Clarithromycin

Identification

Summary

Clarithromycin is a macrolide antibiotic used for the treatment of a wide variety of bacterial infections such as acute otitis, pharyngitis, tonsillitis, respiratory tract infections, uncomplicated skin infections, and helicobacter pylori infection.

Brand Names
Biaxin, Biaxin Bid, Omeclamox, Prevpac
Generic Name
Clarithromycin
DrugBank Accession Number
DB01211
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 747.9534
Monoisotopic: 747.476891299
Chemical Formula
C38H69NO13
Synonyms
  • 6-O-methyl erythromycin
  • 6-O-methylerythromycin
  • 6-O-methylerythromycin A
  • CLA
  • Clarithromycin
  • Clarithromycina
  • Clarithromycine
  • Clarithromycinum
  • Claritromicina
External IDs
  • A-56268
  • ABBOTT-56268
  • TE-031

Pharmacology

Indication

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).

Pharmacology
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Associated Conditions
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Contraindications
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Pharmacodynamics

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.

Mechanism of action

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.

TargetActionsOrganism
A50S ribosomal protein L10
inhibitor
Shigella flexneri
UPotassium voltage-gated channel subfamily H member 2Not AvailableHumans
USolute carrier organic anion transporter family member 1B1Not AvailableHumans
USolute carrier organic anion transporter family member 1B3Not AvailableHumans
Absorption

Clarithromycin is well-absorbed, acid stable and may be taken with food.

Volume of distribution

Not Available

Protein binding

~ 70% protein bound

Metabolism

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

Hover over products below to view reaction partners

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

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

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.

Pathways
PathwayCategory
Clarithromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be decreased when combined with Clarithromycin.
AbametapirThe serum concentration of Clarithromycin can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Clarithromycin can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Clarithromycin.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Clarithromycin.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Clarithromycin.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Clarithromycin.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Clarithromycin.
AcetohexamideThe serum concentration of Acetohexamide can be increased when it is combined with Clarithromycin.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Clarithromycin.
Interactions
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Food Interactions
  • Take with food. Food increases absorption.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Clarithromycin citrate16K08R7NG0848130-51-8MDRWXDRMSKEMRE-AZFLODHXSA-N
Product Images
International/Other Brands
Klacid XL / Klaricid XL / Macladin / Naxy / Veclam / Zeclar
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act Clarithromycin XLTablet, extended release500 mgOralTEVA Canada Limited2014-12-01Not applicableCanada flag
BiaxinGranule, for suspension250 mg/5mLOralAbbVie Inc.1993-12-232017-05-11US flag
BiaxinGranule, for suspension250 mg / 5 mLOralBgp Pharma Ulc2002-05-28Not applicableCanada flag
BiaxinTablet, film coated250 mg/1OralRemedy Repack2012-07-162013-07-16US flag
BiaxinTablet, film coated500 mg/1OralAbbVie Inc.1991-10-312017-07-30US flag0074 258620180814 13942 1gji2l1
BiaxinGranule, for suspension250 mg/5mLOralPhysicians Total Care, Inc.2007-05-01Not applicableUS flag
BiaxinTablet, film coated500 mg/1OralRemedy Repack2012-07-212013-07-21US flag00074 2586 60 nlmimage10 24131228
BiaxinTablet, film coated500 mg/1OralPhysicians Total Care, Inc.1993-06-232011-06-30US flag54868 233820180907 15195 n4t11n
BiaxinGranule, for suspension125 mg/5mLOralAbbVie Inc.1993-12-232014-12-31US flag
BiaxinTablet, film coated, extended release500 mg/1OralA S Medication Solutions2000-03-03Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-clarithromycinTablet500 mgOralApotex Corporation2007-07-26Not applicableCanada flag
Apo-clarithromycinTablet250 mgOralApotex Corporation2007-07-26Not applicableCanada flag
Apo-clarithromycin XLTablet, extended release500 mgOralApotex Corporation2014-09-03Not applicableCanada flag
Ava-clarithromycinTablet250 mgOralAvanstra Inc2011-09-192014-08-21Canada flag
Ava-clarithromycinTablet500 mgOralAvanstra Inc2011-09-192014-08-21Canada flag
ClarithromycinTablet, film coated250 mg/1OralAidarex Pharmaceuticals LLC2006-05-31Not applicableUS flag64679 0954 01 nlmimage10 ac3a5652
ClarithromycinTablet, film coated500 mg/1Oralbryant ranch prepack2015-12-04Not applicableUS flag
ClarithromycinTablet, film coated, extended release500 mg/1OralTeva2006-06-232017-10-31US flag00093 7244 06 nlmimage10 06050368
ClarithromycinTablet, film coated500 mg/1OralRebel Distributors2006-05-31Not applicableUS flag
ClarithromycinTablet, coated250 mg/1OralA-S Medication Solutions2004-11-22Not applicableUS flag54569 568820180907 15195 rysldr
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Apo-lansoprazole-amoxicillin-clarithromycinClarithromycin (500 mg / tab) + Amoxicillin (500 mg / cap) + Lansoprazole (30 mg / cap)Capsule; Capsule, delayed release; Kit; TabletOralApotex Corporation2018-08-03Not applicableCanada flag
HELIPAK 500 + 30 + 1000mg TEDAVİ PAKETİ, 14 TABLETClarithromycin (500 mg) + Amoxicillin (1 g) + Lansoprazole (370 mg)TabletOralTEVA İLAÇLARI SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
HELIPAK 500 + 30 + 1000mg TEDAVİ PAKETİ, 7 TABLETClarithromycin (500 mg) + Amoxicillin (1 g) + Lansoprazole (370 mg)TabletOralTEVA İLAÇLARI SAN.VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
Hp-pacClarithromycin (500 mg / tab) + Amoxicillin (500 mg / cap) + Lansoprazole (30 mg / cap)Capsule; Capsule, delayed release; Kit; TabletOralTakeda1998-08-182021-03-08Canada flag
Lansoprazole, Amoxicillin and ClarithromycinClarithromycin (500 mg/1) + Amoxicillin Trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitOralSandoz Inc2014-03-04Not applicableUS flag
Lansoprazole, Amoxicillin and ClarithromycinClarithromycin (500 mg/1) + Amoxicillin Trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitOralPrasco Laboratories2015-03-032021-02-28US flag
Lansoprazole, Amoxicillin, and ClarithromycinClarithromycin (500 mg/1) + Amoxicillin Trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitOralTeva2013-09-092015-04-30US flag00093 8055 14 nlmimage10 c2386123
Lansoprazole, Amoxicillin, ClarithromycinClarithromycin (500 mg/1) + Amoxicillin Trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitOralRising Health, Llc2016-10-14Not applicableUS flag57237 00120180913 8702 1lfom9c
Omeclamox-PakClarithromycin (500 mg/1) + Amoxicillin Trihydrate (500 mg/1) + Omeprazole (20 mg/1)KitOralPernix Therapeutics2012-04-272016-07-31US flag
Omeclamox-PakClarithromycin (500 mg/1) + Amoxicillin Trihydrate (500 mg/1) + Omeprazole (20 mg/1)KitOralCumberland Pharmaceuticals Inc.2012-04-27Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ClarithromycinClarithromycin (250 mg/1)TabletOralRemedy Repack2009-08-062009-08-06US flag
KLACID 500 MG FILM TABLET, 14 ADETClarithromycin (500 mg)Tablet, film coatedOralABBOTT LABORATUARLARI İTHALAT İHRACAT VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
KLACID MR 7 KONT. SAL. TABLETClarithromycin (500 mg)Tablet, extended releaseOralABBOTT LABORATUARLARI İTHALAT İHRACAT VE TİC. LTD. ŞTİ.2020-08-14Not applicableTurkey flag
KLAMER 500 MG FILM TABLET, 14 ADETClarithromycin (500 mg)Tablet, film coatedOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
A02BD12 — Rabeprazole, amoxicillin and clarithromycinA02BD14 — Vonoprazan, amoxicillin and clarithromycinA02BD07 — Lansoprazole, amoxicillin and clarithromycinA02BD04 — Pantoprazole, amoxicillin and clarithromycinA02BD09 — Lansoprazole, clarithromycin and tinidazoleA02BD05 — Omeprazole, amoxicillin and clarithromycinJ01FA09 — ClarithromycinA02BD06 — Esomeprazole, amoxicillin and clarithromycinA02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
Macrolides and analogues / O-glycosyl compounds / Oxanes / Monosaccharides / Tertiary alcohols / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Amino acids and derivatives / Carboxylic acid esters
show 9 more
Substituents
1,2-aminoalcohol / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino acid or derivatives / Aminoglycoside core / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 22 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
macrolide antibiotic (CHEBI:3732) / Macrolides and lactone polyketides (C06912) / Macrolides and lactone polyketides (LMPK04000014)
Affected organisms
  • Enteric bacteria and other eubacteria
  • Mycobacterium
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Haemophilus influenzae
  • Helicobacter pylori
  • Mycobacterium leprae
  • Mycobacterium avium

Chemical Identifiers

UNII
H1250JIK0A
CAS number
81103-11-9
InChI Key
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)[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

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. [Article]
  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. [Article]
  3. Piscitelli SC, Danziger LH, Rodvold KA: Clarithromycin and azithromycin: new macrolide antibiotics. Clin Pharm. 1992 Feb;11(2):137-52. [Article]
  4. Peters DH, Clissold SP: Clarithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic potential. Drugs. 1992 Jul;44(1):117-64. [Article]
  5. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [Article]
  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. [Article]
Human Metabolome Database
HMDB0015342
KEGG Drug
D00276
KEGG Compound
C06912
PubChem Compound
84029
PubChem Substance
46506489
ChemSpider
10342604
BindingDB
50404044
RxNav
21212
ChEBI
3732
ChEMBL
CHEMBL1741
ZINC
ZINC000085534098
Therapeutic Targets Database
DAP000410
PharmGKB
PA449028
PDBe Ligand
CTY
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Clarithromycin
PDB Entries
1j5a / 5igj / 5igw / 6u18
FDA label
Download (376 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentGastrointestinal Ulcer Haemorrhage / Helicobacter Pylori Infection1
4Active Not RecruitingTreatmentHelicobacter Pylori Infection1
4CompletedPreventionHelicobacter Pylori Infection / Obesity, Morbid1
4CompletedPreventionLung Disorder1
4CompletedSupportive CarePeriodontitis1
4CompletedTreatmentAsthma1
4CompletedTreatmentBorrelia Infection / Lyme Disease1
4CompletedTreatmentChronic Idiopathic Thrombocytopenic Purpura / Helicobacter Pylori Infection1
4CompletedTreatmentCommunity Acquired Pneumonia (CAP)1
4CompletedTreatmentCYP2C19 polymorphism / Helicobacter Pylori Infection / Therapies1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Abbott Laboratories Ltd.
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Cardinal Health
  • DAVA Pharmaceuticals
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Dorx LLC
  • Eon Labs
  • Gallipot
  • Genpharm LP
  • H.J. Harkins Co. Inc.
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Medvantx Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Promex Medical Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sandhills Packaging Inc.
  • Sandoz
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Stat Scripts LLC
  • Teva Pharmaceutical Industries Ltd.
  • Toba Pharma Inc.
  • UDL Laboratories
  • Watson Pharmaceuticals
  • Wockhardt Ltd.
  • Zhejiang Huayi Pharmaceutical Co. Ltd.
Dosage Forms
FormRouteStrength
Syrup
SuspensionOral
Tablet, coatedOral
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
Powder, for suspensionOral2.5 g
For suspensionOral125 mg/5mL
For suspensionOral250 mg/5mL
Granule, for suspensionOral125 mg / 5 mL
Granule, for suspensionOral250 mg / 5 mL
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, coatedOral250 mg/1
Tablet, coatedOral500 mg/1
Tablet, film coatedOral
GranuleOral125 MG/5ML
GranuleOral250 MG/5ML
GranuleOral5 ML
Tablet, film coated, extended releaseOral1000 mg/1
Tablet, extended releaseOral500 mg/1
Injection, powder, for solutionParenteral
Tablet, extended releaseOral
Granule, for suspensionOral
Powder, for solutionOral5 g
Powder, for solutionOral40 g
PowderIntravenous500 mg
Injection, powder, lyophilized, for solutionIntravenous500 mg
Powder, for solution
Powder, for solutionOral12.64 g
Powder, for solutionParenteral500 MG
TabletOral
Granule, for suspensionOral25 MG/ML
Granule, for suspensionOral50 MG/ML
TabletOral250 mg
Powder500 MG
Powder, for suspensionOral5 g
Injection, solutionIntravenous
Powder, for suspensionOral125 mg
GranuleOral250 mg
Capsule; kit; tabletOral
Tablet, film coated, extended releaseOral
Injection, powder, lyophilized, for solutionParenteral500 mg
TabletOral
Capsule; capsule, delayed release; kit; tabletOral
GranuleOral125 mg
Injection
Granule, for suspensionOral500 MG
PowderParenteral500 MG/10ML
Powder, for suspensionOral125 mg/5ml
Tablet, delayed releaseOral500 mg
GranuleOral
Kit; tabletOral
InjectionIntravenous500 mg
Tablet, delayed releaseOral
GranuleOral5 g
TabletOral500 mg
PowderOral2.5 g
Tablet, extended releaseOral500 mg
TabletOral125 mg
Powder, for solutionIntravenous500 MG/10ML
Powder, for solutionOral125 mg
GranuleOral2500 mg
Powder, for suspensionOral
Injection, powder, for solutionIntravenous500 mg
Injection, powder, lyophilized, for solutionIntravenous
KitOral
Granule, for suspensionOral250 MG
Capsule; tabletOral
Powder500 MG/10ML
Tablet, film coatedOral500 mg
Tablet, coatedOral250 mg
Tablet, coatedOral500 mg
Injection, powder, for solution500 mg
Tablet, film coatedOral250 mg
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)Region
CA2471102No2005-02-082017-07-25Canada flag
CA1328609No1994-04-192011-04-19Canada flag
US6010718No2000-01-042017-04-11US flag
US6551616No2003-04-222017-06-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)220 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-3900020000-7d6e24fdb4aaa06a54bd
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0005-0300060900-61dad109d1b621f69b3b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900020000-0595f7fefa3c09c779d2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-8a6bb2526f5f15604524
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-5d02e103d637084e4b49
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0000000900-9b3927ca525e74f19cec
MS/MS Spectrum - , positiveLC-MS/MSsplash10-052e-0800070900-da3f6b9dcca7ec506f23
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0000001900-bcb836ce99019295a00e

Targets

Drugtargets2
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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 cent...
Gene Name
rplJ
Uniprot ID
P0A7J6
Uniprot Name
50S ribosomal protein L10
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. [Article]
  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. [Article]
  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. [Article]
  4. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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 ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
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. [Article]
Kind
Protein
Organism
Humans
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, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
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. [Article]
Kind
Protein
Organism
Humans
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), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
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. [Article]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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. [Article]
  2. Niemi M, Neuvonen PJ, Kivisto KT: The cytochrome P4503A4 inhibitor clarithromycin increases the plasma concentrations and effects of repaglinide. Clin Pharmacol Ther. 2001 Jul;70(1):58-65. doi: 10.1067/mcp.2001.116511. [Article]
  3. Dalboge CS, Nielsen XC, Dalhoff K, Alffenaar JW, Duno M, Buchard A, Uges DR, Jensen AG, Jurgens G, Pressler T, Johansen HK, Hoiby N: Pharmacokinetic variability of clarithromycin and differences in CYP3A4 activity in patients with cystic fibrosis. J Cyst Fibros. 2014 Mar;13(2):179-85. doi: 10.1016/j.jcf.2013.08.008. Epub 2013 Sep 10. [Article]
  4. Akiyoshi T, Ito M, Murase S, Miyazaki M, Guengerich FP, Nakamura K, Yamamoto K, Ohtani H: Mechanism-based inhibition profiles of erythromycin and clarithromycin with cytochrome P450 3A4 genetic variants. Drug Metab Pharmacokinet. 2013;28(5):411-5. Epub 2013 Mar 19. [Article]
  5. Flockhart Table of Drug Interactions [Link]
  6. BIAXIN (clarithromycin) - Drug Monograph [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Flockhart Table of Drug Interactions [Link]

Transporters

Kind
Protein
Organism
Humans
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 sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
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. [Article]
Details
2. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
Uniprot Name
Multidrug resistance protein 1
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. [Article]
  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. [Article]
  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. [Article]
  4. Authors unspecified: Clarithromycin. Tuberculosis (Edinb). 2008 Mar;88(2):92-5. doi: 10.1016/S1472-9792(08)70005-2. [Article]
  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. [Article]
  6. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]

Drug created on June 13, 2005 13:24 / Updated on September 19, 2021 19:53