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doxycycline

 
American Heritage Dictionary:

dox·y·cy·cline

(dŏk'sĭ-sī'klēn', -klĭn) pronunciation
n.
A broad-spectrum antibiotic, C22H24N2O8, derived from tetracycline.

[D(E)OXY- + (TETRA)CYCLINE.]


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Drug Info:

Doxycycline

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Brand names: Adoxa Pak, Adoxa®, Alodox™ , Atridox™, Bio-Tab™, Doryx®, Doxal™, Doxy™, Monodox®, Oracea™, Periostat®, Vibra-Tabs®, Vibramycin®

Chemical formula:



Doxycycline Hyclate Oral capsule

What is this medicine?

DOXYCYCLINE (dox i SYE kleen) is a tetracycline antibiotic. It kills certain bacteria or stops their growth. It is used to treat many kinds of infections, like dental, skin, respiratory, and urinary tract infections. It also treats acne, Lyme disease, malaria, and certain sexually transmitted infections.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

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

They need to know if you have any of these conditions:
•liver disease
•long exposure to sunlight like working outdoors
•stomach problems like colitis
•an unusual or allergic reaction to doxycycline, tetracycline antibiotics, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

Take this medicine by mouth with a full glass of water. Follow the directions on the prescription label. It is best to take this medicine without food, but if it upsets your stomach take it with food. Take your medicine at regular intervals. Do not take your medicine more often than directed. Take all of your medicine as directed even if you think you are better. Do not skip doses or stop your medicine early.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed. While this drug may be prescribed for children as young as 8 years old for selected conditions, precautions do apply.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

•antacids
•barbiturates
•birth control pills
•bismuth subsalicylate
•carbamazepine
•methoxyflurane
•other antibiotics
•phenytoin
•vitamins that contain iron
•warfarin

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Tell your doctor or health care professional if your symptoms do not improve.

Do not treat diarrhea with over the counter products. Contact your doctor if you have diarrhea that lasts more than 2 days or if it is severe and watery.

Do not take this medicine just before going to bed. It may not dissolve properly when you lay down and can cause pain in your throat. Drink plenty of fluids while taking this medicine to also help reduce irritation in your throat.

This medicine can make you more sensitive to the sun. Keep out of the sun. If you cannot avoid being in the sun, wear protective clothing and use sunscreen. Do not use sun lamps or tanning beds/booths.

Birth control pills may not work properly while you are taking this medicine. Talk to your doctor about using an extra method of birth control.

If you are being treated for a sexually transmitted infection, avoid sexual contact until you have finished your treatment. Your sexual partner may also need treatment.

Avoid antacids, aluminum, calcium, magnesium, and iron products for 4 hours before and 2 hours after taking a dose of this medicine.

If you are using this medicine to prevent malaria, you should still protect yourself from contact with mosquitos. Stay in screened-in areas, use mosquito nets, keep your body covered, and use an insect repellent.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•difficulty breathing
•fever
•itching in the rectal or genital area
•pain on swallowing
•redness, blistering, peeling or loosening of the skin, including inside the mouth
•severe stomach pain or cramps
•unusual bleeding or bruising
•unusually weak or tired
•yellowing of the eyes or skin

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•diarrhea
•loss of appetite
•nausea, vomiting

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature, below 30 degrees C (86 degrees F). Protect from light. Keep container tightly closed. Throw away any unused medicine after the expiration date. Taking this medicine after the expiration date can make you seriously ill.

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.


A tetracycline antibiotic used for the treatment of chronic bronchitis, brucellosis, Lyme disease, chlamydial infections, and infections caused by mycoplasmas and rickettsias (see tetracyclines). It is also used to treat mouth ulcers, gum disease, acne, prostatitis, sinusitis, and pelvic inflammatory disease. Doxycycline is also used as a prophylactic protection against malaria, especially in areas, such as southeast Asia, where the malarial parasites are resistant to mefloquine and in people who cannot take chloroquine or mefloquine. Unlike most other tetracyclines, doxycycline does not exacerbate kidney disease and may be taken by those with impaired kidney function. It is available, on prescription only, as tablets, dispersible tablets, capsules, or modified-release capsules.

Side effects and precautions:
see tetracyclines.

Interactions with other drugs:

Antiepileptics: carbamazepine, phenobarbital, phenytoin, and primidone reduce the plasma concentration of doxycycline.

See also tetracyclines.

Proprietary preparations:
Doxylar (capsules); Efracea (modified-release capsules); Periostat (tablets); Vibramycin Acne Pack; Vibramycin-D (dispersible tablets).

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5-hydroxy-6-deoxytetracycline; an antibiotic having a wide range of activity against both Gram-positive and Gram-negative organisms. It is closely similar to tetracycline in structure and mechanism of action. One proprietary name is Vibramycin.





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A second-generation, lipid-soluble tetracycline derivative with greater activity against anaerobes and intracellular bacteria, and a longer half-life. Used as the monohydrate.

Wikipedia on Answers.com:

Doxycycline

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Doxycycline
Systematic (IUPAC) name
(4S,4aR,5S,5aR,6R,12aS)-4-(dimethylamino)- 3,5,10,12,12a-pentahydroxy- 6-methyl- 1,11-dioxo- 1,4,4a,5,5a,6,11,12a-octahydrotetracene- 2-carboxamide
Clinical data
Trade names Vibramycin
AHFS/Drugs.com monograph
MedlinePlus a682063
Licence data US FDA:link
Pregnancy cat. D(US)
Legal status POM (UK) -only (US)
Routes oral, buccal, iv, im
Pharmacokinetic data
Bioavailability 100%
Metabolism hepatic,minimally
Half-life 18-22 hours
Excretion urine, feces
Identifiers
CAS number 564-25-0 YesY
ATC code J01AA02 A01AB22
PubChem CID 11256
DrugBank APRD00597
ChemSpider 10482106 YesY
UNII 334895S862 YesY
KEGG D02129 N
ChEBI CHEBI:60648 YesY
ChEMBL CHEMBL1433 N
Chemical data
Formula C22H24N2O8 
Mol. mass 462.46 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)
Generic 100 mg doxycycline capsules

Doxycycline INN (play /ˌdɒksɨˈskln/ doks-i-sy-kleen) is a member of the tetracycline antibiotics group, and is commonly used to treat a variety of infections. Doxycycline is a semisynthetic tetracycline invented and clinically developed in the early 1960s by Pfizer Inc.[citation needed] and marketed under the brand name Vibramycin.[citation needed] Vibramycin received U.S. Food and Drug Administration approval in 1967,[citation needed] becoming Pfizer's first once-a-day, broad-spectrum antibiotic.[citation needed] Other brand names include Monodox, Microdox, Periostat, Vibra-Tabs, Oracea, Doryx, Vibrox, Adoxa, Doxyhexal, Doxylin, Doxoral,Doxy-1 and Atridox (topical doxycycline hyclate for periodontitis).

Contents

Indicated uses

As well as the general indications for all members of the tetracycline antibiotics group, doxycycline is frequently used to treat chronic prostatitis, sinusitis, syphilis, chlamydia, pelvic inflammatory disease,[1][2] acne, rosacea,[3][4] and rickettsial infections.

Antiprotozoal

It is used in prophylaxis against malaria. It should not be used alone for initial treatment of malaria, even when the parasite is doxycycline-sensitive, because the antimalarial effect of doxycycline is delayed. This delay is related to its mechanism of action, which is to specifically impair the progeny of the apicoplast genes, resulting in their abnormal cell division.[5]

It can be used in a treatment plan in combination with other agents, such as quinine.[6]

Antibacterial

It is used in the treatment and prophylaxis of Bacillus anthracis (anthrax).

It is also effective against Yersinia pestis (the infectious agent of bubonic plague), and is prescribed for the treatment of Lyme disease,[7][8][9][10] ehrlichiosis[11][12] and Rocky Mountain spotted fever. In fact, because doxycycline is one of the few medications shown to be effective in treating Rocky Mountain spotted fever (with the next-best alternative being chloramphenicol), doxycycline is indicated even for use in children for this illness. Otherwise, doxycycline is not indicated for use in children under the age of eight years. Doxycycline, like other antibiotics, will not work for colds, influenza, or other viral infections.

Doxycycline package

When bacteriologic testing indicates appropriate susceptibility to the drug, doxycycline may be used to treat and prevent:

Anthelmintic

Elephantiasis is the end-stage condition of lymphatic filariases caused by one of two genera of filarial nematodes (roundworms): Wuchereria or Brugia (primarily Wuchereria bancrofti). Elephantiasis is characterized by permanently swollen limbs or genitals and permanent damage to the lymph system (often accompanied by severe secondary fungal and bacterial infections). This results from blockage of lymph flow caused by immune response against dead or dying adult worms in the lymphatics. This condition affects over 120 million people worldwide, with 1 billion at risk.[14] Previous antinematode treatments have been limited by poor levels of effectiveness, drug side effects and high costs. Doxycycline was shown in 2003 to kill the symbiotic Wolbachia bacteria in the filarial worms' reproductive tracts, rendering them sterile, thus reducing transmission of the disease.[15] Field trials in 2005 showed doxycycline almost completely eliminates the release of microfilariae when given for an eight-week course.[16][17] However, doxycycline only reduces transmission and the relatively light pathology associated with microfilaraemia; there is currently no cure for lymphatic filariasis.

Cautions and side effects

Cautions and side effects are similar to those of other members of the tetracycline antibiotic group. However, the risk of photosensitivity skin reactions is of particular importance for those intending long-term use for malaria prophylaxis, because it can cause permanent sensitive and thin skin.

Unlike some other members of the tetracycline group, it may be used in those with renal impairment.[18]

Previously, doxycycline was believed to impair the effectiveness of many types of hormonal contraception due to CYP450 induction. Recent research has shown no significant loss of effectiveness in oral contraceptives while using most tetracycline antibiotics (including doxycycline), although many physicians still recommend the use of barrier contraception for people taking the drug to prevent unwanted pregnancy.[19][20][21]

Food, including dairy products, does not interfere with the absorption of doxycycline, unlike most other tetracycline antibiotics.[22]

Doxycycline, like all tetracyclines, is not approved for general use in children, but specific exceptions are made for potentially fatal illnesses where the benefits outweigh the risks and there are few or no other alternatives, such as with Rocky Mountain spotted fever and anthrax.

Expired tetracyclines or tetracyclines allowed to stand at a pH less than 2 are reported to be nephrotoxic due to the formation of a degradation product, anhydro-4-epitetracycline[23][24] causing Fanconi syndrome.[25] In the case of doxycycline, the absence of an hydroxyl group in C-6 prevent the formation of the nephrotoxic compound.[24] Nevertheless, tetracyclines and doxycycline itself have to be taken with precaution in patients with kidney injury, as they can worsen azotemia due to catabolic effects.[25]

Experimental applications

Tet-ON inducible shRNA system

At subantimicrobial doses, doxycycline is an inhibitor of matrix metalloproteases, and has been used in various experimental systems for this purpose, such as for recalcitrant recurrent corneal erosions.[26] Doxycycline has been used successfully in the treatment of one patient with lymphangioleiomyomatosis, an otherwise progressive and fatal disease.[27] Doxycycline has also been shown to attenuate cardiac hypertrophy (in mice), a deadly consequence of prolonged hypertension.[28] In chronic obstructive pulmonary disease, doxycycline has shown to improve lung functions in patients with stable symptoms.[29] Doxycycline is also used in "Tet-on" and "Tet-off" tetracycline-controlled transcriptional activation to regulate transgene expression in organisms and cell cultures.

Other experimental applications include:

References

  1. ^ Sweet RL, Schachter J, Landers DV, Ohm-Smith M, Robbie MO (1988). "Treatment of hospitalized patients with acute pelvic inflammatory disease: comparison of cefotetan plus doxycycline and ana doxycycline". Am. J. Obstet. Gynecol. 158 (3 Pt 2): 736–41. PMID 3162653. 
  2. ^ Gjønnaess H, Holten E (1978). "Doxycycline (Vibramycin) in pelvic inflammatory disease". Acta Obstet Gynecol Scand 57 (2): 137–9. doi:10.3109/00016347809155893. PMID 345730. 
  3. ^ Määttä M, Kari O, Tervahartiala T et al (2006). "Tear fluid levels of MMP-8 are elevated in ocular rosacea--treatment effect of oral doxycycline". Graefes Arch. Clin. Exp. Ophthalmol. 244 (8): 957–62. doi:10.1007/s00417-005-0212-3. PMID 16411105. 
  4. ^ Quarterman MJ, Johnson DW, Abele DC, Lesher JL, Hull DS, Davis LS (1997). "Ocular rosacea. Signs, symptoms, and tear studies before and after treatment with doxycycline". Arch Dermatol 133 (1): 49–54. doi:10.1001/archderm.133.1.49. PMID 9006372. 
  5. ^ Dahl EL, Shock JL, Shenai BR, Gut J, DeRisi JL, Rosenthal PJ (2006). "Tetracyclines specifically target the apicoplast of the malaria parasite Plasmodium falciparum". Antimicrob. Agents Chemother. 50 (9): 3124–31. doi:10.1128/AAC.00394-06. PMC 1563505. PMID 16940111. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1563505. 
  6. ^ Lalloo DG, Shingadia D, Pasvol G et al (February 2007). "UK malaria treatment guidelines". J. Infect. 54 (2): 111–21. doi:10.1016/j.jinf.2006.12.003. PMID 17215045. http://linkinghub.elsevier.com/retrieve/pii/S0163-4453(06)00416-6. 
  7. ^ Nadelman RB, Luger SW, Frank E, Wisniewski M, Collins JJ, Wormser GP (1992). "Comparison of cefuroxime axetil and doxycycline in the treatment of early Lyme disease". Ann. Intern. Med. 117 (4): 273–80. PMID 1637021. 
  8. ^ Luger SW, Paparone P, Wormser GP et al (March 1995). "Comparison of cefuroxime axetil and doxycycline in treatment of patients with early Lyme disease associated with erythema migrans". Antimicrob. Agents Chemother. 39 (3): 661–7. PMC 162601. PMID 7793869. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=162601. 
  9. ^ Nadelman RB, Nowakowski J, Fish D et al (2001). "Prophylaxis with single-dose doxycycline for the prevention of Lyme disease after an Ixodes scapularis tick bite". N. Engl. J. Med. 345 (2): 79–84. doi:10.1056/NEJM200107123450201. PMID 11450675. http://content.nejm.org/cgi/content/full/345/2/79. 
  10. ^ Karlsson M, Hammers-Berggren S, Lindquist L, Stiernstedt G, Svenungsson B (1994). "Comparison of intravenous penicillin G and oral doxycycline for treatment of Lyme neuroborreliosis". Neurologe 44 (7): 1203–7. PMID 8035916. 
  11. ^ Weinstein RS (1996). "Human ehrlichiosis". Am Fam Physician 54 (6): 1971–6. PMID 8900357. 
  12. ^ Karlsson U, Bjöersdorff A, Massung RF, Christensson B (2001). "Human granulocytic ehrlichiosis--a clinical case in Scandinavia". Scand. J. Infect. Dis. 33 (1): 73–4. doi:10.1080/003655401750064130. PMID 11234985. 
  13. ^ Gladwin, Mark (2007). Clinical Microbiology Made Ridiculously Simple 4th ed.. Miami, FL: MedMaster Inc.. pp. 68. ISBN 0-940780-81-X. 
  14. ^ Watkins BM (November 2003). "Drugs for the control of parasitic diseases: current status and development". Trends Parasitol 19 (11): 477–8. doi:10.1016/j.pt.2003.09.010. PMID 14580957. 
  15. ^ Hoerauf A, Mand S, Fischer K et al (2003). "Doxycycline as a novel strategy against bancroftian filariasis-depletion of Wolbachia endosymbionts from Wuchereria bancrofti and stop of microfilaria production". Med. Microbiol. Immunol. 192 (4): 211–6. doi:10.1007/s00430-002-0174-6. PMID 12684759. 
  16. ^ Taylor MJ, Makunde WH, McGarry HF, Turner JD, Mand S, Hoerauf A (2005). "Macrofilaricidal activity after doxycycline treatment of Wuchereria bancrofti: a double-blind, randomised placebo-controlled trial". Lancet 365 (9477): 2116–21. doi:10.1016/S0140-6736(05)66591-9. PMID 15964448. 
  17. ^ Outland, Katrina (24 June 2005). "New Treatment for Elephantitis: Antibiotics". 13. The Journal of Young Investigators. http://www.jyi.org/news/nb.php?id=361. 
  18. ^ Center for Drug Evaluation and Research (November–December 2004). "European recommendations on the use of oral antibiotics for acne". Food and Drug Administration. http://www.jle.com/en/revues/medecine/ejd/e-docs/00/04/07/1B/article.md?type=text.html. Retrieved 2008-01-31. [verification needed]
  19. ^ Archer JS, Archer DF (2002). "Oral contraceptive efficacy and antibiotic interaction: a myth debunked". J. Am. Acad. Dermatol. 46 (6): 917–23. doi:10.1067/mjd.2002.120448. PMID 12063491. 
  20. ^ Dréno B, Bettoli V, Ochsendorf F, Layton A, Mobacken H, Degreef H (November–December 2004). "European recommendations on the use of oral antibiotics for acne". Eur J Dermatol 14 (6): 391–9. PMID 15564203. http://www.jle.com/e-docs/00/04/07/1B/vers_alt/VersionPDF.pdf. 
  21. ^ DeRossi SS, Hersh EV (2002). "Antibiotics and oral contraceptives". Dent. Clin. North Am. 46 (4): 653–64. doi:10.1016/S0011-8532(02)00017-4. PMID 12436822. 
  22. ^ Pharmacological Basis of Therapeutics; Editors: A. G. Gilman, L. S. Goodman, T. W. Rall and F. Murad, 7th edition, MacMillan Publishing Co., New York, 1985, pp. 1170-1198
  23. ^ "Principles and methods for the assessment of nephrotoxicity associated with exposure to chemicals". Environmental health criteria: 119. World Health Organization (WHO). ISBN 92 4 157119 5. ISSN 0250-863X. 1991.
  24. ^ a b Foye's Principles of Medicinal Chemistry; David A. Williams; William O. Foye, Thomas L. Lemke
  25. ^ a b Goodman & Gilman's The Pharmacological Basis of Therapeutics, 12ed, Laurence L. Brunton, Bruce A. Chabner, Björn C. Knollmann
  26. ^ Dursun D, Kim MC, Solomon A, Pflugfelder SC (2001). "Treatment of recalcitrant recurrent corneal erosions with inhibitors of matrix metalloproteinase-9, doxycycline and corticosteroids". Am. J. Ophthalmol. 132 (1): 8–13. doi:10.1016/S0002-9394(01)00913-8. PMID 11438047. 
  27. ^ Moses MA, Harper J, Folkman J (2006). "Doxycycline treatment for lymphangioleiomyomatosis with urinary monitoring for MMPs". N. Engl. J. Med. 354 (24): 2621–2. doi:10.1056/NEJMc053410. PMID 16775248. 
  28. ^ Errami M, Galindo CL, Tassa AT, Dimaio JM, Hill JA, Garner HR (2007). "Doxycycline attenuates isoproterenol- and transverse aortic banding- induced cardiac hypertrophy in mice". J Pharmacol Exp Ther 324 (3): 1196–203. doi:10.1124/jpet.107.133975. PMID 18089841. 
  29. ^ Dalvi PS, Singh A, Trivedi HR et al (2011). "Effect of doxycycline in patients of moderate to severe chronic obstructive pulmonary disease with stable symptoms". Ann Thorac Med 6 (4): 221–6. doi:10.4103/1817-1737.84777. PMC 3183640. PMID 21977068. http://www.thoracicmedicine.org/article.asp?issn=1817-1737;year=2011;volume=6;issue=4;spage=221;epage=226;aulast=Dalvi. 
  30. ^ Saraiva IH, Jones RN, Erwin M, Sader HS (1997). "[Evaluation of antimicrobial sensitivity of 87 clinical isolates of vancomycin-resistant enterococci]" (in Portuguese). Rev Assoc Med Bras 43 (3): 217–22. doi:10.1590/S0104-42301997000300009. PMID 9497549. 
  31. ^ Dibb WL, Digranes A (1981). "Characteristics of 20 human Pasteurella isolates from animal bite wounds". Acta Pathol Microbiol Scand [B] 89 (3): 137–41. PMID 7315339. 
  32. ^ Sreekanth VR, Handa R, Wali JP, Aggarwal P, Dwivedi SN (2000). "Doxycycline in the treatment of rheumatoid arthritis--a pilot study". J Assoc Physicians India 48 (8): 804–7. PMID 11273473. 
  33. ^ Nordström D, Lindy O, Lauhio A, Sorsa T, Santavirta S, Konttinen YT (1998). "Anti-collagenolytic mechanism of action of doxycycline treatment in rheumatoid arthritis". Rheumatol. Int. 17 (5): 175–80. doi:10.1007/s002960050030. PMID 9542777. 
  34. ^ Raza M, Ballering JG, Hayden JM, Robbins RA, Hoyt JC (2006). "Doxycycline decreases monocyte chemoattractant protein-1 in human lung epithelial cells". Exp. Lung Res. 32 (1–2): 15–26. doi:10.1080/01902140600691399. PMID 16809218. 
  35. ^ Chodosh S, Tuck J, Pizzuto D (1988). "Comparative trials of doxycycline versus amoxicillin, cephalexin and enoxacin in bacterial infections in chronic bronchitis and asthma". Scand J Infect Dis Suppl 53: 22–8. PMID 3047855. 
  36. ^ Bachelez H, Senet P, Cadranel J, Kaoukhov A, Dubertret L (2001). "The use of tetracyclines for the treatment of sarcoidosis". Arch Dermatol 137 (1): 69–73. PMID 11176663. http://archderm.ama-assn.org/cgi/content/full/137/1/69. 
  37. ^ El Sayed F, Dhaybi R, Ammoury A (2006). "Subcutaneous nodular sarcoidosis and systemic involvement successfully treated with doxycycline". J Med Liban 54 (1): 42–4. PMID 17044634. 
  38. ^ Briest W, Cooper TK, Tae HJ, Krawczyk M, McDonnell NB, Talan MI (2011). "Doxycycline ameliorates the susceptibility to aortic lesions in a mouse model for the vascular type of ehlers-danlos syndrome". J Pharmacol Exp Ther 337 (3): 621–27. doi:10.1124/jpet.110.177782. PMC 3101011. PMID 21363928. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3101011. 
  39. ^ "Antibiotics 'could help slow MS'". BBC News. 2007-12-11. http://news.bbc.co.uk/2/hi/health/7136088.stm. Retrieved 2008-01-31. 
  40. ^ Mishra GP, Mulani JD. "Doxycycline: An Old Drug With A New Role In Idiopathic Pulmonary Fibrosis". International Journal of Pharma and Bio Sciences. V1(2) 2010. ISSN 0975-6299.

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