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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL888
CHEMBL888
Compound Name GEMCITABINE
ChEMBL Synonyms GEMCITABINE | LY-188011 | GEMCITABINE HYDROCHLORIDE | GEMZAR | Gemzar
Max Phase 4 (Approved)
Trade Names GEMZAR | GEMCITABINE HYDROCHLORIDE
Molecular Formula C9H11F2N3O4

Additional synonyms for CHEMBL888 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)C2(F)F
Standard InChI InChI=1S/C9H11F2N3O4/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12 ...
Download InChI
Standard InChI Key SDUQYLNIPVEERB-QPPQHZFASA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL888

Molecule Features

CHEMBL888 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:Y Oral:N Parenteral:Y Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA polymerase (alpha/delta/epsilon) inhibitor DNA polymerase (alpha/delta/epsilon) DailyMed
Ribonucleoside-diphosphate reductase RR1 inhibitor Ribonucleoside-diphosphate reductase RR1 DailyMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Bile Duct NeoplasmsD001650EFO:0005540bile duct carcinoma1ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
ClinicalTrials
Peritoneal NeoplasmsD010534EFO:1001100peritoneal neoplasm2ClinicalTrials
ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001416cervical adenocarcinoma3ClinicalTrials
Biliary Tract NeoplasmsD001661EFO:0003891biliary tract neoplasm3ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma3ClinicalTrials
ClinicalTrials
CholangiocarcinomaD018281EFO:0005221cholangiocarcinoma3ClinicalTrials
Head and Neck NeoplasmsD006258EFO:0006859head and neck malignant neoplasia2ClinicalTrials
ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma2ClinicalTrials
ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
ClinicalTrials
Nasopharyngeal NeoplasmsD009303EFO:0004252nasopharyngeal neoplasm3ClinicalTrials
ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0003860pancreatic neoplasm3ClinicalTrials
Ureteral NeoplasmsD014516EFO:0003844ureteral neoplasm2ClinicalTrials
AdenocarcinomaD000230EFO:0000228adenocarcinoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma4ClinicalTrials
ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
Colonic NeoplasmsD003110EFO:1001950colon carcinoma2ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma2ClinicalTrials
Gallbladder NeoplasmsD005706EFO:1001956gallbladder carcinoma2ClinicalTrials
Immunoblastic LymphadenopathyD007119EFO:0000255angioimmunoblastic T-cell lymphoma2ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma2ClinicalTrials
MesotheliomaD008654EFO:0000588mesothelioma3ClinicalTrials
ClinicalTrials
OsteosarcomaD012516EFO:0000637osteosarcoma2ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma4ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000707squamous cell carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0005842colorectal cancer2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma2ClinicalTrials
ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000209T-cell acute lymphoblastic leukemia2ClinicalTrials
Lymphoma, T-Cell, PeripheralD016411EFO:0000211unspecified peripheral T-cell lymphoma3ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor2ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma2ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma3ClinicalTrials
ClinicalTrials
Lymphoproliferative DisordersD0082321ClinicalTrials
Triple Negative Breast NeoplasmsD064726EFO:0005537triple-negative breast cancer3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000708squamous cell lung carcinoma3ClinicalTrials
LeiomyosarcomaD007890EFO:0000564leiomyosarcoma2ClinicalTrials
Lymphoma, Large-Cell, AnaplasticD017728EFO:0003032anaplastic large cell lymphoma2ClinicalTrials
Lymphoma, T-Cell, CutaneousD016410EFO:0002913Cutaneous T-cell lymphoma1ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma1ClinicalTrials
Thyroid NeoplasmsD013964EFO:0002892thyroid carcinoma2ClinicalTrials
Vulvar NeoplasmsD014846EFO:0002921vulvar carcinoma2ClinicalTrials
Carcinoma, Pancreatic DuctalD021441EFO:0002517pancreatic ductal adenocarcinoma3ClinicalTrials
ClinicalTrials
Fallopian Tube NeoplasmsD005185EFO:1000251Fallopian Tube Carcinoma2ClinicalTrials
ClinicalTrials
Gallbladder NeoplasmsD005706EFO:0004606gallbladder neoplasm2ClinicalTrials
ClinicalTrials
Gastrointestinal Stromal TumorsD046152Orphanet:44890Gastrointestinal stromal tumor1ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
ClinicalTrials
MelanomaD008545EFO:0000756melanoma2ClinicalTrials
MesotheliomaD008654EFO:0000770malignant pleural mesothelioma3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ClinicalTrials
ATC
ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma4ClinicalTrials
ClinicalTrials
DailyMed
DailyMed
DailyMed
DailyMed
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer2ClinicalTrials
Urethral NeoplasmsD014523EFO:0003846urethral neoplasm3ClinicalTrials
ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000294bladder tumor3ClinicalTrials
Urogenital NeoplasmsD014565EFO:0003863urogenital neoplasm3ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma3ClinicalTrials
ClinicalTrials
Carcinoma, EndometrioidD018269EFO:0000466endometrioid carcinoma2ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
Ovarian NeoplasmsD010051Orphanet:398934Malignant epithelial tumor of ovary3ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia0ClinicalTrials
Testicular NeoplasmsD013736EFO:0005088testicular carcinoma2ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma2ClinicalTrials
Hereditary Breast and Ovarian Cancer SyndromeD061325Orphanet:145Hereditary breast and ovarian cancer syndrome1ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm3ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma3ClinicalTrials
ClinicalTrials
Carcinoma, Large CellD018287EFO:0003050large cell lung carcinoma2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma4ClinicalTrials
ClinicalTrials
DailyMed
CholangiocarcinomaD018281EFO:1001961intrahepatic cholangiocarcinoma3ClinicalTrials
ClinicalTrials
Colorectal NeoplasmsD015179EFO:0000365colorectal adenocarcinoma2ClinicalTrials
Endometrial NeoplasmsD016889EFO:0004230endometrial neoplasm2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Ovarian NeoplasmsD010051EFO:0003893ovarian neoplasm3ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov GEMCITABINE
The Cochrane Collaboration GEMCITABINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL888. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL226 Adenosine A1 receptor Homo sapiens 0.987
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 0.972
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.747
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 0.543
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 0.272

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL4696 Glycogen phosphorylase, muscle form Oryctolagus cuniculus 1.000
CHEMBL318 Adenosine A1 receptor Rattus norvegicus 0.990
CHEMBL1795127 Thymidine kinase Human herpesvirus 1 0.986
CHEMBL226 Adenosine A1 receptor Homo sapiens 0.984
CHEMBL302 Adenosine A2a receptor Rattus norvegicus 0.936
CHEMBL4398 Purinergic receptor P2Y2 Homo sapiens 0.689
CHEMBL5328 Thymidylate synthase Lactobacillus casei 0.645
CHEMBL4714 Pyrimidinergic receptor P2Y6 Homo sapiens 0.621
CHEMBL251 Adenosine A2a receptor Homo sapiens 0.610
CHEMBL2284 Glyceraldehyde-3-phosphate dehydrogenase liver Homo sapiens 0.537
CHEMBL247 Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 0.359
CHEMBL256 Adenosine A3 receptor Homo sapiens 0.208

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
263.2 263.0718 -1.29 2 110.6 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
7 3 0 7 4 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
11.65 4.26 -2.22 -2.22 1 18 0.61

Structural Alerts

There are no structural alerts for CHEMBL888

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01B - ANTIMETABOLITES
L01BC - Pyrimidine analogues
L01BC05 - gemcitabine

ChemSpider ChemSpider:SDUQYLNIPVEERB-QPPQHZFASA-N
DailyMed gemcitabine hydrochloride
PubChem SID: 124893555 SID: 50113286
Wikipedia Gemcitabine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL888



ACToR 95058-81-4
Brenda 72075 2896 40092 149830 154426 16928 1899 153436 29312
ChEBI 175901
ChemicalBook CB4438054
DrugBank DB00441
DrugCentral 1283
EPA CompTox Dashboard DTXSID3040487
FDA SRS B76N6SBZ8R
Guide to Pharmacology 4793
Human Metabolome Database HMDB0014584
IBM Patent System EEFC7DF5CF77B5C2F141464BA4BD72BB
KEGG Ligand C07650
LINCS LSM-5333
MolPort MolPort-003-987-478
Nikkaji J357.909C
PDBe GEO
PharmGKB PA449748
PubChem 60750
PubChem: Thomson Pharma 15221618 15197115
Selleck Gemcitabine(Gemzar)
SureChEMBL SCHEMBL4295
ZINC ZINC000018279854

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/SDUQYLNIPVEERB-QPPQHZFASA-N spacer
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