Pemetrexed

Highest phase reached

Approved

www.ebi.ac.uk

Drug type

Small molecule

www.ebi.ac.uk

First approval year

2004

www.ebi.ac.uk

First approval year: 2004
www.ebi.ac.uk

Listing at source: Listed

Highest phase reached: Approved
www.ebi.ac.uk

Drug type: Small molecule
www.ebi.ac.uk

Drug name: Pemetrexed
www.ebi.ac.uk

Molecular weight: 427.42
www.ebi.ac.uk

Structure (SMILES): Nc1nc2[nH]cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c2c(=O)[nH]1
www.ebi.ac.uk

alimta
Alimta
pemfexy
Pemfexy

adebrelimab pemetrexed carboplatin
ly 231514
LY-231514
ly231514
LY231514
nsc 698037
NSC-698037
pemetrexed
Pemetrexed
PEMETREXED
Pemetrexed (nonsquamous)
Pemetrexed (Pemetrexed Alvogen)
PEMETREXED [EMA EPAR]
PEMETREXED [HSDB]
pemetrexed [INN]
PEMETREXED [MI]
PEMETREXED [ORANGE BOOK]
PEMETREXED [VANDF]
Pemetrexed [WHO-DD]
Pemetrexed 500 mg
Pemetrexed 500 MG
pemetrexed ema epar
pemetrexed hsdb
Pemetrexed injection
pemetrexed inn

And 5 more, listed on the interactive page.

ATC classification codes

L01BA04

Sources for recorded values

www.ebi.ac.uk

CAS registry numbers

137281-23-3

ChEMBL ID: CHEMBL225072
www.ebi.ac.uk

InChIKey: WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
www.ebi.ac.uk

PubChem compound IDs

135410875

FDA ingredient codes (UNII)

04Q9AIZ7NO

68446
2590669

Applicant: AVYXA HOLDINGS
Approval date: 28 Jun 2024
Application number: NDA210661

Status: Authorised
Status date: 20 Sept 2004
Authorisation date: 20 Sept 2004
Approved indications: Malignant pleural mesothelioma Alimta in combination with cisplatin is indicated for the treatment of chemotherapy-naïve patients with unresectable malignant pleural mesothelioma. Non-small-cell lung cancer Alimta in combination with cisplatin is indicated for the first-line treatment of patients with locally advanced or metastatic non-small-cell lung cancer other than predominantly squamous cell histology. Alimta is indicated as monotherapy for the maintenance treatment of locally advanced or metastatic non-small-cell lung cancer other than predominantly squamous cell histology in patients whose disease has not progressed immediately following platinum-based chemotherapy. Alimta is indicated as monotherapy for the second line treatment of patients with locally advanced or metastatic non-small-cell lung cancer other than predominantly squamous cell histology.
Product number: EMEA/H/C/000564
Authorisation holder: Eli Lilly Nederland B.V.
Priority medicines scheme: No
Generic: No
Biosimilar: No
Generic medicines: 5
Biosimilar medicines: 0
Advanced therapy: No
Conditional approval: No
Additional monitoring: No
Accelerated assessment: No
Exceptional circumstances: No

Therapeutic areas

Carcinoma, Non-Small-Cell Lung
Mesothelioma

European medicines record

www.ema.europa.eu

Patents: 3
Designations: 0
Earliest recorded loss of exclusivity: 19 Feb 2036
First in class: No
Fast track: No
Breakthrough designation: No
Orphan designation: No
Priority review: No
Orphan exclusivity: No
Accelerated approval: No
Availability: Prescription only

Pharmacology name: pemetrexed
Type: Synthetic organic
Drug name stem: -trexed
Approval recorded by Guide to Pharmacology: Yes

Administration routes

Parenteral

Action
Inhibition
Action type
Inhibitor
Target
dihydrofolate reductase
Gene symbol
DHFR
Protein identifier
P00374
Median affinity
8.15
Affinity units
pKi
Primary target
Yes
Action
Inhibition
Action type
Inhibitor
Target
thymidylate synthetase
Gene symbol
TYMS
Protein identifier
P04818
Median affinity
6.96
Affinity units
pKi
Mechanism
Dihydrofolate reductase inhibitor
Action type
Inhibitor
Target
Dihydrofolate reductase
Protein identifier
P00374
Mechanism
GAR transformylase inhibitor
Action type
Inhibitor
Target
Trifunctional purine biosynthetic protein adenosine-3
Protein identifier
P22102
Mechanism
Thymidylate synthase inhibitor
Action type
Inhibitor
Target
Thymidylate synthase
Protein identifier
P04818

Mechanism
Dihydrofolate reductase inhibitor
Action type
Inhibitor
Target
Dihydrofolate reductase
Mechanism
GAR transformylase inhibitor
Action type
Inhibitor
Target
Trifunctional purine biosynthetic protein adenosine-3
Mechanism
Thymidylate synthase inhibitor
Action type
Inhibitor
Target
Thymidylate synthase
Mechanism
Thymidylate synthase inhibitor
Action type
Inhibitor
Target
Thymidylate synthase

Action type
Inhibitor
Gene symbol
DHFR
Protein identifier
P00374
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
TYMS
Protein identifier
P04818
Organism
Homo sapiens
Target development level
Clinical
Action type
Inhibitor
Gene symbol
GART
Protein identifier
P22102
Organism
Homo sapiens
Target development level
Clinical

Condition
Stomach Neoplasms
Highest recorded phase
3
Condition identifier
EFO:0000178
Subject identifier
D013274
Condition
Carcinoma, Squamous Cell
Highest recorded phase
2
Condition identifier
EFO:0000181
Subject identifier
D002294
Condition
Adenocarcinoma
Highest recorded phase
2
Condition identifier
EFO:0000228
Subject identifier
D000230
Condition
Carcinoma
Highest recorded phase
3
Condition identifier
EFO:0000313
Subject identifier
D002277
Condition
Lymphoma, Large B-Cell, Diffuse
Highest recorded phase
2
Condition identifier
EFO:0000403
Subject identifier
D016403
Condition
Adenocarcinoma of Lung
Highest recorded phase
3
Condition identifier
EFO:0000571
Subject identifier
D000077192
Condition
Lymphoma
Highest recorded phase
1
Condition identifier
EFO:0000574
Subject identifier
D008223
Condition
Mesothelioma
Highest recorded phase
4
Condition identifier
EFO:0000588
Subject identifier
D008654
Condition
Neoplasms
Highest recorded phase
4
Condition identifier
EFO:0000616
Subject identifier
D009369
Condition
Osteosarcoma
Highest recorded phase
2
Condition identifier
EFO:0000637
Subject identifier
D012516
Condition
Carcinoma, Renal Cell
Highest recorded phase
2
Condition identifier
EFO:0000681
Subject identifier
D002292
Condition
Sarcoma
Highest recorded phase
2
Condition identifier
EFO:0000691
Subject identifier
D012509
Condition
Small Cell Lung Carcinoma
Highest recorded phase
3
Condition identifier
EFO:0000702
Subject identifier
D055752
Condition
Carcinoma, Squamous Cell
Highest recorded phase
2
Condition identifier
EFO:0000708
Subject identifier
D002294
Condition
Mesothelioma
Highest recorded phase
4
Condition identifier
EFO:0000770
Subject identifier
D008654
Condition
Ovarian Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0001075
Subject identifier
D010051
Condition
Uterine Cervical Neoplasms
Highest recorded phase
3
Condition identifier
EFO:0001416
Subject identifier
D002583
Condition
Melanoma
Highest recorded phase
1
Condition identifier
EFO:0002617
Subject identifier
D008545
Condition
Pancreatic Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0002618
Subject identifier
D010190
Condition
Esophageal Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0002916
Subject identifier
D004938
Condition
Medulloblastoma
Highest recorded phase
2
Condition identifier
EFO:0002939
Subject identifier
D008527
Condition
Carcinoma, Large Cell
Highest recorded phase
2
Condition identifier
EFO:0003050
Subject identifier
D018287
Condition
Carcinoma, Non-Small-Cell Lung
Highest recorded phase
3
Condition identifier
EFO:0003060
Subject identifier
D002289
Condition
Urogenital Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0003863
Subject identifier
D014565
Condition
Breast Neoplasms
Highest recorded phase
2
Condition identifier
EFO:0003869
Subject identifier
D001943

And 39 more, listed on the interactive page.

Condition identifier
EFO_0000181
Highest recorded phase
2
Condition identifier
EFO_0000313
Highest recorded phase
3
Condition identifier
EFO_0000571
Highest recorded phase
3
Condition identifier
EFO_0000588
Condition identifier
EFO_0000616
Condition identifier
EFO_0000637
Highest recorded phase
2
Condition identifier
EFO_0000691
Highest recorded phase
2
Condition identifier
EFO_0000702
Highest recorded phase
3
Condition identifier
EFO_0000770
Condition identifier
EFO_0002618
Highest recorded phase
2
Condition identifier
EFO_0003060
Condition identifier
EFO_0003826
Highest recorded phase
1
Condition identifier
EFO_0004142
Highest recorded phase
2
Condition identifier
EFO_0004252
Highest recorded phase
2
Condition identifier
EFO_0005288
Highest recorded phase
1
Condition identifier
EFO_0006859
Highest recorded phase
2
Condition identifier
EFO_0006861
Highest recorded phase
2
Condition identifier
EFO_1000157
Highest recorded phase
2
Condition identifier
EFO_1000657
Highest recorded phase
2
Condition identifier
EFO_1001012
Highest recorded phase
2
Condition identifier
EFO_1001480
Highest recorded phase
2
Condition identifier
EFO_1001901
Highest recorded phase
2
Condition identifier
EFO_1001927
Highest recorded phase
1
Condition identifier
HP_0100526
Condition identifier
MONDO_0000402
Highest recorded phase
2

And 95 more, listed on the interactive page.

Event
acute kidney injury
Reports
349
Reporting signal score
209.696
Event
anaemia
Reports
675
Reporting signal score
572.178
Event
bone marrow failure
Reports
143
Reporting signal score
170.634
Event
colitis
Reports
124
Reporting signal score
112.3
Event
decreased appetite
Reports
281
Reporting signal score
125.891
Event
dehydration
Reports
252
Reporting signal score
128.141
Event
disease progression
Reports
345
Reporting signal score
332.29
Event
febrile neutropenia
Reports
316
Reporting signal score
342.618
Event
general physical health deterioration
Reports
239
Reporting signal score
206.272
Event
injection site pain
Reports
2
Reporting signal score
109.129
Event
interstitial lung disease
Reports
195
Reporting signal score
186.405
Event
leukopenia
Reports
208
Reporting signal score
175.977
Event
lung adenocarcinoma
Reports
56
Reporting signal score
132.879
Event
malignant neoplasm progression
Reports
510
Reporting signal score
844.581
Event
mucosal inflammation
Reports
165
Reporting signal score
199.323
Event
myelosuppression
Reports
103
Reporting signal score
166.231
Event
neutropenia
Reports
502
Reporting signal score
418.765
Event
neutrophil count decreased
Reports
169
Reporting signal score
164.735
Event
non-small cell lung cancer
Reports
89
Reporting signal score
270.596
Event
pancytopenia
Reports
410
Reporting signal score
606.617
Event
pleural effusion
Reports
170
Reporting signal score
122.019
Event
pneumonitis
Reports
138
Reporting signal score
168.065
Event
therapy partial responder
Reports
75
Reporting signal score
141.773
Event
thrombocytopenia
Reports
500
Reporting signal score
460.735
Event
tubulointerstitial nephritis
Reports
118
Reporting signal score
163.228

And 1 more, listed on the interactive page.

NCT00034489
clinicaltrials.gov
NCT03242616
clinicaltrials.gov
NCT03396445
clinicaltrials.gov
NCT00034606
clinicaltrials.gov
NCT00061451
clinicaltrials.gov
NCT00061464
clinicaltrials.gov
NCT00078260
clinicaltrials.gov
NCT00087711
clinicaltrials.gov
NCT00095199
clinicaltrials.gov
NCT00102804
clinicaltrials.gov
NCT00111839
clinicaltrials.gov
NCT00179699
clinicaltrials.gov
NCT00190840
clinicaltrials.gov
NCT00191191
clinicaltrials.gov
NCT00191308
clinicaltrials.gov
NCT00203931
clinicaltrials.gov
NCT00216203
clinicaltrials.gov
NCT00251524
clinicaltrials.gov
NCT00259285
clinicaltrials.gov
NCT00269152
clinicaltrials.gov
NCT00290017
clinicaltrials.gov
NCT00297089
clinicaltrials.gov
NCT00308750
clinicaltrials.gov
NCT00321308
clinicaltrials.gov
NCT00349089
clinicaltrials.gov

And 427 more, listed on the interactive page.

Dose: 500 mg/m2
Route: Intravenous
How often: Once every 3 weeks

Administered over 10 minutes
Dilute with 5% Dextrose in Water, USP or Normal Saline to 100 mL

Hydrogen bond acceptors: 6
Hydrogen bond donors: 6
Polar surface area: 191.26
Calculated partition coefficient (ALogP): 0.67
Calculated partition coefficient (XLogP): 0.2
Prodrug: No
Chirality: Single enantiomer
Inorganic: No
Rule-of-five violations: 1
Rotatable bonds: 9
Heavy atoms: 31
Molecular formula: C20H21N5O6
Monoisotopic mass: 427.14918341
Natural product: Yes

83831-111
83831-112
83831-131
83831-132

Recorded assays: 823
Active assays: 273

Confirmatory
Other

Antineoplastic Agents
id.nlm.nih.gov
Enzyme Inhibitors
id.nlm.nih.gov
Folic Acid Antagonists
id.nlm.nih.gov
Nucleic Acid Synthesis Inhibitors
id.nlm.nih.gov

Distribution coefficient (LogD)

Median: -1.93
Mean: -1.93
Minimum: -1.93
Maximum: -1.93
Unit: unitless
Assays: 1
Standard deviation: 0
Summary method: median
Censored results excluded: 0
Other units excluded: 0
Unknown units excluded: 0

Measurement types

LogD

Related records

Trials (974)

(Concerto) Study of BLU-451 in Advanced Cancers With EGFR Exon 20 Insertion Mutations
(HARMONY) Study of BLU-701 in EGFR-mutant NSCLC
A Clinical and Molecular Risk-Directed Therapy for Newly Diagnosed Medulloblastoma
A Clinical Study of Bemcentinib With Standard of Care Chemoimmunotherapy in Untreated Advanced/Metastatic Non-small Cell Lung Cancer Patients With a Mutation in the STK11 Gene
A Clinical Study of Calderasib (MK-1084) and Other Treatments for Participants With Non-Small Cell Lung Cancer (MK-1084-007/KANDLELIT-007)
A Clinical Study on the Safety and Efficacy of Debio 0932 in Combination With Standard of Care in Patients With Non-small Cell Lung Cancer [NSCLC]
A Clinical Study to Evaluate the Safety and Tolerability of AWT020 in Patients With Advanced Malignancies
A Comparison of Two Doses of Pemetrexed in Patients Who Have Lung Cancer
A Drug Interaction Study to Assess the Effect of LY2603618 on the Metabolic Pathway of Desipramine
A First-in-Human Study of CAN04 in Patients With Solid Malignant Tumors
A Global Phase III Study of Rilvegostomig or Pembrolizumab Plus Chemotherapy for First-Line Treatment of Locally Advanced or Metastatic Non-Squamous NSCLC
A Global Study of Volrustomig (MEDI5752) Plus Chemotherapy Versus Pembrolizumab Plus Chemotherapy for Participants With Metastatic Non-small Cell Lung Cancer.
A Multi-cohort Study of Efbemalenograstim Alfa Injection for Preventing ANC Reduction in Solid Tumor Patients Post Immune-chemotherapy.
A Multicenter Exploratory Clinical Study of Iruplaltinib Combined With Pemetrexed as Neoadjuvant Therapy for Resectable ALK-Positive Non-Squamous Non-Small Cell Lung Cancer
A Neoadjuvant Study of Nivolumab Plus Ipilimumab or Nivolumab Plus Chemotherapy Versus Chemotherapy Alone in Early Stage Non-Small Cell Lung Cancer (NSCLC)
A Personal Cancer Vaccine (NEO-PV-01) With Pembrolizumab and Chemotherapy for Patients With Lung Cancer
A Phase 1 Study in Patients With Solid Tumors
A Phase 1/2 Study Evaluating ABT-751 in Combination With Alimta in Advanced Non-Small Cell Lung Cancer
A Phase 1/2 Study of BA3071 in Patients With Solid Tumors
A Phase 1/2 Study of VS-7375 in Patients With KRAS G12D-Mutated Solid Tumors

Approved for (5)

Cancer
Malignant peritoneal mesothelioma
Malignant pleural mesothelioma
Mesothelioma
Neoplasm

In development for (57)

Adenocarcinoma Phase 2
Biliary tract cancer Phase 2
Breast cancer Phase 2
Breast neoplasm Phase 2
Carcinoma Phase 3
Carcinoma of esophagus Phase 2
Cervical adenocarcinoma Phase 3
Cervical cancer Phase 3
Chordoma Phase 1
Colorectal cancer Phase 2
Colorectal neoplasm Phase 2
Diffuse large B-cell lymphoma Phase 2
Endometrial cancer Phase 1
Esophageal cancer Phase 2
Exocrine pancreatic carcinoma Phase 2
Fallopian tube cancer Phase 2
Fallopian tube carcinoma Phase 2
Gastric cancer Phase 3
Gastric carcinoma Phase 3
Gastric neoplasm Phase 3

Targets (3)

DHFR Dihydrofolate reductase inhibitor
GART GAR transformylase inhibitor
TYMS Thymidylate synthase inhibitor

Pemetrexed

Development status

Names and chemistry

Brand names (4)

Other names (30)

Identifiers

RxNorm IDs (RxCUI) (2)

Regulatory information

United States

European Union

Therapeutic areas

Other regulatory facts

Pharmacology

Drug classification

Administration routes

Mechanisms of action (5)

Open Targets mechanisms (4)

DrugCentral mechanisms (3)

Investigated indications (64)

Open Targets indications (120)

Reported adverse events (26)

Trial references (452)

Dosing

Conditions of use (2)

Chemical properties

National Drug Codes

Evidence counts

Active assay types (2)

Pharmacologic actions

Biological measurements

Observed measurements

Distribution coefficient (LogD)

Measurement types

Related records

Trials (974)

Approved for (5)

In development for (57)

Targets (3)