Gemcitabine hydrochloride
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1996
- First approval year
- 1996
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Gemcitabine hydrochloride
- Molecular weight
- 299.66
- Structure (SMILES)
- Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1
- gemcitabine hydrochloride
- Gemcitabine hydrochloride
- gemzar
- Gemzar
- infugem
- Infugem
- 2 deoxy 2 2 difluorocytidine monohydrochloride beta isomer
- 2'-DEOXY-2',2'-DIFLUOROCYTIDINE MONOHYDROCHLORIDE (.BETA.-ISOMER)
- avgemsi
- AVGEMSI
- cytidine 2 deoxy 2 2 difluoro monohydrochloride
- CYTIDINE, 2'-DEOXY-2',2'-DIFLUORO-, MONOHYDROCHLORIDE
- Gemcitabine (as hydrochloride)
- gemcitabine as hydrochloride
- gemcitabine hcl
- Gemcitabine hcl
- gemcitabine hydrochloride
- Gemcitabine hydrochloride
- GEMCITABINE HYDROCHLORIDE [EP MONOGRAPH]
- GEMCITABINE HYDROCHLORIDE [JAN]
- GEMCITABINE HYDROCHLORIDE [MART.]
- GEMCITABINE HYDROCHLORIDE [MI]
- GEMCITABINE HYDROCHLORIDE [ORANGE BOOK]
- GEMCITABINE HYDROCHLORIDE [USAN]
- GEMCITABINE HYDROCHLORIDE [USP MONOGRAPH]
- GEMCITABINE HYDROCHLORIDE [USP-RS]
- GEMCITABINE HYDROCHLORIDE [VANDF]
- Gemcitabine hydrochloride [WHO-DD]
- gemcitabine hydrochloride ep monograph
- gemcitabine hydrochloride jan
- gemcitabine hydrochloride mart
And 13 more, listed on the interactive page.
- ATC classification codes
- L01BC05
Sources for recorded values
- CAS registry numbers
- 122111-03-9
- ChEMBL ID
- CHEMBL1637
- InChIKey
- OKKDEIYWILRZIA-OSZBKLCCSA-N
- FDA ingredient codes (UNII)
- U347PV74IL
- 60749
- 44558863
- 135501939
- 12574
- 236234
- Applicant
- HOSPIRA INC
- Approval date
- 4 Aug 2011
- Application number
- NDA200795
- Patents
- 6
- Designations
- 1
- Earliest recorded loss of exclusivity
- 19 Aug 2034
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- Yes
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- United States (FDA)
- Approved
- Pharmacology name
- gemcitabine
- Type
- Synthetic organic
- Drug name stem
- -citabine
Administration routes
- Parenteral
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P09884
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P28340
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P49005
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P49642
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P49643
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- P56282
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q07864
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q14181
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q15054
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q9HCU8
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Protein identifier
- Q9NRF9
- Mechanism
- Ribonucleoside-diphosphate reductase RR1 inhibitor
- Action type
- Inhibitor
- Target
- Ribonucleoside-diphosphate reductase RR1
- Protein identifier
- P23921
- Mechanism
- Ribonucleoside-diphosphate reductase RR1 inhibitor
- Action type
- Inhibitor
- Target
- Ribonucleoside-diphosphate reductase RR1
- Protein identifier
- P31350
- Mechanism
- Ribonucleoside-diphosphate reductase RR1 inhibitor
- Action type
- Inhibitor
- Target
- Ribonucleoside-diphosphate reductase RR1
- Protein identifier
- Q7LG56
- Mechanism
- DNA polymerase (alpha/delta/epsilon) inhibitor
- Action type
- Inhibitor
- Target
- DNA polymerase (alpha/delta/epsilon)
- Mechanism
- Ribonucleoside-diphosphate reductase RR1 inhibitor
- Action type
- Inhibitor
- Target
- Ribonucleoside-diphosphate reductase RR1
- Condition
- Lymphoma, Follicular
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000096
- Subject identifier
- D008224
- Condition
- Hodgkin Disease
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000183
- Subject identifier
- D006689
- Condition
- Breast Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000305
- Subject identifier
- D001943
- Condition
- Carcinoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000313
- Subject identifier
- D002277
- Condition
- Lymphoma, Large B-Cell, Diffuse
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000403
- Subject identifier
- D016403
- Condition
- Leukemia
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000565
- Subject identifier
- D007938
- Condition
- Lymphoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000574
- Subject identifier
- D008223
- Condition
- Mesothelioma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000588
- Subject identifier
- D008654
- Condition
- Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Carcinoma, Renal Cell
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000681
- Subject identifier
- D002292
- Condition
- Sarcoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000691
- Subject identifier
- D012509
- Condition
- Carcinoma, Squamous Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000707
- Subject identifier
- D002294
- Condition
- Ovarian Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0001075
- Subject identifier
- D010051
- Condition
- Multiple Myeloma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0001378
- Subject identifier
- D009101
- Condition
- Uterine Cervical Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0001416
- Subject identifier
- D002583
- Condition
- Pancreatic Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0002618
- Subject identifier
- D010190
- Condition
- Lymphoma, T-Cell, Cutaneous
- Highest recorded phase
- 1
- Condition identifier
- EFO:0002913
- Subject identifier
- D016410
- Condition
- Carcinoma, Non-Small-Cell Lung
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003060
- Subject identifier
- D002289
- Condition
- Uterine Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003859
- Subject identifier
- D014594
- Condition
- Nasopharyngeal Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0004252
- Subject identifier
- D009303
- Condition
- Gallbladder Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0004606
- Subject identifier
- D005706
- Condition
- Triple Negative Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0005537
- Subject identifier
- D064726
- Condition
- Lymphoma, Non-Hodgkin
- Highest recorded phase
- 1
- Condition identifier
- EFO:0005952
- Subject identifier
- D008228
- Condition
- Leukemia, Plasma Cell
- Highest recorded phase
- 2
- Condition identifier
- EFO:0006475
- Subject identifier
- D007952
- Condition
- Plasmacytoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0006738
- Subject identifier
- D010954
And 36 more, listed on the interactive page.
- Condition identifier
- EFO_0000183
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000305
- Condition identifier
- EFO_0000313
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000403
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000565
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000574
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000588
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000616
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000691
- Highest recorded phase
- 2
- Condition identifier
- EFO_0001075
- Condition identifier
- EFO_0002618
- Condition identifier
- EFO_0003060
- Condition identifier
- EFO_0003826
- Highest recorded phase
- 2
- Condition identifier
- EFO_0004252
- Condition identifier
- EFO_0005537
- Highest recorded phase
- 3
- Condition identifier
- EFO_0006859
- Condition identifier
- EFO_0006861
- Highest recorded phase
- 2
- Condition identifier
- EFO_1000044
- Highest recorded phase
- 2
- Condition identifier
- EFO_1000359
- Highest recorded phase
- 3
- Condition identifier
- EFO_1000613
- Highest recorded phase
- 2
- Condition identifier
- EFO_1001973
- Highest recorded phase
- 2
- Condition identifier
- HP_0001907
- Highest recorded phase
- 3
- Condition identifier
- MONDO_0000430
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0000607
- Highest recorded phase
- 2
- Condition identifier
- MONDO_0000878
And 75 more, listed on the interactive page.
- Event
- anaemia
- Reports
- 1,390
- Reporting signal score
- 976.546
- Event
- capillary leak syndrome
- Reports
- 109
- Reporting signal score
- 265.864
- Event
- cholangitis
- Reports
- 275
- Reporting signal score
- 639.642
- Event
- disease progression
- Reports
- 1,245
- Reporting signal score
- 1,623.85
- Event
- febrile neutropenia
- Reports
- 743
- Reporting signal score
- 776.482
- Event
- general physical health deterioration
- Reports
- 479
- Reporting signal score
- 335.235
- Event
- haematotoxicity
- Reports
- 275
- Reporting signal score
- 505.333
- Event
- haemolytic uraemic syndrome
- Reports
- 236
- Reporting signal score
- 658.566
- Event
- leukopenia
- Reports
- 589
- Reporting signal score
- 569.97
- Event
- malignant neoplasm progression
- Reports
- 938
- Reporting signal score
- 1,299.54
- Event
- metastases to liver
- Reports
- 259
- Reporting signal score
- 427.304
- Event
- mucosal inflammation
- Reports
- 302
- Reporting signal score
- 284.349
- Event
- neoplasm progression
- Reports
- 302
- Reporting signal score
- 355.141
- Event
- neutropenia
- Reports
- 1,410
- Reporting signal score
- 1,339.18
- Event
- neutrophil count decreased
- Reports
- 347
- Reporting signal score
- 284.536
- Event
- pancytopenia
- Reports
- 508
- Reporting signal score
- 444.129
- Event
- platelet count decreased
- Reports
- 583
- Reporting signal score
- 318.521
- Event
- pleural effusion
- Reports
- 461
- Reporting signal score
- 367.394
- Event
- pneumonitis
- Reports
- 272
- Reporting signal score
- 279.617
- Event
- pyrexia
- Reports
- 1,341
- Reporting signal score
- 504.897
- Event
- recall phenomenon
- Reports
- 133
- Reporting signal score
- 409.398
- Event
- thrombocytopenia
- Reports
- 1,685
- Reporting signal score
- 2,023.29
- Event
- thrombotic microangiopathy
- Reports
- 497
- Reporting signal score
- 1,244.75
- NCT00002998
- NCT00003540
- NCT00005614
- NCT00005991
- NCT00006007
- NCT00006459
- NCT00027989
- NCT00039546
- NCT00059852
- NCT00070278
- NCT00095888
- NCT00100750
- NCT00323063
- NCT00408408
- NCT00470249
- NCT00662129
- NCT00679029
- NCT02479230
- NCT06079983
- NCT06143553
- NCT06255392
- NCT00003001
- NCT00007943
- NCT00276861
- NCT00496704
And 349 more, listed on the interactive page.
- Dose
- 1000 mg/m2
- Route
- Intravenous
- How often
- On Days 1 and 8 of each 21-day cycle
- Hydrogen bond acceptors
- 7
- Hydrogen bond donors
- 3
- Polar surface area
- 110.6
- Calculated partition coefficient (ALogP)
- -1.29
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Molecular formula
- C9H12ClF2N3O4
- Monoisotopic mass
- 299.0484399
- Natural product
- No
- 0143-9340
- 0143-9341
- 0143-9342
- 0409-0181
- 0409-0182
- 0409-0183
- 0409-0185
- 0409-0186
- 0409-0187
- 16714-909
- 16714-930
- 25021-234
- 25021-235
- 25021-239
- 55111-686
- 55111-687
- 63323-102
- 63323-125
- 63323-126
- 67457-616
- 67457-617
- 67457-618
- 68001-342
- 68001-348
- 68001-359
And 9 more, listed on the interactive page.
- Recorded assays
- 1,131
- Active assays
- 274
- Confirmatory
- Other
- Summary
- Antimetabolites, Antineoplastic
Related records
Trials (768)
- 24BRO681 : Alternating Gnp and mFOLFIRINOX for BR-PDAC
- 3-AP and Gemcitabine as Second-Line Therapy in Treating Patients With Stage III or Stage IV Recurrent Non-Small Cell Lung Cancer
- 3-AP and Gemcitabine in Treating Patients With Advanced Solid Tumors or Lymphoma
- 3-AP and Gemcitabine in Treating Patients With Metastatic Non-Small Cell Lung Cancer
- 3-AP and Gemcitabine in Treating Patients With Recurrent, Unresectable, or Metastatic Pancreatic Cancer
- 3-AP and Gemcitabine in Treating Patients With Refractory Metastatic Breast Cancer
- 3-AP and Gemcitabine in Treating Patients With Unresectable or Metastatic Pancreatic Cancer
- A Clinical Study of a Preoperative Translational Therapy for Unresectable Gallbladder Cancer
- A Clinical Study of AL2846 Capsule Combined With Gemzar Injection in the Treatment of Advanced Pancreatic Cancer
- A Clinical Trial of LBL-024 Combination Drug in Patients With Advanced Solid Tumours[Substudy 02(BTC&HCC)]
- A Clinical Trial to Evaluate Tolerability and Security of TQB2858 Injection in Subjects With Advanced Pancreatic Carcinoma
- A Phase 1 Dose Escalation and Dose Expansion Trial of KST-6051 in Participants With Advanced Solid Tumors With Kirsten Rat Sarcoma Viral Oncogene Homolog (KRAS) Mutation
- A Phase 1 Study of Pegilodecakin (LY3500518) in Participants With Advanced Solid Tumors
- A Phase 1/2 Study of VS-7375 in Patients With KRAS G12D-Mutated Solid Tumors
- A Phase 2 Study of siG12D LODER in Combination With Chemotherapy in Patients With Locally Advanced Pancreatic Cancer
- A Phase 2 Trial of Standard Chemotherapy, With or Without BSI-201, in Patients With Triple Negative Metastatic Breast Cancer
- A Phase 3 Clinical Study of SHR-A1912 Combined With R-GemOx Versus R-GemOx in Diffuse Large B-cell Lymphoma
- A Phase 3 Trial of ALIMTA (LY231514, Pemetrexed) Plus GEMZAR Versus GEMZAR in Patients With Unresectable or Metastatic Cancer of the Pancreas.
- A Phase 3, Multi-Center Study of Gemcitabine/Carboplatin, With or Without BSI-201, in Patients With ER-, PR-, and Her2-Negative Metastatic Breast Cancer
- A Phase I Study of Adjuvant Chemotherapy With GC in Biliary Tract Cancer Undergoing Resection Without Major Hepatectomy
Approved for (7)
- Breast cancer
- Breast carcinoma
- Exocrine pancreatic carcinoma
- Malignant pancreatic neoplasm
- Non-small cell lung carcinoma
- Ovarian cancer
- Ovarian carcinoma
In development for (88)
- Acute monocytic leukemia Phase 2
- Adenocarcinoma Phase 2
- Biliary tract cancer Phase 3
- Bladder transitional cell carcinoma Phase 3
- Cancer Phase 3
- Carcinoma Phase 2
- Carcinoma of duodenum Phase 1
- Carcinoma of the ampulla of vater Phase 1
- Cervical adenocarcinoma Phase 3
- Cervical cancer Phase 3
- Cholangiocarcinoma Phase 3
- Chronic myeloid leukemia Phase 2
- Chronic myelomonocytic leukemia Phase 2
- Colorectal cancer Phase 2
- Diffuse large B-cell lymphoma Phase 2
- Duodenum cancer Phase 1
- Endometrial cancer Phase 1
- Endometrium adenocarcinoma Phase 2
- Fallopian tube cancer Phase 2
- Fallopian tube carcinoma Phase 2
Other linked conditions (1)
- Cytomegalovirus retinitis
Targets (14)
- POLA1 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLA2 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLD1 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLD2 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLD3 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLD4 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLE DNA polymerase (alpha/delta/epsilon) inhibitor
- POLE2 DNA polymerase (alpha/delta/epsilon) inhibitor
- POLE3 DNA polymerase (alpha/delta/epsilon) inhibitor
- PRIM1 DNA polymerase (alpha/delta/epsilon) inhibitor
- PRIM2 DNA polymerase (alpha/delta/epsilon) inhibitor
- RRM1 Ribonucleoside-diphosphate reductase RR1 inhibitor
- RRM2 Ribonucleoside-diphosphate reductase RR1 inhibitor
- RRM2B Ribonucleoside-diphosphate reductase RR1 inhibitor