Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C38H69NO13
Monoisotopic mass
747.476891299
InChI
InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
InChI Key
InChIKey=AGOYDEPGAOXOCK-KCBOHYOISA-N
IUPAC Name
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-12,13-dihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-7-methoxy-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
Traditional IUPAC Name
clarithromycin
SMILES
[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[C@H](C)O1)O[C@H]1[C@H](C)[C@@H](O[C@]2([H])O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]1C)OC
pKa (strongest acidic)
12.46
pKa (Strongest Basic)
8.38
Refractivity
190.79 m3·mol-1
Dược Lực Học :
Clarithromycin is a macrolide antibiotic whose spectrum of activity includes many gram-positive (Staphylococcus aureus, S. pneumoniae, and S. pyogenes) and gram-negative aerobic bacteria (Haemophilus influenzae, H. parainfluenzae, and Moraxella catarrhalis), many anaerobic bacteria, some mycobacteria, and some other organisms including Mycoplasma, Ureaplasma, Chlamydia, Toxoplasma, and Borrelia. Other aerobic bacteria that clarithromycin has activity against include C. pneumoniae and M. pneumoniae. Clarithromycin has an in-vitro activity that is similar or greater than that of erythromycin against erythromycin-susceptible organisms. Clarithromycin is usually bacteriostatic, but may be bactericidal depending on the organism and the drug concentration.
Cơ Chế Tác Dụng :
Clarithromycin, a semisynthetic macrolide antibiotic derived from erythromycin, inhibits bacterial protein synthesis by binding to the bacterial 50S ribosomal subunit. Binding inhibits peptidyl transferase activity and interferes with amino acid translocation during the translation and protein assembly process. Clarithromycin may be bacteriostatic or bactericidal depending on the organism and drug concentration.
Clarithromycin is first metabolized to 14-OH clarithromycin, which is active and works synergistically with its parent compound. Like other macrolides, it then penetrates bacteria cell wall and reversibly binds to domain V of the 23S ribosomal RNA of the 50S subunit of the bacterial ribosome, blocking translocation of aminoacyl transfer-RNA and polypeptide synthesis. Clarithromycin also inhibits the hepatic microsomal CYP3A4 isoenzyme and P-glycoprotein, an energy-dependent drug efflux pump.
Dược Động Học :
▧ Absorption :
Clarithromycin is well-absorbed, acid stable and may be taken with food.
▧ Protein binding :
~ 70% protein bound
▧ Metabolism :
Hepatic - predominantly metabolized by CYP3A4 resulting in numerous drug interactions.
▧ Route of Elimination :
After a 250 mg tablet every 12 hours, approximately 20% of the dose is excreted in the urine as clarithromycin, while after a 500 mg tablet every 12 hours, the urinary excretion of clarithromycin is somewhat greater, approximately 30%.
▧ Half Life :
3-4 hours
Độc Tính :
Symptoms of toxicity include diarrhea, nausea, abnormal taste, dyspepsia, and abdominal discomfort. Transient hearing loss with high doses has been observed. Pseudomembraneous colitis has been reported with clarithromycin use. Allergic reactions ranging from urticaria and mild skin eruptions to rare cases of anaphylaxis and Stevens-Johnson syndrome have also occurred. Rare cases of severe hepatic dysfunctions also have been reported. Hepatic failure is usually reversible, but fatalities have been reported. Clarithromycin may also cause tooth decolouration which may be removed by dental cleaning. Fetal abnormalities, such as cardiovascular defects, cleft palate and fetal growth retardation, have been observed in animals. Clarithromycin may cause QT prolongation.
Chỉ Định :
An alternative medication for the treatment of acute otitis media caused by H. influenzae, M. catarrhalis, or S. pneumoniae in patients with a history of type I penicillin hypersensitivity. Also for the treatment of pharyngitis and tonsillitis caused by susceptible Streptococcus pyogenes, as well as respiratory tract infections including acute maxillary sinusitis, acute bacterial exacerbations of chronic bronchitis, mild to moderate community-acquired pneuomia, Legionnaires' disease, and pertussis. Other indications include treatment of uncomplicated skin or skin structure infections, helicobacter pylori infection, duodenal ulcer disease, bartonella infections, early Lyme disease, and encephalitis caused by Toxoplasma gondii (in HIV infected patients in conjunction with pyrimethamine). Clarithromycin may also decrease the incidence of cryptosporidiosis, prevent the occurence of α-hemolytic (viridans group) streptococcal endocarditis, as well as serve as a primary prevention for Mycobacterium avium complex (MAC) bacteremia or disseminated infections (in adults, adolescents, and children with advanced HIV infection).
Tương Tác Thuốc :
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Abiraterone
Strong CYP3A4 inhibitors may increase levels of abiraterone. Monitor concomitant therapy closely.
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Acenocoumarol
The macrolide, clarithromycin, may increase the anticoagulant effect of acenocoumarol.
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Alprazolam
The macrolide, clarithromycin, may increase the effect of the benzodiazepine, alprazolam.
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Alvimopan
Decreases levels by P-glycoprotein (MDR-1) efflux transporter. Can significantly increase systemic exposure to P-glycoprotein substrates.
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Aminophylline
Clarithromycin may increase the effect amd toxicity of aminophylline.
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Amiodarone
Increased risk of cardiotoxicity and arrhythmias
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Anisindione
The macrolide, clarithromycin, may increase the anticoagulant effect of anisindione.
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Aprepitant
The CYP3A4 inhibitor, clarithromycin, may increase the effect and toxicity of aprepitant.
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Artemether
Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
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Astemizole
Increased risk of cardiotoxicity and arrhythmias
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Atazanavir
Atazanavir may increase serum level of clarithromycin.
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Atorvastatin
The macrolide, clarithromycin, may increase the toxicity of the statin, atorvastatin.
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Bretylium
Increased risk of cardiotoxicity and arrhythmias
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Bromazepam
Clarithromycin, a strong CYP3A4 inhibitor, may increase the serum concentration of bromazepam by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of bromazepam if clarithromycin is initiated, discontinued or dose changed. Dosage adjustments may be required.
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Buspirone
Clarithromycin may increase the effect and toxicity of buspirone.
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Cabazitaxel
Concomitant therapy with a strong CYP3A4 inhibitor may increase concentrations of cabazitaxel. Avoid concomitant therapy.
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Carbamazepine
Clarithromycin may decrease the metabolism of carbamazepine. Monitor for changes in the therapeutic or adverse effects of carbamazepine if clarithromycin is initiated, discontinued or dose changed.
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Cerivastatin
The macrolide, clarithromycin, may increase the toxicity of the statin, cerivastatin.
-
Cisapride
Increased risk of cardiotoxicity and arrhythmias
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Citalopram
Possible serotoninergic syndrome with this combination
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Colchicine
Severe colchicine toxicity can occur
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Cyclosporine
The macrolide, clarithromycin, may increase the effect of cyclosporine.
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Dabrafenib
Strong CYP3A4 inhibitors may increase levels of dabrafenib. Consider alternate therapy.
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Dantrolene
Clarithromycin may increase the serum concentration of dantrolene by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of dantrolene if clarithromycin is initiated, discontinued or dose changed.
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Darifenacin
This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
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Darunavir
Increased levels of clarithromycin
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Diazepam
The macrolide, clarithromycin, may increase the effect of the benzodiazepine, diazepam.
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Dicoumarol
The macrolide, clarithromycin, may increase the anticoagulant effect of dicumarol.
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Digoxin
The macrolide, clarithromycin, may increase the effect of digoxin in 10% of patients.
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Dihydroergotamine
Risk of ergotism and severe ischemia with this association
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Disopyramide
Increased risk of cardiotoxicity and arrhythmias
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Dofetilide
Increased risk of cardiotoxicity and arrhythmias
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Dronedarone
Clarithromycin is a strong CYP3A4 inhibitor in which concomitant use with dronedarone will significantly increase its exposure. Avoid concomitant use.
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Dyphylline
Increases the effect and toxicity of theophylline
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Efavirenz
Efavirenz decreases levels of clarithromycin
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Eletriptan
The macrolide, clarithromycin, may increase the effect and toxicity of eletriptan.
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Eplerenone
The macrolide, clarithromycin, may increase the effect and toxicity of eplerenone.
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Ergotamine
Risk of ergotism and severe ischemia with this association
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Erlotinib
This CYP3A4 inhibitor increases levels/toxicity of erlotinib
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Etravirine
Clarithromycin (and other macrolide antibiotics), when used concomitantly with etravirine, may experience a decrease in serum concentration. It is recommended to use alternative antibiotic agents if available. If concurrent therapy cannot be avoided, monitor for reduced effectiveness of clarithromycin.
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Everolimus
The macrolide, clarithromycin, may increase the serum concentration and toxicity of everolimus.
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Fluoxetine
Possible serotoninergic syndrome with this combination
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Fosphenytoin
Clarithromycin may increase the therapeutic and adverse effects of fosphenytoin.
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Gefitinib
This CYP3A4 inhibitor increases levels/toxicity of gefitinib
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Iloperidone
Clarithromycin is a strong CYP3A4 inhibitor that increases serum concentration of iloperidone. Reduce dose of iloperidone by 50%
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Imatinib
The macrolide, clarithromycin, may increase the serum concentration of imatinib.
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Indinavir
Indinavir may decrease the effectiveness of clarithromycin by decreasing the formatin of the active metabolite, 14-hydroxy-clarithromycin. Clarithromycin may increase the serum concentration of indinavir. Indinavir may increase the serum concentration of clarithromycin. Consider alternate therapy or monitor the efficacy and adverse effects of both agents more closely during concomitant therapy.
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Itraconazole
The macrolide, clarithromycin, may increase the effect and toxicity of itraconazole.
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Ivacaftor
Strong CYP3A4 inhibitors may increase levels of ivacaftor. Monitor concomitant therapy closely.
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Lovastatin
The macrolide, clarithromycin, may increase the toxicity of the statin, lovastatin.
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Lurasidone
Concomitant therapy with a strong CYP3A4 inhibitor will increase level or effect of lurasidone. Coadministration with lurasidone is contraindicated.
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Methylprednisolone
The macrolide, clarithromycin, may increase the effect of corticosteroid, methylprednisolone.
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Methysergide
Risk of ergotism and severe ischemia with this association
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Midazolam
The macrolide, clarithromycin, may increase the effect of the benzodiazepine, midazolam.
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Oxtriphylline
Clarithromycin may increase the effect and toxicity of oxtriphylline.
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Pazopanib
Clarithromycin is a strong inhibitor of CYP3A4 thus increasing exposure of pazopanib.
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Phenytoin
Clarithromycin may increase the therapeutic and adverse effects of phenytoin.
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Pimozide
Increased risk of cardiotoxicity and arrhythmias
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Ponatinib
Strong CYP3A4 inhibitors may increase levels of ponatinib. Monitor concomitant therapy closely.
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Quetiapine
The macrolide, clarithromycin, may increase the effect and toxicity of quetiapine.
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Quinidine
Increased risk of cardiotoxicity and arrhythmias
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Quinidine barbiturate
Increased risk of cardiotoxicity and arrhythmias
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Quinupristin
This combination presents an increased risk of toxicity
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Ranolazine
Clarithromycin, a strong CYP3A4 inhibitor, may increase the serum level of ranolazine. Concomitant therapy is contraindicated.
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Regorafenib
Strong CYP3A4 inhibitors may increase levels of regorafenib.
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Repaglinide
Clarithromycin may increase the effect of repaglinide.
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Rifabutin
The rifamycin, rifabutin, may decrease the effect of the macrolide, clarithromycin.
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Rifampicin
The rifamycin, rifampin, may decrease the effect of the macrolide, clarithromycin.
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Saxagliptin
Clarithromycin is an inhibitor of CYP3A4 which increases exposure of saxagliptin. Decrease dose of saxagliptin to 2.5 mg per day.
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Sertraline
Possible serotoninergic syndrome with this combination
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Sildenafil
Increases the effect and toxicity of sildenafil
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Simvastatin
The macrolide, clarithromycin, may increase the toxicity of the statin, simvastatin.
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Sirolimus
The macrolide, clarithromycin, may increase the serum concentration of sirolimus.
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Solifenacin
This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
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Sotalol
Increased risk of cardiotoxicity and arrhythmias
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Sunitinib
Possible increase in sunitinib levels
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Tacrolimus
Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The macrolide antibiotic, Clarithromycin, may also increase the blood concentration of Tacrolimus.
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Tadalafil
Clarithromycin may reduce the metabolism of Tadalafil. Concomitant therapy should be avoided if possible due to high risk of Tadalafil toxicity.
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Tamoxifen
Clarithromycin may increase the serum concentration of Tamoxifen by decreasing its metabolism. Monitor for increased adverse/toxic effects of Tamoxifen.
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Tamsulosin
Clarithromycin, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Clarithromycin is initiated, discontinued, or dose changed.
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Telithromycin
Co-administration may result in altered plasma concentrations of Clarithromycin and/or Telithromycin. Consider alternate therapy or monitor the therapeutic/adverse effects of both agents.
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Temsirolimus
Clarithromycin may inhibit the metabolism and clearance of Temsirolimus. Concomitant therapy should be avoided.
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Teniposide
The strong CYP3A4 inhibitor, Clarithromycin, may decrease the metabolism and clearance of Teniposide, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Teniposide if Clarithromycin is initiated, discontinued or dose changed.
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Terfenadine
Increased risk of cardiotoxicity and arrhythmias
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Theophylline
Clarithromycin may increase the therapeutic and adverse effects of theophylline.
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Thiothixene
May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
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Tiagabine
The strong CYP3A4 inhibitor, Clarithromycin, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Clarithromycin is initiated, discontinued or dose changed.
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Tipranavir
The concentrations of Tipranavir and Clarithromycin increase during concomitant therapy. Dose adjustments are required for patients with renal impairment.
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Tolterodine
Clarithromycin may decrease the metabolism and clearance of Tolterodine. Adjust Tolterodine dose and monitor for efficacy and toxicity.
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Tolvaptan
Clarithromycin is a strong inhibitor of CYP3A4 and will increase serum concentrations of tolvaptan.
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Topotecan
The p-glycoprotein inhibitor, Clarithromycin, may increase the bioavailability of oral Topotecan. A clinically significant effect is also expected with IV Topotecan. Concomitant therapy should be avoided.
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Toremifene
Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
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Tramadol
Clarithromycin may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
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Trazodone
The CYP3A4 inhibitor, Clarithromycin, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Consider alternate therapy or monitor for changes in Trazodone efficacy/toxicity if Clarithromycin is initiated, discontinued or dose changed.
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Triazolam
The macrolide, clarithromycin, may increase the effect of the benzodiazepine, triazolam.
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Trimipramine
Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Clarithromycin, a strong CYP3A4 inhibitor, may also decrease the metabolism and clearance of Trimipramine, a CYP3A4 substrate. Concomitant therapy should be used with caution.
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Valproic Acid
The macrolide antibiotic, Erythromycin, may increase the serum concentratin of Valproic acid. Consider alternate therapy or monitor for changes in Valproic acid therapeutic and adverse effects if Clarithromycin is initiated, discontinued or dose changed.
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Vardenafil
Clarithromycin, a strong CYP3A4 inhibitor, may reduce the metabolism and clearance of Vardenafil. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Vardenafil.
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Vemurafenib
Strong CYP3A4 inhibitors may increase levels of vemurafenib. Monitor concomitant therapy closely.
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Venlafaxine
Clarithromycin, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Venlafaxine, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Venlafaxine if Clarithromycin is initiated, discontinued, or dose changed.
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Verapamil
Clarithromycin, a strong CYP3A4 inhibitor, may increase the serum concentration of Veramapil, a CYP3A4 substrate, by decreasing its metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Verapamil if Clarithromycin is initiated, discontinued or dose changed.
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Vilazodone
CYP3A4 Inhibitors (Strong) may increase the serum concentration of Vilazodone. imit maximum adult vilazodone dose to 20 mg/day in patients receiving strong CYP3A4 inhibitors.
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Vinblastine
Clarithromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinblastine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vinblastine toxicity. Monitor for changes in the therapeutic/adverse effects of Vinblastine if Clarithromycin is initiated, discontinued or dose changed.
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Vincristine
Clarithromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vincristine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vincristine toxicity. Monitor for changes in the therapeutic and adverse effects of Vincristine if Clarithromycin is initiated, discontinued or dose changed.
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Vinorelbine
Clarithromycin, a CYP3A4 and p-glycoprotein inhibitor, may increase the Vinorelbine serum concentration and distribution in certain cells. Consider alternate therapy to avoid Vinorelbine toxicity. Monitor for changes in the therapeutic and adverse effects of Vinorelbine if Clarithromycin is initiated, discontinued or dose changed.
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Vismodegib
P-glycoprotein inhibitors may increase the chance of adverse drug reactions.
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Voriconazole
Additive QTc prolongation may occur. Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of clarithromycin by decreasing its metabolism. Clarithromycin may increase the serum concentration of voriconazole by decreasing its metabolism. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose changed.
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Vorinostat
Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
-
Warfarin
The macrolide, clarithromycin, may increase the anticoagulant effect of warfarin.
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Zidovudine
Clarithromycin may decrease the serum concentration of zidovudine. Increased myelosuppression in mice has been observed. Consider staggering doses during concomitant therapy and closely monitor response to zidovudine therapy.
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Ziprasidone
Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
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Zolpidem
Clarithromycin, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if clarithromycin is initiated, discontinued or dose changed.
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Zonisamide
Clarithromcyin, a strong CYP3A4 inhibitor, may increase the serum concentration of zonisamide by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zonisamide if clarithromycin is initiated, discontinued or dose changed.
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Zopiclone
Clarithromycin, a strong CYP3A4 inhibitor, may increase the serum concentration of zopiclone by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zopiclone if clarithromycin is initiated, discontinued or dose changed.
-
Zuclopenthixol
Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Liều Lượng & Cách Dùng :
Tablet - Oral
Tablet, extended release - Oral
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Nhà Sản Xuất
-
Sản phẩm biệt dược : Biaxin
-
Sản phẩm biệt dược : Biaxin XL
-
Sản phẩm biệt dược : Klacid XL
-
Sản phẩm biệt dược : Klaricid XL
-
Sản phẩm biệt dược : Macladin
-
Sản phẩm biệt dược : Naxy
-
Sản phẩm biệt dược : Veclam
-
Sản phẩm biệt dược : Zeclar
Tài Liệu Tham Khảo Thêm
National Drug Code Directory