Naproxen with lithium

In one study, there was a mean increase of only 17% in healthy volunteers taking celecoxib 200 mg bd (667). When celecoxib was co-administered with lithium, celecoxib concentrations were higher for the first 6 hours after the dose but the AUC was not altered significantly (668). In another review it was mentioned that clinically significant interactions with lithium (increased lithium concentrations) had been identified, but no detail was presented (669). Both celecoxib and naproxen reduced the renal clearance of lithium (used as a measure of proximal tubular sodium reabsorption) (670). 

Care needs to be taken when combining naproxen with other medications. Known adverse drug interactions can occur with aspirin, methotrexate, ACE inhibitors (for high blood pressure), furosemide, lithium, and warfarin (a blood thinner). An overdose of naproxen may cause dizziness, drowsiness, and gastrointestinal problems. High blood pressure, kidney failure, and coma may occur, but are rare. 

Clinically important, potentially hazardous interactions with acitretin, aldesleukin, aminoglycosides, amiodarone, amoxicillin, ampicillin, aspirin, bacampicillin, bismuth, carbenicillin, chloroquine, cisplatin, cloxacillin, co-trimoxazole, dapsone, demeclocycline, dexamethasone, diclofenac, dicloxacillin, etodolac, etoricoxib, etretinate, fenoprofen, flurbiprofen, folic acid antagonists, haloperidol, hydrocortisone, ibuprofen, indomethacin, influenza vaccines, ketoprofen, ketorolac, lithium, magnesium trisalicylate, meclofenamate, mefenamic acid, methicillin, mezlocillin, minocycline, nabumetone, nafcillin, naproxen, NSAIDs, omeprazole, oxacillin, oxaprozin, oxytetracycline, paromomycin, penicillin G, penicillin V, penicillins, phenylbutazone, piperacillin, piroxicam, polypeptide antibiotics, prednisolone, prednisone, probenecid, procarbazine, rofecoxib, salicylates, salsalate, sapropterin, sulfadiazine, sulfamethoxazole, sulfapyridine, sulfasalazine, sulfisoxazole, sulindac, tazobactum, tenoxicam, tetracycline, ticarcillin, tolmetin, trimethoprim, vaccines... 

Internal proton return to lithium enolates from secondary amines which are coordinated to the lithium ion has been used for diastereoselective (Sections 2.1.3.6. and 2.1.4.2.) and enantioselec-tive (Section 2.1.6.1.2.) protonations. A remarkable example of enantioselective internal proton return, with the exclusion of any additional proton source, occurs with racemic Naproxen amides 1l63a. 

Most of the renal tubular reabsorption ofU occurs in the proximal tubule. Nevertheless, Id retention can be increased by any diuretic that leads to depletion of Na, particularly the thiazides (see Chapter 28). Renal excretion can be increased by administration of osmotic diuretics, aceta-zolamide or aminophylline, and triamterene. Spironolactone does not increase the excretion of LiL Some nonsteroidal anti-inflammatory agents can facilitate renal proximal tubular resorption of Id and thereby increase concentrations in plasma to toxic levels. This interaction appears to be particularly prominent with indomethacin, but also may occur with ibuprofen, naproxen, and COX-2 inhibitors, and possibly less so with sulindac and aspirin. A potential drug interaction can occur with angiotensin-converting enzyme inhibitors, causing lithium retention (see Chapter 29). 

Drug interactions occur with many commonly prescribed medications and are mostly due to naproxen s effects on renal prostaglandins and the associated changes in kidney filtration rate, although many other mechanisms exist. Many drug interactions exist, with examples being ACE inhibitors, beta blockers, methotrexate, lithium, probenecid, antiplatelet agents, diuretics, and vancomycin. 

Sb(0S02CF3)3 has been reported as Lewis catalyst for reactions requiring traces of water. Benzoylation of toluene, acylation of m-xylene, and sulfonylation of toluene were examples demonstrating its role in Friedel-Crafts reactions [26]. Also, catalytic amount of Sb(OTf)3 catalyzed the reaction of 2-methoxynaphthalene with acetic anhydride in nitromethane-lithium perchlorate to afford 2-acetyl-6-methoxynaphthalene, a well-known intermediate for the synthesis of naproxen, in a high yield [27]. 

The use of chiral lithium amide bases in combination with achiral protonating agents provides as striking argument for the internal proton return in mixed eno-late aggregates. The concept was verified first by Hogeveen and Zwart [233] and thereafter studied intensively by Vedejs and coworkers who used Lewis acids for reprotonation [234]. The method is illustrated for the deracemization of naproxen amide 466 that is converted into a mixture of cis- and traws-enolates 468 in the ratio of 93 7 by treatment with 2 equiv. of s-butyllithium, followed by 2 equiv. of... 

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