-Flanigan

1. A yellow crystalline compound, C₂₂H₂₄N₂O₈, synthesized or derived from certain microorganisms of the genus Streptomyces and used as a broad-spectrum antibiotic.
2. An antibiotic, such as chlortetracycline and oxytetracycline, having the same basic structure.

[TETRA- + CYCL(IC) + -INE².]

For more information on tetracycline, visit Britannica.com.

A group of closely related antibiotics including tetracycline, oxytetracycline (terramycin), and aureomycin. The last two are used in some countries for preserving food and as growth improvers, added to animal feed at the rate of a few mg per tonne.

An antibiotic produced by certain strains of Streptomyces. Its administration during tooth formation may lead to enamel discoloration.

Brand names: Emtet™Panmycin™SumycinSumycin®Tetra 250™

Chemical formula:

Drug Forms:
• Tetracycline skin ointment (below)
• Tetracycline Hydrochloride Oral tablet
• Tetracycline Hydrochloride Oral capsule

Español:
• Pomada de tetraciclina para la piel
• Clorhidrato de tetraciclina, Tableta oral
• Clorhidrato de tetraciclina, Cápsula oral

Tetracycline skin ointment

What is tetracycline skin ointment?

TETRACYCLINE (Achromycin®) is an antibiotic. Tetracycline ointment stops the growth of certain bacteria that cause skin infections from minor cuts, burns, and wounds. Generic tetracycline skin ointment is not available.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• an unusual or allergic reaction to tetracycline antibiotics, sulfites, other foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I use this medicine?

Tetracycline skin ointment is only for external use on the skin. Do not take by mouth. Follow the directions on the prescription label. Wash hands before and after use. Wash the affected area with soap and water, rinse well and pat dry. Apply a thin layer of the ointment to the affected area as often as prescribed by your prescriber or health care professional. You can cover the area with a sterile gauze dressing (bandage). Finish the full course prescribed by your prescriber or health care professional even if you think your condition is better.

Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.

What drug(s) may interact with tetracycline?

• other antibiotic medicines

Do not use corticosteroid skin products (such as dexamethasone, hydrocortisone and prednisolone) at the same time as this medicine as they can cover up problems. Do not use any other skin products without telling your prescriber or health care professional. Check before starting or stopping any of your medicines or non-prescription products.

What should I watch for while taking tetracycline?

Tell your prescriber or health care professional if your skin does not improve in 2 weeks.

Do not get the ointment in your eyes; if you do, rinse out with plenty of cool tap water.

Do not use this medicine on deep wounds, or serious burns.

This medicine can color your skin yellow. This color will wash off with soap and water, but you should leave the medicine on the skin as long as you can. This yellow color will look worse under ultraviolet light. If you are going to a disco where they use this kind of light, either wash off the medicine before you go, or apply afterwards.

Keep the ointment off your clothes; it can stain them.

What side effects may I notice from using tetracycline?

Side effects with tetracycline skin products are rare. They include:
• skin redness, swelling, pain, blistering or peeling

Where can I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F); do not freeze. Protect from light. Throw away any unused medicine after the expiration date.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

Definition

Tetracyclines are a group of antibiotics that are useful in treatment of many bacterial infections.

Description

Tetracyclines are called broad-spectrum antibiotics because they can be used to treat a wide variety of infections. Physicians may prescribe these drugs to treat eye infections, pneumonia, gonorrhea, Rocky Mountain spotted fever, urinary tract infections, certain bacteria that could be used in biological weapons, and other infections caused by bacteria. The medicine is also used to treat acne. The tetracyclines will not work for colds, flu, and other infections caused by viruses. Tetracyclines are generally a low-cost alternative among antibiotics.

There are five drugs in the tetracycline class:

• demeclocycline
• doxycycline
• minocycline
• oxytetracycline
• tetracycline

General Use

All tetracyclines are used for treatment of infections in patients over the age of eight years. They may be used in several forms, including capsules, injections, ointments, eye and ear drops.

Tetracyclines are bacteriostatic. They do not kill bacteria; they prevent bacteria from growing, so that the body's natural defenses are better able to deal with an infection. For this reason, tetracyclines are not used in patients with impaired immune systems.

Although all tetracyclines are similar, and can do most of the same work, there are some differences. Doxycycline requires only one dose a day and can be used even when the patient has kidney problems. Demeclocycline and minocycline penetrate the skin better than other tetracyclines and may be preferred for treatment of acne. Demeclocycline is effective for the syndrome of inappropriate anti-diuretic hormone (SIDAH), although it is not officially approved for this purpose.

In addition to their role in treating infections, tetracyclines have a wide range of other uses. These include protection against some types of malaria and treatment of some of the infections that might be used in bioterrorism. Some tetracycline derivatives have been useful in cancer therapy. Tetracyclines have been useful in prevention of gum diseases of the mouth.

Precautions

Tetracyclines should normally not be used in children under the age of eight because some tetracyclines can be absorbed into the bones and teeth and give the teeth a mottled appearance. Some experts believe that tetracyclines should be avoided in children younger than ten.

Side Effects

Not all tetracyclines have the same side effects, but the following list includes some of the most common problems:

• dizziness and lightheadedness
• diarrhea
• stomach upset
• nausea
• vomiting
• photosensitivity
• fungus infections
• tooth discoloration
• mouth irritation
• skin discoloration

On rare occasions tetracyclines may cause more severe adverse effects, including kidney damage and drug-induced lupus.

Patients taking tetracyclines should avoid prolonged sun exposure. Standard sunscreens are not adequate to protect against severe sunburn in patients taking tetracyclines.

Interactions

Tetracyclines should not be used at the same time the patient is receiving a live vaccine. The antibiotics may prevent the vaccine from growing, and this may keep the vaccine from producing immunity.

Moreover, tetracyclines may reduce the effectiveness of oral contraceptives.

Many antibiotics share tetracyclines' interaction with neuromuscular blocking agents. Tetracyclines should not be used at the same time as neuromuscular blocking agents since the antibiotics can increase the strength of the neuromuscular blocker, which can make breathing difficult. While this interaction is severe, it is rare, since the neuromuscular blocking agents are usually used only in surgery.

Tetracyclines should not be taken at the same time as foods containing calcium or foods containing iron, magnesium, or aluminum. The metals bind to the tetracycline, and the combination has reduced effect on bacteria.

The common interaction between tetracyclines and minerals can be avoided by taking tetracycline on an empty stomach, one hour before or two hours after meals, with water.

Parental Concerns

Although it is recommended that tetracyclines not be given to children under the age of eight, the drug is sometimes required in severe infections. Tetracyclines may be required for children who have developed infections either in hospitals or while traveling overseas.

Parents should carefully check the expiration date of tetracycline and not use the drug past the expiration date. Expired tetracycline has been known to cause a severe kidney problem called Fanconi syndrome. Expired tetracycline should be disposed of, not saved.

Because tetracyclines can cause photosensitization, patients taking these drugs should use sunscreen and avoid direct sunlight.

Because of their interaction with metals, tetracyclines should always be taken on an empty stomach with only water. Patients should particularly avoid calcium-containing dairy products and antacids as well as multivitamin-mineral supplements.

Tetracyclines inhibit the growth of many bacteria and other microorganisms which can lead to overgrowth of other microorganisms. Possible symptoms are discoloration of the tongue and diarrhea. Parents should report these problems to the prescriber immediately.

Parents should alert all health-care professionals about all drugs their children are taking. Both tetracycline and oral contraceptives are used to treat acne in teenage girls, but these drugs should not be used together.

See also Penicillins.

Resources

Books

Beers, Mark H., and Robert Berkow, eds. The Merck Manual, 2nd home ed. West Point, PA: Merck & Co., 2004.

Mcevoy, Gerald K., et al. AHFS Drug Information 2004. Bethesda, MD: American Society of Healthsystems Pharmacists, 2004.

Siberry, George K., and Robert Iannone, eds. The Harriet Lane Handbook, 15th ed. Philadelphia: Mosby, 2000.

Periodicals

Black, Douglas J., and Allan Ellsworth. "Practical overview of antibiotics for family physicians." Clinics in Family Practice 6, no. 1 (March 2004): 265–89.

Cronquist, Steven D. "Tularemia: The disease and the weapon." Dermatologic Clinics 22, no. 3 (July 2004): 313–320.

Izzedine, Hassane, et al. "Drug-induced Fanconi's syndrome." American Journal of Kidney Disease 41, no. 2 (February 1, 2003): 292–309.

Sanfilippo, Angela M., et al. "Common pediatric and adolescent skin conditions." Journal of Pediatric and Adolescent Gynecology 16, no. 5 (October 1, 2003): 269–83.

Thompson, Matthew J., and Christopher Sanford. "Travel-related infections in primary care." Clinics in Family Practice 6, no. 1 (March 2004): 235–64.

Organizations

American Academy of Pediatrics. 141 Northwest Point Boulevard, Elk Grove Village, IL 60007–1098. Web site: www.aap.org.

Web Sites

The Pediatric Infectious Disease Journal. Available online at www.medscape.com/viewpublication/769_index (accessed September 30, 2004).

[Article by: Samuel Uretsky, PharmD]

An antibiotic produced by cultures of Streptomyces aureofaciens and S. rimosus. It is effective against many different microorganisms, including rickettsiae, certain viruses, and both gram-negative and gram-positive microorganisms. Preparations include chlortetracycline hydrochloride (Aureomycin), oxytetracycline hydrochloride (Terramycin), tetracycline hydrochloride (Achromycin), and demethylchlortetracycline (Declomycin). Administration of these compounds is associated with pigmentation of developing teeth and bones, and in horses with a severe colitis.

• t. stain — discoloration of dentine and enamel caused by systemic treatment with tetracycline during dental development; usually yellow to brown or green to gray.

This article deals with the specific antibiotic called tetracycline. For the group of antibiotics known as the tetracyclines, see tetracycline antibiotics.

Tetracycline

Systematic (IUPAC) name
2-(amino-hydroxy-methylidene)-4-dimethylamino- 6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5, 5a-tetrahydrotetracene-1,3,12-trione OR 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro- 3,6,10,12,12a-pentahydroxy- 1,11-dioxo-naphthacene-2-carboxamide OR (4S,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
Identifiers
CAS number	60-54-8 64-75-5 (hydrochloride)
ATC code	A01AB13 D06AA04 J01AA07 S01AA09 S02AA08 S03AA02 QG01AA90 QG51AA02 QJ51AA07
PubChem	643969
DrugBank	APRD00572
ChemSpider	10257122
Chemical data
Formula	C22H24N2O8
Mol. mass	444.435 g/mol
Pharmacokinetic data
Bioavailability	60-80% Oral, while fasting <40% Intramuscular
Metabolism	Not metabolised
Half life	6-11 hours
Excretion	Fecal and Renal
Therapeutic considerations
Pregnancy cat.	D(AU) D(US)
Legal status	℞ Prescription only
Routes	oral, topical (skin & eye), im, iv
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Tetracycline (INN) (pronounced /ˌtɛtrəˈsaɪkliːn/) is a broad-spectrum polyketide antibiotic produced by the Streptomyces genus of Actinobacteria, indicated for use against many bacterial infections. It is a protein synthesis inhibitor. It is commonly used to treat acne today, and more recently, rosacea, and played a historical role in stamping out cholera in the developed world. It is sold under the brand names Sumycin, Terramycin, Tetracyn, and Panmycin, among others. Actisite is a thread-like fiber form, used in dental applications. It is also used to produce several semi-synthetic derivatives, which together are known as the tetracycline antibiotics.

Contents 1 Mechanism of action 2 History 3 Cautions, contraindications, side effects 4 Indication 5 Other uses 6 Cell culture 7 Notes

Mechanism of action

Tetracycline antiporter system

Tetracyclines work by binding the 30S ribosomal subunit and through an interaction with 16S rRNA, they prevent the docking of amino-acylated tRNA.

Resistance to tetracyclines can arise through drug efflux, ribosomal protection proteins, 16S rRNA mutation, and drug inactivation through the action of a monooxygenase^[1].

History

The tetracyclines are a large family of antibiotics that were discovered as natural products by Benjamin Minge Duggar and first described in 1948.^[2] Under Yellapragada Subbarao, Benjamin Duggar made his discovery of the world's first tetracycline antibiotic, Aureomycin, in 1945. Tetracycline was then discovered by Lloyd Conover in the research departments of Pfizer. The patent for tetracycline, U.S. Patent 2,699,054, was first issued in 1950. However, Nubian mummies have been studied in the 1990s and were found to contain significant levels of tetracycline; there is evidence that the beer brewed at the time could have been the source.^[3] Tetracycline sparked the development of many chemically altered antibiotics and in doing so has proved to be one of the most important discoveries made in the field of antibiotics. It is used to treat many gram-positive and gram-negative bacteria and some protozoa. It, like some other antibiotics, is also used in the treatment of acne.

Cautions, contraindications, side effects

Are as those of the tetracycline antibiotics group:

• Can stain developing teeth (even when taken by the mother during pregnancy)
• Can cause permanent teeth discoloration (yellow-gray-brown). Infancy and childhood to eight (8) years old
• Inactivated by Ca²⁺ ion, not to be taken with milk or yogurt
• Inactivated by aluminium, iron and zinc, not to be taken at the same time as indigestion remedies
• Inactivated by common antacids and over-the-counter heartburn medicines.
• Skin photosensitivity; exposure to the Sun or intense light is not recommended
• Drug-induced lupus, and hepatitis
• Tinnitus
• May interfere with methotrexate by displacing it from the various protein binding sites
• Can cause breathing complications as well as anaphylactic shock in some individuals
• Should be avoided during pregnancy as it may affect bone growth of fetus.
• Passes into breast milk and is harmful to breast-fed infants, and should therefore be avoided during breastfeeding if possible.^[4]

Indication

It is first-line therapy for Rocky Mountain spotted fever (Rickettsia), Q fever (Coxiella), Psittacosis and Lymphogranuloma venereum (Chlamydia), and to eradicate nasal carriage of meningococci. ^[5]

Doxycycline is also one (of many) recommended drugs for chemoprophylatic treatment of malaria in travels to areas of the world where malaria is endemic. ^[6]

Other uses

Since tetracycline is absorbed into bone, it is used as a marker of bone growth for biopsies in humans, and as a biomarker in wildlife to detect consumption of medicine- or vaccine-containing baits.^[7] The presence of tetracycline in bone is detected by its fluorescence.^[8]

In genetic engineering tetracycline is used in transcriptional activation. Tetracycline is also one of the antibiotics used to treat ulcers caused by bacterial infections. In cancer research at Harvard Medical School, tetracycline has been used to reliably cause regression of advanced stages of leukemia in mice, by placing it in their drinking water.^[9]

Cell culture

Tetracycline is used in cell biology as selective agent in cell culture systems. It is toxic to prokaryotic and eukaryotic cells and selects for cells harboring the bacterial tet^r gene, which encodes a 399-amino acid membrane associated protein. This protein actively exports tetracycline out of the cell rendering cells harboring this gene more resistant to the drug. The yellow crystalline powder can be dissolved in water (20 mg/ml) or ethanol (5 mg/ml) and is routinely used at 10 mg/l in cell culture. In cell culture at 37 °C it is stable for 4 days.

Notes

1. ^ Zakeri, B. & Wright, G. D. Chemical biology of tetracycline antibiotics. Biochem. Cell Biol. 86, 124-136 (2008).
2. ^ Klajn, Rafal, Chemistry and chemical biology of tetracyclines, retrieved 20 June 2007.
3. ^ George Armelagos (May, 2000). "Take Two Beers and Call Me in 1,600 Years - use of tetracycline by Nubians and Ancient Egyptians". American Museum of Natural History. http://www.findarticles.com/p/articles/mi_m1134/is_4_109/ai_62324477. Retrieved 2007-12-19. 
4. ^ kidsgrowth.org --> Drugs and Other Substances in Breast Milk Retrieved on June 19, 2009
5. ^ Lippincott's Illustrated Reviews: Pharmacology, 4th ed. Harvery RA, Champe, PC. Lippincott, Williams & Wilkins, 2009
6. ^ http://wwwn.cdc.gov/TRAVEL/yellowBookCh4-Malaria.aspx
7. ^ Olson CA, et al. Bait ingestion by free-ranging raccoons and nontarget species in an oral rabies vaccine field trial in Florida. J Wildl Dis. 2000 Oct;36(4):734-43.
8. ^ Mayton CA. Tetracycline labeling of bone
9. ^ William J. Cromie (February 10, 2000). "Researchers Switch Cancer Off and On -- In Mice". http://www.hno.harvard.edu/gazette/2000/02.10/leukemia.html. Retrieved 2008-10-25. 

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