Details of the Drug

General Information of Drug (ID: DMSE3I7)

Drug Name
Gemcitabine
Synonyms
Gemcitabine hydrochloride; DDFC; DFdC; DFdCyd; Folfugem; GEO; Gamcitabine; GemLip; Gemcel; Gemcin; Gemcitabina; Gemcitabinum; Gemtro; Gemzar; Zefei; Gemcitabine HCl; Gemcitabine stereoisomer; LY 188011; LY188011; Gemcitabina [INN-Spanish]; Gemcitabinum [INN-Latin]; Gemzar (TN); Gemzar (hydrochloride); Inno-D07001; LY-188011; Gemcitabine (USAN/INN)
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Approved [1], [2]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 263.2
Topological Polar Surface Area (xlogp) -1.5
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 32 mL/min/kg [4]
Elimination
Within a week following administration of a single dose of 1000 mg/m2 infused over 30 minutes, about 92-98% of the dose was recovered in urine where 89% of the recovered dose was excreted as difluorodeoxyuridine (dFdU) and less than 10% as gemcitabine [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 0.7 - 1.6 hours [6]
Metabolism
The drug is metabolized via the deoxycytidine kinase [7]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 93.9 micromolar/kg/day [8]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.5 L/kg [4]
Water Solubility
The ability of drug to dissolve in water is measured as 15 mg/mL [3]
Chemical Identifiers
Formula
C9H11F2N3O4
IUPAC Name
4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Canonical SMILES
C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
InChI
InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17)/t4-,6-,7-/m1/s1
InChIKey
SDUQYLNIPVEERB-QPPQHZFASA-N
Cross-matching ID
PubChem CID
60750
ChEBI ID
CHEBI:175901
CAS Number
95058-81-4
DrugBank ID
DB00441
TTD ID
D03UVS
VARIDT ID
DR00063
INTEDE ID
DR0765

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Ribonucleoside-diphosphate reductase M2 (RRM2) TTBWDI0 RIR2_HUMAN Modulator [9]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Concentrative nucleoside transporter 1 (SLC28A1) DT0EQPW S28A1_HUMAN Substrate [10]
Multidrug resistance-associated protein 5 (ABCC5) DTYVM24 MRP5_HUMAN Substrate [11]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [12]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytidine aminohydrolase (CDA) DEKEDRC CDD_HUMAN Substrate [13]
Cytidine deaminase (cdd) DETX3A5 CDD_ECOLI Substrate [14]
Cytidine deaminase (cdd) DEFVABT CDD_KLEP7 Substrate [14]
Uridine/cytidine monophosphate kinase (UMPK) DEMPH4I KCY_HUMAN Substrate [15]
Cytidine deaminase (cdd) DEYILK4 E0TLJ6_MYCHH Substrate [16]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Solid tumour/cancer
ICD Disease Classification 2A00-2F9Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Ribonucleoside-diphosphate reductase M2 (RRM2) DTT RRM2 1.66E-04 2.66 1.68
Multidrug resistance-associated protein 5 (ABCC5) DTP MRP5 8.28E-03 6.40E-01 7.46E-01
P-glycoprotein 1 (ABCB1) DTP P-GP 2.74E-01 -2.19E-01 -3.03E-01
Concentrative nucleoside transporter 1 (SLC28A1) DTP CNT1 2.99E-02 -3.24E-01 -1.02E+00
Uridine/cytidine monophosphate kinase (UMPK) DME CMPK1 2.73E-04 5.37E-01 1.41E+00
Cytidine aminohydrolase (CDA) DME CDA 1.62E-05 4.67E-01 8.77E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Gemcitabine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [47]
Coadministration of a Drug Treating the Disease Different from Gemcitabine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [48]
Roflumilast DMPGHY8 Moderate Additive immunosuppressive effects by the combination of Gemcitabine and Roflumilast. Asthma [CA23] [47]
Ofloxacin DM0VQN3 Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Ofloxacin. Bacterial infection [1A00-1C4Z] [49]
Ciprofloxacin XR DM2NLS9 Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Ciprofloxacin XR. Bacterial infection [1A00-1C4Z] [49]
Trovafloxacin DM6AN32 Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Trovafloxacin. Bacterial infection [1A00-1C4Z] [49]
Sparfloxacin DMB4HCT Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Sparfloxacin. Bacterial infection [1A00-1C4Z] [49]
Gemifloxacin DMHT34O Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Gemifloxacin. Bacterial infection [1A00-1C4Z] [49]
Norfloxacin DMIZ6W2 Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Norfloxacin. Bacterial infection [1A00-1C4Z] [49]
ABT-492 DMJFD2I Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by ABT-492. Bacterial infection [1A00-1C4Z] [49]
Levofloxacin DMS60RB Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Levofloxacin. Bacterial infection [1A00-1C4Z] [49]
Lomefloxacin DMVRH9C Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Lomefloxacin. Bacterial infection [1A00-1C4Z] [49]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Gemcitabine and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [50]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Cannabidiol. Epileptic encephalopathy [8A62] [47]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Brentuximab vedotin. Hodgkin lymphoma [2B30] [51]
Efavirenz DMC0GSJ Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Efavirenz. Human immunodeficiency virus disease [1C60-1C62] [52]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Gemcitabine and Mipomersen. Hyper-lipoproteinaemia [5C80] [53]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Gemcitabine and Teriflunomide. Hyper-lipoproteinaemia [5C80] [54]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Gemcitabine and BMS-201038. Hyper-lipoproteinaemia [5C80] [55]
Methotrexate DM2TEOL Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Methotrexate. Leukaemia [2A60-2B33] [47]
Denosumab DMNI0KO Moderate Additive myelosuppressive effects by the combination of Gemcitabine and Denosumab. Low bone mass disorder [FB83] [56]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [57]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Idelalisib. Mature B-cell leukaemia [2A82] [58]
Clofarabine DMCVJ86 Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Clofarabine. Mature B-cell lymphoma [2A85] [59]
Thalidomide DM70BU5 Major Additive thrombogenic effects by the combination of Gemcitabine and Thalidomide. Multiple myeloma [2A83] [60]
Tecfidera DM2OVDT Moderate Additive immunosuppressive effects by the combination of Gemcitabine and Tecfidera. Multiple sclerosis [8A40] [61]
Siponimod DM2R86O Major Additive immunosuppressive effects by the combination of Gemcitabine and Siponimod. Multiple sclerosis [8A40] [62]
Fingolimod DM5JVAN Major Additive immunosuppressive effects by the combination of Gemcitabine and Fingolimod. Multiple sclerosis [8A40] [63]
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Gemcitabine and Ocrelizumab. Multiple sclerosis [8A40] [64]
Ozanimod DMT6AM2 Major Additive immunosuppressive effects by the combination of Gemcitabine and Ozanimod. Multiple sclerosis [8A40] [47]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive immunosuppressive effects by the combination of Gemcitabine and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [65]
Gatifloxacin DMSL679 Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Gatifloxacin. Respiratory infection [CA07-CA4Z] [49]
Canakinumab DM8HLO5 Moderate Additive immunosuppressive effects by the combination of Gemcitabine and Canakinumab. Rheumatoid arthritis [FA20] [66]
Rilonacept DMGLUQS Moderate Additive immunosuppressive effects by the combination of Gemcitabine and Rilonacept. Rheumatoid arthritis [FA20] [66]
Golimumab DMHZV7X Major Additive immunosuppressive effects by the combination of Gemcitabine and Golimumab. Rheumatoid arthritis [FA20] [67]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Gemcitabine and Leflunomide. Rheumatoid arthritis [FA20] [54]
Anthrax vaccine DM9GSWY Moderate Antagonize the effect of Gemcitabine when combined with Anthrax vaccine. Sepsis [1G40-1G41] [68]
Naltrexone DMUL45H Moderate Increased risk of hepatotoxicity by the combination of Gemcitabine and Naltrexone. Substance abuse [6C40] [69]
Azathioprine DMMZSXQ Moderate Additive immunosuppressive effects by the combination of Gemcitabine and Azathioprine. Transplant rejection [NE84] [62]
Cinoxacin DM4EWNS Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Cinoxacin. Urinary tract infection [GC08] [49]
Nalidixic acid DMRM0JV Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Nalidixic acid. Urinary tract infection [GC08] [49]
Enoxacin DMYTE6L Minor Decreased absorption of Gemcitabine due to intestinal mucosa variation caused by Enoxacin. Urinary tract infection [GC08] [49]
Ganciclovir DM1MBYQ Moderate Additive myelosuppressive effects by the combination of Gemcitabine and Ganciclovir. Virus infection [1A24-1D9Z] [62]
Valganciclovir DMS2IUH Moderate Additive myelosuppressive effects by the combination of Gemcitabine and Valganciclovir. Virus infection [1A24-1D9Z] [62]
⏷ Show the Full List of 43 DDI Information of This Drug

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