Roxithromycin

Identification

Summary

Roxithromycin is an antibiotic used to treat a variety of susceptible bacterial infections.

Generic Name
Roxithromycin
DrugBank Accession Number
DB00778
Background

Roxithromycin is a semi-synthethic macrolide antibiotic that is structurally and pharmacologically similar to erythromycin, azithromycin, or clarithromycin. It was shown to be more effective against certain Gram-negative bacteria, particularly Legionella pneumophila. Roxithromycin exerts its antibacterial action by binding to the bacterial ribosome and interfering with bacterial protein synthesis. It is marketed in Australia as a treatment for respiratory tract, urinary and soft tissue infections.

Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Structure
Weight
Average: 837.0465
Monoisotopic: 836.524569772
Chemical Formula
C41H76N2O15
Synonyms
  • (9E)-erythromycin 9-(O-((2-methoxyethoxy)methyl)oxime)
  • Roxithromycin
  • Roxithromycine
  • Roxithromycinum
  • Roxitromicina
External IDs
  • RU 28965
  • RU 965

Pharmacology

Indication

Used to treat respiratory tract, urinary and soft tissue infections.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofLower respiratory tract and lung infections••••••••••••••••••• •••• ••••••
Treatment ofRespiratory tract infections (rti)••••••••••••••••••• •••• ••••••
Treatment ofSkin infections••••••••••••••••••• •••• ••••••
Treatment ofEar, nose and throat infections••••••••••••••••••• •••• ••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Roxithromycin has the following antibacterial spectrum in vitro: Streptococcus agalactiae, Streptococcus pneumoniae (Pneumococcus), Neisseria meningitides (Meningococcus), Listeria monocytogenes, Mycoplasma pneumoniae, Chlamydia trachomatis, Ureaplasma urealyticum, Legionella pneumophila, Helicobacter (Campylobacter), Gardnerella vaginalis, Bordetella pertussis, Moraxella catarrhalis (Branhamella Catarrhalis), and Haemophilus ducreyi. Roxithromycin is highly concentrated in polymorphonuclear leukocytes and macrophages, achieving intracellular concentrations greater than those outside the cell. Roxithromycin enhances the adhesive and chemotactic functions of these cells which in the presence of infection produce phagocytosis and bacterial lysis. Roxithromycin also possesses intracellular bactericidal activity.

Mechanism of action

Roxithromycin prevents bacterial growth by interfering with their protein synthesis. It binds to the 50S subunit of bacterial ribosomes and inhibits the translocation of peptides.

TargetActionsOrganism
A50S ribosomal protein L10
inhibitor
Shigella flexneri
UP-glycoprotein 1Not AvailableHumans
Absorption

Very rapidly absorbed and diffused into most tissues and phagocytes.

Volume of distribution

Not Available

Protein binding

96%, mainly to alpha1-acid glycoproteins

Metabolism

Hepatic. Roxithromycin is only partially metabolised, more than half the parent compound being excreted unchanged. Three metabolites have been identified in urine and faeces: the major metabolite is descladinose roxithromycin, with N-mono and N-di-demethyl roxithromycin as minor metabolites. The respective percentage of roxithromycin and these three metabolites is similar in urine and faeces.

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Route of elimination

Not Available

Half-life

12 hours

Clearance

Not Available

Adverse Effects
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Toxicity

Roxithromycin primarily causes gastrointestinal adverse events, such as diarrhoea, nausea, abdominal pain and vomiting. Less common adverse events include headaches, rashes, abnormal liver function values and alteration in senses of smell and taste.

Pathways
PathwayCategory
Roxithromycin 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
AbametapirThe serum concentration of Roxithromycin can be increased when it is combined with Abametapir.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Roxithromycin.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Roxithromycin.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Roxithromycin.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Roxithromycin.
Food Interactions
Not Available

Products

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International/Other Brands
Acevor (Help) / Actirox (Active HC) / Ai Luo Xin (Huashen Pharmaceutical) / Allolide (Roman Industries) / Ammirox (MacroPhar) / Anti-Bio (Kon/Nos Leon) / Ao Ge Shen (Jianfa Pharmaceutical) / Aparox (Siza) / Arbid (Hetero) / Aroxe (Global) / Asmetic (Farmilia) / Assoral (Savio I.B.N.) / Aswad (Robins) / Azuril (Pharmanel) / Bazuctril (Chrispa) / BD-Rox (Panacea) / Bei Ke (Aoda Pharmaceuticals) / Bei Sha (Huipusen Medical Biological Technology) / Bi Ai Di (Siping Aimo Pharmaceutical) / Biaxsig (Sanofi-Aventis) / Bicofen (Pharmex) / Biostatik (Pharos) / Claramid (Pfizer) / Coroxin / Delitroxin (Pharmathen) / Delos (Dallas) / Dorolid (Domesco) / Elrox (Biopharm M.J.) / Erybros (Bros) / Eslid (Shin Poong) / Guamil (P T Interbat) / Heng Te (Hanson Pharmaceutical) / Hycin (Saga) / I-Throcin (T.C. Pharma-Chem) / Infectoroxit (Infectopharm) / Inrox (Intra) / Ixor (Soho) / Klomicina (Klonal) / Ladlid (Choseido Pharmaceutical) / Lang Su (Shandong Dayin Yanghai Bio-Pharmaceutical Co.) / Le Er Tai (Tianji Biological Pharmaceutical) / Le Xi Qing (Zhangshu Santai Pharmaceutical) / Li Fu (Suzhou Chung-Hwa Chemical & Pharmaceutical Industrial) / Lizhuxing (Livzon Zhuhai) / Ludin (Vellpharm) / Luo Jun Qing (Fusen Pharmaceutical) / Luo Shi Li (Xi'an Detian Pharmaceutical Co.) / Luo Si Mei (Yabo Pharmaceutical Co.) / Luprex (Lupin) / Macrol (UAP) / Macrolid (Rafarm) / Marulide (Pasteur) / Neo-Suxigal (Anfarm) / Nirox (Gabriel Health) / Odirox (Cipla) / Overal (Lusofarmaco) / Pedilid (Incepta) / Pedrox (Beximco) / Pinsheng (Xincat) / Plethirox (Sel-J) / Poliroxin (Polipharm) / Pu Hong (Shyndec) / Pymeroxitil (PMP) / Qi Wei (Lanling Pharmaceutical Production) / Ramivan (Medipharm) / Redotrin (Coup) / Remora (Nobel) / Ren Su (Yangtze River Pharma) / Renicin (Sandoz) / Ridinfect (Medicraft) / Ritosin (Münir Sahin) / Rocin (Pasteur) / Rokithrid (Taiyo Pharmaceutical) / Roksimin (Il-Ko) / Rolexit (Nufarindo) / Rolicyn (Polfa Tarchomin) / Romac (Saiph) / Romicin (Dae Woo) / Romycin (Livzon Zhuhai) / Romyk (Lindopharm) / Ropit (Epitome) / Rossitrol (Sanofi-Aventis) / Rothricin (Siam Bheasach) / Rotram (Ranbaxy) / Rovenal (Leciva) / Roxamed (Dar Al Dawa) / Roxar (Sigma) / Roxcin (Biolab) / Roxemicin (Han Mi) / Roxeptin (Ipca Laboratories Ltd.) / Roxetomin (Sun) / Roxi (Dae Won) / Roxi-Fatol (Riemser) / Roxi-Puren (Actavis) / Roxi-Q (Juta) / Roxi-saar (MIP) / Roxibest (Blue Cross) / Roxibeta (Betapharm) / Roxibron (Viofar) / Roxicin (Atlantic Lab) / Roxicur (Velka) / Roxicure (Pharmaceutical) / Roxid (Alembic) / Roxide (Sandoz) / Roxidura (Mylan dura) / Roxigamma (Wörwag Pharma) / Roxigrün (Grünenthal) / Roxihexal (Salutas) / Roxikid (Ahn-Gook) / Roxil (YSS) / Roxilan (Olan-Kemed) / Roximac (Ram Pharmaceutical) / Roximain (Towa Yakuhin) / Roximax (Pharmaghreb) / Roximed (Medhaus) / Roximerck (Mylan Seiyaku) / Roximic (Acto) / Roximin (Novis Pharmaceutical) / Roximisan (Slaviamed) / Roximol (Torrent) / Roximycin (Alphapharm) / Roxinga (Roxinga) / Roxinox (Charoen Bhaesaj) / Roxiratio (ratiopharm) / Roxirocin (Korea Arlico) / Roxisara (Abbott) / Roxistad (Aliud) / Roxitas (Intas) / Roxitazon (Alice Loren) / Roxithrin (Kuk Je) / Roxithro (Millimed) / Roxithrostad (STADA) / Roxitil (Kolon) / Roxitin (T P Drug) / Roxitis (Medley) / Roxitop (Farmaline) / Roxitran (Neo Quimica) / Roxitrom (Biolab) / Roxitromycine (Sandoz) / Roxitron (ICN) / Roxivar (Zota) / Roxivinol (Pheracon) / Roxivista (Cadila) / Roxl-150 / Roxo / Roxomycin / Roxy (Ind-Swift) / Roxy-150 (Cipla) / Rulid / Rulide (Sanofi-Aventis) / Rulide D (Sanofi-Aventis) / Surlid (Sanofi-Aventis) / Tirabicin / Xthrocin

Categories

ATC Codes
J01FA06 — Roxithromycin
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 / Monosaccharides / Oxanes / Tertiary alcohols / Secondary alcohols / Amino acids and derivatives / Carboxylic acid esters / Lactones / Trialkylamines
show 11 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
erythromycin derivative, semisynthetic derivative, macrolide (CHEBI:48844)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
21KOF230FA
CAS number
80214-83-1
InChI Key
RXZBMPWDPOLZGW-XMRMVWPWSA-N
InChI
InChI=1S/C41H76N2O15/c1-15-29-41(10,49)34(45)24(4)31(42-53-21-52-17-16-50-13)22(2)19-39(8,48)36(58-38-32(44)28(43(11)12)18-23(3)54-38)25(5)33(26(6)37(47)56-29)57-30-20-40(9,51-14)35(46)27(7)55-30/h22-30,32-36,38,44-46,48-49H,15-21H2,1-14H3/b42-31+/t22-,23-,24+,25+,26-,27+,28+,29-,30+,32-,33+,34-,35+,36-,38+,39-,40-,41-/m1/s1
IUPAC Name
(3R,4S,5S,6R,7R,9R,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-10-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
SMILES
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@@H]([C@H]2O)N(C)C)[C@](C)(O)C[C@@H](C)C(=NOCOCCOC)[C@H](C)[C@@H](O)[C@]1(C)O

References

Synthesis Reference

Murali Krishna Madala, Suresh Babu Meduri, Ketan Dhansukhlal Vyas, Ashok Krishna Kulkarni, "Process for preparing erythromycin derivative, such as roxithromycin, from the corresponding oxime." U.S. Patent US6051695, issued September, 1998.

US6051695
General References
  1. Gentry LO: Roxithromycin, a new macrolide antibiotic, in the treatment of infections in the lower respiratory tract: an overview. J Antimicrob Chemother. 1987 Nov;20 Suppl B:145-52. [Article]
  2. Link [Link]
KEGG Drug
D01710
KEGG Compound
C13173
PubChem Compound
6915744
PubChem Substance
46507676
ChemSpider
5291557
BindingDB
50248154
RxNav
9478
ChEBI
48935
ChEMBL
CHEMBL1214185
ZINC
ZINC000096006016
Therapeutic Targets Database
DAP000885
PharmGKB
PA164750505
PDBe Ligand
ROX
Wikipedia
Roxithromycin
PDB Entries
1jzz

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4CompletedTreatmentRheumatoid Arthritis1
4Unknown StatusPreventionBacterial Infections / Pacemaker Complication1
4Unknown StatusPreventionRupture of Membranes; Premature, Affecting Fetus1
3CompletedTreatmentQuality of Life (QOL) / Respiratory Function Tests1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral50 MG
Powder, for suspensionOral1.5 mg
Tablet, for suspensionOral50 MG
TabletOral150 mg
TabletOral
Tablet, film coatedOral50 MG
Powder, for suspensionOral3 g
Tablet, film coatedOral
GranuleOral50 mg
Tablet, solubleOral50 mg
Powder, for suspensionOral1.5 g
CapsuleOral150 MG
TabletOral300 mg
Tablet, film coatedOral300 mg
Tablet, film coatedOral150 mg
Tablet, coatedOral300 mg
Tablet, coatedOral150 mg
Tablet, coatedOral100 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility0.0189 mg/L at 25 °C (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))Not Available
logP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.187 mg/mLALOGPS
logP2.9ALOGPS
logP3Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.45Chemaxon
pKa (Strongest Basic)9.08Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area216.89 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity211.24 m3·mol-1Chemaxon
Polarizability91.83 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5
Blood Brain Barrier-0.9659
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8875
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IIInhibitor0.5625
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8339
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.708
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9615
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8676
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.9728 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9792
hERG inhibition (predictor II)Inhibitor0.6433
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-MSsplash10-0avj-9400000330-28b6678f1cbca323b0c9
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0aor-3911000000-4cbf211b5d9e86f931c0
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00xr-0000493040-58979c13aa08aabece66
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0000090010-6a8aec8cf2250a61f51e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00fr-0000095000-b6d63d80187aeea8a81f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00b9-0000159000-4d5697a33fe979ce33e3
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-2911101000-e3794cff943215a188cb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0aor-3911000000-4cbf211b5d9e86f931c0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0000000690-70aa08973751f58c3c7c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-0000003590-b166581b462301c15dd1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-07er-3700001980-9e611403eaf682d40a1f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002s-1900001340-789609c05354de23c2e4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bt9-5900001200-feb2c7814e5aeb7ab99c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-054x-8700000940-c40a3bde5842ac7810f6
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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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. Bertho G, Gharbi-Benarous J, Delaforge M, Girault JP: Transferred nuclear Overhauser effect study of macrolide-ribosome interactions: correlation between antibiotic activities and bound conformations. Bioorg Med Chem. 1998 Feb;6(2):209-21. [Article]
  2. Yam WK, Wahab HA: Molecular insights into 14-membered macrolides using the MM-PBSA method. J Chem Inf Model. 2009 Jun;49(6):1558-67. doi: 10.1021/ci8003495. [Article]
  3. Mabe S, Eller J, Champney WS: Structure-activity relationships for three macrolide antibiotics in Haemophilus influenzae. Curr Microbiol. 2004 Oct;49(4):248-54. [Article]
Kind
Protein
Organism
Humans
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
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Beltinger J, Haschke M, Kaufmann P, Michot M, Terracciano L, Krahenbuhl S: Hepatic veno-occlusive disease associated with immunosuppressive cyclophosphamide dosing and roxithromycin. Ann Pharmacother. 2006 Apr;40(4):767-70. Epub 2006 Mar 7. [Article]
  2. Kaufmann P, Haschke M, Torok M, Beltinger J, Bogman K, Wenk M, Terracciano L, Krahenbuhl S: Mechanisms of venoocclusive disease resulting from the combination of cyclophosphamide and roxithromycin. Ther Drug Monit. 2006 Dec;28(6):766-74. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Kaufmann P, Haschke M, Torok M, Beltinger J, Bogman K, Wenk M, Terracciano L, Krahenbuhl S: Mechanisms of venoocclusive disease resulting from the combination of cyclophosphamide and roxithromycin. Ther Drug Monit. 2006 Dec;28(6):766-74. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
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. Yamazaki H, Shimada T: Comparative studies of in vitro inhibition of cytochrome P450 3A4-dependent testosterone 6beta-hydroxylation by roxithromycin and its metabolites, troleandomycin, and erythromycin. Drug Metab Dispos. 1998 Nov;26(11):1053-7. [Article]
  2. Yamazaki H, Hiroki S, Urano T, Inoue K, Shimada T: Effects of roxithromycin, erythromycin and troleandomycin on their N-demethylation by rat and human cytochrome P450 enzymes. Xenobiotica. 1996 Nov;26(11):1143-53. doi: 10.3109/00498259609050259. [Article]
  3. Ohno Y, Hisaka A, Suzuki H: General framework for the quantitative prediction of CYP3A4-mediated oral drug interactions based on the AUC increase by coadministration of standard drugs. Clin Pharmacokinet. 2007;46(8):681-96. doi: 10.2165/00003088-200746080-00005. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:55