pemetrexed Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antineoplastics; thymidylate synthetase inhibitors 2073 137281-23-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • LY231514
  • pemetrexed diacid monohydrate
  • pemetrexed sodium
  • pemetrexed sodium hydrate
  • pemetrexed
  • pemetrexed disodium
  • alimta
  • pemetrexed disodium heptahydrate
Pemetrexed is a folate analog metabolic inhibitor that disrupts folate-dependent metabolic processes essential for cell replication. In vitro studies show that pemetrexed inhibits thymidylate synthase (TS), dihydrofolate reductase, and glycinamide ribonucleotide formyltransferase (GARFT), 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.
  • Molecular weight: 427.42
  • Formula: C20H21N5O6
  • CLOGP: -1.17
  • LIPINSKI: 2
  • HAC: 11
  • HDO: 6
  • TPSA: 186.97
  • ALOGS: -3.97
  • ROTB: 9

  • Status: ONP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 90 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 80 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.38 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.15 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.19 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.85 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 20, 2004 EMA ELI LILLY NEDERLAND B.V.
Feb. 4, 2004 FDA LILLY

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Malignant neoplasm progression 781.84 17.94 390 14979 71151 53262546
Disease progression 276.18 17.94 231 15138 101689 53232008
Pancytopenia 197.79 17.94 182 15187 90746 53242951
Anaemia 170.92 17.94 294 15075 276424 53057273
Neutropenia 156.27 17.94 210 15159 158975 53174722
Drug resistance 149.89 17.94 85 15284 19877 53313820
Thrombocytopenia 131.50 17.94 180 15189 138547 53195150
Metastases to central nervous system 123.16 17.94 63 15306 11994 53321703
Bone marrow failure 122.44 17.94 87 15282 30028 53303669
Neoplasm progression 116.06 17.94 84 15285 29835 53303862
Non-small cell lung cancer 115.31 17.94 42 15327 3491 53330206
Febrile neutropenia 103.68 17.94 139 15230 104797 53228900
Lung adenocarcinoma 94.12 17.94 39 15330 4579 53329118
Acquired gene mutation 88.44 17.94 24 15345 753 53332944
Pneumonitis 85.48 17.94 71 15298 30817 53302880
Mucosal inflammation 78.38 17.94 78 15291 42706 53290991
Tubulointerstitial nephritis 74.83 17.94 51 15318 16453 53317244
Nephropathy toxic 73.91 17.94 40 15329 8532 53325165
Metastases to adrenals 70.71 17.94 20 15349 733 53332964
Dehydration 67.03 17.94 149 15220 168261 53165436
Rheumatoid arthritis 63.42 17.94 8 15361 314523 53019174
Metastases to meninges 60.89 17.94 23 15346 2116 53331581
Non-small cell lung cancer metastatic 59.97 17.94 17 15352 628 53333069
Pleural effusion 59.56 17.94 98 15271 88481 53245216
Therapy partial responder 59.46 17.94 31 15338 6132 53327565
Hepatocellular injury 59.26 17.94 57 15312 29929 53303768
Lung neoplasm malignant 57.66 17.94 44 15325 16908 53316789
Death 55.99 17.94 227 15142 357005 52976692
Arthralgia 55.25 17.94 29 15340 439754 52893943
EGFR gene mutation 54.99 17.94 13 15356 230 53333467
Haematotoxicity 54.90 17.94 32 15337 7865 53325832
Renal tubular necrosis 51.08 17.94 35 15334 11384 53322313
Lung adenocarcinoma stage IV 50.72 17.94 12 15357 213 53333484
Malignant pleural effusion 49.95 17.94 21 15348 2556 53331141
Pain 49.71 17.94 58 15311 588340 52745357
Myelosuppression 49.68 17.94 36 15333 12792 53320905
Haemoptysis 49.28 17.94 50 15319 27989 53305708
Colitis 48.76 17.94 60 15309 41492 53292205
Posterior reversible encephalopathy syndrome 48.59 17.94 39 15330 16121 53317576
Renal tubular disorder 47.82 17.94 21 15348 2842 53330855
Melanoderma 47.69 17.94 11 15358 174 53333523
Joint swelling 47.19 17.94 6 15363 234632 53099065
Neutrophil count decreased 46.84 17.94 64 15305 49034 53284663
Immune-mediated lung disease 46.19 17.94 12 15357 317 53333380
Interstitial lung disease 45.09 17.94 69 15300 58553 53275144
Fall 44.45 17.94 24 15345 358416 52975281
Pulmonary embolism 44.08 17.94 100 15269 114342 53219355
Lung cancer metastatic 43.80 17.94 19 15350 2497 53331200
Vomiting 43.67 17.94 268 15101 496871 52836826
Product dose omission issue 43.55 17.94 3 15366 191617 53142080
Drug hypersensitivity 42.33 17.94 12 15357 265230 53068467
Drug ineffective 42.25 17.94 110 15259 817135 52516562
Nausea 41.44 17.94 364 15005 755727 52577970
General physical health deterioration 41.44 17.94 114 15255 146828 53186869
Metastases to bone 40.58 17.94 38 15331 19290 53314407
Malignant transformation 40.53 17.94 11 15358 345 53333352
Immune-mediated pancreatitis 40.48 17.94 8 15361 57 53333640
Myocarditis 40.37 17.94 27 15342 8441 53325256
Hepatitis 39.86 17.94 49 15320 33845 53299852
Blood creatinine increased 38.45 17.94 78 15291 82584 53251113
Subacute cutaneous lupus erythematosus 38.36 17.94 17 15352 2351 53331346
Renal failure 37.55 17.94 96 15273 118356 53215341
Osteonecrosis of jaw 37.35 17.94 49 15320 36097 53297600
Performance status decreased 35.18 17.94 18 15351 3425 53330272
Non-small cell lung cancer stage IV 34.82 17.94 9 15360 233 53333464
Secondary hypertension 34.03 17.94 8 15361 138 53333559
Gamma-glutamyltransferase increased 33.92 17.94 45 15324 33510 53300187
Decreased appetite 33.89 17.94 137 15232 214837 53118860
Maternal exposure during pregnancy 33.78 17.94 3 15366 155636 53178061
White blood cell count decreased 33.53 17.94 95 15274 124380 53209317
Abdominal discomfort 33.46 17.94 11 15358 221051 53112646
Nephritis 33.14 17.94 15 15354 2180 53331517
Radiation pneumonitis 33.11 17.94 13 15356 1327 53332370
Off label use 32.64 17.94 240 15129 471972 52861725
Hypertransaminasaemia 32.57 17.94 18 15351 3998 53329699
Acute kidney injury 32.54 17.94 152 15217 253716 53079981
Hepatotoxicity 32.28 17.94 40 15329 27840 53305857
Sinusitis 32.26 17.94 5 15364 168559 53165138
Adenocarcinoma 30.88 17.94 15 15354 2554 53331143
Metastases to lung 30.50 17.94 26 15343 11678 53322019
Multiple-drug resistance 30.43 17.94 16 15353 3219 53330478
Lymphangiosis carcinomatosa 30.38 17.94 12 15357 1244 53332453
Gene mutation 30.14 17.94 12 15357 1271 53332426
Nasopharyngitis 30.11 17.94 9 15360 192286 53141411
Transaminases increased 29.82 17.94 40 15329 30092 53303605
BRAF V600E mutation positive 29.75 17.94 6 15363 48 53333649
Skin toxicity 29.55 17.94 17 15352 4076 53329621
Platelet count decreased 28.62 17.94 82 15287 108017 53225680
Metastases to liver 28.43 17.94 33 15336 21463 53312234
Contraindicated product administered 28.42 17.94 3 15366 135626 53198071
Peripheral swelling 28.26 17.94 12 15357 206096 53127601
Hepatitis toxic 28.03 17.94 15 15354 3126 53330571
Weight increased 27.91 17.94 12 15357 204555 53129142
Rash maculo-papular 27.19 17.94 38 15331 29711 53303986
Pericardial effusion 26.67 17.94 36 15333 27242 53306455
Sarcomatoid carcinoma 26.65 17.94 5 15364 26 53333671
Immune-mediated hepatic disorder 26.25 17.94 6 15363 91 53333606
Systemic lupus erythematosus 25.70 17.94 3 15366 125411 53208286
Neonatal respiratory depression 25.55 17.94 6 15363 103 53333594
Oesophagitis 25.47 17.94 26 15343 14651 53319046
Tracheal fistula 24.47 17.94 5 15364 43 53333654
Paronychia 24.02 17.94 16 15353 4968 53328729
Jaw operation 23.97 17.94 9 15360 814 53332883
Insomnia 23.93 17.94 12 15357 187060 53146637
Leukoencephalopathy 23.90 17.94 15 15354 4209 53329488
Leukopenia 22.70 17.94 59 15310 73404 53260293
Lung adenocarcinoma recurrent 22.38 17.94 4 15365 15 53333682
Hepatic function abnormal 22.35 17.94 39 15330 36860 53296837
Gastrointestinal toxicity 22.26 17.94 15 15354 4747 53328950
Skin hyperpigmentation 22.15 17.94 16 15353 5656 53328041
Focal segmental glomerulosclerosis 21.69 17.94 10 15359 1515 53332182
Renal salt-wasting syndrome 21.64 17.94 6 15363 204 53333493
Diverticular perforation 21.51 17.94 13 15356 3412 53330285
Carcinoembryonic antigen increased 21.50 17.94 10 15359 1547 53332150
Meningitis herpes 21.26 17.94 6 15363 218 53333479
Sepsis 21.23 17.94 91 15278 146338 53187359
Somnolence 21.09 17.94 11 15358 167723 53165974
Dermatitis bullous 20.99 17.94 18 15351 8145 53325552
Febrile bone marrow aplasia 20.87 17.94 17 15352 7172 53326525
Immune-mediated hepatitis 20.05 17.94 8 15361 852 53332845
Feeling abnormal 19.99 17.94 7 15362 135294 53198403
Metastasis 19.98 17.94 14 15355 4717 53328980
Muscle spasms 19.87 17.94 7 15362 134788 53198909
Peripheral ischaemia 19.75 17.94 14 15355 4805 53328892
Therapeutic product effect decreased 19.45 17.94 6 15363 125649 53208048
Nephrogenic diabetes insipidus 19.38 17.94 8 15361 929 53332768
Swelling 19.33 17.94 16 15353 191089 53142608
Immune-mediated enterocolitis 19.17 17.94 8 15361 956 53332741
Glossodynia 19.12 17.94 3 15366 100288 53233409
Hypothyroidism 19.12 17.94 36 15333 36071 53297626
Asthenia 18.96 17.94 166 15203 343424 52990273
Dizziness 18.44 17.94 51 15318 372208 52961489
Pneumonia moraxella 18.29 17.94 4 15365 49 53333648
Nephropathy 18.28 17.94 14 15355 5403 53328294
Anaplastic lymphoma kinase gene mutation 18.16 17.94 3 15366 6 53333691
Epistaxis 18.05 17.94 52 15317 68658 53265039

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Malignant neoplasm progression 735.60 16.74 556 24862 77940 32410168
Pancytopenia 363.16 16.74 400 25018 90835 32397273
Interstitial lung disease 227.70 16.74 267 25151 64734 32423374
Thrombocytopenia 222.99 16.74 408 25010 147891 32340217
Neutropenia 222.47 16.74 398 25020 141777 32346331
Anaemia 207.69 16.74 505 24913 223119 32264989
Bone marrow failure 157.86 16.74 154 25264 30250 32457858
Disease progression 157.70 16.74 260 25158 86602 32401506
Mucosal inflammation 149.16 16.74 156 25262 33278 32454830
Non-small cell lung cancer 127.33 16.74 62 25356 3875 32484233
Lung adenocarcinoma 126.63 16.74 65 25353 4549 32483559
Febrile neutropenia 123.57 16.74 282 25136 119284 32368824
General physical health deterioration 120.39 16.74 273 25145 114986 32373122
Neoplasm progression 116.17 16.74 107 25311 19551 32468557
Myelosuppression 113.90 16.74 85 25333 11591 32476517
Pneumonitis 102.39 16.74 122 25296 30012 32458096
Febrile bone marrow aplasia 102.19 16.74 70 25348 8345 32479763
Pleural effusion 84.49 16.74 189 25229 78803 32409305
Leukopenia 78.39 16.74 156 25262 59966 32428142
Decreased appetite 72.84 16.74 283 25135 160530 32327578
Metastases to central nervous system 68.30 16.74 53 25365 7655 32480453
Neutrophil count decreased 67.15 16.74 127 25291 47012 32441096
Drug ineffective 66.94 16.74 124 25294 383353 32104755
Enteritis 60.19 16.74 48 25370 7213 32480895
Immune-mediated lung disease 57.26 16.74 21 25397 642 32487466
Completed suicide 56.84 16.74 4 25414 92513 32395595
Dehydration 55.95 16.74 224 25194 128734 32359374
Haematotoxicity 54.48 16.74 44 25374 6732 32481376
Skin toxicity 54.27 16.74 35 25383 3771 32484337
Diarrhoea 52.72 16.74 474 24944 364328 32123780
Aplasia 51.68 16.74 36 25382 4406 32483702
Drug interaction 51.35 16.74 57 25361 218128 32269980
Platelet count decreased 51.26 16.74 201 25217 114390 32373718
Immune-mediated adverse reaction 51.26 16.74 18 25400 484 32487624
Headache 47.55 16.74 50 25368 196147 32291961
Product dose omission issue 47.43 16.74 11 25407 102564 32385544
Neutropenic sepsis 47.42 16.74 54 25364 12645 32475463
Large intestine perforation 43.69 16.74 42 25376 8088 32480020
Fall 43.21 16.74 54 25364 196147 32291961
Septic shock 42.93 16.74 135 25283 68854 32419254
Vomiting 42.46 16.74 322 25096 235235 32252873
Colitis 41.72 16.74 86 25332 33865 32454243
Pulmonary embolism 40.89 16.74 151 25267 83508 32404600
Haemoptysis 40.11 16.74 84 25334 33441 32454667
Overdose 38.96 16.74 10 25408 87067 32401041
Pneumothorax 37.89 16.74 57 25361 17513 32470595
Superior vena cava syndrome 37.72 16.74 15 25403 574 32487534
Lung disorder 37.42 16.74 82 25336 33672 32454436
Tubulointerstitial nephritis 37.32 16.74 60 25358 19517 32468591
Radiation pneumonitis 36.60 16.74 23 25395 2369 32485739
Bradycardia 36.60 16.74 6 25412 71556 32416552
Immune-mediated enterocolitis 35.84 16.74 20 25398 1655 32486453
Hepatocellular injury 35.76 16.74 68 25350 25250 32462858
Nausea 35.62 16.74 395 25023 320454 32167654
White blood cell count decreased 35.26 16.74 153 25265 91045 32397063
Immune-mediated hepatic disorder 34.53 16.74 11 25407 217 32487891
Respiratory failure 34.21 16.74 170 25248 107012 32381096
Lung cancer metastatic 34.15 16.74 23 25395 2665 32485443
EGFR gene mutation 32.10 16.74 9 25409 112 32487996
Small intestinal perforation 31.88 16.74 19 25399 1780 32486328
Pain in extremity 31.44 16.74 28 25390 118873 32369235
Metastases to bone 30.95 16.74 40 25378 10670 32477438
Pleural mesothelioma malignant 30.49 16.74 8 25410 76 32488032
Hiccups 30.24 16.74 38 25380 9857 32478251
Muscle spasms 29.79 16.74 9 25409 70409 32417699
Epistaxis 29.13 16.74 103 25315 55752 32432356
Pneumonia 28.98 16.74 413 25005 354839 32133269
Sepsis 28.48 16.74 217 25201 158617 32329491
Peripheral swelling 28.44 16.74 9 25409 68336 32419772
Toxicity to various agents 27.99 16.74 61 25357 177980 32310128
Rash 27.56 16.74 267 25151 209066 32279042
Tremor 26.93 16.74 15 25403 81262 32406846
Purpura 26.87 16.74 37 25381 10488 32477620
Lung neoplasm malignant 26.51 16.74 46 25372 15917 32472191
Rhabdomyolysis 26.02 16.74 10 25408 67255 32420853
Therapy partial responder 25.61 16.74 25 25393 4905 32483203
Performance status decreased 25.55 16.74 23 25395 4075 32484033
Nasopharyngitis 25.49 16.74 9 25409 63778 32424330
Dyspnoea 24.55 16.74 408 25010 361637 32126471
Blood pressure increased 24.40 16.74 16 25402 79338 32408770
Rheumatoid nodule 24.33 16.74 17 25401 2090 32486018
Off label use 24.10 16.74 354 25064 305966 32182142
Drug resistance 23.44 16.74 54 25364 22911 32465197
Feeling abnormal 23.34 16.74 9 25409 60414 32427694
Peritonitis 23.34 16.74 53 25365 22277 32465831
Renal failure 23.13 16.74 182 25236 134296 32353812
Myalgia 22.85 16.74 18 25400 81212 32406896
Malignant pleural effusion 22.74 16.74 14 25404 1391 32486717
Nephritis 22.62 16.74 17 25401 2340 32485768
Aphthous ulcer 22.06 16.74 22 25396 4429 32483679
Disseminated intravascular coagulation 22.03 16.74 53 25365 23123 32464985
Opsoclonus myoclonus 21.91 16.74 6 25412 68 32488040
Dysphagia 21.39 16.74 100 25318 61376 32426732
Vasculitis 21.35 16.74 30 25388 8663 32479445
Pericardial effusion 21.22 16.74 52 25366 22950 32465158
Eastern Cooperative Oncology Group performance status worsened 21.18 16.74 10 25408 583 32487525
Non-small cell lung cancer metastatic 21.10 16.74 10 25408 588 32487520
Musculoskeletal stiffness 20.73 16.74 3 25415 39261 32448847
Gastrointestinal perforation 20.72 16.74 20 25398 3870 32484238
Mesothelioma 20.44 16.74 9 25409 446 32487662
Lichenoid keratosis 20.20 16.74 16 25402 2380 32485728
Hyperpyrexia 20.18 16.74 17 25401 2757 32485351
Hallucination 20.06 16.74 8 25410 52611 32435497
Arthralgia 20.06 16.74 55 25363 148393 32339715
Myocarditis 20.04 16.74 34 25384 11556 32476552
Depression 20.01 16.74 28 25390 97032 32391076
Acute kidney injury 19.96 16.74 331 25087 293137 32194971
Asthma 19.82 16.74 5 25413 44060 32444048
Lymphangiosis carcinomatosa 19.41 16.74 11 25407 938 32487170
Tumour necrosis 19.29 16.74 12 25406 1214 32486894
Occipital neuralgia 19.10 16.74 5 25413 47 32488061
Acquired gene mutation 19.10 16.74 12 25406 1235 32486873
Cardiac failure congestive 19.01 16.74 23 25395 84829 32403279
Pseudocellulitis 18.73 16.74 5 25413 51 32488057
Hypercreatininaemia 18.65 16.74 9 25409 551 32487557
Metastases to meninges 18.49 16.74 12 25406 1306 32486802
Lung adenocarcinoma recurrent 18.46 16.74 3 25415 0 32488108
Weight increased 18.40 16.74 23 25395 83640 32404468
Pulmonary toxicity 18.38 16.74 21 25397 4932 32483176
Cardiac disorder 18.35 16.74 5 25413 41861 32446247
Agitation 18.33 16.74 11 25407 57225 32430883
Pericarditis 18.23 16.74 29 25389 9344 32478764
Cachexia 18.16 16.74 25 25393 7084 32481024
Bicytopenia 18.07 16.74 14 25404 2017 32486091
Hypoglycaemia 18.06 16.74 10 25408 54372 32433736
Nephropathy toxic 18.01 16.74 33 25385 11913 32476195
Laryngeal leukoplakia 18.00 16.74 5 25413 60 32488048
Insomnia 17.80 16.74 32 25386 100316 32387792
Radiation oesophagitis 17.69 16.74 8 25410 422 32487686
Anxiety 17.58 16.74 30 25388 95975 32392133
Pyrexia 17.57 16.74 349 25069 319619 32168489
Rash maculo-papular 17.56 16.74 55 25363 27967 32460141
Immune thrombocytopenia 17.51 16.74 27 25391 8470 32479638
Pericarditis malignant 17.47 16.74 4 25414 20 32488088
Diaphragmatic rupture 17.47 16.74 4 25414 20 32488088
Tumour pseudoprogression 17.41 16.74 8 25410 438 32487670
Metastases to liver 17.36 16.74 34 25384 12898 32475210
Tracheo-oesophageal fistula 17.31 16.74 8 25410 444 32487664
Human chorionic gonadotropin increased 17.31 16.74 4 25414 21 32488087
Extremity necrosis 17.00 16.74 13 25405 1837 32486271
Electrocardiogram QT prolonged 16.88 16.74 5 25413 39636 32448472

Pharmacologic Action:

SourceCodeDescription
ATC L01BA04 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Folic acid analogues
FDA MoA N0000000111 Folic Acid Metabolism Inhibitors
FDA EPC N0000175584 Folate Analog Metabolic Inhibitor
MeSH PA D000970 Antineoplastic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D005493 Folic Acid Antagonists
MeSH PA D019384 Nucleic Acid Synthesis Inhibitors
CHEBI has role CHEBI:35221 antimetabolite
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:50683 7,8-dihydrofolate reductase inhibitors
CHEBI has role CHEBI:63720 EC 2.1.1.45 inhibitors
CHEBI has role CHEBI:63721 glycinamide ribonucleotide formyltransferase inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Non-small cell lung cancer indication 254637007 DOID:3908
Malignant mesothelioma of pleura indication 254645002 DOID:7474
Kidney disease contraindication 90708001 DOID:557
Impaired renal function disorder contraindication 197663003
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.34 acidic
pKa2 5.15 acidic
pKa3 9.45 acidic
pKa4 13.09 acidic
pKa5 3.95 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
500MG/20ML (25MG/ML) PEMFEXY EAGLE PHARMS N209472 Feb. 8, 2020 RX SOLUTION INTRAVENOUS 7772209 May 24, 2022 USE OF PEMETREXED WITH PRIOR AND/OR REPEATED VITAMIN B12 AND FOLIC ACID ADMINISTRATION IN PATIENTS WITH MESOTHELIOMA
500MG/20ML (25MG/ML) PEMFEXY EAGLE PHARMS N209472 Feb. 8, 2020 RX SOLUTION INTRAVENOUS 7772209 May 24, 2022 USE OF PEMETREXED WITH PRIOR AND/OR REPEATED VITAMIN B12 AND FOLIC ACID ADMINISTRATION IN PATIENTS WITH NON-SQUAMOUS NON-SMALL CELL LUNG CANCER

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Thymidylate synthase Enzyme INHIBITOR IC50 6.47 WOMBAT-PK CHEMBL
Dihydrofolate reductase Enzyme INHIBITOR IC50 5.18 WOMBAT-PK CHEMBL
Trifunctional purine biosynthetic protein adenosine-3 Enzyme INHIBITOR Ki 6.42 CHEMBL DRUG LABEL
Serine hydroxymethyltransferase, cytosolic Enzyme Kd 4.77 CHEMBL
Folate receptor beta Membrane receptor IC50 7.22 CHEMBL
Proton-coupled folate transporter Transporter Ki 7.03 CHEMBL
Folate transporter 1 Transporter IC50 6.86 CHEMBL
Folate receptor alpha Membrane receptor IC50 7.38 CHEMBL
Folylpolyglutamate synthase, mitochondrial Enzyme WOMBAT-PK
Bifunctional dihydrofolate reductase-thymidylate synthase Enzyme IC50 6.37 CHEMBL
Dihydrofolate reductase Enzyme Ki 6.25 CHEMBL
Dihydrofolate reductase Enzyme IC50 5.64 CHEMBL
Thymidylate synthase Enzyme IC50 4.82 CHEMBL
Dihydrofolate reductase Enzyme IC50 5.64 CHEMBL
Thymidylate synthase Enzyme Ki 6.47 CHEMBL
Thymidylate synthase Enzyme IC50 4.70 CHEMBL
Thymidylate synthase Enzyme Ki 6.26 CHEMBL
Dihydrofolate reductase Enzyme IC50 5.64 CHEMBL
Thymidylate synthase Enzyme IC50 5.96 CHEMBL
Thymidylate synthase (EC 2.1.1.45) (TS) (TSase) Enzyme IC50 4.12 CHEMBL
Trifunctional purine biosynthetic protein adenosine-3 Enzyme INHIBITOR Ki 5.03 IUPHAR

External reference:

IDSource
4021417 VUID
N0000148831 NUI
D03828 KEGG_DRUG
150399-23-8 SECONDARY_CAS_RN
4021417 VANDF
C0210657 UMLSCUI
CHEBI:63724 CHEBI
LYA PDB_CHEM_ID
CHEMBL225072 ChEMBL_ID
CHEMBL2360464 ChEMBL_ID
D000068437 MESH_DESCRIPTOR_UI
DB00642 DRUGBANK_ID
135410875 PUBCHEM_CID
6837 IUPHAR_LIGAND_ID
7675 INN_ID
04Q9AIZ7NO UNII
1666923 RXNORM
17856 MMSL
32871 MMSL
48646 MMSL
d05047 MMSL
008494 NDDF
008495 NDDF
409159000 SNOMEDCT_US
411089001 SNOMEDCT_US
735172002 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Alimta HUMAN PRESCRIPTION DRUG LABEL 1 0002-7623 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS NDA 33 sections
Alimta HUMAN PRESCRIPTION DRUG LABEL 1 0002-7640 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 100 mg INTRAVENOUS NDA 33 sections