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Identification
NameTelithromycin
Accession NumberDB00976  (APRD00483)
TypeSmall Molecule
GroupsApproved
Description

Telithromycin, a semi-synthetic erythromycin derivative, belongs to a new chemical class of antibiotics called ketolides. Ketolides have been recently added to the macrolide-lincosamide-streptogramin class of antibiotics. Similar to the macrolide antibiotics, telithromycin prevents bacterial growth by interfering with bacterial protein synthesis. Telithromycin binds to the 50S subunit of the 70S bacterial ribosome and blocks further peptide elongation. Binding occurs simultaneously at to two domains of 23S RNA of the 50S ribosomal subunit, domain II and V, where older macrolides bind only to one. It is used to treat mild to moderate respiratory infections.

Structure
Thumb
SynonymsNot Available
External Identifiers
  • HMR 3647
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ketektablet, film coated300 mg/1oralSanofi Aventis U.S. Llc2010-06-01Not applicableUs
Ketektablet400 mgoralSanofi Aventis Canada Inc2003-05-292011-08-15Canada
Ketektablet, film coated400 mg/1oralPhysicians Total Care, Inc.2004-10-27Not applicableUs
Ketektablet, film coated400 mg/1oralSanofi Aventis U.S. Llc2010-06-01Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIKI8H7H19WL
CAS number191114-48-4
WeightAverage: 812.018
Monoisotopic: 811.473143313
Chemical FormulaC43H65N5O10
InChI KeyLJVAJPDWBABPEJ-PNUFFHFMSA-N
InChI
InChI=1S/C43H65N5O10/c1-12-33-43(8)37(48(41(53)58-43)19-14-13-18-47-23-31(45-24-47)30-16-15-17-44-22-30)27(4)34(49)25(2)21-42(7,54-11)38(28(5)35(50)29(6)39(52)56-33)57-40-36(51)32(46(9)10)20-26(3)55-40/h15-17,22-29,32-33,36-38,40,51H,12-14,18-21H2,1-11H3/t25-,26-,27+,28+,29-,32+,33-,36-,37-,38-,40+,42-,43-/m1/s1
IUPAC Name
(3aS,4R,7R,9R,10R,11R,13R,15R,15aR)-10-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-4-ethyl-11-methoxy-3a,7,9,11,13,15-hexamethyl-1-{4-[4-(pyridin-3-yl)-1H-imidazol-1-yl]butyl}-tetradecahydro-1H-oxacyclotetradeca[4,3-d][1,3]oxazole-2,6,8,14-tetrone
SMILES
[H][C@@]12[C@@H](C)C(=O)[[email protected]](C)C[C@@](C)(OC)[[email protected]](O[C@@H]3O[[email protected]](C)C[C@@H]([[email protected]]3O)N(C)C)[C@@H](C)C(=O)[C@@H](C)C(=O)O[[email protected]](CC)[C@@]1(C)OC(=O)N2CCCCN1C=NC(=C1)C1=CC=CN=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • N-substituted imidazole
  • Oxane
  • Oxazolidinone
  • Pyridine
  • 1,3-dicarbonyl compound
  • Azole
  • Cyclic alcohol
  • Imidazole
  • Oxazolidine
  • Heteroaromatic compound
  • Carbamic acid ester
  • 1,2-aminoalcohol
  • Carboxylic acid ester
  • Tertiary amine
  • Ketone
  • Lactone
  • Tertiary aliphatic amine
  • Cyclic ketone
  • Amino acid or derivatives
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Ether
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Dialkyl ether
  • Amine
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of Pneumococcal infection, acute sinusitis, acute bacterial tonsillitis, acute bronchitis and bronchiolitis, lower respiratory tract infection and lobar (pneumococcal) pneumonia.
PharmacodynamicsTelithromycin is a ketolide antibiotic which has an antimicrobial spectrum similar or slightly broader than that of penicillin. It is often used as an alternative in patients who have an allergy to penicillins. For respiratory tract infections, it has better coverage of atypical organisms, including mycoplasma. Telithromycin prevents bacterial growth by binding to bacterial 50S ribosomal subunits and interfering with bacterial peptide translocation and elongation.
Mechanism of actionTelithromycin acts by binding to domains II and V of 23S rRNA of the 50S ribosomal subunit. By binding at domain II, telithromycin retains activity against gram-positive cocci (e.g. Streptococcus pneumoniae) in the presence of resistance mediated by methylases (erm genes) that alter the binding site at domain V. Telithromycin may also inhibit the assembly of nascent ribosomal units. Compared to erythromycin A, telithromycin binds to the 23S rRNA with 10 times greater affinity in erythromycin-susceptible organisms and 25 times greater affinity in macrolide-resistant strains. This increased binding affinity may be conferred by the C11-12 carbamate side chain of telithromycin. The side chain appears to maintain binding at domain II in the presence of resistance mediated by alterations in domain V.
Related Articles
AbsorptionAbsolute bioavailability is approximately 57%. Maximal concentrations are reached 0.5 - 4 hours following oral administration. Food intake does not affected absorption.
Volume of distribution
  • 2.9 L/kg
Protein binding60 - 70% bound primarily to human serum albumin
Metabolism

Hepatic - estimated 50% metabolized by CYP3A4 and 50% metabolized independent of cytochrome P450

Route of eliminationThe systemically available telithromycin is eliminated by multiple pathways as follows: 7% of the dose is excreted unchanged in feces by biliary and/or intestinal secretion; 13% of the dose is excreted unchanged in urine by renal excretion; and 37% of the dose is metabolized by the liver.
Half lifeMain elimination half-life is 2-3 hours; terminal elimination half-life is 10 hours
ClearanceNot Available
ToxicityLD50>2000 mg/kg (PO in rats). Adverse effects are similar to those of clarithormycin and erithromycin and include diarrhea, nausea, vomiting, loose stools, abdominal pain, flatulence and dyspepsia. It may also cause dizziness, headache and taste disturbances.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Telithromycin Action PathwayDrug actionSMP00252
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9904
Blood Brain Barrier-0.8608
Caco-2 permeable-0.8958
P-glycoprotein substrateSubstrate0.8472
P-glycoprotein inhibitor IInhibitor0.8737
P-glycoprotein inhibitor IIInhibitor0.7653
Renal organic cation transporterNon-inhibitor0.8479
CYP450 2C9 substrateNon-substrate0.7872
CYP450 2D6 substrateNon-substrate0.8617
CYP450 3A4 substrateSubstrate0.7538
CYP450 1A2 substrateNon-inhibitor0.8288
CYP450 2C9 inhibitorNon-inhibitor0.7157
CYP450 2D6 inhibitorNon-inhibitor0.8675
CYP450 2C19 inhibitorNon-inhibitor0.6476
CYP450 3A4 inhibitorNon-inhibitor0.8407
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7749
Ames testNon AMES toxic0.7687
CarcinogenicityNon-carcinogens0.8998
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7843 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9399
hERG inhibition (predictor II)Non-inhibitor0.6053
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral400 mg
Tablet, film coatedoral300 mg/1
Tablet, film coatedoral400 mg/1
Prices
Unit descriptionCostUnit
Ketek pak 400 mg tablet6.12USD tablet
Ketek 400 mg tablet5.87USD tablet
Ketek 300 mg tablet5.76USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2102457 No2002-01-222013-11-04Canada
CA2189271 No2005-12-272015-05-02Canada
US5635485 No1998-04-012018-04-01Us
USD459798 No1995-09-242015-09-24Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point176-188 °CNot Available
water solubility300 mg/LNot Available
logP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0283 mg/mLALOGPS
logP4.21ALOGPS
logP5.13ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)7.65ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area171.85 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity214.68 m3·mol-1ChemAxon
Polarizability90.44 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Suhas Sohani, Mandar Deodhar, Nishant Patel, Manish Patel, Mahesh Davadra, Vinodhamar Kansal, “Process for the Preparation of Telithromycin.” U.S. Patent US20070260066, issued November 08, 2007.

US20070260066
General References
  1. Clay KD, Hanson JS, Pope SD, Rissmiller RW, Purdum PP 3rd, Banks PM: Brief communication: severe hepatotoxicity of telithromycin: three case reports and literature review. Ann Intern Med. 2006 Mar 21;144(6):415-20. Epub 2006 Feb 15. [PubMed:16481451 ]
External Links
ATC CodesJ01FA15
AHFS Codes
  • 08:12.12.12
PDB EntriesNot Available
FDA labelDownload (1.6 MB)
MSDSDownload (201 KB)
Interactions
Drug Interactions
Drug
AlfentanilThe serum concentration of Alfentanil can be increased when it is combined with Telithromycin.
AlfuzosinThe serum concentration of Alfuzosin can be increased when it is combined with Telithromycin.
AlmotriptanThe serum concentration of Almotriptan can be increased when it is combined with Telithromycin.
AlosetronThe serum concentration of Alosetron can be increased when it is combined with Telithromycin.
AlprazolamThe serum concentration of Alprazolam can be increased when it is combined with Telithromycin.
AmlodipineThe metabolism of Amlodipine can be decreased when combined with Telithromycin.
AmrinoneThe metabolism of Amrinone can be decreased when combined with Telithromycin.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Telithromycin.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Telithromycin.
AstemizoleThe serum concentration of Astemizole can be increased when it is combined with Telithromycin.
AtorvastatinThe serum concentration of Atorvastatin can be increased when it is combined with Telithromycin.
AvanafilThe serum concentration of Avanafil can be increased when it is combined with Telithromycin.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Telithromycin.
BarnidipineThe serum concentration of Barnidipine can be increased when it is combined with Telithromycin.
BedaquilineThe serum concentration of Bedaquiline can be increased when it is combined with Telithromycin.
BepridilThe metabolism of Bepridil can be decreased when combined with Telithromycin.
BexaroteneThe serum concentration of Telithromycin can be decreased when it is combined with Bexarotene.
BortezomibThe serum concentration of Bortezomib can be increased when it is combined with Telithromycin.
BosentanThe serum concentration of Telithromycin can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Telithromycin.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Telithromycin.
BrexpiprazoleThe serum concentration of Brexpiprazole can be increased when it is combined with Telithromycin.
BrinzolamideThe serum concentration of Brinzolamide can be increased when it is combined with Telithromycin.
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Telithromycin.
BuspironeThe metabolism of Buspirone can be decreased when combined with Telithromycin.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Telithromycin.
CabozantinibThe serum concentration of Cabozantinib can be increased when it is combined with Telithromycin.
CarbamazepineThe metabolism of Carbamazepine can be decreased when combined with Telithromycin.
CeritinibThe serum concentration of Ceritinib can be increased when it is combined with Telithromycin.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Telithromycin.
CisaprideThe metabolism of Cisapride can be decreased when combined with Telithromycin.
CitalopramTelithromycin may increase the QTc-prolonging activities of Citalopram.
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Telithromycin.
ClozapineThe metabolism of Clozapine can be decreased when combined with Telithromycin.
CobicistatThe serum concentration of Cobicistat can be increased when it is combined with Telithromycin.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Telithromycin.
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Telithromycin.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Telithromycin.
DabrafenibThe serum concentration of Telithromycin can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Daclatasvir can be increased when it is combined with Telithromycin.
DapoxetineThe serum concentration of Dapoxetine can be increased when it is combined with Telithromycin.
DasatinibThe serum concentration of Dasatinib can be increased when it is combined with Telithromycin.
DeferasiroxThe serum concentration of Telithromycin can be decreased when it is combined with Deferasirox.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Telithromycin.
DienogestThe serum concentration of Dienogest can be increased when it is combined with Telithromycin.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Telithromycin.
DisopyramideTelithromycin may increase the QTc-prolonging activities of Disopyramide.
DofetilideTelithromycin may increase the QTc-prolonging activities of Dofetilide.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Telithromycin.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Telithromycin.
DronabinolThe serum concentration of Dronabinol can be increased when it is combined with Telithromycin.
DronedaroneThe serum concentration of Dronedarone can be increased when it is combined with Telithromycin.
DrospirenoneThe serum concentration of Drospirenone can be increased when it is combined with Telithromycin.
DutasterideThe serum concentration of Dutasteride can be increased when it is combined with Telithromycin.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Telithromycin.
EplerenoneThe serum concentration of Eplerenone can be increased when it is combined with Telithromycin.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Telithromycin.
EstazolamThe serum concentration of Estazolam can be increased when it is combined with Telithromycin.
EtizolamThe serum concentration of Etizolam can be increased when it is combined with Telithromycin.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Telithromycin.
FelodipineThe metabolism of Felodipine can be decreased when combined with Telithromycin.
FentanylThe serum concentration of Fentanyl can be increased when it is combined with Telithromycin.
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Telithromycin.
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Telithromycin.
FluconazoleThe metabolism of Telithromycin can be decreased when combined with Fluconazole.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Telithromycin.
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Telithromycin.
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Telithromycin.
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Telithromycin.
Fusidic AcidThe serum concentration of Telithromycin can be increased when it is combined with Fusidic Acid.
GabapentinThe metabolism of Gabapentin can be decreased when combined with Telithromycin.
GoserelinGoserelin may increase the QTc-prolonging activities of Telithromycin.
GuanfacineThe serum concentration of Guanfacine can be increased when it is combined with Telithromycin.
HalofantrineThe serum concentration of Halofantrine can be increased when it is combined with Telithromycin.
HydrocodoneThe serum concentration of Hydrocodone can be increased when it is combined with Telithromycin.
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Telithromycin.
IdelalisibThe serum concentration of Telithromycin can be increased when it is combined with Idelalisib.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Telithromycin resulting in a loss in efficacy.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Telithromycin.
ImidafenacinThe serum concentration of Imidafenacin can be increased when it is combined with Telithromycin.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be increased when Irinotecan is used in combination with Telithromycin.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be increased when Isavuconazonium is used in combination with Telithromycin.
IsradipineThe metabolism of Isradipine can be decreased when combined with Telithromycin.
ItraconazoleThe serum concentration of Telithromycin can be increased when it is combined with Itraconazole.
IvabradineThe serum concentration of Ivabradine can be increased when it is combined with Telithromycin.
IvacaftorThe serum concentration of Ivacaftor can be increased when it is combined with Telithromycin.
IxabepiloneThe serum concentration of Ixabepilone can be increased when it is combined with Telithromycin.
KetoconazoleThe serum concentration of Telithromycin can be increased when it is combined with Ketoconazole.
LacosamideThe serum concentration of Lacosamide can be increased when it is combined with Telithromycin.
LamotrigineThe metabolism of Lamotrigine can be decreased when combined with Telithromycin.
LapatinibThe serum concentration of Lapatinib can be increased when it is combined with Telithromycin.
LercanidipineThe serum concentration of Lercanidipine can be increased when it is combined with Telithromycin.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Telithromycin.
LevobupivacaineThe serum concentration of Levobupivacaine can be increased when it is combined with Telithromycin.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Telithromycin.
LomitapideThe serum concentration of Lomitapide can be increased when it is combined with Telithromycin.
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Telithromycin.
LuliconazoleThe serum concentration of Telithromycin can be increased when it is combined with Luliconazole.
LurasidoneThe serum concentration of Lurasidone can be increased when it is combined with Telithromycin.
MacitentanThe serum concentration of MACITENTAN can be increased when it is combined with Telithromycin.
Magnesium SulfateThe metabolism of Magnesium Sulfate can be decreased when combined with Telithromycin.
MaravirocThe serum concentration of Maraviroc can be increased when it is combined with Telithromycin.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be increased when it is combined with Telithromycin.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Telithromycin.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Telithromycin.
MifepristoneMifepristone may increase the QTc-prolonging activities of Telithromycin.
MitotaneThe serum concentration of Telithromycin can be decreased when it is combined with Mitotane.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Telithromycin.
NelfinavirThe metabolism of Telithromycin can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Telithromycin can be increased when it is combined with Netupitant.
NicardipineThe metabolism of Nicardipine can be decreased when combined with Telithromycin.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Telithromycin.
NimodipineThe serum concentration of Nimodipine can be increased when it is combined with Telithromycin.
NisoldipineThe serum concentration of Nisoldipine can be increased when it is combined with Telithromycin.
NitrendipineThe metabolism of Nitrendipine can be decreased when combined with Telithromycin.
OctreotideOctreotide may increase the QTc-prolonging activities of Telithromycin.
OlaparibThe serum concentration of Olaparib can be increased when it is combined with Telithromycin.
OspemifeneThe serum concentration of Ospemifene can be increased when it is combined with Telithromycin.
OxybutyninThe serum concentration of Oxybutynin can be increased when it is combined with Telithromycin.
OxycodoneThe risk or severity of adverse effects can be increased when Telithromycin is combined with Oxycodone.
PalbociclibThe serum concentration of Palbociclib can be increased when it is combined with Telithromycin.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Telithromycin.
ParecoxibThe serum concentration of Parecoxib can be increased when it is combined with Telithromycin.
ParicalcitolThe serum concentration of Paricalcitol can be increased when it is combined with Telithromycin.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Telithromycin.
PerhexilineThe metabolism of Perhexiline can be decreased when combined with Telithromycin.
PhenytoinThe metabolism of Telithromycin can be increased when combined with Phenytoin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Telithromycin.
PimecrolimusThe metabolism of Pimecrolimus can be decreased when combined with Telithromycin.
PimozideTelithromycin may increase the QTc-prolonging activities of Pimozide.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Telithromycin.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Telithromycin.
PranlukastThe serum concentration of Pranlukast can be increased when it is combined with Telithromycin.
PrasugrelThe serum concentration of the active metabolites of Prasugrel can be reduced when Prasugrel is used in combination with Telithromycin resulting in a loss in efficacy.
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Telithromycin.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Telithromycin.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Telithromycin.
PrenylamineThe metabolism of Prenylamine can be decreased when combined with Telithromycin.
QuinidineTelithromycin may increase the QTc-prolonging activities of Quinidine.
QuinineThe serum concentration of Quinine can be increased when it is combined with Telithromycin.
RamelteonThe serum concentration of Ramelteon can be increased when it is combined with Telithromycin.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Telithromycin.
RegorafenibThe serum concentration of Regorafenib can be increased when it is combined with Telithromycin.
RepaglinideThe serum concentration of Repaglinide can be increased when it is combined with Telithromycin.
RetapamulinThe serum concentration of Retapamulin can be increased when it is combined with Telithromycin.
RifabutinThe metabolism of Rifabutin can be decreased when combined with Telithromycin.
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Telithromycin.
RisedronateThe metabolism of Risedronate can be decreased when combined with Telithromycin.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Telithromycin.
RuxolitinibThe serum concentration of Ruxolitinib can be increased when it is combined with Telithromycin.
SalmeterolThe serum concentration of Salmeterol can be increased when it is combined with Telithromycin.
SaxagliptinThe serum concentration of Saxagliptin can be increased when it is combined with Telithromycin.
SildenafilThe serum concentration of Sildenafil can be increased when it is combined with Telithromycin.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Telithromycin.
SiltuximabThe serum concentration of Telithromycin can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Simeprevir can be increased when it is combined with Telithromycin.
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Telithromycin.
SirolimusThe metabolism of Sirolimus can be decreased when combined with Telithromycin.
SonidegibThe serum concentration of Sonidegib can be increased when it is combined with Telithromycin.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Telithromycin.
St. John's WortThe serum concentration of Telithromycin can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Telithromycin can be increased when it is combined with Stiripentol.
SuvorexantThe serum concentration of Suvorexant can be increased when it is combined with Telithromycin.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Telithromycin.
TadalafilThe serum concentration of Tadalafil can be increased when it is combined with Telithromycin.
TamsulosinThe serum concentration of Tamsulosin can be increased when it is combined with Telithromycin.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Telithromycin.
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Telithromycin.
TemsirolimusThe risk or severity of adverse effects can be increased when Telithromycin is combined with Temsirolimus.
TerfenadineTelithromycin may increase the QTc-prolonging activities of Terfenadine.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Telithromycin resulting in a loss in efficacy.
TocilizumabThe serum concentration of Telithromycin can be decreased when it is combined with Tocilizumab.
TofacitinibThe serum concentration of Tofacitinib can be increased when it is combined with Telithromycin.
TolterodineThe serum concentration of Tolterodine can be increased when it is combined with Telithromycin.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Telithromycin.
ToremifeneThe risk or severity of adverse effects can be increased when Telithromycin is combined with Toremifene.
TrabectedinThe serum concentration of Trabectedin can be increased when it is combined with Telithromycin.
TramadolThe serum concentration of Tramadol can be increased when it is combined with Telithromycin.
Trastuzumab emtansineThe serum concentration of the active metabolites of ado-trastuzumab emtansine can be increased when ado-trastuzumab emtansine is used in combination with Telithromycin.
TriazolamThe serum concentration of Triazolam can be increased when it is combined with Telithromycin.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Telithromycin.
VardenafilThe serum concentration of Vardenafil can be increased when it is combined with Telithromycin.
VemurafenibThe serum concentration of Vemurafenib can be increased when it is combined with Telithromycin.
VerapamilTelithromycin may increase the bradycardic activities of Verapamil.
VilazodoneThe serum concentration of Vilazodone can be increased when it is combined with Telithromycin.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Telithromycin.
VorapaxarThe serum concentration of Vorapaxar can be increased when it is combined with Telithromycin.
ZopicloneThe serum concentration of Zopiclone can be increased when it is combined with Telithromycin.
Food Interactions
  • Take without regard to meals.

Targets

1. 23S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
Actions
inhibitor
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Reinert RR, Al-Lahham A: Time-kill study of the activity of telithromycin against macrolide-resistant Streptococcus pneumoniae Isolates with 23S rRNA mutations and changes in ribosomal proteins L4 and L22. Antimicrob Agents Chemother. 2005 Jul;49(7):3011-3. [PubMed:15980387 ]
  4. Farrell DJ, Shackcloth J, Barbadora KA, Green MD: Streptococcus pyogenes isolates with high-level macrolide resistance and reduced susceptibility to telithromycin associated with 23S rRNA mutations. Antimicrob Agents Chemother. 2006 Feb;50(2):817-8. [PubMed:16436755 ]
  5. Hirakata Y, Mizuta Y, Wada A, Kondoh A, Kurihara S, Izumikawa K, Seki M, Yanagihara K, Miyazaki Y, Tomono K, Kohno S: The first telithromycin-resistant Streptococcus pneumoniae isolate in Japan associated with erm(B) and mutations in 23S rRNA and riboprotein L4. Jpn J Infect Dis. 2007 Feb;60(1):48-50. [PubMed:17314426 ]
  6. Champney WS, Mentens N, Zurawick K: An examination of the differential sensitivity to ketolide antibiotics in ermB strains of Streptococcus pyogenes and Streptococcus pneumoniae. Curr Microbiol. 2004 Oct;49(4):239-47. [PubMed:15386111 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Bearden DT, Neuhauser MM, Garey KW: Telithromycin: an oral ketolide for respiratory infections. Pharmacotherapy. 2001 Oct;21(10):1204-22. [PubMed:11601667 ]
  2. Zhanel GG, Walters M, Noreddin A, Vercaigne LM, Wierzbowski A, Embil JM, Gin AS, Douthwaite S, Hoban DJ: The ketolides: a critical review. Drugs. 2002;62(12):1771-804. [PubMed:12149046 ]
  3. Reed M, Wall GC, Shah NP, Heun JM, Hicklin GA: Verapamil toxicity resulting from a probable interaction with telithromycin. Ann Pharmacother. 2005 Feb;39(2):357-60. Epub 2004 Dec 14. [PubMed:15598962 ]
  4. Shi J, Chapel S, Montay G, Hardy P, Barrett JS, Sica D, Swan SK, Noveck R, Leroy B, Bhargava VO: Effect of ketoconazole on the pharmacokinetics and safety of telithromycin and clarithromycin in older subjects with renal impairment. Int J Clin Pharmacol Ther. 2005 Mar;43(3):123-33. [PubMed:15792396 ]
  5. Nguyen M, Chung EP: Telithromycin: the first ketolide antimicrobial. Clin Ther. 2005 Aug;27(8):1144-63. [PubMed:16199242 ]
  6. 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 ]
  7. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 01:51