PEMETREXED

Search structure
Trade Names:
Synonyms:
Status: Approved (2004)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01BA04
UNII: 04Q9AIZ7NO

Structure
InChI Key WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
Smile Nc1nc2[nH]cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c2c(=O)[nH]1
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H21N5O6
Molecular Weight 427.42
AlogP 0.67
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 6.0
Number of Rotational Bond 9.0
Polar Surface Area 191.26
Molecular species ACID
Aromatic Rings 3.0
Heavy Atoms 31.0

Pharmacology

Primary Target
dihydrofolate reductase
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Ligase
- 12-30000 - 380-1000 -
Enzyme Oxidoreductase
- 68-66000 - 7-7 -
Enzyme Transferase
- 5700-29000 16900 1-340 -
Enzyme
- 5700-29000 16900 380-1000 -
Membrane receptor
- 42-894 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC19 family of vitamin transporters
- 24-138 - - 60
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC46 family of folate transporters
- 8-67 - 94-2540 40-85

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Mesothelioma 4 D008654 ClinicalTrials
Mesothelioma 4 D008654 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Head and Neck Neoplasms 3 D006258 ClinicalTrials
Carcinoma 3 D002277 ClinicalTrials
Adenocarcinoma of Lung 3 D000077192 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Small Cell Lung Carcinoma 3 D055752 ClinicalTrials
Head and Neck Neoplasms 3 D006258 ClinicalTrials
Neoplasm Metastasis 2 D009362 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Neuroendocrine Tumors 2 D018358 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Adenocarcinoma 2 D000230 ClinicalTrials
Osteosarcoma 2 D012516 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Urogenital Neoplasms 2 D014565 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Nasopharyngeal Neoplasms 2 D009303 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Biliary Tract Neoplasms 2 D001661 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Esophageal Neoplasms 2 D004938 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Chordoma 1 D002817 ClinicalTrials
Lymphoma 1 D008223 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Lymphoma, Non-Hodgkin 1 D008228 ClinicalTrials
Thymus Neoplasms 1 D013953 ClinicalTrials
Meningeal Carcinomatosis 1 D055756 ClinicalTrials
Thymoma 1 D013945 ClinicalTrials
Glioma 0 D005910 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt
Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Asthenia 87.0
General disorders and administration site conditions Fatigue 87.0
Gastrointestinal disorders Nausea 84.0
General disorders and administration site conditions Asthenia 81.0
General disorders and administration site conditions Fatigue 81.0
General disorders and administration site conditions Asthenia 80.0
General disorders and administration site conditions Fatigue 80.0
Gastrointestinal disorders Nausea 79.0
Gastrointestinal disorders Nausea 77.0
General disorders and administration site conditions Asthenia 74.0
General disorders and administration site conditions Fatigue 74.0
Cardiac disorders Dyspnoea 66.0
General disorders and administration site conditions Decreased appetite 62.0
Cardiac disorders Dyspnoea 62.0
General disorders and administration site conditions Decreased appetite 58.0
Blood and lymphatic system disorders Neutropenia 58.0
Gastrointestinal disorders Vomiting 58.0
Blood and lymphatic system disorders Leukopenia 55.0
Gastrointestinal disorders Vomiting 52.0
Gastrointestinal disorders Vomiting 50.0
Blood and lymphatic system disorders Neutropenia 45.0
Gastrointestinal disorders Constipation 44.0
Skin and subcutaneous tissue disorders Alopecia 42.0
General disorders and administration site conditions Asthenia 42.0
General disorders and administration site conditions Fatigue 42.0
Cardiac disorders Chest pain 40.0
Blood and lymphatic system disorders Neutropenia 40.0
Gastrointestinal disorders Constipation 39.0
Gastrointestinal disorders Nausea 39.0
Blood and lymphatic system disorders Agranulocytosis 38.0
Skin and subcutaneous tissue disorders Alopecia 38.0
Blood and lymphatic system disorders Neutropenia 38.0
General disorders and administration site conditions Asthenia 36.0
General disorders and administration site conditions Fatigue 36.0
General disorders and administration site conditions Decreased appetite 35.0
General disorders and administration site conditions Asthenia 34.0
Gastrointestinal disorders Diarrhoea 34.0
General disorders and administration site conditions Fatigue 34.0
Blood and lymphatic system disorders Leukopenia 34.0
Gastrointestinal disorders Vomiting 34.0
Blood and lymphatic system disorders Anaemia 33.0
Blood and lymphatic system disorders Neutropenia 32.0
Gastrointestinal disorders Nausea 31.0
Gastrointestinal disorders Vomiting 31.0
Cardiac disorders Chest pain 30.0
Gastrointestinal disorders Constipation 30.0
Gastrointestinal disorders Pharyngitis 28.0
Gastrointestinal disorders Stomatitis 28.0
Blood and lymphatic system disorders Leukopenia 27.0
Blood and lymphatic system disorders Thrombocytopenia 27.0
Investigations Body temperature increased 26.0
Gastrointestinal disorders Diarrhoea 26.0
General disorders and administration site conditions Asthenia 25.0
General disorders and administration site conditions Decreased appetite 25.0
General disorders and administration site conditions Fatigue 25.0
Gastrointestinal disorders Nausea 25.0
Gastrointestinal disorders Vomiting 25.0
General disorders and administration site conditions Decreased appetite 24.0
Gastrointestinal disorders Diarrhoea 24.0
Blood and lymphatic system disorders Neutropenia 24.0
General disorders and administration site conditions Oedema 24.0
Blood and lymphatic system disorders Agranulocytosis 23.0
Gastrointestinal disorders Constipation 23.0
Blood and lymphatic system disorders Neutropenia 23.0
Gastrointestinal disorders Pharyngitis 23.0
Gastrointestinal disorders Stomatitis 23.0
Blood and lymphatic system disorders Anaemia 22.0
General disorders and administration site conditions Decreased appetite 22.0
Skin and subcutaneous tissue disorders Dermatitis 22.0
Skin and subcutaneous tissue disorders Rash 22.0
Skin and subcutaneous tissue disorders Skin exfoliation 22.0
Gastrointestinal disorders Diarrhoea 21.0
Blood and lymphatic system disorders Leukopenia 20.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 20.0
Musculoskeletal and connective tissue disorders Myalgia 20.0
Gastrointestinal disorders Pharyngitis 20.0
Gastrointestinal disorders Stomatitis 20.0
Blood and lymphatic system disorders Anaemia 19.0
Investigations Body temperature increased 19.0
General disorders and administration site conditions Decreased appetite 19.0
Gastrointestinal disorders Nausea 19.0
Blood and lymphatic system disorders Neutropenia 19.0
General disorders and administration site conditions Oedema 19.0
Gastrointestinal disorders Vomiting 19.0
General disorders and administration site conditions Asthenia 18.0
Investigations Creatinine renal clearance decreased 18.0
General disorders and administration site conditions Fatigue 18.0
General disorders and administration site conditions Asthenia 17.0
Investigations Body temperature increased 17.0
General disorders and administration site conditions Fatigue 17.0
Blood and lymphatic system disorders Leukopenia 17.0
Gastrointestinal disorders Nausea 17.0
Nervous system disorders Neuropathy peripheral 17.0
Gastrointestinal disorders Pharyngitis 17.0
Gastrointestinal disorders Stomatitis 17.0
General disorders and administration site conditions Asthenia 16.0
Gastrointestinal disorders Diarrhoea 16.0
General disorders and administration site conditions Fatigue 16.0
Blood and lymphatic system disorders Neutropenia 16.0
Gastrointestinal disorders Vomiting 16.0
Blood and lymphatic system disorders Anaemia 15.0
Nervous system disorders Neuropathy peripheral 15.0
Gastrointestinal disorders Pharyngitis 15.0
Gastrointestinal disorders Stomatitis 15.0
Blood and lymphatic system disorders Anaemia 14.0
General disorders and administration site conditions Asthenia 14.0
General disorders and administration site conditions Decreased appetite 14.0
Skin and subcutaneous tissue disorders Dermatitis 14.0
General disorders and administration site conditions Fatigue 14.0
Blood and lymphatic system disorders Leukopenia 14.0
Psychiatric disorders Mood swings 14.0
Skin and subcutaneous tissue disorders Rash 14.0
Skin and subcutaneous tissue disorders Skin exfoliation 14.0
Musculoskeletal and connective tissue disorders Arthralgia 13.0
Gastrointestinal disorders Diarrhoea 13.0
Blood and lymphatic system disorders Leukopenia 13.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 13.0
Musculoskeletal and connective tissue disorders Myalgia 13.0
Blood and lymphatic system disorders Neutropenia 13.0
General disorders and administration site conditions Asthenia 12.0
General disorders and administration site conditions Fatigue 12.0
Blood and lymphatic system disorders Leukopenia 12.0
Gastrointestinal disorders Nausea 12.0
Gastrointestinal disorders Vomiting 12.0
Skin and subcutaneous tissue disorders Alopecia 11.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Infections and infestations Infection 11.0
Blood and lymphatic system disorders Leukopenia 11.0
Gastrointestinal disorders Nausea 11.0
Blood and lymphatic system disorders Neutropenia 11.0
Gastrointestinal disorders Vomiting 11.0
Investigations Alanine aminotransferase increased 10.0
Blood and lymphatic system disorders Anaemia 10.0
Skin and subcutaneous tissue disorders Dermatitis 10.0
Cardiac disorders Dyspnoea 10.0
Nervous system disorders Neuropathy peripheral 10.0
Skin and subcutaneous tissue disorders Rash 10.0
Skin and subcutaneous tissue disorders Skin exfoliation 10.0
Blood and lymphatic system disorders Thrombocytopenia 10.0
Gastrointestinal disorders Vomiting 10.0
General disorders and administration site conditions Asthenia 9.0
Investigations Body temperature increased 9.0
General disorders and administration site conditions Decreased appetite 9.0
Metabolism and nutrition disorders Dehydration 9.0
Skin and subcutaneous tissue disorders Dermatitis 9.0
Gastrointestinal disorders Diarrhoea 9.0
General disorders and administration site conditions Fatigue 9.0
Blood and lymphatic system disorders Febrile neutropenia 9.0
Psychiatric disorders Mood swings 9.0
Nervous system disorders Neuropathy peripheral 9.0
Blood and lymphatic system disorders Neutropenia 9.0
Gastrointestinal disorders Pharyngitis 9.0
Skin and subcutaneous tissue disorders Rash 9.0
Skin and subcutaneous tissue disorders Skin exfoliation 9.0
Gastrointestinal disorders Stomatitis 9.0
Blood and lymphatic system disorders Thrombocytopenia 9.0
Gastrointestinal disorders Vomiting 9.0
Investigations Alanine aminotransferase increased 8.0
Musculoskeletal and connective tissue disorders Arthralgia 8.0
Investigations Aspartate aminotransferase increased 8.0
Investigations Body temperature increased 8.0
Cardiac disorders Chest pain 8.0
Gastrointestinal disorders Diarrhoea 8.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 8.0
Blood and lymphatic system disorders Neutropenia 8.0
Blood and lymphatic system disorders Thrombocytopenia 8.0
Investigations Aspartate aminotransferase increased 7.0
Gastrointestinal disorders Constipation 7.0
General disorders and administration site conditions Decreased appetite 7.0
Metabolism and nutrition disorders Dehydration 7.0
Gastrointestinal disorders Dysphagia 7.0
Vascular disorders Embolism 7.0
General disorders and administration site conditions Mucosal inflammation 7.0
Gastrointestinal disorders Odynophagia 7.0
Gastrointestinal disorders Oesophagitis 7.0
Skin and subcutaneous tissue disorders Pruritus 7.0
Gastrointestinal disorders Stomatitis 7.0
Vascular disorders Thrombosis 7.0
Skin and subcutaneous tissue disorders Alopecia 6.0
Blood and lymphatic system disorders Anaemia
Blood and lymphatic system disorders Anaemia 6.0
Investigations Body temperature increased 6.0
Gastrointestinal disorders Constipation 6.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
Gastrointestinal disorders Dysgeusia 6.0
Gastrointestinal disorders Dysphagia 6.0
Infections and infestations Infection 6.0
Blood and lymphatic system disorders Leukopenia 6.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 6.0
Blood and lymphatic system disorders Neutropenia 6.0
Gastrointestinal disorders Odynophagia 6.0
Gastrointestinal disorders Oesophagitis 6.0
Gastrointestinal disorders Pharyngitis 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Skin and subcutaneous tissue disorders Skin exfoliation 6.0
Gastrointestinal disorders Stomatitis 6.0
Gastrointestinal disorders Vomiting 6.0
Blood and lymphatic system disorders Anaemia 5.0
General disorders and administration site conditions Asthenia 5.0
Investigations Blood creatinine decreased 5.0
Cardiac disorders Chest pain 5.0
General disorders and administration site conditions Decreased appetite
Skin and subcutaneous tissue disorders Dermatitis 5.0
Gastrointestinal disorders Diarrhoea 5.0
Gastrointestinal disorders Dysphagia 5.0
Cardiac disorders Dyspnoea 5.0
General disorders and administration site conditions Fatigue 5.0
Infections and infestations Infection 5.0
General disorders and administration site conditions Mucosal inflammation 5.0
Blood and lymphatic system disorders Neutropenia 5.0
Gastrointestinal disorders Odynophagia 5.0
General disorders and administration site conditions Oedema 5.0
Gastrointestinal disorders Oesophagitis 5.0
Skin and subcutaneous tissue disorders Rash 5.0
Gastrointestinal disorders Stomatitis 5.0
Blood and lymphatic system disorders Thrombocytopenia 5.0
Blood and lymphatic system disorders Anaemia
Blood and lymphatic system disorders Anaemia 4.8
General disorders and administration site conditions Asthenia 4.5
General disorders and administration site conditions Fatigue 4.5
Investigations Alanine aminotransferase increased
Blood and lymphatic system disorders Anaemia 4.0
Investigations Aspartate aminotransferase increased
Gastrointestinal disorders Constipation 4.0
General disorders and administration site conditions Decreased appetite 4.0
Metabolism and nutrition disorders Dehydration 4.0
Gastrointestinal disorders Diarrhoea 4.0
Vascular disorders Embolism 4.0
Infections and infestations Infection 4.0
Blood and lymphatic system disorders Leukopenia 4.0
Gastrointestinal disorders Nausea 4.0
Nervous system disorders Neuropathy peripheral
Blood and lymphatic system disorders Neutropenia 4.0
Blood and lymphatic system disorders Thrombocytopenia 4.0
Vascular disorders Thrombosis 4.0
Gastrointestinal disorders Vomiting 4.0
Blood and lymphatic system disorders Neutropenia 3.9
General disorders and administration site conditions Oedema
Blood and lymphatic system disorders Anaemia 3.0
Musculoskeletal and connective tissue disorders Arthralgia 3.0
General disorders and administration site conditions Decreased appetite 3.0
Metabolism and nutrition disorders Dehydration 3.0
Skin and subcutaneous tissue disorders Dermatitis
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 3.0
Vascular disorders Embolism 3.0
Blood and lymphatic system disorders Febrile neutropenia 3.0
Infections and infestations Infection 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Musculoskeletal and connective tissue disorders Myalgia 3.0
Cardiac disorders Myocardial ischaemia 3.0
Gastrointestinal disorders Nausea 3.0
Blood and lymphatic system disorders Neutropenia 3.0
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Skin exfoliation
Vascular disorders Thrombosis 3.0
General disorders and administration site conditions Mucosal inflammation
Gastrointestinal disorders Nausea
Gastrointestinal disorders Stomatitis
Investigations Alanine aminotransferase increased 2.0
Blood and lymphatic system disorders Anaemia 2.0
General disorders and administration site conditions Asthenia 2.0
Gastrointestinal disorders Constipation 2.0
Investigations Creatinine renal clearance decreased 2.0
General disorders and administration site conditions Decreased appetite 2.0
Cardiac disorders Dyspnoea 2.0
Vascular disorders Embolism 2.0
General disorders and administration site conditions Fatigue 2.0
Blood and lymphatic system disorders Febrile neutropenia 2.0
Immune system disorders Hypersensitivity 2.0
Infections and infestations Infection
Infections and infestations Infection 2.0
Blood and lymphatic system disorders Leukopenia 2.0
General disorders and administration site conditions Mucosal inflammation
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.0
Musculoskeletal and connective tissue disorders Myalgia 2.0
Cardiac disorders Myocardial ischaemia 2.0
Gastrointestinal disorders Nausea 2.0
Blood and lymphatic system disorders Neutropenia 2.0
Gastrointestinal disorders Pharyngitis 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Renal and urinary disorders Renal failure 2.0
Gastrointestinal disorders Stomatitis
Gastrointestinal disorders Stomatitis 2.0
Blood and lymphatic system disorders Thrombocytopenia 2.0
Vascular disorders Thrombosis 2.0
Gastrointestinal disorders Vomiting 2.0
Gastrointestinal disorders Vomiting
Investigations Alanine aminotransferase increased 1.0
Blood and lymphatic system disorders Anaemia
Blood and lymphatic system disorders Anaemia 1.0
Musculoskeletal and connective tissue disorders Arthralgia 1.0
Investigations Aspartate aminotransferase increased 1.0
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Asthenia 1.0
Investigations Blood creatinine decreased 1.0
Investigations Body temperature increased 1.0
Cardiac disorders Chest pain 1.0
Eye disorders Conjunctivitis 1.0
Gastrointestinal disorders Constipation 1.0
General disorders and administration site conditions Decreased appetite 1.0
Metabolism and nutrition disorders Dehydration 1.0
Skin and subcutaneous tissue disorders Dermatitis 1.0
Gastrointestinal disorders Diarrhoea 1.0
Gastrointestinal disorders Dyspepsia 1.0
Gastrointestinal disorders Dysphagia 1.0
Cardiac disorders Dyspnoea 1.0
Vascular disorders Embolism 1.0
General disorders and administration site conditions Fatigue
General disorders and administration site conditions Fatigue 1.0
Blood and lymphatic system disorders Febrile neutropenia 1.0
Immune system disorders Hypersensitivity 1.0
Infections and infestations Infection 1.0
Blood and lymphatic system disorders Leukopenia
Blood and lymphatic system disorders Leukopenia 1.0
Psychiatric disorders Mood swings 1.0
General disorders and administration site conditions Mucosal inflammation 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Cardiac disorders Myocardial ischaemia 1.0
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 1.0
Nervous system disorders Neuropathy peripheral 1.0
Blood and lymphatic system disorders Neutropenia 1.0
Gastrointestinal disorders Odynophagia 1.0
General disorders and administration site conditions Oedema 1.0
Gastrointestinal disorders Oesophagitis 1.0
Gastrointestinal disorders Pharyngitis 1.0
Skin and subcutaneous tissue disorders Rash 1.0
Renal and urinary disorders Renal failure 1.0
Skin and subcutaneous tissue disorders Skin exfoliation 1.0
Gastrointestinal disorders Stomatitis 1.0
Blood and lymphatic system disorders Thrombocytopenia 1.0
Vascular disorders Thrombosis 1.0
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Vomiting 1.0
Blood and lymphatic system disorders Anaemia
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Fatigue
Blood and lymphatic system disorders Neutropenia
General disorders and administration site conditions Mucosal inflammation 0.3
Gastrointestinal disorders Nausea 0.3
Gastrointestinal disorders Stomatitis 0.3

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
66.67
General disorders and administration site conditions
33.33

Cross References

Resources Reference
CAS NUMBER 137281-23-3
ChEBI 63616
ChEMBL CHEMBL225072
DrugBank DB00642
DrugCentral 2073
EPA CompTox DTXSID2048329
FDA SRS 04Q9AIZ7NO
Guide to Pharmacology 6837
PDB LYA
PubChem 135410875
SureChEMBL SCHEMBL7968
ZINC ZINC000001540998
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