Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H21N5O6 |
Molecular Weight | 427.4106 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC2=C(C(CCC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CN2)C(=O)N1
InChI
InChIKey=WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m0/s1
Molecular Formula | C20H21N5O6 |
Molecular Weight | 427.4106 |
Charge | 0 |
Count |
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Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9762351
https://www.ncbi.nlm.nih.gov/pubmed/17308042
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9762351
https://www.ncbi.nlm.nih.gov/pubmed/17308042
Pemetrexed is a new-generation antifolate, approved for the treatment of mesothelioma and non-small cell lung cancer, currently being evaluated for the treatment of a variety of other solid tumors.
Pemetrexed, is a folate analog metabolic inhibitor that exerts its action by disrupting folate-dependent metabolic processes essential for cell replication. In vitro studies have shown that pemetrexed inhibits thymidylate synthase (TS), dihydrofolate reductase (DHFR), glycinamide ribonucleotide formyltransferase (GARFT) and and to a lesser extent aminoimidazole carboxamide ribonucleotide formyltransferase (AICARFT), which are folate-dependent enzymes involved in the de novo biosynthesis of thymidine and purine nucleotides. Pemetrexed is taken into cells by membrane carriers such as the reduced folate carrier and membrane folate binding protein transport systems. Once in the cell, pemetrexed is converted to polyglutamate forms by the enzyme folylpolyglutamate synthetase. The polyglutamate forms are retained in cells and are inhibitors of TS and GARFT. Polyglutamation is a time- and concentration-dependent process that occurs in tumor cells and, is thought to occur to a lesser extent, in normal tissues. Polyglutamated metabolites are thought to have an increased intracellular half-life resulting in prolonged drug action in malignant cells.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15987831 | https://www.ncbi.nlm.nih.gov/pubmed/23297298
Curator's Comment: Known to be CNS penetrant in rodents
https://www.ncbi.nlm.nih.gov/pubmed/15987831
https://www.ncbi.nlm.nih.gov/pubmed/23297298
Human data not available, but is known that pemetrexed-based treatments controls of brain metastases in the treatment of non-small-cell lung cancer https://www.ncbi.nlm.nih.gov/pubmed/21831719
Originator
Sources: http://adisinsight.springer.com/drugs/800003871
Curator's Comment: # Eli Lilly
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1952 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9762351 |
109.0 nM [Ki] | ||
Target ID: CHEMBL202 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9762351 |
7.0 nM [Ki] | ||
Target ID: CHEMBL3972 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9762351 |
9300.0 nM [Ki] | ||
Target ID: CHEMBL2518 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9762351 |
3580.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ALIMTA Approved UseALIMTA® is a folate analog metabolic inhibitor indicated for: Locally Advanced or Metastatic Nonsquamous Non-Small Cell Lung Cancer: Initial treatment in combination with cisplatin. (1.1) Maintenance treatment of patients whose disease has not progressed after four cycles of platinum-based first-line chemotherapy. (1.2) After prior chemotherapy as a single-agent. (1.3) Mesothelioma: in combination with cisplatin. (1.4) Limitations of Use: ALIMTA is not indicated for the treatment of patients with squamous cell non-small cell lung cancer. (1.5) 1.1 Nonsquamous Non-Small Cell Lung Cancer – Combination with Cisplatin ALIMTA® is indicated in combination with cisplatin therapy for the initial treatment of patients with locally advanced or metastatic nonsquamous non-small cell lung cancer. 1.2 Nonsquamous Non-Small Cell Lung Cancer – Maintenance ALIMTA is indicated for the maintenance treatment of patients with locally advanced or metastatic nonsquamous non-small cell lung cancer whose disease has not progressed after four cycles of platinum-based first-line chemotherapy. 1.3 Nonsquamous Non-Small Cell Lung Cancer – After Prior Chemotherapy ALIMTA is indicated as a single-agent for the treatment of patients with locally advanced or metastatic nonsquamous non-small cell lung cancer after prior chemotherapy. 1.4 Mesothelioma ALIMTA in combination with cisplatin is indicated for the treatment of patients with malignant pleural mesothelioma whose disease is unresectable or who are otherwise not candidates for curative surgery. 1.5 Limitations of Use ALIMTA is not indicated for the treatment of patients with squamous cell non-small cell lung cancer. [see Clinical Studies (14.1, 14.2, 14.3) Launch Date2004 |
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Primary | ALIMTA Approved UseALIMTA® is a folate analog metabolic inhibitor indicated for: Locally Advanced or Metastatic Nonsquamous Non-Small Cell Lung Cancer: Initial treatment in combination with cisplatin. (1.1) Maintenance treatment of patients whose disease has not progressed after four cycles of platinum-based first-line chemotherapy. (1.2) After prior chemotherapy as a single-agent. (1.3) Mesothelioma: in combination with cisplatin. (1.4) Limitations of Use: ALIMTA is not indicated for the treatment of patients with squamous cell non-small cell lung cancer. (1.5) 1.1 Nonsquamous Non-Small Cell Lung Cancer – Combination with Cisplatin ALIMTA® is indicated in combination with cisplatin therapy for the initial treatment of patients with locally advanced or metastatic nonsquamous non-small cell lung cancer. 1.2 Nonsquamous Non-Small Cell Lung Cancer – Maintenance ALIMTA is indicated for the maintenance treatment of patients with locally advanced or metastatic nonsquamous non-small cell lung cancer whose disease has not progressed after four cycles of platinum-based first-line chemotherapy. 1.3 Nonsquamous Non-Small Cell Lung Cancer – After Prior Chemotherapy ALIMTA is indicated as a single-agent for the treatment of patients with locally advanced or metastatic nonsquamous non-small cell lung cancer after prior chemotherapy. 1.4 Mesothelioma ALIMTA in combination with cisplatin is indicated for the treatment of patients with malignant pleural mesothelioma whose disease is unresectable or who are otherwise not candidates for curative surgery. 1.5 Limitations of Use ALIMTA is not indicated for the treatment of patients with squamous cell non-small cell lung cancer. [see Clinical Studies (14.1, 14.2, 14.3) Launch Date2004 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
137 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16391300 |
500 mg/m² other, intravenous dose: 500 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: |
PEMETREXED blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
164 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16391300 |
500 mg/m² other, intravenous dose: 500 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: |
PEMETREXED blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.71 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/16391300 |
500 mg/m² other, intravenous dose: 500 mg/m² route of administration: Intravenous experiment type: OTHER co-administered: |
PEMETREXED blood | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19% |
PEMETREXED plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg/m2 1 times / 2 weeks multiple, intravenous Highest studied dose Dose: 1200 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 1200 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 63.7 years (range: 47–77 years) n = 7 Health Status: unhealthy Condition: Recurrent or Progressive Central Nervous System Lymphoma Age Group: 63.7 years (range: 47–77 years) Sex: M+F Population Size: 7 Sources: |
DLT: Lymphopenia... Other AEs: Neutropenia, Fatigue... Dose limiting toxicities: Lymphopenia (grade 4, 2 patients) Other AEs:Neutropenia (grade 3-4) Sources: Fatigue (grade 3-4) |
900 mg/m2 1 times / 2 weeks multiple, intravenous MTD Dose: 900 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 900 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 63.7 years (range: 47–77 years) n = 4 Health Status: unhealthy Condition: Recurrent or Progressive Central Nervous System Lymphoma Age Group: 63.7 years (range: 47–77 years) Sex: M+F Population Size: 4 Sources: |
Disc. AE: Transaminases increased... AEs leading to discontinuation/dose reduction: Transaminases increased (1 patient) Sources: |
600 mg/m2 1 times / 2 weeks multiple, intravenous Dose: 600 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 600 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 63.7 years (range: 47–77 years) n = 6 Health Status: unhealthy Condition: Recurrent or Progressive Central Nervous System Lymphoma Age Group: 63.7 years (range: 47–77 years) Sex: M+F Population Size: 6 Sources: |
DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fatigue | grade 3-4 | 1200 mg/m2 1 times / 2 weeks multiple, intravenous Highest studied dose Dose: 1200 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 1200 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 63.7 years (range: 47–77 years) n = 7 Health Status: unhealthy Condition: Recurrent or Progressive Central Nervous System Lymphoma Age Group: 63.7 years (range: 47–77 years) Sex: M+F Population Size: 7 Sources: |
Neutropenia | grade 3-4 | 1200 mg/m2 1 times / 2 weeks multiple, intravenous Highest studied dose Dose: 1200 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 1200 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 63.7 years (range: 47–77 years) n = 7 Health Status: unhealthy Condition: Recurrent or Progressive Central Nervous System Lymphoma Age Group: 63.7 years (range: 47–77 years) Sex: M+F Population Size: 7 Sources: |
Lymphopenia | grade 4, 2 patients DLT |
1200 mg/m2 1 times / 2 weeks multiple, intravenous Highest studied dose Dose: 1200 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 1200 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 63.7 years (range: 47–77 years) n = 7 Health Status: unhealthy Condition: Recurrent or Progressive Central Nervous System Lymphoma Age Group: 63.7 years (range: 47–77 years) Sex: M+F Population Size: 7 Sources: |
Transaminases increased | 1 patient Disc. AE |
900 mg/m2 1 times / 2 weeks multiple, intravenous MTD Dose: 900 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 900 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 63.7 years (range: 47–77 years) n = 4 Health Status: unhealthy Condition: Recurrent or Progressive Central Nervous System Lymphoma Age Group: 63.7 years (range: 47–77 years) Sex: M+F Population Size: 4 Sources: |
Neutropenia | grade 4, 1 patient DLT, Disc. AE |
600 mg/m2 1 times / 2 weeks multiple, intravenous Dose: 600 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 600 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 63.7 years (range: 47–77 years) n = 6 Health Status: unhealthy Condition: Recurrent or Progressive Central Nervous System Lymphoma Age Group: 63.7 years (range: 47–77 years) Sex: M+F Population Size: 6 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
not significant | ||||
not significant | ||||
not significant | ||||
not significant | ||||
yes [Ki 300 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Page: 17.0 |
yes | |||
Page: 17.0 |
yes | weak (co-administration study) Comment: coadministration with ibuprofen decreased the clearance of pemetrexed and increased its expsoure (AUC) by ~ 20% Page: 17.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 73.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Pemetrexed disodium: a novel antifolate clinically active against multiple solid tumors. | 2001 |
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A new route to 7-substituted derivatives of n-[4-(2-[2-amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimidin-5-yl]ethyl)benzoyl]-L-glutamic acid [ALIMTA (LY231514, MTA)]. | 2001 Jun 1 |
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Pemetrexed (Alimta): a novel multitargeted antifolate agent. | 2003 Apr |
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Design, synthesis, and biological activities of classical N-[4-[2-(2-amino-4-ethylpyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-l-glutamic acid and its 6-methyl derivative as potential dual inhibitors of thymidylate synthase and dihydrofolate reductase and as potential antitumor agents. | 2003 Feb 13 |
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Accumulation of 5-phosphoribosyl-1-pyrophosphate in human CCRF-CEM leukaemia cells treated with antifolates. | 2004 Mar |
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Pemetrexed: a review of its use in the management of advanced non-squamous non-small cell lung cancer. | 2009 Nov 12 |
Sample Use Guides
Combination ALIMTA (pemetrexed disodium) use in Non-Small Cell Lung Cancer and Mesothelioma: Recommended dose of ALIMTA is 500 mg/m2 i.v. on Day 1 of each 21-day cycle in combination with cisplatin 75 mg/m2 i.v. beginning 30 minutes after ALIMTA administration.
Single-Agent use in Non-Small Cell Lung Cancer: Recommended dose of ALIMTA is 500 mg/m2 i.v. on Day 1 of each 21-day cycle. Dose Reductions: Dose reductions or discontinuation may be needed based on toxicities from the preceding cycle of therapy.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23179091
pemetrexed has a potent cytotoxic effect against human peripheral blood lymphocytes at concentrations 25, 50, 75 and 100 μg/mL (concentrations roughly 2,25–9 times less than the maximum plasma level (225 μg/mL) achieved in patients receiving this drug) based on the top concentration (100 μg/mL)
Substance Class |
Chemical
Created
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Record UNII |
04Q9AIZ7NO
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EMA ASSESSMENT REPORTS |
PEMETREXED LILLY (AUTHORIZED: CARCINOMA, NON-SMALL-CELL LUNG, MESOTHELIOMA)
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EMA ASSESSMENT REPORTS |
ALIMTA (AUTHORIZED: CARCINOMA, NON-SMALL-CELL LUNG, MESOTHELIOMA)
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WHO-ATC |
L01BA04
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NDF-RT |
N0000000111
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LIVERTOX |
NBK548117
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NCI_THESAURUS |
C2021
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EMA ASSESSMENT REPORTS |
PEMETREXED HOSPIRA (AUTHORIZED: CARCINOMA, NON-SMALL-CELL LUNG, MESOTHELIOMA)
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NCI_THESAURUS |
C511
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NDF-RT |
N0000175584
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WHO-VATC |
QL01BA04
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EMA ASSESSMENT REPORTS |
PEMETREXED MEDAC (AUTHORIZED: CARCINOMA, NON-SMALL-CELL LUNG, MESOTHELIOMA)
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Pemetrexed
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CHEMBL1201258
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
URINE
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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TARGET -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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SOLVATE->ANHYDROUS | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Vdss | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Elimination: CrCl 40-59 mL/minute PHARMACOKINETIC PHARMACOKINETIC |
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