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Tetracycline antibiotics

tetracycline antibiotics, tetracycline antibiotics drugs
Tetracyclines are broad-spectrum antibiotics whose general usefulness has been reduced with the onset of antibiotic resistance Despite this, they remain the treatment of choice for some specific indications

They are so named for their four "tetra-" hydrocarbon rings "-cycl-" derivation "-ine" To be specific, they are defined as "a subclass of polyketides having an octahydrotetracene-2-carboxamide skeleton" They are collectively known as "derivatives of polycyclic naphthacene carboxamide"

Contents

  • 1 Medical uses
  • 2 Side effects
    • 21 Cautions
    • 22 Contraindications
  • 3 Mechanism of action
  • 4 Mechanism of resistance
  • 5 Administration
  • 6 History
  • 7 Examples
    • 71 Experimental tetracyclines in clinical trials
  • 8 Use as a research reagent
  • 9 See also
  • 10 References
  • 11 External links

Medical uses

Tetracyclines are generally used in the treatment of infections of the urinary tract, respiratory tract, and the intestines and are also used in the treatment of chlamydia, especially in patients allergic to β-lactams and macrolides; however, their use for these indications is less popular than it once was due to widespread development of resistance in the causative organisms

Their most common current use is in the treatment of moderately severe acne and rosacea tetracycline, oxytetracycline, doxycycline or minocycline

Anaerobic bacteria are not as susceptible to tetracyclines as are aerobic bacteria

Doxycycline is also used as a prophylactic treatment for infection by Bacillus anthracis anthrax and is effective against Yersinia pestis, the infectious agent of bubonic plague It is also used for malaria treatment and prophylaxis, as well as treating elephantitis filariasis

Tetracyclines remain the treatment of choice for infections caused by chlamydia trachoma, psittacosis, salpingitis, urethritis and L venereum infection, Rickettsia typhus, Rocky Mountain spotted fever, brucellosis and spirochetal infections borreliosis, syphilis and Lyme disease In addition, they may be used to treat anthrax, plague, tularemia and Legionnaires' disease They are also used in veterinary medicine

They may have a role in reducing the duration and severity of cholera, although drug-resistance is mounting and their effect on overall mortality is questioned

Tetracycline derivatives are currently being investigated for the treatment of certain inflammatory disorders

Side effects

Side-effects from tetracyclines are not common, but of particular note is phototoxicity It increases the risk of sunburn under exposure to light from the sun or other sources This may be of particular importance for those intending to take on vacations long-term doxycycline as a malaria prophylaxis

They may cause stomach or bowel upsets, and, on rare occasions, allergic reactions Very rarely, severe headache and vision problems may be signs of dangerous secondary intracranial hypertension, also known as idiopathic intracranial hypertension

Tetracyclines are teratogens due to the likelihood of causing teeth discolouration in the fetus as they develop in infancy For this same reason, tetracyclines are contraindicated for use in children under 8 years of age Some adults also experience teeth discoloration mild grey hue after use They are, however, safe to use in the first 18 weeks of pregnancy

Some patients taking tetracyclines require medical supervision because they can cause steatosis and liver toxicity

Cautions

Tetracyclines should be used with caution in those with liver impairment and those that are soluble in water and urine worsen renal failure this is not true of the lipid-soluble agents doxycycline and minocycline They may increase muscle weakness in myasthenia gravis and exacerbate systemic lupus erythematosus Antacids containing aluminium and calcium reduce the absorption of all tetracyclines, and dairy products reduce absorption greatly for all but minocycline

The breakdown products of tetracyclines are toxic and can cause Fanconi syndrome, a potentially fatal disease affecting proximal tubular function in the nephrons of the kidney Prescriptions of these drugs should be discarded once expired because they can cause hepatotoxicity

It was once believed that tetracycline antibiotics impair the effectiveness of many types of hormonal contraception Recent research has shown no significant loss of effectiveness in oral contraceptives while using most tetracyclines Despite these studies, many physicians still recommend the use of barrier contraception for people taking any tetracyclines to prevent unwanted pregnancy

Contraindications

Tetracycline use should be avoided in pregnant or lactating women, and in children with developing teeth because they may result in permanent staining dark yellow-gray teeth with a darker horizontal band that goes across the top and bottom rows of teeth, and possibly affect the growth of teeth and bones

Usage during the first 12 weeks of pregnancy does not appear to increase the risk of any major birth defects There may be a small increased risk for minor birth defects such as an inguinal hernia, but the number of reports is too small to be sure if there actually is any risk

In tetracycline preparation, stability must be considered in order to avoid formation of toxic epi-anhydrotetracyclines

Mechanism of action

Tetracycline antibiotics are protein synthesis inhibitors, inhibiting the binding of aminoacyl-tRNA to the mRNA-ribosome complex They do so mainly by binding to the 30S ribosomal subunit in the mRNA translation complex

Tetracyclines also have been found to inhibit matrix metalloproteinases This mechanism does not add to their antibiotic effects, but has led to extensive research on chemically modified tetracyclines or CMTs like incyclinide for the treatment of rosacea, acne, diabetes and various types of neoplasms Incyclinide was announced to be ineffective for rosacea in September 2007

Several trials have examined modified and unmodified tetracyclines for the treatment of human cancers; of those, very promising results were achieved with CMT-3 for patients with Kaposi Sarcoma

Mechanism of resistance

Tetracycline inhibits cell growth by inhibiting translation It binds to the 16S part of the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome The binding is reversible in nature

Cells become resistant to tetracycline by at least three mechanisms: enzymatic inactivation of tetracycline, efflux, and ribosomal protection Inactivation is the rarest type of resistance, where an acetyl group is added to the molecule, causing inactivation of the drug In efflux, a resistance gene encodes a membrane protein that actively pumps tetracycline out of the cell This is the mechanism of action of the tetracycline resistance gene on the artificial plasmid pBR322 In ribosomal protection, a resistance gene encodes a protein that can have several effects, depending on what gene is transferred Six classes of ribosomal protection genes/proteins have been found, all with high sequence homology, suggesting a common evolutionary ancestor

Possible mechanisms of action of these protective proteins include:

  1. blocking tetracyclines from binding to the ribosome
  2. binding to the ribosome and distorting the structure to still allow t-RNA binding while tetracycline is bound
  3. binding to the ribosome and dislodging tetracycline

All of these changes to ribosomes are reversible non-covalent because ribosomes isolated from both tetracycline-resistant and susceptible organisms bind tetracycline equally well in vitro

Administration

When ingested, it is usually recommended that the more water-soluble, short-acting tetracyclines plain tetracycline, chlortetracycline, oxytetracycline, demeclocycline and methacycline be taken with a full glass of water, either two hours after eating or two hours before eating This is partly because most tetracyclines bind with food and also easily with magnesium, aluminium, iron and calcium, which reduces their ability to be completely absorbed by the body Dairy products, antacids and preparations containing iron should be avoided near the time of taking the drug Partial exceptions to these rules occur for doxycycline and minocycline, which may be taken with food though not iron, antacids, or calcium supplements Minocycline can be taken with dairy products because it does not chelate calcium as readily, although dairy products do decrease absorption of minocycline slightly

History

The first member of the group to be discovered is chlortetracycline Aureomycin in the late 1940s by Benjamin Minge Duggar, a scientist employed by American Cyanamid - Lederle Laboratories, under the leadership of Yellapragada Subbarow, who derived the substance from a golden-colored, fungus-like, soil-dwelling bacterium named Streptomyces aureofaciens Oxytetracycline Terramycin was discovered shortly afterwards by AC Finlay et al; it came from a similar soil bacterium named Streptomyces rimosus Robert Burns Woodward determined the structure of oxytetracycline, enabling Lloyd H Conover to successfully produce tetracycline itself as a synthetic product The development of many chemically altered antibiotics formed this group In June 2005, tigecycline, the first member of a new subgroup of tetracyclines named glycylcyclines, was introduced to treat infections that are resistant to other antimicrobics including conventional tetracyclines While tigecycline is the first tetracycline approved in over 20 years, other, newer versions of tetracyclines are currently in human clinical trials

A research conducted by anthropologist George J Armelagos and his team at Emory University showed that ancient Nubians from the post-Meroitic period around 350 CE had deposits of tetracycline in their bones, detectable through analyses of cross sections through ultraviolet light - the deposits are fluorescent, just as modern ones Armelagos suggested that this was due to ingestion of the local ancient beer very much like the Egyptian beer, made from contaminated stored grains

Examples

According to source:

  • Naturally occurring
    • Tetracycline
    • Chlortetracycline
    • Oxytetracycline
    • Demeclocycline
  • Semi-synthetic
    • Lymecycline
    • Meclocycline
    • Methacycline
    • Minocycline
    • Rolitetracycline

According to duration of action:

  • Short-acting half-life is 6–8 hours
    • Tetracycline
    • Chlortetracycline
    • Oxytetracycline
  • Intermediate-acting half-life is ~12 hours
    • Demeclocycline
    • Methacycline
  • Long-acting half-life is 16 hours or more
    • Doxycycline
    • Minocycline
    • Tigecycline

Tigecycline is a tetracycline antibiotic, but is also more specifically classified as a glycylcycline antibiotic

Experimental tetracyclines in clinical trials

  • Omadacycline formerly known as PTK-0796 in phase III clinical trials for acute bacterial skin and skin structure infections ABSSSI and community acquired bacterial pneumonia CABP
  • Sarecycline formerly known as WC 3035 in phase III clinical trials for acne vulgaris

Use as a research reagent

Members of the tetracycline class of antibiotics are often used as research reagents in in vitro and in vivo biomedical research experiments involving bacteria as well in experiments in eukaryotic cells and organisms with inducible protein expression systems using tetracycline-controlled transcriptional activation The mechanism of action for the antibacterial effect of tetracyclines relies on disrupting protein translation in bacteria, thereby damaging the ability of microbes to grow and repair; however protein translation is also disrupted in eukaryotic mitochondria leading to effects that may confound experimental results

It can be used as an artificial biomarker in wildlife to check if wild animals are consuming a bait that contains a vaccine or medication Since it is fluorescent and binds to calcium, a UV lamp can be used to check if it is in a tooth pulled from an animal For example, it was used to check uptake of oral rabies vaccine baits by raccoons in the USA However, this is an invasive procedure for the animal and labour-intensive for the researcher Therefore, other dyes such as rhodamine B that can be detected in hair and whiskers are preferred

See also

  • Glycylcycline
  • Eravacycline
  • Tetracycline controlled transcriptional activation
  • Animal Drug Availability Act 1996

References

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed the "Gold Book" 1997 Online corrected version:  2006– "tetracyclines"
  2. ^ Sloan, Barry; Scheinfeld, Noah September 2008 "The use and safety of doxycycline hyclate and other second-generation tetracyclines" Expert Opinion on Drug Safety 7 5: 571–577 doi:101517/1474033875571 ISSN 1744-764X PMID 18759709 
  3. ^ Resistance,, WHO Advisory Group on Integrated Surveillance of Antimicrobial Critically important antimicrobials for human medicine : ranking of antimicrobial agents for risk management of antimicrobial resistance due to non-human use World Health Organization, 5th revision 2016 ed ISBN 9789241512220 OCLC 982301334 
  4. ^ Chow, Anthony W; Patten, Valerie; Guze, Lucien B 1975-01-01 "Comparative Susceptibility of Anaerobic Bacteria to Minocycline, Doxycycline, and Tetracycline" Antimicrobial Agents and Chemotherapy 7 1: 46–49 doi:101128/aac7146 ISSN 0066-4804 PMC 429070  PMID 1137358 
  5. ^ "Antibiotic treatment successful against elephantiasis" Retrieved 13 March 2017 
  6. ^ Bhattacharya SK, National Institute of Cholera and Enteric Diseases 2003 "An evaluation of current cholera treatment" Expert Opin Pharmacother 4 2: 141–6 doi:101517/1465656642141 PMID 12562304 
  7. ^ Parsi VK 2001 "Cholera" Prim Care Update Ob Gyns 8 3: 106–109 doi:101016/S1068-607X0000086-X PMID 11378428 
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  9. ^
  10. ^ Deboyser D, Goethals F, Krack G, Roberfroid M 1989 "Investigation into the mechanism of tetracycline-induced steatosis: study in isolated hepatocytes" Toxicology and Applied Pharmacology 97 3: 473–9 doi:101016/0041-008X8990252-4 PMID 2609344 
  11. ^ Amacher DE, Martin BA 1997 "Tetracycline-induced steatosis in primary canine hepatocyte cultures" Fundamental and Applied Toxicology 40 2: 256–63 doi:101006/faat19972389 PMID 9441722 
  12. ^ Ekwall B, Acosta D 1982 "In vitro comparative toxicity of selected drugs and chemicals in HeLa cells, Chang liver cells, and rat hepatocytes" Drug and Chemical Toxicology 5 3: 219–31 doi:103109/01480548209041054 PMID 7151717 
  13. ^ Archer JS, Archer DF June 2002 "Oral contraceptive efficacy and antibiotic interaction: a myth debunked" Journal of the American Academy of Dermatology 46 6: 917–23 doi:101067/mjd2002120448 PMID 12063491 
  14. ^ Dréno B, Bettoli V, Ochsendorf F, Layton A, Mobacken H, Degreef H 2004 "European recommendations on the use of oral antibiotics for acne" European Journal of Dermatology 14 6: 391–9 PMID 15564203 
  15. ^ DeRossi SS, Hersh EV October 2002 "Antibiotics and oral contraceptives" Dental clinics of North America 46 4: 653–64 doi:101016/S0011-85320200017-4 PMID 12436822 
  16. ^ a b Tetracycline and Pregnancy Archived 2011-08-27 at the Wayback Machine from Organization of Teratology Information Specialists July 2010
  17. ^ "Mechanism of Action of Tetracyclines - Animations - PharmaXChangeinfo" 27 May 2011 Retrieved 13 March 2017 
  18. ^ H Spreitzer July 2, 2007 "Neue Wirkstoffe - Incyclinid" Österreichische Apothekerzeitung in German 14/2007: 655 
  19. ^ Viera MH, Perez OA, Berman B 2007 "Incyclinide" Drugs of the Future 32 3: 209–214 doi:101358/dof2007032031083308 
  20. ^ Ryan, M E; Usman, A; Ramamurthy, N S; Golub, L M; Greenwald, R A 2001 "Excessive matrix metalloproteinase activity in diabetes: Inhibition by tetracycline analogues with zinc reactivity" Current medicinal chemistry 8 3: 305–316 doi:102174/0929867013373598 PMID 11172685 
  21. ^ "CollaGenex says incyclinide ineffective for rosacea" 26 September 2016 Retrieved 13 March 2017 – via Reuters 
  22. ^ Richards, C; Pantanowitz, L; Dezube, B J 2011 "Antimicrobial and non-antimicrobial tetracyclines in human cancer trials" Pharmacological Research 63 2: 151–156 doi:101016/jphrs201010008 PMID 20951804 
  23. ^ Piscitelli, Stephen C; Keith Rodvold 2005 Drug Interactions in Infectious Diseases Humana Press ISBN 1-58829-455-2 
  24. ^ The Pharmaceutical Century
  25. ^ Finlay, A C; Hobby, G L; P'an, S Y; Regna, P P; Routien, J B; Seeley, D B; Shull, G M; Sobin, B A; Solomons, I A; Vinson, J W; Kane, J H 1 January 1950 "Terramycin, a New Antibiotic" Science 111: 85 doi:101126/science111287485 Retrieved 13 March 2017 – via NASA ADS 
  26. ^ "Lemelson-MIT Program" Retrieved 13 March 2017 
  27. ^ Olson MW, Ruzin A, Feyfant E, Rush TS, O'Connell J, Bradford PA June 2006 "Functional, biophysical, and structural bases for antibacterial activity of tigecycline" Antimicrobial Agents and Chemotherapy 50 6: 2156–66 doi:101128/AAC01499-05 PMC 1479133  PMID 16723578 
  28. ^ "How Paratek hopes to succeed in antibiotics despite Tetraphase's fail" Bizjournalscom Retrieved 2017-03-13 
  29. ^ Samuel D 1996 "Archaeology of ancient Egypt beer" PDF Journal of the American Society of Brewing Chemists 54 1: 3–12 
  30. ^ Bassett E J; Keith M S; Armelagos G J; Martin D L; Villanueva A R 1980 "Tetracycline-labeled human bone from ancient Sudanese Nubia AD 350" PDF Science 209 4464: 1532–1534 doi:101126/science7001623 
  31. ^ Nelson, Mark L; Levy, Stuart B 22 December 2011 "The history of the tetracyclines" PDF Annals of the New York Academy of Sciences 1241: 17–32 doi:101111/j1749-6632201106354x 
  32. ^ "Antibiotic Firm Paratek Joins IPO Queue; Aiming for $92M" Retrieved 13 March 2017 
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  34. ^ "Study to Evaluate Safety & Efficacy of Sarecycline in Treatment of Acne - Full Text View - ClinicalTrialsgov" Retrieved 13 March 2017 
  35. ^ Zhu, Z, Zheng, T, Lee, C G, Homer, R J, & Elias, J A 2002 Tetracycline-controlled transcriptional regulation systems: advances and application in transgenic animal modeling Seminars in Cell & Developmental Biology, 132, 121-128 doi:101016/s1084-95210200018-6
  36. ^ Moullan N, Mouchiroud L, Wang X, Ryu D, Williams EG, Mottis A, Jovaisaite V, Frochaux MV, Quiros PM, Deplancke B, Houtkooper RH, Auwerx J 2015 "Tetracyclines Disturb Mitochondrial Function across Eukaryotic Models: A Call for Caution in Biomedical Research" Celll Reports 10 10: 1681–91 doi:101016/jcelrep201502034 PMID 25772356 
  37. ^ Chatzispyrou IA, Held NM, Mouchiroud L, Auwerx J, Houtkooper RH 2015 "Tetracycline antibiotics impair mitochondrial function and its experimental use confounds research" Cancer Research 75 21: 4446–9 doi:101158/0008-5472CAN-15-1626 PMID 26475870 
  38. ^ Fry, Tricia L; Dunbar, Mike R 2007 "A REVIEW OF BIOMARKERS USED FOR WILDLIFE DAMAGE AND DISEASE MANAGEMENT" PDF Proceedings of the 12th Wildlife Damage Management Conference: 217–222 Retrieved 2017-05-03 

External links

  • Media related to Tetracycline antibiotics at Wikimedia Commons

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