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Trametinib
Identification
- Name
- Trametinib
- Accession Number
- DB08911
- Description
Trametinib dimethyl sulfoxide is a kinase inhibitor. Each 1-mg tablet contains 1.127 mg trametinib dimethyl sulfoxide equivalent to 1 mg of trametinib non-solvated parent. FDA approved on May 29, 2013 4.
The U.S. Food and Drug Administration approved Dabrafenib(Tafilnar) and Mekinist (trametinib), administered together, for the treatment of anaplastic thyroid cancer (ATC) that cannot be removed by surgery or has spread to other parts of the body (metastatic), and has a type of abnormal gene, BRAF V600E (BRAF V600E mutation-positive) 3.
Thyroid cancer is a disease in which cancer cells form in the tissues of the thyroid. Anaplastic thyroid cancer is a rare, aggressive type of thyroid cancer. The National Institutes of Health (NIH) estimates there will be 53,990 new cases of thyroid cancer and an estimated 2,060 deaths from the disease in the United States in 2018. Anaplastic thyroid cancer accounts for approximately 1 to 2 percent of all thyroid cancers 3.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Trametinib (DB08911)
- Weight
- Average: 615.3948
Monoisotopic: 615.077875874 - Chemical Formula
- C26H23FIN5O4
- Synonyms
- Tramétinib
- Trametinib
- Trametinibum
- External IDs
- GSK 1120212
- GSK-1120212
- GSK1120212
- JTP 74057
- JTP-74057
Pharmacology
- Indication
Trametinib is indicated for the treatment of unresectable or metastatic melanoma with BRAF V600E or V600K mutations, as detected by an FDA-approved test [FDA].
In May 2018, it was approved for use with Dabrafenib for the treatment of treat anaplastic thyroid cancer caused by an abnormal BRAF V600E gene 3.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Trametinib is an anticancer agent which causes apoptosis (or programmed cell death) and inhibits cell proliferation, which are both important in the treatment of malignancies 2.
- Mechanism of action
Trametinib is a reversible, allosteric inhibitor of mitogen-activated extracellular signal regulated kinase 1 (MEK1) and MEK2 activation and of_ MEK1_ and MEK2 kinase activity. MEK proteins are upstream regulators of the extracellular signal-related kinase (ERK) pathway, which promotes cellular proliferation. Trametinib helps with melanoma with the BRAF V600E or V600K as the mutation results in the constitutive activation of the BRAF pathway which includes MEK1 and MEK2 Label.
Target Actions Organism ADual specificity mitogen-activated protein kinase kinase 1 antagonistinhibitorHumans ADual specificity mitogen-activated protein kinase kinase 2 antagonistinhibitorHumans - Absorption
Trametinib is readily absorbed. When an oral administration of trametinib was given to patients with BRAF V600 mutation-positive melanoma, peak plasma concentration occurred 1.5 hours post-dose (Tmax). A single 2 mg oral dose has a bioavailability of 72%. When a dose of 2mg/day is given, the peak plasma concentration (Cmax) is 22.2 ng/mL Label.
- Volume of distribution
Apparent volume of distribution (Vd/F) = 214 L Label
- Protein binding
97.4% bound to human plasma proteins Label
- Metabolism
Trametinib is metabolized predominantly via deacetylation alone or with mono-oxygenation or in combination with glucuronidation biotransformation pathways in vitro. Deacetylation is likely mediated by hydrolytic enzymes, such as carboxyl-esterases or amidases. The cytochrome P450 enzyme system is not involved with the metabolism of trametinib. The predominant circulating component in the plasma is the parent drug Label.
- Route of elimination
80% of the dose is excreted in the feces. <20% of the dose is excreted in the urine with <0.1% of the excreted dose in the form of the parent compound Label.
- Half-life
Elimination half-life = 3.9-4.8 days Label.
- Clearance
Apparent clearance = 4.9 L/h Label
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Most common adverse reactions (≥20%) for trametinib include rash, diarrhea, and lymphedema Label.
The most common adverse reactions (≥20%) for Tafinlar in combination with Trametinib are pyrexia, chills, fatigue, rash, nausea, vomiting, diarrhea, abdominal pain, peripheral edema, cough, headache, arthralgia, night sweats, decreased appetite, constipation, and myalgia Label.
The following is a list of toxicities that may occur with the combination of Dabrafenib and Trametinib:
New primary malignancies: These may occur when Tafinlar is administered as a single agent or in combination with Trametinib. Monitor patients for new malignancies prior to initiation of therapy, while on therapy, and following discontinuation of TAFINLAR or the combination therapy. Tumor Promotion in BRAF Wild-Type Melanoma: Increased cell proliferation can occur with BRAF inhibitors Label.
Hemorrhage: Major hemorrhagic events can occur in patients receiving TAFINLAR in combination with trametinib. Monitor for signs and symptoms of bleeding Label.
Venous Thromboembolism: Deep vein thrombosis and pulmonary embolism can occur in patients receiving the drug combination Label.
Cardiomyopathy: Assess LVEF before treatment with TAFINLAR in combination with trametinib, after one month of treatment, then every 2 to 3 months thereafter Label.
Ocular toxicities: Perform an ophthalmologic evaluation for any visual disturbances Label.
Serious Febrile Reactions: Incidence and severity of pyrexia are increased with TAFINLAR in combination with trametinib Label.
Serious Skin Toxicity: Monitor for skin toxicities and for secondary infections. Discontinue for intolerable Grade 2, or Grade 3 or 4 rash not improving within 3 weeks despite the interruption of TAFINLAR Label.
Hyperglycemia: Monitor serum glucose levels in patients with pre-existing diabetes or hyperglycemia Label.
Glucose-6-Phosphate Dehydrogenase Deficiency: Closely monitor for hemolytic anemia Label.
Embryofetal Toxicity: Can cause fetal harm. Advise females of reproductive potential of potential risk to a fetus. TAFINLAR may render hormonal contraceptives less effective and an alternative method of contraception should be used Label.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- 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.
Drug Interaction Unlock Additional DataAbacavir Abacavir may decrease the excretion rate of Trametinib which could result in a higher serum level. Abiraterone The metabolism of Abiraterone can be increased when combined with Trametinib. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Trametinib. Acarbose Acarbose may decrease the excretion rate of Trametinib which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Trametinib which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Trametinib which could result in a higher serum level. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Trametinib. Acetaminophen Acetaminophen may decrease the excretion rate of Trametinib which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Trametinib which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Trametinib which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take separate from meals. Take at least one hour before or two hours after a meal.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Trametinib dimethyl sulfoxide BSB9VJ5TUT 1187431-43-1 OQUFJVRYDFIQBW-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataMekinist Tablet, film coated 2 mg Oral Novartis Europharm Limited 2014-06-30 Not applicable EU 
Mekinist Tablet 1 mg Oral Novartis Not applicable Not applicable Canada 
Mekinist Tablet, film coated 0.5 mg Oral Novartis Europharm Limited 2014-06-30 Not applicable EU Mekinist Tablet, film coated 2 mg/1 Oral Novartis Pharmaceuticals Corporation 2016-03-17 Not applicable US 
Mekinist Tablet, film coated 0.5 mg Oral Novartis Europharm Limited 2014-06-30 Not applicable EU Mekinist Tablet, film coated 2 mg/1 Oral GlaxoSmithKline Manufacturing SpA 2013-06-17 Not applicable US Mekinist Tablet, film coated 2 mg/1 Oral Glaxosmithkline Inc 2013-06-17 2016-12-31 US Mekinist Tablet, film coated 2 mg Oral Novartis Europharm Limited 2014-06-30 Not applicable EU Mekinist Tablet, film coated 2 mg Oral Novartis Europharm Limited 2014-06-30 Not applicable EU Mekinist Tablet 2 mg Oral Novartis 2013-08-28 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- L01XE25 — Trametinib
- Drug Categories
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strong)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Kinase Inhibitor
- MAP Kinase Kinase 1, antagonists & inhibitors
- MAP Kinase Kinase 2, antagonists & inhibitors
- Narrow Therapeutic Index Drugs
- Protein Kinase Inhibitors
- Pyridines
- Pyrimidines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyridopyrimidines. These are compounds containing a pyridopyrimidine, which consists of a pyridine fused to a pyrimidine. Pyridine is 6-membered ring consisting of five carbon atoms and a nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridopyrimidines
- Sub Class
- Not Available
- Direct Parent
- Pyridopyrimidines
- Alternative Parents
- Acetanilides / N-acetylarylamines / Aniline and substituted anilines / Aminopyridines and derivatives / Pyrimidones / Pyridinones / Fluorobenzenes / Methylpyridines / Iodobenzenes / Aryl fluorides show 16 more
- Substituents
- Acetamide / Acetanilide / Amine / Amino acid or derivatives / Aminopyridine / Anilide / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide show 34 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organofluorine compound, organoiodine compound, acetamides, aromatic amine, cyclopropanes, ring assembly, pyridopyrimidine (CHEBI:75998)
Chemical Identifiers
- UNII
- 33E86K87QN
- CAS number
- 871700-17-3
- InChI Key
- LIRYPHYGHXZJBZ-UHFFFAOYSA-N
- InChI
- InChI=1S/C26H23FIN5O4/c1-13-22-21(23(31(3)24(13)35)30-20-10-7-15(28)11-19(20)27)25(36)33(17-8-9-17)26(37)32(22)18-6-4-5-16(12-18)29-14(2)34/h4-7,10-12,17,30H,8-9H2,1-3H3,(H,29,34)
- IUPAC Name
- N-(3-{3-cyclopropyl-5-[(2-fluoro-4-iodophenyl)amino]-6,8-dimethyl-2,4,7-trioxo-1H,2H,3H,4H,6H,7H-pyrido[4,3-d]pyrimidin-1-yl}phenyl)acetamide
- SMILES
- CN1C(=O)C(C)=C2N(C(=O)N(C3CC3)C(=O)C2=C1NC1=CC=C(I)C=C1F)C1=CC(NC(C)=O)=CC=C1
References
- General References
- Salama AK, Kim KB: Trametinib (GSK1120212) in the treatment of melanoma. Expert Opin Pharmacother. 2013 Apr;14(5):619-27. doi: 10.1517/14656566.2013.770475. Epub 2013 Feb 23. [PubMed:23432625]
- Infante JR, Fecher LA, Falchook GS, Nallapareddy S, Gordon MS, Becerra C, DeMarini DJ, Cox DS, Xu Y, Morris SR, Peddareddigari VG, Le NT, Hart L, Bendell JC, Eckhardt G, Kurzrock R, Flaherty K, Burris HA 3rd, Messersmith WA: Safety, pharmacokinetic, pharmacodynamic, and efficacy data for the oral MEK inhibitor trametinib: a phase 1 dose-escalation trial. Lancet Oncol. 2012 Aug;13(8):773-81. doi: 10.1016/S1470-2045(12)70270-X. Epub 2012 Jul 16. [PubMed:22805291]
- FDA approves new uses for two drugs administered together for the treatment of BRAF-positive anaplastic thyroid cancer [Link]
- [email protected]: FDA Approved Drug Products [Link]
- External Links
- KEGG Drug
- D10175
- PubChem Compound
- 11707110
- PubChem Substance
- 175427149
- ChemSpider
- 9881833
- 1425099
- ChEBI
- 75998
- ChEMBL
- CHEMBL2103875
- ZINC
- ZINC000043100709
- PharmGKB
- PA166115364
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Trametinib
- AHFS Codes
- 10:00.00 — Antineoplastic Agents
- FDA label
- Download (517 KB)
- MSDS
- Download (120 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 0.5 mg Tablet Oral 1 mg Tablet Oral 2 mg Tablet, film coated Oral .5 mg/1 Tablet, film coated Oral 0.5 mg/1 Tablet, film coated Oral 0.5 mg Tablet, film coated Oral 1 MG Tablet, film coated Oral 1 mg/1 Tablet, film coated Oral 2 mg Tablet, film coated Oral 2 mg/1 Tablet, coated 0.5 mg Tablet, coated 2 mg Tablet, coated Oral 0.5 mg Tablet, coated Oral 2 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS8703781 No 2014-04-22 2030-10-15 US US8835443 No 2014-09-16 2025-09-13 US US9271941 No 2016-03-01 2032-01-28 US US9155706 No 2015-10-13 2032-01-28 US US7378423 No 2008-05-27 2025-09-13 US US8580304 No 2013-11-12 2032-01-28 US US8952018 No 2015-02-10 2030-10-15 US US9399021 No 2016-07-26 2032-01-28 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 293-303 MSDS - Predicted Properties
Property Value Source Water Solubility 0.0307 mg/mL ALOGPS logP 3.45 ALOGPS logP 3.18 ChemAxon logS -4.3 ALOGPS pKa (Strongest Acidic) 12.6 ChemAxon pKa (Strongest Basic) -3.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 102.06 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 156.38 m3·mol-1 ChemAxon Polarizability 55.43 Å3 ChemAxon Number of Rings 5 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 + 0.9733 Blood Brain Barrier + 0.8217 Caco-2 permeable - 0.5193 P-glycoprotein substrate Non-substrate 0.5945 P-glycoprotein inhibitor I Non-inhibitor 0.6449 P-glycoprotein inhibitor II Non-inhibitor 0.8622 Renal organic cation transporter Non-inhibitor 0.899 CYP450 2C9 substrate Non-substrate 0.7215 CYP450 2D6 substrate Non-substrate 0.8232 CYP450 3A4 substrate Substrate 0.5735 CYP450 1A2 substrate Non-inhibitor 0.8599 CYP450 2C9 inhibitor Non-inhibitor 0.5775 CYP450 2D6 inhibitor Non-inhibitor 0.9521 CYP450 2C19 inhibitor Non-inhibitor 0.8769 CYP450 3A4 inhibitor Non-inhibitor 0.836 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9337 Ames test AMES toxic 0.5498 Carcinogenicity Non-carcinogens 0.8078 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3412 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9539 hERG inhibition (predictor II) Non-inhibitor 0.6602
Spectra
- Mass Spec (NIST)
- Not Available
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistInhibitor
- General Function
- Receptor signaling protein tyrosine phosphatase activity
- Specific Function
- Dual specificity protein kinase which acts as an essential component of the MAP kinase signal transduction pathway. Binding of extracellular ligands such as growth factors, cytokines and hormones t...
- Gene Name
- MAP2K1
- Uniprot ID
- Q02750
- Uniprot Name
- Dual specificity mitogen-activated protein kinase kinase 1
- Molecular Weight
- 43438.65 Da
References
- Salama AK, Kim KB: Trametinib (GSK1120212) in the treatment of melanoma. Expert Opin Pharmacother. 2013 Apr;14(5):619-27. doi: 10.1517/14656566.2013.770475. Epub 2013 Feb 23. [PubMed:23432625]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistInhibitor
- General Function
- Scaffold protein binding
- Specific Function
- Catalyzes the concomitant phosphorylation of a threonine and a tyrosine residue in a Thr-Glu-Tyr sequence located in MAP kinases. Activates the ERK1 and ERK2 MAP kinases (By similarity).
- Gene Name
- MAP2K2
- Uniprot ID
- P36507
- Uniprot Name
- Dual specificity mitogen-activated protein kinase kinase 2
- Molecular Weight
- 44423.735 Da
References
- Salama AK, Kim KB: Trametinib (GSK1120212) in the treatment of melanoma. Expert Opin Pharmacother. 2013 Apr;14(5):619-27. doi: 10.1517/14656566.2013.770475. Epub 2013 Feb 23. [PubMed:23432625]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
Drug created on June 24, 2013 15:36 / Updated on September 17, 2020 23:28
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