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Identification
NameClarithromycin
Accession NumberDB01211  (APRD00181)
TypeSmall Molecule
GroupsApproved
Description

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.

Structure
Thumb
Synonyms
6-O-methyl erythromycin
6-O-Methylerythromycin
6-O-Methylerythromycin a
CLA
CLARITHROMYCIN
Clarithromycina
Clarithromycine
Clarithromycinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel-clarithromycingranules for suspension250 mgoralAccel Pharma Inc2012-09-04Not applicableCanada
Accel-clarithromycingranules for suspension125 mgoralAccel Pharma Inc2012-09-04Not applicableCanada
Act Clarithromycin XLtablet (extended-release)500 mgoralActavis Pharma Company2014-12-01Not applicableCanada
Ava-clarithromycintablet500 mgoralAvanstra Inc2011-09-192014-08-21Canada
Ava-clarithromycintablet250 mgoralAvanstra Inc2011-09-192014-08-21Canada
Biaxintablet, film coated500 mg/1oralA S Medication Solutions Llc1991-10-31Not applicableUs
Biaxintablet, film coated500 mg/1oralAbb Vie Inc.1991-10-31Not applicableUs
Biaxintablet, film coated250 mg/1oralREMEDYREPACK INC.2013-03-13Not applicableUs
Biaxintablet, film coated500 mg/1oralREMEDYREPACK INC.2013-02-25Not applicableUs
Biaxintablet, film coated500 mg/1oralCardinal Health1991-10-31Not applicableUs
Biaxintablet, film coated250 mg/1oralAbb Vie Inc.1991-10-31Not applicableUs
Biaxintablet, film coated, extended release500 mg/1oralPhysicians Total Care, Inc.2000-11-03Not applicableUs
Biaxingranule, for suspension250 mg/5mLoralAbb Vie Inc.1993-12-23Not applicableUs
Biaxingranule, for suspension250 mg/5mLoralPhysicians Total Care, Inc.2007-05-01Not applicableUs
Biaxintablet, film coated, extended release500 mg/1oralAbb Vie Inc.2000-03-03Not applicableUs
Biaxingranules for suspension250 mgoralBgp Pharma Ulc2002-05-28Not applicableCanada
Biaxintablet, film coated, extended release500 mg/1oralA S Medication Solutions Llc2000-03-03Not applicableUs
Biaxingranule, for suspension125 mg/5mLoralAbb Vie Inc.1993-12-23Not applicableUs
Biaxingranules for suspension125 mgoralBgp Pharma Ulc1995-12-31Not applicableCanada
Biaxin Bidtablet250 mgoralBgp Pharma Ulc1992-12-31Not applicableCanada
Biaxin Bidtablet500 mgoralBgp Pharma Ulc1994-12-31Not applicableCanada
Biaxin XLtablet (extended-release)500 mgoralBgp Pharma Ulc2002-05-22Not applicableCanada
Clarithromycinfor suspension250 mg/5mLoralZydus Pharmaceuticals USA Inc1991-10-31Not applicableUs
Clarithromycintablet500 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Clarithromycinfor suspension125 mg/5mLoralZydus Pharmaceuticals USA Inc1991-10-31Not applicableUs
Clarithromycintablet250 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Clarithromycintablet, film coated500 mg/1oralZydus Pharmaceuticals USA Inc1991-10-31Not applicableUs
Clarithromycintablet500 mgoralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
Clarithromycintablet250 mgoralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
Clarithromycintablet, film coated250 mg/1oralZydus Pharmaceuticals USA Inc1991-10-31Not applicableUs
Clarithromycintablet500 mg/1oralKAISER FOUNDATION HOSPITALS2009-10-01Not applicableUs
Clarithromycintablet500 mgoralPro Doc Limitee2009-10-08Not applicableCanada
Clarithromycingranules for suspension250 mgoralSanis Health Inc2013-09-05Not applicableCanada
Clarithromycintablet250 mgoralPro Doc Limitee2009-10-08Not applicableCanada
Clarithromycingranules for suspension125 mgoralSanis Health Inc2013-09-05Not applicableCanada
Dom-clarithromycintablet500 mgoralDominion Pharmacal2010-10-01Not applicableCanada
Mylan-clarithromycintablet500 mgoralMylan Pharmaceuticals Ulc2007-07-26Not applicableCanada
Mylan-clarithromycintablet250 mgoralMylan Pharmaceuticals Ulc2007-07-26Not applicableCanada
PMS-clarithromycintablet500 mgoralPharmascience Inc2007-08-10Not applicableCanada
PMS-clarithromycintablet250 mgoralPharmascience Inc2007-08-10Not applicableCanada
Ran-clarithromycintablet500 mgoralRanbaxy Pharmaceuticals Canada Inc.2011-02-01Not applicableCanada
Ran-clarithromycintablet250 mgoralRanbaxy Pharmaceuticals Canada Inc.2011-02-01Not applicableCanada
Ran-clarithromycingranules for suspension125 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Ran-clarithromycingranules for suspension250 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Ran-clarithromycin XLtablet (extended-release)500 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Ratio-clarithromycintablet500 mgoralRatiopharm Inc Division Of Teva Canada Limited2007-07-262014-09-19Canada
Ratio-clarithromycintablet250 mgoralRatiopharm Inc Division Of Teva Canada Limited2007-07-262014-09-19Canada
Riva-clarithromycintablet500 mgoralLaboratoire Riva Inc2010-06-16Not applicableCanada
Riva-clarithromycintablet250 mgoralLaboratoire Riva Inc2010-06-162013-07-31Canada
Sandoz Clarithromycintablet500 mgoralSandoz Canada Incorporated2008-06-06Not applicableCanada
Sandoz Clarithromycintablet250 mgoralSandoz Canada Incorporated2008-06-06Not applicableCanada
Sandoz Clarithromycin XLtablet (extended-release)500 mgoralSandoz Canada IncorporatedNot applicableNot applicableCanada
Teva-clarithromycintablet500 mgoralTeva Canada Limited2012-05-09Not applicableCanada
Teva-clarithromycintablet250 mgoralTeva Canada Limited2012-05-09Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-clarithromycintablet500 mgoralApotex Inc2007-07-26Not applicableCanada
Apo-clarithromycintablet250 mgoralApotex Inc2007-07-26Not applicableCanada
Apo-clarithromycin XLtablet (extended-release)500 mgoralApotex Inc2014-09-03Not applicableCanada
Clarithromycintablet500 mg/1oralRebel Distributors Corp.2005-08-25Not applicableUs
Clarithromycintablet250 mg/1oralRebel Distributors Corp.2005-10-18Not applicableUs
Clarithromycintablet, film coated250 mg/1oralLannett Company, Inc.2015-12-04Not applicableUs
Clarithromycintablet, coated250 mg/1oralRoxane Laboratories, Inc2004-11-22Not applicableUs
Clarithromycintablet, film coated500 mg/1oralWockhardt USA LLC.2006-05-31Not applicableUs
Clarithromycintablet, film coated250 mg/1oralApotex Corp2007-09-13Not applicableUs
Clarithromycintablet500 mg/1oralAvera Mc Kennan Hospital2015-03-02Not applicableUs
Clarithromycintablet, film coated500 mg/1oralREMEDYREPACK INC.2014-03-03Not applicableUs
Clarithromycintablet, film coated500 mg/1oralAllied Pharma Inc2012-12-31Not applicableUs
Clarithromycintablet, film coated250 mg/1oralWockhardt USA LLC.2006-05-31Not applicableUs
Clarithromycintablet, film coated, extended release500 mg/1oralDepartment Of State Health Services, Pharmacy Branch2008-01-01Not applicableUs
Clarithromycintablet, film coated500 mg/1oralREMEDYREPACK INC.2013-05-092016-04-05Us
Clarithromycintablet, film coated250 mg/1oralSunshine Lake Pharma Co., Ltd.2015-09-29Not applicableUs
Clarithromycintablet, coated500 mg/1oralBlenheim Pharmacal, Inc.2015-12-02Not applicableUs
Clarithromycintablet, film coated500 mg/1oralKAISER FOUNDATION HOSPITALS2010-10-27Not applicableUs
Clarithromycintablet250 mg/1oralbryant ranch prepack2005-10-18Not applicableUs
Clarithromycintablet, film coated500 mg/1oralApotex Corp2007-09-13Not applicableUs
Clarithromycintablet, film coated500 mg/1oralProficient Rx LP2012-07-25Not applicableUs
Clarithromycintablet, film coated250 mg/1oralAllied Pharma Inc2012-12-31Not applicableUs
Clarithromycintablet, film coated500 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-11-15Not applicableUs
Clarithromycintablet, film coated500 mg/1oralSunshine Lake Pharma Co., Ltd.2015-09-29Not applicableUs
Clarithromycinfor suspension250 mg/5mLoralSandoz Inc2007-09-04Not applicableUs
Clarithromycintablet, film coated500 mg/1oralTeva Pharmaceuticals USA Inc2014-12-16Not applicableUs
Clarithromycintablet, coated500 mg/1oralbryant ranch prepack2004-05-25Not applicableUs
Clarithromycintablet500 mg/1oralClinical Solutions Wholesale2005-08-25Not applicableUs
Clarithromycintablet500 mg/1oralLife Line Home Care Services, Inc.2011-12-08Not applicableUs
Clarithromycintablet, film coated250 mg/1oralREMEDYREPACK INC.2011-05-12Not applicableUs
Clarithromycintablet, film coated, extended release500 mg/1oralPd Rx Pharmaceuticals, Inc.2008-01-01Not applicableUs
Clarithromycintablet, extended release500 mg/1oralbryant ranch prepack2009-05-30Not applicableUs
Clarithromycintablet, film coated250 mg/1oralWockhardt Limited2006-05-31Not applicableUs
Clarithromycintablet500 mg/1oralPreferred Pharmaceuticals, Inc2005-10-05Not applicableUs
Clarithromycintablet500 mg/1oralREMEDYREPACK INC.2011-07-08Not applicableUs
Clarithromycintablet500 mg/1oralPd Rx Pharmaceuticals, Inc.2005-08-25Not applicableUs
Clarithromycinfor suspension125 mg/5mLoralSandoz Inc2007-09-04Not applicableUs
Clarithromycintablet, film coated250 mg/1oralTeva Pharmaceuticals USA Inc2014-12-16Not applicableUs
Clarithromycintablet500 mg/1oralAmerican Health Packaging2014-04-16Not applicableUs
Clarithromycintablet250 mg/1oralREMEDYREPACK INC.2011-06-27Not applicableUs
Clarithromycintablet, film coated, extended release500 mg/1oralPd Rx Pharmaceuticals, Inc.2008-01-01Not applicableUs
Clarithromycintablet500 mg/1oralSandoz Inc2005-08-25Not applicableUs
Clarithromycintablet, film coated, extended release500 mg/1oralTeva Pharmaceuticals USA Inc2006-06-23Not applicableUs
Clarithromycingranule, for suspension250 mg/5mLoralRanbaxy Pharmaceuticals Inc.2007-10-03Not applicableUs
Clarithromycintablet, film coated500 mg/1oralWockhardt Limited2006-05-31Not applicableUs
Clarithromycintablet250 mg/1oralREMEDYREPACK INC.2011-06-01Not applicableUs
Clarithromycintablet, film coated500 mg/1oralRebel Distributors Corp2006-05-31Not applicableUs
Clarithromycintablet250 mg/1oralSandoz Inc2005-10-18Not applicableUs
Clarithromycintablet, film coated500 mg/1oralTeva Pharmaceuticals USA Inc2005-06-28Not applicableUs
Clarithromycingranule, for suspension125 mg/5mLoralRanbaxy Pharmaceuticals Inc.2007-10-03Not applicableUs
Clarithromycintablet, film coated500 mg/1oralPd Rx Pharmaceuticals, Inc.2006-05-31Not applicableUs
Clarithromycintablet250 mg/1oralAvera Mc Kennan Hospital2015-05-01Not applicableUs
Clarithromycintablet, film coated, extended release500 mg/1oralDispensing Solutions, Inc.2008-01-01Not applicableUs
Clarithromycintablet, film coated500 mg/1oralREMEDYREPACK INC.2011-05-04Not applicableUs
Clarithromycintablet, film coated250 mg/1oralAidarex Pharmaceuticals LLC2006-05-31Not applicableUs
Clarithromycintablet, film coated, extended release500 mg/1oralActavis Pharma, Inc.2008-01-01Not applicableUs
Clarithromycintablet, film coated250 mg/1oralTeva Pharmaceuticals USA Inc2005-06-28Not applicableUs
Clarithromycintablet, film coated500 mg/1oralRanbaxy Pharmaceuticals Inc.2005-05-25Not applicableUs
Clarithromycintablet500 mg/1oralPhysicians Total Care, Inc.2005-10-05Not applicableUs
Clarithromycintablet, film coated500 mg/1oralBlenheim Pharmacal, Inc.2012-10-05Not applicableUs
Clarithromycintablet, film coated500 mg/1oralAurobindo Pharma Limited2012-07-25Not applicableUs
Clarithromycintablet, film coated500 mg/1oralCitron Pharma LLC2012-07-25Not applicableUs
Clarithromycintablet500 mg/1oralREMEDYREPACK INC.2011-04-20Not applicableUs
Clarithromycintablet, film coated500 mg/1oralAidarex Pharmaceuticals LLC2006-05-31Not applicableUs
Clarithromycintablet, film coated500 mg/1oralLannett Company, Inc.2015-12-04Not applicableUs
Clarithromycintablet, coated500 mg/1oralRoxane Laboratories, Inc2004-05-25Not applicableUs
Clarithromycintablet, film coated250 mg/1oralRanbaxy Pharmaceuticals Inc.2005-05-25Not applicableUs
Clarithromycinfor suspension250 mg/5mLoralPhysicians Total Care, Inc.2008-03-04Not applicableUs
Clarithromycintablet, film coated500 mg/1oralAmerican Health Packaging2013-06-202015-11-30Us
Clarithromycintablet, film coated250 mg/1oralAurobindo Pharma Limited2012-07-25Not applicableUs
Clarithromycintablet, film coated250 mg/1oralCitron Pharma LLC2012-07-25Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Klacid XLNot Available
Klaricid XLNot Available
MacladinNot Available
NaxyNot Available
VeclamNot Available
ZeclarNot Available
Brand mixtures
NameLabellerIngredients
Hp-pacTakeda Pharmaceuticals America Inc
Lansoprazole, Amoxicillin, and ClarithromycinTeva Pharmaceuticals USA Inc
Omeclamox-pakPernix Therapeutics, LLC
SaltsNot Available
Categories
UNIIH1250JIK0A
CAS number81103-11-9
WeightAverage: 747.9534
Monoisotopic: 747.476891299
Chemical FormulaC38H69NO13
InChI KeyInChIKey=AGOYDEPGAOXOCK-KCBOHYOISA-N
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
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
SMILES
[H][C@@]1(C[C@@](C)(OC)[C@@H](O)[[email protected]](C)O1)O[[email protected]]1[[email protected]](C)[C@@H](O[C@]2([H])O[[email protected]](C)C[C@@H]([[email protected]]2O)N(C)C)[C@@](C)(C[C@@H](C)C(=O)[[email protected]](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]1C)OC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Amino sugar
  • Desosamine
  • Amino saccharide
  • Oxane
  • Monosaccharide
  • Tertiary alcohol
  • Cyclic ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationAn 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).
PharmacodynamicsClarithromycin 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.
Mechanism of actionClarithromycin 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.
Related Articles
AbsorptionClarithromycin is well-absorbed, acid stable and may be taken with food.
Volume of distributionNot Available
Protein binding~ 70% protein bound
Metabolism

Hepatic - predominantly metabolized by CYP3A4 resulting in numerous drug interactions.

SubstrateEnzymesProduct
Clarithromycin
14-hydroxyclarithromycinDetails
Clarithromycin
N-desmethylclarithromycinDetails
Route of eliminationAfter 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 life3-4 hours
ClearanceNot Available
ToxicitySymptoms 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.
Affected organisms
  • Enteric bacteria and other eubacteria
  • Mycobacterium
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Haemophilus influenzae
  • Helicobacter pylori
  • Mycobacterium leprae
  • Mycobacterium avium
Pathways
PathwayCategorySMPDB ID
Clarithromycin Action PathwayDrug actionSMP00248
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5434
Blood Brain Barrier-0.987
Caco-2 permeable-0.8674
P-glycoprotein substrateSubstrate0.7714
P-glycoprotein inhibitor IInhibitor0.8475
P-glycoprotein inhibitor IINon-inhibitor0.622
Renal organic cation transporterNon-inhibitor0.8987
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9161
CYP450 3A4 substrateSubstrate0.6672
CYP450 1A2 substrateNon-inhibitor0.8973
CYP450 2C9 inhibitorNon-inhibitor0.8851
CYP450 2D6 inhibitorNon-inhibitor0.9258
CYP450 2C19 inhibitorNon-inhibitor0.8835
CYP450 3A4 inhibitorNon-inhibitor0.5524
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.898
Ames testNon AMES toxic0.8967
CarcinogenicityNon-carcinogens0.9294
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7236 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9883
hERG inhibition (predictor II)Non-inhibitor0.9038
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Granules for suspensionoral125 mg
Granules for suspensionoral250 mg
Granule, for suspensionoral125 mg/5mL
Granule, for suspensionoral250 mg/5mL
Tablet, film coatedoral250 mg/1
Tablet, film coatedoral500 mg/1
Tablet, film coated, extended releaseoral500 mg/1
Tabletoral250 mg
Tabletoral500 mg
Tablet (extended-release)oral500 mg
For suspensionoral125 mg/5mL
For suspensionoral250 mg/5mL
Tabletoral250 mg/1
Tabletoral500 mg/1
Tablet, coatedoral250 mg/1
Tablet, coatedoral500 mg/1
Tablet, extended releaseoral500 mg/1
Kit; capsule; capsule (sustained-release); tabletoral
Kit
Prices
Unit descriptionCostUnit
Biaxin 60 250 mg tablet Bottle379.5USD bottle
Clarithromycin 250 mg/5ml Suspension 100ml Bottle86.23USD bottle
Clarithromycin 250 mg/5ml Suspension 50ml Bottle46.56USD bottle
Clarithromycin 125 mg/5ml Suspension 100ml Bottle45.24USD bottle
Clarithromycin 125 mg/5ml Suspension 50ml Bottle27.99USD bottle
Biaxin XL 500 mg 24 Hour tablet6.77USD tablet
Biaxin xl 500 mg tablet6.57USD tablet
Biaxin 250 mg tablet6.42USD tablet
Biaxin 500 mg tablet6.37USD tablet
Clarithromycin 500 mg 24 Hour tablet5.21USD tablet
Clarithromycin er 500 mg tablet5.01USD tablet
Clarithromycin 250 mg tablet4.61USD tablet
Clarithromycin 500 mg tablet4.61USD tablet
Biaxin Bid 500 mg Tablet3.41USD tablet
Biaxin Xl 500 mg Extended-Release Tablet2.63USD tablet
Mylan-Clarithromycin 500 mg Tablet1.91USD tablet
Pms-Clarithromycin 500 mg Tablet1.91USD tablet
Ratio-Clarithromycin 500 mg Tablet1.91USD tablet
Sandoz Clarithromycin 500 mg Tablet1.91USD tablet
Biaxin Bid 250 mg Tablet1.73USD tablet
Clarithromycin 100% powder1.56USD g
Biaxin 50 mg/ml Suspension0.59USD ml
Biaxin 25 mg/ml Suspension0.3USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1328609 No1994-04-192011-04-19Canada
CA2471102 No2005-02-082017-07-25Canada
US6010718 No1997-04-112017-04-11Us
US6551616 No1997-06-152017-06-15Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point220 dec °CPhysProp
water solubility0.33 mg/LNot Available
logP3.16MCFARLAND,JW ET AL. (1997)
pKa8.99 (at 25 °C)MCFARLAND,JW ET AL. (1997)
Predicted Properties
PropertyValueSource
Water Solubility0.217 mg/mLALOGPS
logP3.18ALOGPS
logP3.24ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)12.46ChemAxon
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area182.91 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity190.79 m3·mol-1ChemAxon
Polarizability82.03 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Jih-Hua Liu, David A. Riley, “Preparation of crystal form II of clarithromycin.” U.S. Patent US5844105, issued May, 1997.

US5844105
General References
  1. Malhotra-Kumar S, Lammens C, Coenen S, Van Herck K, Goossens H: Effect of azithromycin and clarithromycin therapy on pharyngeal carriage of macrolide-resistant streptococci in healthy volunteers: a randomised, double-blind, placebo-controlled study. Lancet. 2007 Feb 10;369(9560):482-90. [PubMed:17292768 ]
  2. Zuckerman JM, Qamar F, Bono BR: Macrolides, ketolides, and glycylcyclines: azithromycin, clarithromycin, telithromycin, tigecycline. Infect Dis Clin North Am. 2009 Dec;23(4):997-1026, ix-x. doi: 10.1016/j.idc.2009.06.013. [PubMed:19909895 ]
  3. Piscitelli SC, Danziger LH, Rodvold KA: Clarithromycin and azithromycin: new macrolide antibiotics. Clin Pharm. 1992 Feb;11(2):137-52. [PubMed:1312921 ]
  4. Peters DH, Clissold SP: Clarithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic potential. Drugs. 1992 Jul;44(1):117-64. [PubMed:1379907 ]
  5. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [PubMed:18486039 ]
  6. Stephenson GA, Stowell JG, Toma PH, Pfeiffer RR, Byrn SR: Solid-state investigations of erythromycin A dihydrate: structure, NMR spectroscopy, and hygroscopicity. J Pharm Sci. 1997 Nov;86(11):1239-44. [PubMed:9383733 ]
External Links
ATC CodesA02BD04A02BD05A02BD06A02BD07A02BD09A02BD11J01FA09
AHFS Codes
  • 08:12.12.92
PDB EntriesNot Available
FDA labelDownload (376 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Clarithromycin.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Clarithromycin.
AlfentanilThe serum concentration of Alfentanil can be increased when it is combined with Clarithromycin.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Clarithromycin.
AlmotriptanThe serum concentration of Almotriptan can be increased when it is combined with Clarithromycin.
AlosetronThe serum concentration of Alosetron can be increased when it is combined with Clarithromycin.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Clarithromycin.
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Clarithromycin.
AmlodipineThe metabolism of Amlodipine can be decreased when combined with Clarithromycin.
AmrinoneThe metabolism of Amrinone can be decreased when combined with Clarithromycin.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Clarithromycin.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Clarithromycin.
AstemizoleThe serum concentration of Astemizole can be increased when it is combined with Clarithromycin.
AtazanavirThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Atazanavir.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Clarithromycin.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Clarithromycin.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Clarithromycin.
BarnidipineThe serum concentration of Barnidipine can be increased when it is combined with Clarithromycin.
BatimastatThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Batimastat.
BedaquilineThe serum concentration of Bedaquiline can be increased when it is combined with Clarithromycin.
BepridilThe metabolism of Bepridil can be decreased when combined with Clarithromycin.
BexaroteneThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Bexarotene.
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Clarithromycin.
BortezomibThe serum concentration of Bortezomib can be increased when it is combined with Clarithromycin.
BosentanThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Clarithromycin.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Clarithromycin.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Clarithromycin.
BrinzolamideThe serum concentration of Brinzolamide can be increased when it is combined with Clarithromycin.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Clarithromycin.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Clarithromycin.
BuspironeThe metabolism of Buspirone can be decreased when combined with Clarithromycin.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Clarithromycin.
CabergolineThe serum concentration of Cabergoline can be increased when it is combined with Clarithromycin.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Clarithromycin.
CarbamazepineThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Carbamazepine.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Clarithromycin.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Clarithromycin.
CisaprideThe metabolism of Cisapride can be decreased when combined with Clarithromycin.
CitalopramClarithromycin may increase the QTc-prolonging activities of Citalopram.
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Clarithromycin.
ClozapineThe metabolism of Clozapine can be decreased when combined with Clarithromycin.
CobicistatThe serum concentration of Cobicistat can be increased when it is combined with Clarithromycin.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Clarithromycin.
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Clarithromycin.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Clarithromycin.
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Clarithromycin.
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be increased when it is combined with Clarithromycin.
DabrafenibThe serum concentration of Clarithromycin can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Clarithromycin.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Clarithromycin.
DarunavirThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Darunavir.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Clarithromycin.
DeferasiroxThe serum concentration of Clarithromycin can be decreased when it is combined with Deferasirox.
DexamethasoneThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Dexamethasone.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Clarithromycin.
DienogestThe serum concentration of Dienogest can be increased when it is combined with Clarithromycin.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Clarithromycin.
DihydroergotamineThe serum concentration of Dihydroergotamine can be increased when it is combined with Clarithromycin.
DiltiazemThe metabolism of Diltiazem can be decreased when combined with Clarithromycin.
DisopyramideClarithromycin may increase the QTc-prolonging activities of Disopyramide.
DofetilideClarithromycin may increase the QTc-prolonging activities of Dofetilide.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Clarithromycin.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Clarithromycin.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Clarithromycin.
DronedaroneThe serum concentration of Dronedarone can be increased when it is combined with Clarithromycin.
DrospirenoneThe serum concentration of Drospirenone can be increased when it is combined with Clarithromycin.
DutasterideThe serum concentration of Dutasteride can be increased when it is combined with Clarithromycin.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Clarithromycin.
EfavirenzThe serum concentration of Clarithromycin can be decreased when it is combined with Efavirenz.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Clarithromycin.
EnzalutamideThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Enzalutamide.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Clarithromycin.
Ergoloid mesylateThe serum concentration of Ergoloid mesylate can be increased when it is combined with Clarithromycin.
ErgonovineThe serum concentration of Ergonovine can be increased when it is combined with Clarithromycin.
ErgotamineThe serum concentration of Ergotamine can be increased when it is combined with Clarithromycin.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Clarithromycin.
Eslicarbazepine acetateThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Eslicarbazepine acetate.
EstazolamThe serum concentration of Estazolam can be increased when it is combined with Clarithromycin.
EtizolamThe serum concentration of Etizolam can be increased when it is combined with Clarithromycin.
EtravirineThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Etravirine.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Clarithromycin.
FelodipineThe metabolism of Felodipine can be decreased when combined with Clarithromycin.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Clarithromycin.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Clarithromycin.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Clarithromycin.
FluconazoleThe metabolism of Clarithromycin can be decreased when combined with Fluconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Clarithromycin.
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Clarithromycin.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Clarithromycin.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Clarithromycin.
FosamprenavirThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Fosamprenavir.
FosphenytoinThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Fosphenytoin.
Fusidic AcidThe serum concentration of Clarithromycin can be increased when it is combined with Fusidic Acid.
GabapentinThe metabolism of Gabapentin can be decreased when combined with Clarithromycin.
GlipizideThe serum concentration of Glipizide can be increased when it is combined with Clarithromycin.
GlyburideThe serum concentration of Glyburide can be increased when it is combined with Clarithromycin.
GoserelinGoserelin may increase the QTc-prolonging activities of Clarithromycin.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Clarithromycin.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Clarithromycin.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Clarithromycin.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Clarithromycin.
IdelalisibThe serum concentration of Clarithromycin can be increased when it is combined with Idelalisib.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Clarithromycin resulting in a loss in efficacy.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Clarithromycin.
ImidafenacinThe serum concentration of Imidafenacin can be increased when it is combined with Clarithromycin.
IndinavirThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Indinavir.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Clarithromycin.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be increased when Isavuconazonium is used in combination with Clarithromycin.
IsoflurophateThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Isoflurophate.
IsradipineThe metabolism of Isradipine can be decreased when combined with Clarithromycin.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Clarithromycin.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Clarithromycin.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Clarithromycin.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Clarithromycin.
LamotrigineThe metabolism of Lamotrigine can be decreased when combined with Clarithromycin.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Clarithromycin.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Clarithromycin.
LercanidipineThe serum concentration of Lercanidipine can be increased when it is combined with Clarithromycin.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Clarithromycin.
LevobupivacaineThe serum concentration of Levobupivacaine can be increased when it is combined with Clarithromycin.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Clarithromycin.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Clarithromycin.
LopinavirClarithromycin may increase the QTc-prolonging activities of Lopinavir.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Clarithromycin.
LuliconazoleThe serum concentration of Clarithromycin can be increased when it is combined with Luliconazole.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Clarithromycin.
MacitentanThe serum concentration of MACITENTAN can be increased when it is combined with Clarithromycin.
Magnesium SulfateThe metabolism of Magnesium Sulfate can be decreased when combined with Clarithromycin.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Clarithromycin.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be increased when it is combined with Clarithromycin.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Clarithromycin.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Clarithromycin.
MifepristoneMifepristone may increase the QTc-prolonging activities of Clarithromycin.
MitotaneThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Mitotane.
ModafinilThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Modafinil.
NafcillinThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Nafcillin.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Clarithromycin.
NelfinavirThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Nelfinavir.
NetupitantThe serum concentration of Clarithromycin can be increased when it is combined with Netupitant.
NicardipineThe metabolism of Nicardipine can be decreased when combined with Clarithromycin.
NifedipineThe metabolism of Nifedipine can be decreased when combined with Clarithromycin.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Clarithromycin.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Clarithromycin.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Clarithromycin.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Clarithromycin.
NitrendipineThe metabolism of Nitrendipine can be decreased when combined with Clarithromycin.
OctreotideOctreotide may increase the QTc-prolonging activities of Clarithromycin.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Clarithromycin.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Clarithromycin.
OxybutyninThe serum concentration of Oxybutynin can be increased when it is combined with Clarithromycin.
OxycodoneThe risk or severity of adverse effects can be increased when Clarithromycin is combined with Oxycodone.
PalbociclibThe serum concentration of Palbociclib can be increased when it is combined with Clarithromycin.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Clarithromycin.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Clarithromycin.
ParicalcitolThe serum concentration of Paricalcitol can be increased when it is combined with Clarithromycin.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Clarithromycin.
PerhexilineThe metabolism of Perhexiline can be decreased when combined with Clarithromycin.
PhenobarbitalThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Phenobarbital.
PhenytoinThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Phenytoin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Clarithromycin.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Clarithromycin.
PimozideClarithromycin may increase the QTc-prolonging activities of Pimozide.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Clarithromycin.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Clarithromycin.
PranlukastThe serum concentration of Pranlukast can be increased when it is combined with Clarithromycin.
PrasugrelThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Clarithromycin resulting in a loss in efficacy.
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Clarithromycin.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Clarithromycin.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Clarithromycin.
PrenylamineThe metabolism of Prenylamine can be decreased when combined with Clarithromycin.
PrimidoneThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Primidone.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Clarithromycin.
QuinidineClarithromycin may increase the QTc-prolonging activities of Quinidine.
QuinineThe serum concentration of Quinine can be increased when it is combined with Clarithromycin.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Clarithromycin.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Clarithromycin.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Clarithromycin.
RepaglinideThe serum concentration of Repaglinide can be increased when it is combined with Clarithromycin.
RetapamulinThe serum concentration of Retapamulin can be increased when it is combined with Clarithromycin.
RifabutinThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Rifabutin.
RifampicinThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Rifampicin.
RifapentineThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Rifapentine.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Clarithromycin.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Clarithromycin.
RisedronateThe metabolism of Risedronate can be decreased when combined with Clarithromycin.
RitonavirThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Ritonavir.
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Clarithromycin.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Clarithromycin.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Clarithromycin.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Clarithromycin.
SaquinavirThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Saquinavir.
SaxagliptinThe serum concentration of Saxagliptin can be increased when it is combined with Clarithromycin.
SertralineThe metabolism of Sertraline can be decreased when combined with Clarithromycin.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Clarithromycin.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Clarithromycin.
SiltuximabThe serum concentration of Clarithromycin can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Clarithromycin.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Clarithromycin.
SirolimusThe metabolism of Sirolimus can be decreased when combined with Clarithromycin.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Clarithromycin.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Clarithromycin.
St. John's WortThe serum concentration of Clarithromycin can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Clarithromycin can be increased when it is combined with Stiripentol.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Clarithromycin.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Clarithromycin.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Clarithromycin.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Clarithromycin.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Clarithromycin.
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Clarithromycin.
TemsirolimusThe risk or severity of adverse effects can be increased when Clarithromycin is combined with Temsirolimus.
TerfenadineClarithromycin may increase the QTc-prolonging activities of Terfenadine.
TheophyllineThe metabolism of Theophylline can be decreased when combined with Clarithromycin.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Clarithromycin resulting in a loss in efficacy.
TipranavirThe therapeutic efficacy of Clarithromycin can be decreased when used in combination with Tipranavir.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Clarithromycin.
TocilizumabThe serum concentration of Clarithromycin can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Clarithromycin.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Clarithromycin.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Clarithromycin.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Clarithromycin.
ToremifeneThe risk or severity of adverse effects can be increased when Clarithromycin is combined with Toremifene.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Clarithromycin.
TramadolThe serum concentration of Tramadol can be increased when it is combined with Clarithromycin.
Trastuzumab emtansineThe serum concentration of the active metabolites of ado-trastuzumab emtansine can be increased when ado-trastuzumab emtansine is used in combination with Clarithromycin.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Clarithromycin.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Clarithromycin.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Clarithromycin.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Clarithromycin.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Clarithromycin.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Clarithromycin.
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Clarithromycin.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Clarithromycin.
VindesineThe serum concentration of Vindesine can be increased when it is combined with Clarithromycin.
VinorelbineThe serum concentration of Vinorelbine can be increased when it is combined with Clarithromycin.
VorapaxarThe serum concentration of Vorapaxar can be increased when it is combined with Clarithromycin.
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Clarithromycin.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Clarithromycin.
ZidovudineClarithromycin may increase the myelosuppressive activities of Zidovudine.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Clarithromycin.
Food Interactions
  • Biaxin - take without regard to meals (however absorption appears to be improved when drug is taken with food).
  • Biaxin XL - take with a meal, taking it on an empty stomach is associated with total product exposure 30% inferior to that observed when administered with food.

Targets

Kind
Protein
Organism
Shigella flexneri
Pharmacological action
yes
Actions
inhibitor
General Function:
Structural constituent of ribosome
Specific Function:
Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA (By similarity).Forms part of the ribosomal stalk, playing a central role in the interaction of the ribosome with GTP-bound translation factors.
Gene Name:
rplJ
Uniprot ID:
P0A7J6
Molecular Weight:
17711.38 Da
References
  1. Morimura T, Hashiba M, Kameda H, Takami M, Takahama H, Ohshige M, Sugawara F: Identification of macrolide antibiotic-binding Human_p8 protein. J Antibiot (Tokyo). 2008 May;61(5):291-6. doi: 10.1038/ja.2008.41. [PubMed:18653994 ]
  2. Champney WS, Burdine R: Macrolide antibiotic inhibition of translation and 50S ribosomal subunit assembly in methicillin-resistant Staphylococcus aureus cells. Microb Drug Resist. 1998 Fall;4(3):169-74. [PubMed:9818968 ]
  3. Zuckerman JM, Qamar F, Bono BR: Macrolides, ketolides, and glycylcyclines: azithromycin, clarithromycin, telithromycin, tigecycline. Infect Dis Clin North Am. 2009 Dec;23(4):997-1026, ix-x. doi: 10.1016/j.idc.2009.06.013. [PubMed:19909895 ]
  4. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [PubMed:18486039 ]
  5. Champney WS, Burdine R: Macrolide antibiotics inhibit 50S ribosomal subunit assembly in Bacillus subtilis and Staphylococcus aureus. Antimicrob Agents Chemother. 1995 Sep;39(9):2141-4. [PubMed:8540733 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular Weight:
126653.52 Da
References
  1. Keseru GM: Prediction of hERG potassium channel affinity by traditional and hologram qSAR methods. Bioorg Med Chem Lett. 2003 Aug 18;13(16):2773-5. [PubMed:12873512 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Fontana E, Dansette PM, Poli SM: Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr Drug Metab. 2005 Oct;6(5):413-54. [PubMed:16248836 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP: Structure-based identification of OATP1B1/3 inhibitors. Mol Pharmacol. 2013 Jun;83(6):1257-67. doi: 10.1124/mol.112.084152. Epub 2013 Apr 9. [PubMed:23571415 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP). Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular Weight:
77402.175 Da
References
  1. De Bruyn T, van Westen GJ, Ijzerman AP, Stieger B, de Witte P, Augustijns PF, Annaert PP: Structure-based identification of OATP1B1/3 inhibitors. Mol Pharmacol. 2013 Jun;83(6):1257-67. doi: 10.1124/mol.112.084152. Epub 2013 Apr 9. [PubMed:23571415 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Zuckerman JM, Qamar F, Bono BR: Macrolides, ketolides, and glycylcyclines: azithromycin, clarithromycin, telithromycin, tigecycline. Infect Dis Clin North Am. 2009 Dec;23(4):997-1026, ix-x. doi: 10.1016/j.idc.2009.06.013. [PubMed:19909895 ]
  2. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [PubMed:18486039 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  4. Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA: Comparative metabolic capabilities of CYP3A4, CYP3A5, and CYP3A7. Drug Metab Dispos. 2002 Aug;30(8):883-91. [PubMed:12124305 ]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
  2. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
  3. Egashira K, Ohtani H, Itoh S, Koyabu N, Tsujimoto M, Murakami H, Sawada Y: Inhibitory effects of pomelo on the metabolism of tacrolimus and the activities of CYP3A4 and P-glycoprotein. Drug Metab Dispos. 2004 Aug;32(8):828-33. [PubMed:15258108 ]
  4. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [PubMed:18486039 ]
  5. Dey S, Gunda S, Mitra AK: Pharmacokinetics of erythromycin in rabbit corneas after single-dose infusion: role of P-glycoprotein as a barrier to in vivo ocular drug absorption. J Pharmacol Exp Ther. 2004 Oct;311(1):246-55. Epub 2004 Jun 2. [PubMed:15175422 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular Weight:
60025.025 Da
References
  1. Kobayashi Y, Sakai R, Ohshiro N, Ohbayashi M, Kohyama N, Yamamoto T: Possible involvement of organic anion transporter 2 on the interaction of theophylline with erythromycin in the human liver. Drug Metab Dispos. 2005 May;33(5):619-22. Epub 2005 Feb 11. [PubMed:15708966 ]
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Drug created on June 13, 2005 07:24 / Updated on June 28, 2016 01:52