General Information of Drug (ID: DMMX2E6)

Drug Name
Pemetrexed
Synonyms
Alimta; LYA; LY 231514; LY231514; Alimta (TN); LY 231,514; LY-2315; LY-231514; Pemetrexed (INN); Pemetrexed [INN:BAN]; LY-231,514; N-(4-(2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimdin-5-yl)ethyl)benzoyl)glutamic acid; N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1h-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-d-glutamic acid; (2R)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid; (2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid; 2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid; 2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-PENTANEDIOIC ACID
Indication
Disease Entry ICD 11 Status REF
Malignant pleural mesothelioma 2C26.0 Approved [1], [2], [3], [4], [5]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 427.4
Topological Polar Surface Area (xlogp) 0.2
Rotatable Bond Count (rotbonds) 9
Hydrogen Bond Donor Count (hbonddonor) 6
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [6]
Clearance
The drug present in the plasma can be removed from the body at the rate of 1.3 mL/min/kg [7]
Elimination
80% of drug is excreted from urine in the unchanged form [6]
Half-life
The concentration or amount of drug in body reduced by one-half in 3.5 hours [7]
Metabolism
The drug is metabolized via the cytochrome P450 Enzymes [8]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1.377 micromolar/kg/day [9]
Unbound Fraction
The unbound fraction of drug in plasma is 0.19% [7]
Vd
The volume of distribution (Vd) of drug is 16.1 L [10]
Water Solubility
The ability of drug to dissolve in water is measured as 90 mg/mL [6]
Chemical Identifiers
Formula
C20H21N5O6
IUPAC Name
(2S)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
Canonical SMILES
C1=CC(=CC=C1CCC2=CNC3=C2C(=O)NC(=N3)N)C(=O)N[C@@H](CCC(=O)O)C(=O)O
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
InChIKey
WBXPDJSOTKVWSJ-ZDUSSCGKSA-N
Cross-matching ID
PubChem CID
135410875
ChEBI ID
CHEBI:63616
CAS Number
137281-23-3
DrugBank ID
DB00642
TTD ID
D0Y4GO
VARIDT ID
DR00318

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Candida Thymidylate synthase (Candi TMP1) TTU6BFZ TYSY_CANAL Inhibitor [11]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Folate transporter 1 (SLC19A1) DTOSN46 S19A1_HUMAN Substrate [12]
Proton-coupled folate transporter (SLC46A1) DTDJEMI PCFT_HUMAN Substrate [13]
Multidrug resistance-associated protein 5 (ABCC5) DTYVM24 MRP5_HUMAN Substrate [14]
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [15]
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [16]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [17]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Pemetrexed (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Framycetin DMF8DNE Moderate Decreased renal excretion of Pemetrexed caused by Framycetin mediated nephrotoxicity. Alcoholic liver disease [DB94] [69]
Inotersen DMJ93CT Moderate Decreased renal excretion of Pemetrexed caused by Inotersen mediated nephrotoxicity. Amyloidosis [5D00] [69]
Roflumilast DMPGHY8 Moderate Additive immunosuppressive effects by the combination of Pemetrexed and Roflumilast. Asthma [CA23] [70]
Kanamycin DM2DMPO Moderate Decreased renal excretion of Pemetrexed caused by Kanamycin mediated nephrotoxicity. Bacterial infection [1A00-1C4Z] [69]
Streptomycin DME1LQN Moderate Decreased renal excretion of Pemetrexed caused by Streptomycin mediated nephrotoxicity. Bacterial infection [1A00-1C4Z] [69]
Gentamicin DMKINJO Moderate Decreased renal excretion of Pemetrexed caused by Gentamicin mediated nephrotoxicity. Bacterial infection [1A00-1C4Z] [69]
Netilmicin DMRD1QK Moderate Decreased renal excretion of Pemetrexed caused by Netilmicin mediated nephrotoxicity. Bacterial infection [1A00-1C4Z] [69]
Tobramycin DMUI0CH Moderate Decreased renal excretion of Pemetrexed caused by Tobramycin mediated nephrotoxicity. Bacterial infection [1A00-1C4Z] [69]
Etidronic acid DM1XHYJ Moderate Decreased renal excretion of Pemetrexed caused by Etidronic acid mediated nephrotoxicity. Bone paget disease [FB85] [69]
Methoxyflurane DML0RAE Moderate Decreased renal excretion of Pemetrexed caused by Methoxyflurane mediated nephrotoxicity. Corneal disease [9A76-9A78] [69]
Pentamidine DMHZJCG Moderate Decreased renal excretion of Pemetrexed caused by Pentamidine mediated nephrotoxicity. Fungal infection [1F29-1F2F] [69]
Amphotericin B DMTAJQE Moderate Decreased renal excretion of Pemetrexed caused by Amphotericin B mediated nephrotoxicity. Fungal infection [1F29-1F2F] [69]
Teriflunomide DMQ2FKJ Major Additive immunosuppressive effects by the combination of Pemetrexed and Teriflunomide. Hyper-lipoproteinaemia [5C80] [71]
Givosiran DM5PFIJ Moderate Decreased renal excretion of Pemetrexed caused by Givosiran mediated nephrotoxicity. Inborn porphyrin/heme metabolism error [5C58] [69]
Balsalazide DMO091F Moderate Decreased renal excretion of Pemetrexed caused by Balsalazide mediated nephrotoxicity. Indeterminate colitis [DD72] [69]
Denosumab DMNI0KO Moderate Additive myelosuppressive effects by the combination of Pemetrexed and Denosumab. Low bone mass disorder [FB83] [72]
Moxetumomab pasudotox DMN63DZ Moderate Decreased renal excretion of Pemetrexed caused by Moxetumomab pasudotox mediated nephrotoxicity. Mature B-cell leukaemia [2A82] [69]
Exjade DMHPRWG Moderate Decreased renal excretion of Pemetrexed caused by Exjade mediated nephrotoxicity. Mineral absorption/transport disorder [5C64] [69]
Gallium nitrate DMF9O6B Moderate Decreased renal excretion of Pemetrexed caused by Gallium nitrate mediated nephrotoxicity. Mineral excesses [5B91] [69]
Thalidomide DM70BU5 Major Additive thrombogenic effects by the combination of Pemetrexed and Thalidomide. Multiple myeloma [2A83] [73]
Tecfidera DM2OVDT Moderate Additive immunosuppressive effects by the combination of Pemetrexed and Tecfidera. Multiple sclerosis [8A40] [74]
Siponimod DM2R86O Major Additive immunosuppressive effects by the combination of Pemetrexed and Siponimod. Multiple sclerosis [8A40] [75]
Fingolimod DM5JVAN Major Additive immunosuppressive effects by the combination of Pemetrexed and Fingolimod. Multiple sclerosis [8A40] [76]
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Pemetrexed and Ocrelizumab. Multiple sclerosis [8A40] [77]
Ozanimod DMT6AM2 Major Additive immunosuppressive effects by the combination of Pemetrexed and Ozanimod. Multiple sclerosis [8A40] [70]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive myelosuppressive effects by the combination of Pemetrexed and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [78]
Temsirolimus DMS104F Moderate Decreased renal excretion of Pemetrexed caused by Temsirolimus mediated nephrotoxicity. Renal cell carcinoma [2C90] [69]
Colistimethate DMZ9BMU Moderate Decreased renal excretion of Pemetrexed caused by Colistimethate mediated nephrotoxicity. Respiratory infection [CA07-CA4Z] [69]
Canakinumab DM8HLO5 Moderate Additive immunosuppressive effects by the combination of Pemetrexed and Canakinumab. Rheumatoid arthritis [FA20] [79]
Rilonacept DMGLUQS Moderate Additive immunosuppressive effects by the combination of Pemetrexed and Rilonacept. Rheumatoid arthritis [FA20] [79]
Golimumab DMHZV7X Major Additive immunosuppressive effects by the combination of Pemetrexed and Golimumab. Rheumatoid arthritis [FA20] [80]
Sulfasalazine DMICA9H Moderate Decreased renal excretion of Pemetrexed caused by Sulfasalazine mediated nephrotoxicity. Rheumatoid arthritis [FA20] [69]
Leflunomide DMR8ONJ Major Additive immunosuppressive effects by the combination of Pemetrexed and Leflunomide. Rheumatoid arthritis [FA20] [71]
Anthrax vaccine DM9GSWY Moderate Antagonize the effect of Pemetrexed when combined with Anthrax vaccine. Sepsis [1G40-1G41] [81]
Telavancin DM58VQX Moderate Decreased renal excretion of Pemetrexed caused by Telavancin mediated nephrotoxicity. Staphylococcal/streptococcal disease [1B5Y] [69]
Sirolimus DMGW1ID Moderate Decreased renal excretion of Pemetrexed caused by Sirolimus mediated nephrotoxicity. Transplant rejection [NE84] [69]
Azathioprine DMMZSXQ Moderate Additive immunosuppressive effects by the combination of Pemetrexed and Azathioprine. Transplant rejection [NE84] [75]
Tacrolimus DMZ7XNQ Moderate Decreased renal excretion of Pemetrexed caused by Tacrolimus mediated nephrotoxicity. Transplant rejection [NE84] [69]
Olsalazine DMZW9HA Moderate Decreased renal excretion of Pemetrexed caused by Olsalazine mediated nephrotoxicity. Ulcerative colitis [DD71] [69]
Plazomicin DMKMBES Moderate Decreased renal excretion of Pemetrexed caused by Plazomicin mediated nephrotoxicity. Urinary tract infection [GC08] [69]
Ganciclovir DM1MBYQ Moderate Additive myelosuppressive effects by the combination of Pemetrexed and Ganciclovir. Virus infection [1A24-1D9Z] [75]
Valganciclovir DMS2IUH Moderate Additive myelosuppressive effects by the combination of Pemetrexed and Valganciclovir. Virus infection [1A24-1D9Z] [75]
⏷ Show the Full List of 42 DDI Information of This Drug

References

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