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Identification
- Summary
Telithromycin is an ketolide used to treat community acquired pneumonia of mild to moderate severity.
- Brand Names
- Ketek
- Generic Name
- Telithromycin
- DrugBank Accession Number
- DB00976
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Telithromycin (DB00976)
- Weight
- Average: 812.018
Monoisotopic: 811.473143313 - Chemical Formula
- C43H65N5O10
- Synonyms
- Telithromycin
- telitromicina
- External IDs
- HMR 3647
Pharmacology
- Indication
For the treatment of Pneumococcal infection, acute sinusitis, acute bacterial tonsillitis, acute bronchitis and bronchiolitis, lower respiratory tract infection and lobar (pneumococcal) pneumonia.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Mild community-acquired pneumonia •••••••••••• Treatment of Moderate community-acquired pneumonia •••••••••••• - Contraindications & Blackbox Warnings
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Telithromycin 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 action
Telithromycin 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.
Target Actions Organism A23S ribosomal RNA inhibitorEnteric bacteria and other eubacteria - Absorption
Absolute 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 binding
60 - 70% bound primarily to human serum albumin
- Metabolism
Hepatic - estimated 50% metabolized by CYP3A4 and 50% metabolized independent of cytochrome P450
- Route of elimination
The 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-life
Main elimination half-life is 2-3 hours; terminal elimination half-life is 10 hours
- Clearance
Not Available
- Adverse Effects
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LD50>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.
- Pathways
Pathway Category Telithromycin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 3A4 CYP3A4*20 Not Available 1461_1462insA Effect Inferred Poor drug metabolizer. Details Cytochrome P450 3A4 CYP3A4*26 Not Available 802C>T Effect Inferred Poor drug metabolizer. Details
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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The metabolism of 1,2-Benzodiazepine can be decreased when combined with Telithromycin. Abametapir The serum concentration of Telithromycin can be increased when it is combined with Abametapir. Abatacept The metabolism of Telithromycin can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Telithromycin. Abiraterone The metabolism of Abiraterone can be decreased when combined with Telithromycin. - Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ketek Tablet 400 mg Oral Sanofi Aventis Deutschland Gmb H 2003-05-29 2011-08-15 Canada 
Ketek Tablet, film coated 400 mg/1 Oral Physicians Total Care, Inc. 2004-10-27 Not applicable US 
Ketek Tablet, film coated 300 mg/1 Oral Sanofi Aventis Deutschland Gmb H 2010-06-01 2016-06-30 US Ketek Tablet, film coated 400 mg/1 Oral Sanofi Aventis Deutschland Gmb H 2010-06-01 2016-06-30 US
Categories
- ATC Codes
- J01FA15 — Telithromycin
- Drug Categories
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strong)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Erythromycin and similars
- Ketolide Antibacterial
- Ketolides
- Lactones
- Macrolides
- Macrolides, Lincosamides and Streptogramins
- Moderate Risk QTc-Prolonging Agents
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- Polyketides
- Protein Synthesis Inhibitors
- QTc Prolonging Agents
- 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
- Pyridines and derivatives / Oxazolidinones / Oxanes / 1,3-dicarbonyl compounds / N-substituted imidazoles / Carbamate esters / Heteroaromatic compounds / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols show 12 more
- Substituents
- 1,2-aminoalcohol / 1,3-dicarbonyl compound / Acetal / Alcohol / Amine / Amino acid or derivatives / Aminoglycoside core / Aromatic heteropolycyclic compound / Azacycle / Azole show 28 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- KI8H7H19WL
- CAS number
- 191114-48-4
- InChI Key
- LJVAJPDWBABPEJ-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)[C@H](C)C[C@@](C)(OC)[C@H](O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C)[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@H](CC)[C@@]1(C)OC(=O)N2CCCCN1C=NC(=C1)C1=CC=CN=C1
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
- 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. [Article]
- External Links
- KEGG Drug
- D01078
- KEGG Compound
- C12009
- PubChem Compound
- 3002190
- PubChem Substance
- 46504510
- ChemSpider
- 2273373
- BindingDB
- 50378137
- 274786
- ChEBI
- 29688
- ChEMBL
- CHEMBL1136
- ZINC
- ZINC000009574770
- Therapeutic Targets Database
- DAP000109
- PharmGKB
- PA10202
- PDBe Ligand
- TEL
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Telithromycin
- PDB Entries
- 1p9x / 1yij / 4v7s / 4v7z / 4wf9 / 6ha1 / 6ha8 / 6xhy / 7azy / 7nsq … show 2 more
- FDA label
- Download (1.6 MB)
- MSDS
- Download (201 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Drug Induced Liver Injury 1 somestatus stop reason just information to hide 4 Completed Diagnostic Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 4 Completed Treatment Acute Exacerbation of Chronic Bronchitis (AECB) / Community Acquired Pneumonia (CAP) 1 somestatus stop reason just information to hide 4 Completed Treatment Chronic Bronchitis 2 somestatus stop reason just information to hide 4 Completed Treatment Pneumonia 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- A-S Medication Solutions LLC
- Murfreesboro Pharmaceutical Nursing Supply
- Physicians Total Care Inc.
- Sanofi-Aventis Inc.
- Southwood Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet Oral 400 mg Tablet, film coated Oral 300 mg/1 Tablet, film coated Oral 400 mg/1 Tablet, film coated Oral 400 MG Tablet, film coated Oral - Prices
Unit description Cost Unit Ketek pak 400 mg tablet 6.12USD tablet Ketek 400 mg tablet 5.87USD tablet Ketek 300 mg tablet 5.76USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2189271 No 2005-12-27 2015-05-02 Canada CA2102457 No 2002-01-22 2013-11-04 Canada US5635485 No 1997-06-03 2018-04-01 US USD459798 No 2002-07-02 2015-09-24 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 176-188 °C Not Available water solubility 300 mg/L Not Available logP 3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0283 mg/mL ALOGPS logP 4.21 ALOGPS logP 5.13 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 8.84 Chemaxon pKa (Strongest Basic) 7.65 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 171.85 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 214.68 m3·mol-1 Chemaxon Polarizability 90.44 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9904 Blood Brain Barrier - 0.8608 Caco-2 permeable - 0.8958 P-glycoprotein substrate Substrate 0.8472 P-glycoprotein inhibitor I Inhibitor 0.8737 P-glycoprotein inhibitor II Inhibitor 0.7653 Renal organic cation transporter Non-inhibitor 0.8479 CYP450 2C9 substrate Non-substrate 0.7872 CYP450 2D6 substrate Non-substrate 0.8617 CYP450 3A4 substrate Substrate 0.7538 CYP450 1A2 substrate Non-inhibitor 0.8288 CYP450 2C9 inhibitor Non-inhibitor 0.7157 CYP450 2D6 inhibitor Non-inhibitor 0.8675 CYP450 2C19 inhibitor Non-inhibitor 0.6476 CYP450 3A4 inhibitor Non-inhibitor 0.8407 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7749 Ames test Non AMES toxic 0.7687 Carcinogenicity Non-carcinogens 0.8998 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7843 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9399 hERG inhibition (predictor II) Non-inhibitor 0.6053
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 304.252215 predictedDarkChem Lite v0.1.0 [M-H]- 271.027 predictedDeepCCS 1.0 (2019) [M+H]+ 302.620415 predictedDarkChem Lite v0.1.0 [M+H]+ 272.7507 predictedDeepCCS 1.0 (2019) [M+Na]+ 303.891015 predictedDarkChem Lite v0.1.0 [M+Na]+ 279.07968 predictedDeepCCS 1.0 (2019)
Targets
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Yes
Inhibitor
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Bearden DT, Neuhauser MM, Garey KW: Telithromycin: an oral ketolide for respiratory infections. Pharmacotherapy. 2001 Oct;21(10):1204-22. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Nguyen M, Chung EP: Telithromycin: the first ketolide antimicrobial. Clin Ther. 2005 Aug;27(8):1144-63. [Article]
- Flockhart Table of Drug Interactions [Link]
- Telithromycin FDA Label [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Kalliokoski A, Niemi M: Impact of OATP transporters on pharmacokinetics. Br J Pharmacol. 2009 Oct;158(3):693-705. doi: 10.1111/j.1476-5381.2009.00430.x. Epub 2009 Sep 25. [Article]
- Konig J: Uptake transporters of the human OATP family: molecular characteristics, substrates, their role in drug-drug interactions, and functional consequences of polymorphisms. Handb Exp Pharmacol. 2011;(201):1-28. doi: 10.1007/978-3-642-14541-4_1. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10779507, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (17-beta-glucuronosyl estradiol, dehydroepiandrosterone sulfate (DHEAS), and estrone 3-sulfate), as well as eicosanoid leukotriene C4, prostaglandin E2 and L-thyroxine (T4) (PubMed:10779507, PubMed:11159893, PubMed:12568656, PubMed:15159445, PubMed:17412826, PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463). Shows a pH-sensitive substrate specificity towards sulfated steroids, taurocholate and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Involved in the clearance of bile acids and organic anions from the liver (PubMed:22232210). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins) such as pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:15159445). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drugs methotrexate and paclitaxel (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Kalliokoski A, Niemi M: Impact of OATP transporters on pharmacokinetics. Br J Pharmacol. 2009 Oct;158(3):693-705. doi: 10.1111/j.1476-5381.2009.00430.x. Epub 2009 Sep 25. [Article]
- Konig J: Uptake transporters of the human OATP family: molecular characteristics, substrates, their role in drug-drug interactions, and functional consequences of polymorphisms. Handb Exp Pharmacol. 2011;(201):1-28. doi: 10.1007/978-3-642-14541-4_1. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 02, 2024 21:47