Identification

Name
Clarithromycin
Accession Number
DB01211  (APRD00181)
Type
Small Molecule
Groups
Approved
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
  • Clarithromycina
  • Clarithromycine
  • Clarithromycinum
  • Claritromicina
External IDs
A-56268 / ABBOTT-56268 / TE-031
Product Ingredients
IngredientUNIICASInChI Key
Clarithromycin citrate16K08R7NG0848130-51-8MDRWXDRMSKEMRE-AZFLODHXSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Clarithromycin XLTablet, extended release500 mgOralActavis Pharma Company2014-12-01Not applicableCanada
BiaxinTablet, film coated, extended release500 mg/1OralA S Medication Solutions2000-03-03Not applicableUs
BiaxinGranule, for suspension125 mg/5mLOralAbbvie1993-12-232014-12-31Us
BiaxinGranule, for suspension125 mgOralBgp Pharma Ulc1995-12-31Not applicableCanada
BiaxinGranule, for suspension125 mg/5mLOralPhysicians Total Care, Inc.2003-12-032011-06-30Us
BiaxinTablet, film coated250 mg/1OralAbbvie1991-10-312017-04-26Us
BiaxinTablet, film coated500 mg/1OralPhysicians Total Care, Inc.1993-06-232011-06-30Us54868 233820180907 15195 n4t11n
BiaxinTablet, film coated500 mg/1OralRemedy Repack2012-07-212013-07-21Us00074 2586 60 nlmimage10 24131228
BiaxinTablet, film coated, extended release500 mg/1OralAbbvie2000-03-032014-12-10Us
BiaxinTablet, film coated500 mg/1OralA S Medication Solutions1991-10-31Not applicableUs54569 343920180907 15195 1awpoea
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-clarithromycinTablet500 mgOralApotex Corporation2007-07-26Not applicableCanada
Apo-clarithromycinTablet250 mgOralApotex Corporation2007-07-26Not applicableCanada
Apo-clarithromycin XLTablet, extended release500 mgOralApotex Corporation2014-09-03Not applicableCanada
Ava-clarithromycinTablet500 mgOralAvanstra Inc2011-09-192014-08-21Canada
Ava-clarithromycinTablet250 mgOralAvanstra Inc2011-09-192014-08-21Canada
ClarithromycinTablet, film coated250 mg/1OralMylan Pharmaceuticals2013-03-042014-02-28Us
ClarithromycinTablet, film coated500 mg/1OralRemedy Repack2018-04-25Not applicableUs
ClarithromycinTablet, film coated250 mg/1OralTeva Pharmaceuticals USA, Inc.2014-12-16Not applicableUs
ClarithromycinTablet, film coated250 mg/1OralTeva2005-06-282016-08-31Us0093 715720180907 15195 8v71pr
ClarithromycinTablet, film coated500 mg/1OralA-S Medication Solutions2012-07-25Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-lansoprazole-amoxicillin-clarithromycinClarithromycin (500 mg) + Amoxicillin (500 mg) + Lansoprazole (30 mg)Capsule; Capsule, delayed release; Kit; TabletOralApotex CorporationNot applicableNot applicableCanada
Hp-pacClarithromycin (500 mg) + Amoxicillin (500 mg) + Lansoprazole (30 mg)Capsule; Capsule, delayed release; Kit; TabletOralTakeda1998-08-18Not applicableCanada
Lansoprazole, Amoxicillin and ClarithromycinClarithromycin (500 mg/1) + Amoxycillin trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitSandoz2014-03-04Not applicableUs
Lansoprazole, Amoxicillin and ClarithromycinClarithromycin (500 mg/1) + Amoxycillin trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitPrasco, Laboratories2015-03-03Not applicableUs
Lansoprazole, Amoxicillin, and ClarithromycinClarithromycin (500 mg/1) + Amoxycillin trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitTeva2013-09-092015-04-30Us00093 8055 14 nlmimage10 c2386123
Lansoprazole, Amoxicillin, ClarithromycinClarithromycin (500 mg/1) + Amoxycillin trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitRising Health, Llc.2016-10-14Not applicableUs57237 00120180913 8702 1lfom9c
Omeclamox-PakClarithromycin (500 mg/1) + Amoxycillin trihydrate (500 mg/1) + Omeprazole (20 mg/1)KitCumberland Pharmaceuticals2012-04-27Not applicableUs
Omeclamox-PakClarithromycin (500 mg/1) + Amoxycillin trihydrate (500 mg/1) + Omeprazole (20 mg/1)KitPernix Therapeutics2012-04-272016-07-31Us
PrevpacClarithromycin (500 mg/1) + Amoxycillin trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitPhysicians Total Care, Inc.2005-05-20Not applicableUs
PrevpacClarithromycin (500 mg/1) + Amoxycillin trihydrate (500 mg/1) + Lansoprazole (30 mg/1)KitTap Pharmaceutical Products Inc.2007-06-262007-06-26Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ClarithromycinClarithromycin (250 mg/1)TabletOralRemedy Repack2009-08-062009-08-06Us
International/Other Brands
Klacid XL / Klaricid XL / Macladin / Naxy / Veclam / Zeclar
Categories
UNII
H1250JIK0A
CAS number
81103-11-9
Weight
Average: 747.9534
Monoisotopic: 747.476891299
Chemical Formula
C38H69NO13
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

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).

Associated Conditions
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 AvailableHuman
USolute carrier organic anion transporter family member 1B1Not AvailableHuman
USolute carrier organic anion transporter family member 1B3Not AvailableHuman
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.

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
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.

Affected organisms
  • Enteric bacteria and other eubacteria
  • Mycobacterium
  • Streptococcus pyogenes
  • Streptococcus pneumoniae
  • Haemophilus influenzae
  • Helicobacter pylori
  • Mycobacterium leprae
  • Mycobacterium avium
Pathways
PathwayCategory
Clarithromycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Clarithromycin.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Clarithromycin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Clarithromycin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Clarithromycin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Clarithromycin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Clarithromycin.
6-Deoxyerythronolide BThe metabolism of Clarithromycin can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Clarithromycin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Clarithromycin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when 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.

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
Human Metabolome Database
HMDB0015342
KEGG Drug
D00276
KEGG Compound
C06912
PubChem Compound
84029
PubChem Substance
46506489
ChemSpider
10342604
BindingDB
50404044
ChEBI
3732
ChEMBL
CHEMBL1741
Therapeutic Targets Database
DAP000410
PharmGKB
PA449028
HET
CTY
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Clarithromycin
ATC Codes
A02BD05 — Omeprazole, amoxicillin and clarithromycinA02BD06 — Esomeprazole, amoxicillin and clarithromycinA02BD09 — Lansoprazole, clarithromycin and tinidazoleA02BD07 — Lansoprazole, amoxicillin and clarithromycinA02BD04 — Pantoprazole, amoxicillin and clarithromycinA02BD11 — Pantoprazole, amoxicillin, clarithromycin and metronidazoleJ01FA09 — Clarithromycin
AHFS Codes
  • 08:12.12.92 — Other Macrolides
PDB Entries
1j5a / 5igj / 5igw
FDA label
Download (376 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
0Unknown StatusBasic ScienceCancer, Breast1
1CompletedNot AvailableDrug-drug Interaction Study1
1CompletedNot AvailableHealthy Volunteers7
1CompletedBasic ScienceAnovulatory cycle / Cytochrome P450 CYP3A Enzyme Deficiency / Disorder Due Cytochrome P450 CYP2D6 Variant1
1CompletedBasic ScienceDrug Drug Interaction (DDI) / Pharmacodynamics / Pharmacokinetics1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedBasic ScienceNeoplasms / Neoplasms Metastasis1
1CompletedBasic SciencePharmacokinetics1
1CompletedBasic ScienceVenous Thromboembolism (VTE)1
1CompletedScreeningOxidative Stress1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
1CompletedTreatmentDrug Interaction Potentiation1
1CompletedTreatmentHealthy Volunteers11
1CompletedTreatmentHelicobacter Pylori1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
1CompletedTreatmentMajor Depressive Disorder (MDD)1
1CompletedTreatmentMalignant Lymphomas / Nonhematologic Malignancies1
1Not Yet RecruitingTreatmentHIV-1-infection1
1RecruitingBasic ScienceHealthy Volunteers2
1RecruitingTreatmentProstate Cancer1
1TerminatedBasic ScienceAdvanced Solid Tumors1
1, 2CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
1, 2RecruitingOtherParkinson's Disease (PD)1
1, 2RecruitingTreatmentPlasma Cell Myeloma1
2Active Not RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2Active Not RecruitingTreatmentMultiple Myeloma (MM)5
2Active Not RecruitingTreatmentRefractory Multiple Myeloma / Stage I Multiple Myeloma / Stage II Multiple Myeloma / Stage III Multiple Myeloma1
2CompletedNot AvailableMalignant Lymphomas1
2CompletedPreventionMultiple Myeloma and Plasma Cell Neoplasm1
2CompletedTreatmentCystic Fibrosis (CF)1
2CompletedTreatmentDS Stage I Plasma Cell Myeloma / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare4
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Toxoplasmosis, Cerebral1
2CompletedTreatmentHypersomnia / Idiopathic Hypersomnia / Narcolepsy1
2CompletedTreatmentInfection, Mycobacterium Avium-Intracellulare1
2CompletedTreatmentMalignant Lymphomas2
2Not Yet RecruitingTreatmentAcid Dyspepsia / Gastritis1
2Not Yet RecruitingTreatmentAlcohol Use Disorder (AUD)1
2RecruitingTreatmentAppendiceal Neoplasms / Pseudomyxoma Peritonei1
2RecruitingTreatmentGastric Diffuse Large B-cell Lymphoma1
2RecruitingTreatmentInfection NOS / Multiple Myeloma (MM)1
2RecruitingTreatmentInfluenza A Virus Infection1
2RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Non-squamous Cell Lung Cancer / Squamous Cell Carcinoma of Lung1
2RecruitingTreatmentMucosa Associated Lymphoid Tissue (MALT) Lymphoma1
2RecruitingTreatmentMultiple Myeloma (MM)1
2TerminatedPreventionUreaplasma/Mycoplasma Positive / Very Low Birth Weight Infant1
2TerminatedSupportive CareCachexia / Lung Cancers1
2TerminatedTreatmentMultiple Myeloma (MM)1
2Unknown StatusTreatmentMalignant Lymphomas1
2WithdrawnTreatmentRelapse/Refractory Multiple Myeloma1
2, 3Active Not RecruitingTreatmentMycobacterium Ulcerans Infection1
2, 3CompletedTreatmentAggressive Periodontitis, Generalized1
2, 3CompletedTreatmentPeriodontitis, Aggressive1
2, 3Unknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer (GU) / Gastritis / Helicobacter Infections1
3CompletedTreatmentAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB)1
3CompletedTreatmentAcute Bacterial Sinusitis (ABS)1
3CompletedTreatmentAcute Obliterating Bronchiolitis / Obliterative Bronchiolitis1
3CompletedTreatmentAsthma Bronchial1
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
3CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases1
3CompletedTreatmentCrohn's Disease (CD)1
3CompletedTreatmentHelicobacter Infections1
3CompletedTreatmentHelicobacter Pylori Gastritis1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare4
3CompletedTreatmentPeptic ulcer haemorrhage1
3CompletedTreatmentPneumonia4
3CompletedTreatmentPneumonia, Bacterial1
3CompletedTreatmentPreterm Premature Rupture of the Membranes1
3CompletedTreatmentSepsis / Severe Sepsis / Shock, Septic1
3RecruitingBasic ScienceAutism Spectrum Conditions/Disorders1
3RecruitingTreatmentAtypical; Mycobacterium, Pulmonary, Tuberculous1
3RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
3RecruitingTreatmentBiomarkers / Gram-Negative Bacteria Infection / Multiple Organ Failure / Pneumonia / Respiratory Distress Syndrome (RDS) / Sepsis / The Mortality Rate1
3RecruitingTreatmentDuodenal Ulcer1
3RecruitingTreatmentHelicobacter-associated Gastritis1
3RecruitingTreatmentLung Infection / Mycobacterium avium complex infection1
3RecruitingTreatmentMultiple Myeloma (MM)3
3RecruitingTreatmentPreterm Premature Rupture of Membranes1
3TerminatedTreatmentHelicobacter Infections / Motor Fluctuations / Parkinson's Disease (PD)1
3Unknown StatusPreventionChronic Lung Disease of Prematurity1
3Unknown StatusTreatmentDuodenal Ulcer / Gastric Ulcer (GU) / Gastritis / Helicobacter Infections1
3Unknown StatusTreatmentMalignant Lymphomas / Non-Hodgkin's Lymphoma (NHL)1
3Unknown StatusTreatmentMalignant Neoplasm of Stomach1
4Active Not RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4CompletedPreventionChronic Lung Diseases1
4CompletedTreatmentAsthma Bronchial1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)8
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Chronic Idiopathic Thrombocytopenic Purpura1
4CompletedTreatmentBorrelia Infection / Lyme Disease1
4CompletedTreatmentFunctional Dyspepsia / Helicobacter Pylori / Peptic Ulcers1
4CompletedTreatmentGastritis / Indigestion / Peptic Ulcers2
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentHelicobacter Infections1
4CompletedTreatmentHelicobacter Pylori / Indigestion / Peptic Ulcers1
4CompletedTreatmentIndigestion / Peptic Ulcers1
4CompletedTreatmentPeptic Ulcers1
4CompletedTreatmentSepsis / Ventilator-associated Bacterial Pneumonia1
4Enrolling by InvitationTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Not Yet RecruitingTreatmentAntimicrobial Susceptibility Testing / Triple Therapy1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4Not Yet RecruitingTreatmentGastro-esophageal Reflux Disease (GERD)1
4Not Yet RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4RecruitingTreatmentAntimicrobial Susceptibility Testing / Bacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)6
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Complications, Pregnancy / Iron Deficiency Anemia (IDA)1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastric Polyps1
4RecruitingTreatmentHelicobacter Pylori1
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Functional Dyspepsia1
4Unknown StatusTreatmentCrohn's Disease (CD)1
4Unknown StatusTreatmentEradication Rates of the Two Regimens1
4Unknown StatusTreatmentGastritis, Gastric Ulcer, and Duodenal Ulcer1
4Unknown StatusTreatmentHelicobacter Pylori1
4Unknown StatusTreatmentMycobacterium Avium Complex Lung Disease1
4Unknown StatusTreatmentMycobacterium avium complex infection / Non-Tuberculous Mycobacteria1
Not AvailableActive Not RecruitingBasic ScienceVitamin D and Calcium Homeostasis1
Not AvailableCompletedNot AvailableHealthy Volunteers3
Not AvailableCompletedNot AvailableLower Respiratory Tract Infection (LRTI)1
Not AvailableCompletedNot AvailableRespiratory Tract Infections (RTI)3
Not AvailableCompletedSupportive CareGlomerulonephritis / Glomerulonephritis membranous / Glomerulonephritis minimal lesion1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)6
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Functional Dyspepsia1
Not AvailableCompletedTreatmentChronic Rhinosinusitis / Endoscopic Sinus Surgery1
Not AvailableCompletedTreatmentGastric MALT Lymphoma1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Mycobacterium Avium-intracellular Infection2
Not AvailableCompletedTreatmentInduction of Labour1
Not AvailableCompletedTreatmentInfection NOS2
Not AvailableCompletedTreatmentPeriodontitis, Aggressive1
Not AvailableCompletedTreatmentUlcerative Colitis (UC)1
Not AvailableNot Yet RecruitingDiagnosticHyperaldosteronism1
Not AvailableNot Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableRecruitingPreventionMotility Disorders / Staphylococcus Aureus1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)4
Not AvailableRecruitingTreatmentHelicobacter Infection1
Not AvailableUnknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1

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
Tablet, extended releaseOral500 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
For suspensionOral125 mg/5mL
For suspensionOral250 mg/5mL
Granule, for suspensionOral125 mg
Granule, for suspensionOral250 mg
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, coatedOral250 mg/1
Tablet, coatedOral500 mg/1
Tablet, film coated, extended releaseOral1000 mg/1
Capsule; capsule, delayed release; kit; tabletOral
TabletOral250 mg
TabletOral500 mg
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
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2471102No2005-02-082017-07-25Canada
CA1328609No1994-04-192011-04-19Canada
US6010718No2000-01-042017-04-11Us
US6551616No2003-04-222017-06-15Us

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

Taxonomy

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
Aminoglycoside core / Macrolide / Glycosyl compound / O-glycosyl compound / Oxane / Monosaccharide / Tertiary alcohol / 1,2-aminoalcohol / Amino acid or derivatives / 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)

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 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. [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
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. [PubMed:12873512]
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, 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. [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), 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. [PubMed:23571415]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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. [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. 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]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  2. Flockhart Table - Indiana University [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
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]
  2. Furuta T, Sagehashi Y, Shirai N, Sugimoto M, Nakamura A, Kodaira M, Kenmotsu K, Nagano M, Egashira T, Ueda K, Yoneyama M, Ohashi K, Ishizaki T, Hishida A: Influence of CYP2C19 polymorphism and Helicobacter pylori genotype determined from gastric tissue samples on response to triple therapy for H pylori infection. Clin Gastroenterol Hepatol. 2005 Jun;3(6):564-73. [PubMed:15952098]
  3. Saito M, Yasui-Furukori N, Uno T, Takahata T, Sugawara K, Munakata A, Tateishi T: Effects of clarithromycin on lansoprazole pharmacokinetics between CYP2C19 genotypes. Br J Clin Pharmacol. 2005 Mar;59(3):302-9. doi: 10.1111/j.1365-2125.2004.02329.x. [PubMed:15752376]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  2. Flockhart Table - Indiana University [Link]

Transporters

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 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. [PubMed:15708966]
Kind
Protein
Organism
Human
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. [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
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. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on November 18, 2018 13:31