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10-SEPTEMBER-2008 16:47:15 - Diclofenac Diclofenac Systematic IUPAC name 2-2-2,6-dichlorophenylaminophenylacetic acid Identifiers CAS number 15307-86-5 ATC code M01AB05 M02AA15, S01BC03 PubChem 3033 DrugBank APRD00527 Chemical data Formula C14H11Cl2NO2 Mol. mass 296.148 g/mol Pharmacokinetic data Bioavailability 100% Protein binding more than 99% Metabolism hepatic, no active metabolites exist Half life 1.2-2 hr 35% of the drug enters enterohepatic recirculation Excretion biliary, only 1% in urine Therapeutic considerations Pregnancy cat. AAU B 1st. and 2nd. trimenon, X third trimenon Legal status POMUK Rx-only most preparations/countries. Limited OTC some countries Routes oral, rectal, im, iv renal- and gallstones, topical Diclofenac marketed as MOBIDIC, Flector patch, Voltaren, Voltarol, Diclon, Dicloflex Difen, Difene, Cataflam, Pennsaid, Rhumalgan, Modifenac, Abitren, Olfen, Voveran, Arthrotec, Dedolor, Deflamat and Zolterol, with various drug dose combinations is a non-steroidal anti-inflammatory drug NSAID taken to reduce inflammation and as an analgesic reducing pain in conditions such as arthritis or acute injury. It can also be used to reduce menstrual pain, dysmenorrhea. The name is derived from its chemical name: 2-2,6-dichloranilino phenylacetic acid In the United Kingdom, India, and the United States, it may be supplied as either the sodium or potassium salt, in China most often as the sodium salt, while in some other countries only as the potassium salt. Diclofenac is available as a generic drug in a number of formulations. Over the counter OTC use is approved in some countries for minor aches and pains and fever associated with common infections. Contents 1 Mechanism of action 2 Indications 2.1 Off label/investigational uses 3 Contraindications 4 Side effects 4.1 Cardiac 4.2 Gastrointestinal 4.3 Hepatic 4.4 Renal 4.5 Other 5 Formulations 6 Ecological problems 7 References 8 External links Mechanism of action The action of one single dose is much longer 6 to 8 hours than the very short half-life that the drug indicates. This could partly be due to a particular high concentration achieved in synovial fluids. The exact mechanism of action is not entirely known, but it is thought that the primary mechanism responsible for its anti-inflammatory / antipyretic / analgesic action is inhibition of prostaglandin synthesis by inhibition of cyclooxygenase COX. Inhibition of COX also decreases prostaglandins in the epithelium of the stomach, making it more sensitive to corrosion by gastric acid. This is also the main side effect of diclofenac. Diclofenac has a low to moderate preference to block the COX2-isoenzyme approximately 10-fold and is said to have therefore a somewhat lower incidence of gastrointestinal complaints than noted with indomethacin and aspirin. Diclofenac may also be a unique member of the NSAIDs. There is some evidence that diclofenac inhibits the lipoxygenase pathways, thus reducing formation of the leukotrienes also pro-inflammatory autacoids. There is also speculation that diclofenac may inhibit phospholipase A2 as part of its mechanism of action. These additional actions may explain the high potency of diclofenac - it is the most potent NSAID on a broad basis. There are marked differences among NSAIDs in their selective inhibition of the two subtypes of cyclo-oxygenase, COX-1 and COX-2. Much pharmaceutical drug design has attempted to focus on selective COX-2 inhibition as a way to minimize the gastrointestinal side effects of NSAIDs like aspirin. In practice, use of some COX-2 inhibitors due to their adverse effects has led to massive numbers of patient family lawsuits alleging wrongful death by heart attack, yet other significantly COX-selective NSAIDs like diclofenac have been well-tolerated by most of the population. Besides the well-known and often cited COX-inhibition, a number of other molecular targets of diclofenac have recently been identified which could contribute to its pain-relieving actions. These include: -Blockade of voltage-dependent sodium channels after activation of the channel, diclofenac inhibits its reactivation -Blockade of acid-sensing ion channels ASICs -Positive allosteric modulation of KCNQ- and BK-potassium channels diclofenac opens these channels, leading to hyperpolarization of the cell membrane Indications Combined Diclofenac sodium and misoprostol tablets. Combined Diclofenac sodium and misoprostol tablets. Diclofenac is used for musculoskeletal complaints, especially arthritis rheumatoid arthritis, osteoarthritis, spondylarthritis, ankylosing spondylitis, gout attacks, and pain management in case of kidney stones and gallstones. An additional indication is the treatment of acute migraines. Diclofenac is used commonly to treat mild to moderate post-operative or post-traumatic pain, particularly when inflammation is also present, and is effective against menstrual pain. Diclofenac suppositories Diclofenac suppositories As long-term use of diclofenac and similar NSAIDs predisposes for peptic ulcer, many patients at risk for this complication are prescribed a combination Arthrotec of diclofenac and misoprostol, a synthetic prostaglandin analogue, to protect the gastric mucosa. An external, gel-based formulation containing 3% of diclofenac Solareze is available for the treatment of facial actinic keratosis which is caused by over-exposure to sunlight. Some countries have also approved the external use of diclofenac 1% gel to treat musculoskeletal conditions. Over-the-counter use against minor aches and pains and fever associated with common infections is also licensed in some countries, such as Australia and New Zealand. In many countries eye-drops are sold to treat acute and chronic non-bacterial inflammations of the anterior part of the eyes e.g. postoperative states. A common brand name is Voltaren-ophta. Off label/investigational uses Diclofenac is often used to treat chronic pain associated with cancer, particularly if inflammation is also present Step I of the World Health Organisation WHO Scheme for treatment of chronic pain. Good results sometimes better than those with opioids have been seen in female breast cancer and in the pain associated with bony metastases. Diclofenac can be combined with opioids if needed. In Europe Combaren exists, a fixed combination of diclofenac and codeine 50 mg each for cancer treatment. Combinations with psychoactive drugs such as chlorprothixene and/or amitriptyline have also been investigated and found useful in a number of cancer patients. Fever due to malignant lymphogranulomatosis Hodgkin's lymphoma often responds to diclofenac. Treatment can be terminated as soon as the usual treatment with radiation and/or chemotherapy causes remission of fever. Diclofenac may prevent the development of Alzheimer's disease if given daily in small doses during many years. All investigations were stopped after it was found that some of the other investigated NSAIDs naproxen, rofecoxib caused a higher incidence of death cases due to cardiovascular events and stroke compared to placebo. Diclofenac has been found to increase the blood pressure in patients with Shy-Drager syndrome autonomous hypotension often seen in diabetic patients. Currently, this use is highly investigational and cannot be recommended as routine treatment. Diclofenac has been found to be effective against all strains of multi drug resistant E. coli, with a MIC of 25 microg/mL. Therefore, it may be suggested that diclofenac has the capacity to treat UTI uncomplicated urinary tract infections caused by E. coli.1 It has also been shown to be effective in treating Salmonella infections in mice 2 and is under investigation for the treatment of tuberculosis3. Its mechanism of action is not clear yet but it appears to inhibit DNA systhesis. 4 Contraindications Hypersensitivity against diclofenac History of allergic reactions bronchospasm, shock, rhinitis, urticaria following the use of Aspirin or another NSAID Third-trimester pregnancy Active stomach and/or duodenal ulceration or gastrointestinal bleeding Inflammative intestinal disorders such as Crohn's disease or ulcerative colitis Severe insufficiency of the heart NYHA III/IV Recently, a warning has been issued by FDA not to use to treat patients recovering from heart surgery Severe liver insufficiency Child-Pugh Class C Severe renal insufficiency creatinine clearance 30 ml/min Caution in patients with preexisting hepatic porphyria, as diclofenac may trigger attacks Caution in patients with severe, active bleeding such as cerebral hemorrhage NSAIDs in general should be avoided during Dengue Fever. Side effects Diclofenac is among the better tolerated NSAIDs. Though 20% of patients on long-term treatment experience side effects, only 2% have to discontinue the drug, mostly due to gastrointestinal complaints. Cardiac Following the identification of increased risks of heart attacks with the selective COX-2 inhibitor rofecoxib in 2004, attention has focused on all the other members of the NSAIDs group, including Diclofenac. Research results are mixed with a meta-analysis of papers and reports up to April 2006 suggesting a relative increased rate of heart disease of 1.63 compared to non users.5 Professor Peter Weissberg, Medical Director of the British Heart Foundation said, However, the increased risk is small and many patients with chronic debilitating pain may well feel that this small risk is worth taking to relieve their symptoms. Only Aspirin was found not to increase the risk of heart disease, however this is known to have a higher rate of gastric ulceration than Diclofenac. A subsequent large study of 74,838 users of NSAIDs or coxibs, published in May 2006 found no additional cardiovascular risk from Diclofenac use.6 Diclonefac has similar COX-2 selectivity to celecoxib 7. Perhaps related to this selectivity, a review of this constantly changing topic by FDA Medical Officer David Graham concluded in September, 2006 that Diclofenac does increase the risk of myocardial infarction 8. Gastrointestinal Gastrointestinal complaints are most often noted see above. The development of ulceration and/or bleeding requires immediate termination of treatment with diclofenac. Most patients receive an ulcer-protective drug as prophylaxis during long-term treatment misoprostol, ranitidine 150mg at bedtime or omeprazole 20 mg at bedtime. Hepatic Liver damage occurs infrequently, and is usually reversible. Hepatitis may occur rarely without any warning symptoms and may be fatal. Patients with osteoarthritis more often develop symptomatic liver disease than patients with rheumatoid arthritis. Liver function should be monitored regularly during long-term treatment. If used for the short term treatment of pain or fever, diclofenac has not been found to be more hepatotoxic than other NSAIDs. Renal Studies in Pakistan showed that diclofenac caused acute kidney failure in vultures when they ate the carcasses of animals that had recently been treated with it see below at Ecological problems. Species and individual humans that are drug sensitive are initially assumed to lack genes expressing specific drug detoxification enzymes. Because elderly humans have reduced expression levels of all enzymes, elderly human metabolisms may gradually approach those of vultures, thus unexpectedly becoming more diclofenac intolerant. NSAIDs are associated with adverse renal kidney effects caused by the reduction in synthesis of renal prostaglandins9 in sensitive persons or animal species, and potentially during long term use in non-sensitive persons if resistance to side effects decreases with age. Unfortunately this side effect can't be avoided merely by using a COX-2 selective inhibitor because, Both isoforms of COX, COX-1 and COX-2, are expressed in the kidney... Consequently, the same precautions regarding renal risk that are followed for nonselective NSAIDs should be used when selective COX-2 inhibitors are administered.9 Other Bone marrow depression is noted infrequently leukopenia, agranulocytosis, thrombopenia with/without purpura, aplastic anemia. These conditions may be life-threatening and/or irreversible, if detected too late. All patients should be monitored closely. Diclofenac is a weak and reversible inhibitor of thrombocytic aggregation needed for normal coagulation. Diclofenac may disrupt the normal menstrual cycle. Formulations Enteric Coated Diclofenac Sodium tablets by Dexel-Pharma Ltd. Enteric Coated Diclofenac Sodium tablets by Dexel-Pharma Ltd. Flector Patch is a minimally systemic topical patch formulation of diclofenac. It is indicated for acute pain due to minor sprains, strains, and contusions. The patch has been approved in many other countries outside the U.S.A under different brand names. Voltaren and Voltarol contain the sodium salt of diclofenac. In the United Kingdom Voltarol can be supplied with either the sodium salt or potassium salt, while Cataflam in some other countries is the potassium salt only. Diclofenac is available in stomach acid resistant formulations 25 and 50 mg, fast disintegrating oral formulations 50 mg, slow- and controlled-release forms 75, 100 or 150 mg, suppositories 50 and 100 mg, and injectable forms 50 and 75 mg. Diclofenac is also available over the counter OTC in some countries: Voltaren dolo 12.5 mg diclofenac as potassium salt in Switzerland and Germany, and preparations containing 25 mg diclofenac in New Zealand, and in Sweden Voltaren 25mg Diclofenac is also available in Suppository formulation. NB: Diclofenac is known in the Baltic States as Diclofenacum. Ecological problems Use of diclofenac in animals has been reported to have led to a sharp decline in the vulture population in the Indian subcontinent, up to 95% in some areas.10 The mechanism is probably renal failure, a known side-effect of diclofenac. Vultures eat the carcasses of domesticated animals that have been administered veterinary diclofenac, and are poisoned by the accumulated chemical. At a meeting of the National Wildlife Board in March 2005, the Government of India announced that it intended to phase out the veterinary use of diclofenac.11 Meloxicam is a safer though more expensive candidate to replace use of diclofenac.12 The loss of tens of millions of vultures over the last decade has had major ecological consequences across the Indian subcontinent that pose a potential threat to human health. In many places, populations of feral dogs Canis familiaris sic have increased sharply from the disappearance of Gyps vultures as the main scavenger of wild and domestic ungulate carcasses. Associated with the rise in dog numbers is an increased risk of rabies12 and casualties of almost 50,000 people.13 The Government of India cites one of those major consequences as a vulture species extinction.11 A major shift in transfer of corpse pathogens from vultures to feral dogs and rats can lead to a disease pandemic causing millions of deaths in a crowded country like India. The loss of vultures has had a social impact on the Indian Zoroastrian Parsi community, who traditionally use vultures to dispose of human corpses in sky burials Towers of Silence, and are now having to seek alternative disposal methods.12 Diclofenac was shown also to cause harm to freshwater fish species as rainbow trout Schwaiger et al. 2004. Aquat. Toxicol. 682: 141-150;Triebskorn et al. 2004. Aquat. Toxicol. 682: 151-166; Schwaiger Triebskorn 2005. UBA-Berichte 29/05: 217-226. Triebskorn et al. 2007. Analyt. Bioanalyt. Chem. 3874: 1405-1416. References ^ Mazumdar K, Dutta NK, Dastidar SG, Motohashi N, Shirataki Y 2006. Diclofenac in the management of E. coli urinary tract infections. In Vivo 20 5: 613-619. PMID 17091768. ^ Dutta NK, Annadurai S, Mazumdar K, Dastidar SG, Kristiansen JE, Molnar J, Martins M, Amaral L. 2007. Potential management of resistant microbial infections with a novel non-antibiotic: the anti-inflammatory drug diclofenac sodium. Int. J. Antimicrob. Agents 30 3: 242-249. ^ Dutta NK, Mazumdar K, Dastidar SG, Park JH 2007. Activity of diclofenac used alone and in combination with streptomycin against Mycobacterium tuberculosis in mice. Int. J. Antimicrob. Agents 30 4: 336-340. ^ Dutta NK, Annadurai S, Mazumdar K, Dastidar SG, Kristiansen JE, Molnar J, Martins M, Amaral L 2000. The anti-bacterial action of diclofenac shown by inhibition of DNA synthesis. Int. J. Antimicrob. Agents 14 3: 249-51. ^ Kearney P, Baigent C, Godwin J, Halls H, Emberson J, Patrono C 2006. Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ 332 7553: 1302-8. doi:10.1136/bmj.332.7553.1302. PMID 16740558. ^ Solomon D, Avorn J, Stürmer T, Glynn R, Mogun H, Schneeweiss S 2006. Cardiovascular outcomes in new users of coxibs and nonsteroidal antiinflammatory drugs: high-risk subgroups and time course of risk. Arthritis Rheum 54 5: 1378-89. doi:10.1002/art.21887. PMID 16645966. ^ FitzGerald G, Patrono C 2001. The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med 345 6: 433-42. doi:10.1056/NEJM200108093450607. PMID 11496855. ^ Graham D 2006. COX-2 inhibitors, other NSAIDs, and cardiovascular risk: the seduction of common sense. JAMA 296 13: 1653-6. doi:10.1001/jama.296.13.jed60058. PMID 16968830. ^ a b Brater DC 2002. Renal effects of cyclooxygyenase-2-selective inhibitors. J Pain Symptom Manage 23 4 Suppl: S15-20; discussion S21-3. doi:10.1016/S0885-39240200370-6. PMID 11992745. ^ Oaks JL, Gilbert M, Virani MZ, Watson RT, Meteyer CU, Rideout BA, Shivaprasad HL, Ahmed S, Chaudhry MJ, Arshad M, Mahmood S, Ali A, Khan AA 2004. Diclofenac residues as the cause of vulture population decline in Pakistan. Nature 427 6975: 630-3. doi:10.1038/nature02317. PMID 14745453. ^ a b Press Information Bureau, Government of India 2005-05-16. Saving the Vultures from Extiction. Press release. Retrieved on 2006-05-12. ^ a b c Swan G, Naidoo V, Cuthbert R, Green RE, Pain DJ, Swarup D, Prakash V, Taggart M, Bekker L, Das D, Diekmann J, Diekmann M, Killian E, Meharg A, Patra RC, Saini M, Wolter K 2006. Removing the threat of diclofenac to critically endangered Asian vultures. PLoS Biol 4 3: e66. doi:10.1371/journal.pbio.0040066. PMID 16435886. ^ Rabies follows disruption in food cycle External links v d e Non-steroidal anti-inflammatory drug NSAID products primarily M01A and M02A, also N02BA Salicylates Aspirin acetylsalicylic acid · Aloxiprin · Benorylate · Diflunisal · Ethenzamide · Magnesium salicylate · Methyl salicylate · Salsalate · Salicin · Salicylamide · Sodium salicylate Arylalkanoic acids Diclofenac · Aceclofenac · Acemetacin · Alclofenac · Bromfenac · Etodolac · Indometacin · Indometacin farnesil · Nabumetone · Oxametacin · Proglumetacin · Sulindac · Tolmetin 2-Arylpropionic acids profens Ibuprofen · Alminoprofen · Benoxaprofen · Carprofen · Dexibuprofen · Dexketoprofen · Fenbufen · Fenoprofen · Flunoxaprofen · Flurbiprofen · Ibuproxam · Indoprofen†· Ketoprofen · Ketorolac · Loxoprofen · Miroprofen · Naproxen · Oxaprozin · Pirprofen · Suprofen · Tarenflurbil · Tiaprofenic acid N-Arylanthranilic acids fenamic acids Mefenamic acid · Flufenamic acid · Meclofenamic acid · Tolfenamic acid Pyrazolidine derivatives Phenylbutazone · Ampyrone · Azapropazone · Clofezone · Kebuzone · Metamizole†· Mofebutazone · Oxyphenbutazone · Phenazone · Sulfinpyrazone Oxicams Piroxicam · Droxicam · Lornoxicam · Meloxicam · Tenoxicam · Ampiroxicam COX-2 inhibitors Celecoxib · Deracoxib‡ · Etoricoxib · Firocoxib‡ · Lumiracoxib†· Parecoxib · Rofecoxib†· Valdecoxib†Sulphonanilides Nimesulide Topically used products Bendazac · Diclofenac · Etofenamate · Felbinac · Flurbiprofen · Ibuprofen · Indometacin · Ketoprofen · Naproxen · Piroxicam · Suprofen Others Fluproquazone · COX-inhibiting nitric oxide donator Items listed in bold indicate initially developed compounds of specific groups. †Withdrawn drugs. ‡Veterinary use medications. v d e Anti-inflammatory and antirheumatic products M01 Anti-inflammatory and antirheumatic products, non-steroids See also: NSAIDs Pyrazolidine/Butylpyrazolidines: · Ampyrone · Clofezone · Kebuzone · Metamizole · Mofebutazone · Oxyphenbutazone · Phenazone · Phenylbutazone · Sulfinpyrazone · Acetic acid derivatives and related substances: · Aceclofenac · Acemetacin · Alclofenac · Bromfenac · Bumadizone · Bufexamac · Diclofenac · Difenpiramide · Etodolac · Fentiazac · Indometacin · Ketorolac · Lonazolac · Oxametacin · Proglumetacin · Sulindac · Tolmetin · Zomepirac · Oxicams: · Ampiroxicam · Droxicam · Lornoxicam · Meloxicam · Piroxicam · Tenoxicam · Propionic acid derivatives: · Alminoprofen · Benoxaprofen · Dexibuprofen · Dexketoprofen · Fenbufen · Fenoprofen · Flunoxaprofen · Flurbiprofen · Ibuprofen · Ibuproxam · Indoprofen · Ketoprofen · Naproxen · Oxaprozin · Pirprofen · Suprofen · Tiaprofenic acid · Fenamates: · Flufenamic acid · Meclofenamic acid · Mefenamic acid · Tolfenamic acid · Coxibs: · Celecoxib · Etoricoxib · Lumiracoxib · Parecoxib · Rofecoxib · Valdecoxib · other anti-inflammatory and antirheumatic agents, non-steroids: · Nabumetone · Niflumic acid · Azapropazone · Glucosamine · Benzydamine · Glycosaminoglycan · Magnesium salicylate · Proquazone · Superoxide dismutase/Orgotein · Nimesulide · Feprazone · Diacerein · Morniflumate · Tenidap · Oxaceprol · Chondroitin sulfate · Specific antirheumatic agents Quinolines: · Oxycinchophen · Gold preparations: · Sodium aurothiomalate · Sodium aurothiosulfate · Auranofin · Aurothioglucose · Aurotioprol · Penicillamine/Bucillamine v d e Topical products for joint and muscular pain M02 Anti-inflammatory preparations, non-steroids Butylpyrazolidines: Phenylbutazone - Mofebutazone - Clofezone - Oxyphenbutazone Acetic acid derivatives: Tolmetin - Diclofenac - Fentiazac other: Benzydamine - Etofenamate - Piroxicam - Felbinac - Bufexamac - Ketoprofen - Bendazac - Naproxen - Ibuprofen - Feprazone - Niflumic acid - Meclofenamic acid - Flurbiprofen - Suxibuzone - Indometacin - Nifenazone Other Tolazoline - Dimethyl sulfoxide v d e Analgesic products N02A, N02B Opioids See also: Opioids template Opium Alkaloids Thereof Codeine · Morphine · Opium · Laudanum · Paregoric Semi-Synthetic Opium Derivatives Acetyldihydrocodeine · Benzylmorphine · Desomorphine · Dihydrocodeine · Dihydromorphine · Ethylmorphine · Diamorphine · Hydrocodone · Hydromorphinol · Hydromorphone · Nicocodeine · Nicodicodeine · Nicomorphine · Oxycodone · Oxymorphone · Thebacon Synthetic Opioids Alphaprodine · Anileridine · Buprenorphine · Butorphanol · Dextromoramide · Dextropropoxyphene · Dezocine · Fentanyl · Ketobemidone · Levorphanol · Methadone · Meptazinol · Nalbuphine · Pentazocine · Propoxyphene · Propiram · Pethidine · Phenazocine · Piminodine · Piritramide · Tapentadol · Tilidine · Tramadol Pyrazolones Ampyrone/Aminophenazone · Metamizole · Phenazone Cannabinoids Ajulemic acid · AM404 · Cannabidiol · Cannabis · Nabilone · Tetrahydrocannabinol Anilides Paracetamol acetaminophen · Phenacetin · Propacetamol Non-Steroidal Anti-Inflammatories See also: NSAIDs template Propionic Acid NSAIDs Fenoprofen · Flurbiprofen · Ibuprofen · Ketoprofen · Naproxen · Oxaprozin Oxicam NSAIDs Meloxicam · Piroxicam · Acetic Acid NSAIDs Diclofenac · Indometacin · Ketorolac · Sulindac · Tolmetin COX-2 NSAIDs Celecoxib · Rofecoxib Anthranilic Acid Fenamate NSAIDS Meclofenamate · Mefenamic acid Salicylate NSAIDS Aspirin Acetylsalicylic Acid · Benorylate · Diflunisal · Ethenzamide · Magnesium Salicylate · Salicin · Salicylamide · Salsalate · Trisalate Other NSAIDS Nabumetone Atypical, Adjunct Miscellaneous Bicifadine · Clonidine · Cyclobenzaprine · Duloxetine · Flupirtine · Gabapentin · Glafenine · Nefopam · Orphenadrine · Tebanicline · Trazodone · Ziconotide Retrieved from http://en..org/wiki/Diclofenac Categories: Carboxylic acids | Non-steroidal anti-inflammatory drugs | Organochlorides Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Türkçe Deutsch Español Esperanto Français Italiano Magyar Nederlands 日本語 Polski Português Română РуÑ?Ñ?кий Suomi Svenska ไทย Tiếng Việt Türkçe This page was last modified on 18 August 2008, at 22:13
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