Identification
- Summary
Eltrombopag is a thrombopoietin receptor agonist used to treat thrombocytopenia or aplastic anemia associated with various etiologies.
- Brand Names
- Promacta
- Generic Name
- Eltrombopag
- DrugBank Accession Number
- DB06210
- Background
Eltrombopag is used to treat low blood platelet counts in adults with chronic immune (idiopathic) thrombocytopenia (ITP), when certain other medicines, or surgery to remove the spleen, have not worked well enough. ITP is a condition that may cause unusual bruising or bleeding due to an abnormally low number of platelets in the blood. Eltrombopag has also been recently approved (late 2012) for the treatment of thrombocytopenia (low blood platelet counts) in patients with chronic hepatitis C to allow them to initiate and maintain interferon-based therapy.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Eltrombopag (DB06210)
- Weight
- Average: 442.4666
Monoisotopic: 442.164105212 - Chemical Formula
- C25H22N4O4
- Synonyms
- Eltrombopag
- Eltrombopagum
- External IDs
- SB 497115
- SB-497115
- SB497115
Pharmacology
- Indication
Thrombopoietin receptor agonists are pharmaceutical agents that stimulate platelet production in the bone marrow. In this, they differ from the previously discussed agents that act by attempting to curtail platelet destruction.
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- Associated Therapies
- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Eltrombopag is an orally bioavailable, small-molecule TPO-receptor agonist that interacts with the transmembrane domain of the human TPO-receptor. Eltrombopag is a stimulator of STAT and JAK phosphorylation. Unlike recombinant TPO or romiplostim, Eltrombopag does not activate the AKT pathway in any way. It should be noted that when given to patients with aplastic anemia, other lineages besides platelet count were increased, suggesting that either eltrombopag enhanced the effect of TPO in vivo; or there is a yet uncovered mechanism of action at work.
Target Actions Organism UThrombopoietin receptor agonistHumans - Absorption
Peak absorption of Eltrombopag occurs around 2-6 hours following oral administration, and the total oral absorption of drug-related material following a 75 mg dose was estimated to be at least 52%.
- Volume of distribution
Based on a radiolabel study, the concentration of eltrombopag in blood cells is approximately 50% to 79% of plasma concentrations.
- Protein binding
Eltrombopag is highly protein bound (>99%).
- Metabolism
Eltrombopag is predominantly through pathways including cleavage, oxidation, and conjugation with glucuronic acid, glutathione, or cysteine. In vitro studies suggest that CYP1A2 and CYP2C8 are responsible for the oxidative metabolism of eltrombopag. UGT1A1 and UGT1A3 are responsible for the glucuronidation of eltrombopag.
- Route of elimination
Eltrombopag is eliminated primarily via the feces (59%), along with 31% being renally excreted.
- Half-life
About 21-32 hours in healthy patients. About 26-35 hours in patients with idiopathic thrombocytopenic purpura.
- Clearance
Not Available
- Adverse Effects
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Eltrombopag may cause hepatotoxicity, especially if administered in combination with interferon and ribavirin in patients with chronic hepatitis C (may increase the risk of hepatic decompensation).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Coagulation factor V Factor V Leiden (A;A) / (A;G) A allele ADR Directly Studied Patients who carry this polymorphism in F5 are associated with an increased risk of thromboembolism when treated with eltrombopag. Details Antithrombin-III --- (T;T) C > T ADR Directly Studied Patients who carry this polymorphism in SERPINC1 are associated with antithrombin III deficiency and an increased risk of thromboembolism when treated with eltrombopag. 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 softwareAbacavir The metabolism of Abacavir can be decreased when combined with Eltrombopag. Abametapir The serum concentration of Eltrombopag can be increased when it is combined with Abametapir. Abatacept The metabolism of Eltrombopag can be increased when combined with Abatacept. Abemaciclib Eltrombopag may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Abiraterone The serum concentration of Eltrombopag can be increased when it is combined with Abiraterone. Acemetacin The metabolism of Acemetacin can be decreased when combined with Eltrombopag. Acenocoumarol The metabolism of Eltrombopag can be decreased when combined with Acenocoumarol. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Eltrombopag. Acetylsalicylic acid The metabolism of Acetylsalicylic acid can be decreased when combined with Eltrombopag. Acyclovir The metabolism of Eltrombopag can be decreased when combined with Acyclovir. 
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- Avoid multivalent ions. Polyvalent cations in food or supplements will be chelated by eltrombopag; therefore, they should be separated by 4 hours before or 2 hours after taking eltrombopag.
- Take on an empty stomach. Separate the administration of eltrombopag from food by at least 1 hour before and 2 hours after eating.
Products
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Ingredient UNII CAS InChI Key Eltrombopag olamine 4U07F515LG 496775-62-3 PLILLUUXAVKBPY-SBIAVEDLSA-N - Product Images
- International/Other Brands
- Promacta / Revolade
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Promacta Tablet, film coated 100 mg/1 Oral GlaxoSmithKline LLC 2012-11-16 2012-11-16 US 
Promacta Tablet, film coated 75 mg/1 Oral Glaxosmithkline Inc 2009-01-05 2019-03-31 US 
Promacta Powder, for suspension 12.5 mg/1 Oral Novartis Pharmaceuticals Corporation 2018-09-27 Not applicable US Promacta Powder, for suspension 25 mg/1 Oral Novartis Pharmaceuticals Corporation 2018-09-27 Not applicable US Promacta Tablet, film coated 12.5 mg/1 Oral Glaxosmithkline Inc 2012-01-02 2019-04-30 US Promacta Tablet, film coated 25 mg/1 Oral Novartis Pharmaceuticals Corporation 2016-05-24 Not applicable US Promacta Powder, for suspension 25 mg/1 Oral Glaxosmithkline Inc 2016-11-27 2016-11-28 US Promacta Tablet, film coated 50 mg/1 Oral Glaxosmithkline Inc 2008-11-24 2019-04-30 US 
Promacta Tablet, film coated 75 mg/1 Oral Novartis Pharmaceuticals Corporation 2016-04-01 Not applicable US Promacta Tablet, film coated 12.5 mg/1 Oral Novartis Pharmaceuticals Corporation 2016-08-22 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-eltrombopag Tablet 50 mg Oral Apotex Corporation 2023-05-23 Not applicable Canada 
Apo-eltrombopag Tablet 25 mg Oral Apotex Corporation 2023-05-23 Not applicable Canada
Categories
- ATC Codes
- B02BX05 — Eltrombopag
- Drug Categories
- Acids, Carbocyclic
- BCRP/ABCG2 Inhibitors
- Benzene Derivatives
- Blood and Blood Forming Organs
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (moderate)
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Hematinics
- Hemostatics
- Increased Megakaryocyte Maturation
- Increased Platelet Production
- OATP1B1/SLCO1B1 Inhibitors
- Organic Anion Transporting Polypeptide 1B1 Inhibitors
- Thrombopoietin Receptor Agonist
- Thrombopoietin Receptor Agonists
- UGT1A1 Inhibitors
- UGT1A1 Substrates
- UGT1A3 Inhibitors
- UGT1A3 substrates
- UGT1A4 Inhibitors
- UGT1A6 Inhibitors
- UGT1A9 Inhibitors
- UGT2B15 Inhibitors
- UGT2B7 Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Biphenyls and derivatives
- Direct Parent
- Biphenyls and derivatives
- Alternative Parents
- Benzoic acids / o-Xylenes / Phenylhydrazines / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / Pyrazolones / Monocarboxylic acids and derivatives / Hydrazones / Carboxylic acids / Azacyclic compounds show 4 more
- Substituents
- 1-hydroxy-4-unsubstituted benzenoid / Aromatic heteromonocyclic compound / Azacycle / Benzoic acid / Benzoic acid or derivatives / Benzoyl / Biphenyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrazoles, hydrazines, benzoic acids (CHEBI:85010)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- S56D65XJ9G
- CAS number
- 496775-61-2
- InChI Key
- XDXWLKQMMKQXPV-QYQHSDTDSA-N
- InChI
- InChI=1S/C25H22N4O4/c1-14-10-11-19(12-15(14)2)29-24(31)22(16(3)28-29)27-26-21-9-5-8-20(23(21)30)17-6-4-7-18(13-17)25(32)33/h4-13,26,30H,1-3H3,(H,32,33)/b27-22-
- IUPAC Name
- 3'-{2-[(4Z)-1-(3,4-dimethylphenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-ylidene]hydrazin-1-yl}-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
- SMILES
- CC1=NN(C(=O)\C1=N/NC1=CC=CC(C2=CC=CC(=C2)C(O)=O)=C1O)C1=CC=C(C)C(C)=C1
References
- Synthesis Reference
http://doc.sciencenet.cn/upload/file/2011531154034454.pdf
- General References
- Zekry A, Freiman J: Eltrombopag: Is this "24 karat gold platelet" treatment for thrombocytopenia in cirrhosis associated with hepatitis C? Hepatology. 2008 Apr;47(4):1418-21. doi: 10.1002/hep.22300. [Article]
- Mondelli MU: Eltrombopag: an effective remedy for thrombocytopaenia? J Hepatol. 2008 Jun;48(6):1030-2. doi: 10.1016/j.jhep.2008.03.008. Epub 2008 Mar 31. [Article]
- Tarantino MD, Fogarty P, Mayer B, Vasey SY, Brainsky A: Efficacy of eltrombopag in management of bleeding symptoms associated with chronic immune thrombocytopenia. Blood Coagul Fibrinolysis. 2013 Apr;24(3):284-96. doi: 10.1097/MBC.0b013e32835fac99. [Article]
- Kiang TK, Ensom MH, Chang TK: UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther. 2005 Apr;106(1):97-132. Epub 2005 Jan 12. [Article]
- Deng Y, Madatian A, Wire MB, Bowen C, Park JW, Williams D, Peng B, Schubert E, Gorycki F, Levy M, Gorycki PD: Metabolism and disposition of eltrombopag, an oral, nonpeptide thrombopoietin receptor agonist, in healthy human subjects. Drug Metab Dispos. 2011 Sep;39(9):1734-46. doi: 10.1124/dmd.111.040170. Epub 2011 Jun 6. [Article]
- Kuter DJ: The biology of thrombopoietin and thrombopoietin receptor agonists. Int J Hematol. 2013 Jul;98(1):10-23. doi: 10.1007/s12185-013-1382-0. Epub 2013 Jul 3. [Article]
- Eltrombopag [File]
- External Links
- KEGG Drug
- D03978
- PubChem Compound
- 9846180
- PubChem Substance
- 175427059
- ChemSpider
- 19879943
- 711942
- ChEBI
- 85010
- ChEMBL
- CHEMBL461101
- ZINC
- ZINC000011679756
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Eltrombopag
- FDA label
- Download (197 KB)
- MSDS
- Download (33.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Diagnostic Immune Thrombocytopenia (ITP) 1 4 Completed Treatment Aplastic Anemia 1 4 Completed Treatment Eltrombopag 1 4 Completed Treatment Purpura, Thrombocytopaenic, Idiopathic 1 4 Completed Treatment Thrombocytopenia 1 4 Recruiting Treatment Immune Thrombocytopenia Purpura 1 4 Recruiting Treatment Previously Treated Primary Immune Thrombocytopenia 1 4 Unknown Status Treatment Immune Thrombocytopenia (ITP) 1 4 Unknown Status Treatment Neoplasms, Hematologic 1 4 Unknown Status Treatment Primary Immune Thrombocytopenia (ITP) 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder, for suspension Oral 12.5 mg/1 Powder, for suspension Oral 25 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 12.5 mg/1 Tablet, film coated Oral 25 mg/1 Tablet, film coated Oral 50 mg/1 Tablet, film coated Oral 75 mg/1 Tablet, film coated Oral Tablet, film coated Oral 31.9 MG Tablet, film coated Oral 63.8 MG Powder, for suspension Oral 25 MG Tablet Oral 12.5 mg Tablet Oral 25 mg Tablet Oral 50 mg Tablet Oral 75 mg Tablet, film coated Oral 25 MG Tablet, film coated Oral 50 MG Tablet, film coated Oral 75 MG Tablet, film coated Oral 12.5 mg Tablet, coated Oral 25 mg Tablet, coated Oral 50 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8052995 Yes 2011-11-08 2028-02-01 US US6280959 Yes 2001-08-28 2019-04-30 US US7790704 Yes 2010-09-07 2021-11-24 US US7452874 Yes 2008-11-18 2021-11-24 US US7473686 Yes 2009-01-06 2021-11-24 US US7160870 Yes 2007-01-09 2023-05-20 US US7795293 Yes 2010-09-14 2023-11-21 US US7547719 Yes 2009-06-16 2026-01-13 US US7332481 Yes 2008-02-19 2021-11-24 US US8062665 Yes 2011-11-22 2028-02-01 US US8052994 Yes 2011-11-08 2028-02-01 US US8071129 Yes 2011-12-06 2028-02-01 US US8052993 Yes 2011-11-08 2028-02-01 US US8828430 Yes 2014-09-09 2028-02-01 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Eltrombopag olamine is practically insoluble in aqueous buffer across a pH range of 1 to 7.4, and is sparingly soluble in water. FDA Label - Predicted Properties
Property Value Source Water Solubility 0.0103 mg/mL ALOGPS logP 4.02 ALOGPS logP 6.03 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 3.97 Chemaxon pKa (Strongest Basic) -0.12 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 114.59 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 126.48 m3·mol-1 Chemaxon Polarizability 47.7 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6946 Blood Brain Barrier - 0.6616 Caco-2 permeable - 0.5811 P-glycoprotein substrate Non-substrate 0.6578 P-glycoprotein inhibitor I Non-inhibitor 0.8297 P-glycoprotein inhibitor II Non-inhibitor 0.9187 Renal organic cation transporter Non-inhibitor 0.944 CYP450 2C9 substrate Non-substrate 0.5991 CYP450 2D6 substrate Non-substrate 0.8495 CYP450 3A4 substrate Substrate 0.5424 CYP450 1A2 substrate Non-inhibitor 0.8173 CYP450 2C9 inhibitor Inhibitor 0.6357 CYP450 2D6 inhibitor Non-inhibitor 0.8982 CYP450 2C19 inhibitor Non-inhibitor 0.7625 CYP450 3A4 inhibitor Non-inhibitor 0.7595 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6304 Ames test Non AMES toxic 0.5993 Carcinogenicity Non-carcinogens 0.5481 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.1796 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9862 hERG inhibition (predictor II) Non-inhibitor 0.6936
Spectra
- Mass Spec (NIST)
- Download (91.2 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Transmembrane signaling receptor activity
- Specific Function
- Receptor for thrombopoietin. May represent a regulatory molecule specific for TPO-R-dependent immune responses.
- Gene Name
- MPL
- Uniprot ID
- P40238
- Uniprot Name
- Thrombopoietin receptor
- Molecular Weight
- 71244.08 Da
References
- Kuter DJ: Thrombopoietin and thrombopoietin mimetics in the treatment of thrombocytopenia. Annu Rev Med. 2009;60:193-206. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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 un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- 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
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Kuter DJ: The biology of thrombopoietin and thrombopoietin receptor agonists. Int J Hematol. 2013 Jul;98(1):10-23. doi: 10.1007/s12185-013-1382-0. Epub 2013 Jul 3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
Drug created at March 19, 2008 16:17 / Updated at September 28, 2023 01:14