gemcitabine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
nucleosides antiviral or antineoplastic agents, cytarabine or azacitidine derivatives 1283 95058-81-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • gemcitabine
  • gamcitabine
  • gemcitabine hydrochloride
  • gemcitabine HCl
Gemcitabine kills cells undergoing DNA synthesis and blocks the progression of cells through the G1/S-phase boundary. Gemcitabine is metabolized by nucleoside kinases to diphosphate (dFdCDP) and triphosphate (dFdCTP) nucleosides. Gemcitabine diphosphate inhibits ribonucleotide reductase, an enzyme responsible for catalyzing the reactions that generate deoxynucleoside triphosphates for DNA synthesis, resulting in reductions in deoxynucleotide concentrations, including dCTP. Gemcitabine triphosphate competes with dCTP for incorporation into DNA. The reduction in the intracellular concentration of dCTP by the action of the diphosphate enhances the incorporation of gemcitabine triphosphate into DNA (selfpotentiation). After the gemcitabine nucleotide is incorporated into DNA, only one additional nucleotide is added to the growing DNA strands, which eventually results in the initiation of apoptotic cell death.
  • Molecular weight: 263.20
  • Formula: C9H11F2N3O4
  • CLOGP: -0.71
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 108.38
  • ALOGS: -1.07
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 15 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 8 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 93.90 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 32 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 18, 2019 PMDA Eli Lilly Japan K.K.
May 15, 1996 FDA LILLY

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Thrombocytopenia 1861.62 49.66 584 7754 18547 2331200
Malignant neoplasm progression 1681.30 49.66 487 7851 11641 2338106
Neutropenia 1491.94 49.66 509 7829 21039 2328708
Anaemia 1408.46 49.66 553 7785 34239 2315508
Pyrexia 1105.86 49.66 530 7808 53178 2296569
Disease progression 1065.13 49.66 374 7964 16721 2333026
Vomiting 1040.31 49.66 558 7780 71044 2278703
Nausea 924.95 49.66 606 7732 111583 2238164
Thrombotic microangiopathy 793.72 49.66 173 8165 1174 2348573
Pleural effusion 747.24 49.66 261 8077 11407 2338340
Haemolytic uraemic syndrome 679.20 49.66 133 8205 481 2349266
Abdominal pain 628.30 49.66 314 8024 34060 2315687
Platelet count decreased 624.01 49.66 248 8090 15565 2334182
Dehydration 612.31 49.66 270 8068 22025 2327722
Febrile neutropenia 603.83 49.66 219 8119 10663 2339084
Diarrhoea 588.10 49.66 411 7927 83153 2266594
Dyspnoea 574.36 49.66 396 7942 78337 2271410
Ascites 561.16 49.66 176 8162 5444 2344303
General physical health deterioration 489.50 49.66 202 8136 13937 2335810
Asthenia 478.88 49.66 292 8046 46634 2303113
Pulmonary embolism 441.67 49.66 202 8136 17881 2331866
Leukopenia 440.64 49.66 171 8167 10025 2339722
Metastases to liver 440.34 49.66 126 8212 2815 2346932
Interstitial lung disease 432.10 49.66 157 8181 7655 2342092
Haemoglobin decreased 431.52 49.66 199 8139 17952 2331795
Pneumonia 425.59 49.66 276 8062 49020 2300727
Posterior reversible encephalopathy syndrome 406.26 49.66 114 8224 2366 2347381
Acute kidney injury 404.09 49.66 219 8119 27903 2321844
Sepsis 403.24 49.66 191 8147 18297 2331450
Pancytopenia 397.43 49.66 164 8174 11288 2338459
Haematotoxicity 382.06 49.66 93 8245 1074 2348673
Fatigue 368.27 49.66 314 8024 84559 2265188
Oedema peripheral 366.31 49.66 194 8144 23569 2326178
Neoplasm progression 362.91 49.66 121 8217 4547 2345200
White blood cell count decreased 360.28 49.66 176 8162 18032 2331715
Neutrophil count decreased 355.67 49.66 130 8208 6437 2343310
Bone marrow failure 331.97 49.66 119 8219 5567 2344180
Cholangitis 328.97 49.66 78 8260 798 2348949
Pneumonitis 323.12 49.66 107 8231 3932 2345815
Pseudocirrhosis 297.57 49.66 51 8287 62 2349685
Decreased appetite 296.93 49.66 181 8157 28710 2321037
Acute myeloid leukaemia 295.94 49.66 91 8247 2619 2347128
Neuropathy peripheral 295.47 49.66 133 8205 11299 2338448
Recall phenomenon 290.00 49.66 55 8283 159 2349588
Capillary leak syndrome 287.38 49.66 60 8278 319 2349428
Deep vein thrombosis 279.79 49.66 133 8205 12799 2336948
Thrombotic thrombocytopenic purpura 268.26 49.66 65 8273 734 2349013
Hypertension 259.69 49.66 163 8175 27198 2322549
Aspartate aminotransferase increased 258.51 49.66 125 8213 12487 2337260
Death 246.74 49.66 247 8091 81221 2268526
Metastases to lung 244.84 49.66 71 8267 1660 2348087
Metastases to bone 242.68 49.66 75 8263 2194 2347553
Alanine aminotransferase increased 237.13 49.66 122 8216 13910 2335837
Pancreatic carcinoma metastatic 229.71 49.66 52 8286 425 2349322
Renal failure 229.08 49.66 128 8210 17221 2332526
Off label use 222.42 49.66 223 8115 73375 2276372
Blood alkaline phosphatase increased 214.20 49.66 90 8248 6455 2343292
Neutropenic sepsis 203.27 49.66 59 8279 1383 2348364
Constipation 200.41 49.66 127 8211 21502 2328245
Pulmonary toxicity 195.63 49.66 49 8289 640 2349107
Respiratory failure 192.78 49.66 105 8233 13423 2336324
Cellulitis 190.87 49.66 92 8246 9109 2340638
Chills 189.75 49.66 109 8229 15443 2334304
Hepatic failure 188.72 49.66 79 8259 5610 2344137
Mucosal inflammation 188.37 49.66 77 8261 5147 2344600
Tachycardia 181.69 49.66 108 8230 16301 2333446
Pulmonary oedema 181.65 49.66 83 8255 7280 2342467
Pericardial effusion 179.14 49.66 69 8269 3940 2345807
Hypoxia 178.58 49.66 78 8260 6149 2343598
Metastases to central nervous system 176.07 49.66 58 8280 2090 2347657
Cough 168.69 49.66 135 8203 32982 2316765
Palmar-plantar erythrodysaesthesia syndrome 162.02 49.66 65 8273 4136 2345611
Blood creatinine increased 161.90 49.66 86 8252 10447 2339300
Blood bilirubin increased 159.94 49.66 69 8269 5276 2344471
Septic shock 159.92 49.66 75 8263 6979 2342768
Pancreatic carcinoma 156.00 49.66 48 8290 1381 2348366
Metastases to lymph nodes 155.59 49.66 44 8294 936 2348811
Generalised oedema 154.19 49.66 54 8284 2349 2347398
Hypokalaemia 152.58 49.66 83 8255 10571 2339176
Infection 150.01 49.66 99 8239 17930 2331817
Myositis 146.39 49.66 45 8293 1290 2348457
Urinary tract infection 145.95 49.66 119 8219 29823 2319924
Hypotension 145.82 49.66 123 8215 32313 2317434
Breast cancer metastatic 144.58 49.66 50 8288 2094 2347653
Thrombocytosis 139.87 49.66 40 8298 887 2348860
Lung infiltration 134.31 49.66 48 8290 2216 2347531
Epistaxis 133.98 49.66 74 8264 9705 2340042
Biliary sepsis 132.36 49.66 25 8313 70 2349677
Hypoalbuminaemia 131.99 49.66 42 8296 1352 2348395
Rash 131.23 49.66 153 8185 59405 2290342
Erythema 131.08 49.66 104 8234 25055 2324692
Toxicity to various agents 130.60 49.66 116 8222 32638 2317109
Confusional state 125.46 49.66 100 8238 24244 2325503
Blood lactate dehydrogenase increased 124.35 49.66 51 8287 3433 2346314
Acute respiratory distress syndrome 123.69 49.66 50 8288 3242 2346505
Colitis 122.87 49.66 57 8281 5169 2344578
Disseminated intravascular coagulation 122.85 49.66 50 8288 3300 2346447
Stomatitis 120.86 49.66 69 8269 9641 2340106
Haematocrit decreased 120.23 49.66 53 8285 4265 2345482
Gastrointestinal haemorrhage 120.00 49.66 75 8263 12360 2337387
Oedema 117.68 49.66 69 8269 10134 2339613
Jaundice 113.92 49.66 55 8283 5453 2344294
Chronic kidney disease 112.90 49.66 50 8288 4068 2345679
Small intestinal obstruction 112.84 49.66 42 8296 2178 2347569
Metastases to peritoneum 112.40 49.66 29 8309 429 2349318
Portal hypertension 111.79 49.66 30 8308 521 2349226
Performance status decreased 107.76 49.66 30 8308 601 2349146
Peripheral ischaemia 107.27 49.66 31 8307 714 2349033
Dyspnoea exertional 106.01 49.66 53 8285 5667 2344080
Pain 105.82 49.66 140 8198 61717 2288030
Atrial fibrillation 105.80 49.66 72 8266 13696 2336051
Device occlusion 104.00 49.66 31 8307 798 2348949
Pneumothorax 103.98 49.66 40 8298 2272 2347475
Hypophagia 101.46 49.66 46 8292 3954 2345793
Hyponatraemia 100.77 49.66 69 8269 13256 2336491
Malaise 98.44 49.66 128 8210 55457 2294290
Polyneuropathy 95.66 49.66 35 8303 1728 2348019
Metastases to skin 94.57 49.66 22 8316 205 2349542
Intestinal obstruction 94.28 49.66 45 8293 4348 2345399
Cholestasis 91.88 49.66 42 8296 3679 2346068
Chest pain 91.48 49.66 89 8249 28048 2321699
Nephrotic syndrome 90.68 49.66 30 8308 1094 2348653
Pneumocystis jirovecii pneumonia 90.49 49.66 36 8302 2237 2347510
Hypocalcaemia 90.17 49.66 42 8296 3841 2345906
Cardiomyopathy 89.76 49.66 38 8300 2769 2346978
Proteinuria 89.20 49.66 38 8300 2812 2346935
Neurotoxicity 85.72 49.66 34 8304 2096 2347651
Ileus 85.07 49.66 34 8304 2138 2347609
Hepatotoxicity 85.03 49.66 39 8299 3442 2346305
Ovarian cancer recurrent 84.43 49.66 20 8318 203 2349544
Cardiac failure 82.96 49.66 59 8279 12035 2337712
Gastrointestinal toxicity 82.66 49.66 24 8314 562 2349185
Lung disorder 82.28 49.66 46 8292 6166 2343581
Neoplasm malignant 82.21 49.66 43 8295 5050 2344697
Second primary malignancy 81.76 49.66 27 8311 979 2348768
Subacute cutaneous lupus erythematosus 81.60 49.66 22 8316 389 2349358
Abdominal pain upper 81.55 49.66 75 8263 22025 2327722
Blood albumin decreased 80.52 49.66 31 8307 1764 2347983
Myelodysplastic syndrome 79.67 49.66 34 8304 2526 2347221
Ovarian cancer 78.48 49.66 28 8310 1285 2348462
Lymphoedema 78.33 49.66 27 8311 1118 2348629
Cerebral ischaemia 77.31 49.66 27 8311 1163 2348584
C-reactive protein increased 76.60 49.66 44 8294 6211 2343536
Breast cancer 76.13 49.66 51 8287 9444 2340303
Carbohydrate antigen 19-9 increased 75.10 49.66 15 8323 61 2349686
Encephalopathy 75.02 49.66 39 8299 4522 2345225
Blood sodium decreased 73.43 49.66 34 8304 3066 2346681
Hepatitis 73.41 49.66 43 8295 6294 2343453
Cerebral infarction 73.15 49.66 38 8300 4399 2345348
Embolism 70.99 49.66 26 8312 1287 2348460
Multiple organ dysfunction syndrome 70.95 49.66 45 8293 7596 2342151
Syncope 69.60 49.66 61 8277 16814 2332933
Product use in unapproved indication 68.53 49.66 51 8287 11149 2338598
Skin necrosis 67.14 49.66 24 8314 1107 2348640
White blood cell count increased 66.50 49.66 42 8296 7036 2342711
Drug ineffective 65.20 49.66 149 8189 101475 2248272
Haemolysis 64.89 49.66 23 8315 1035 2348712
Hepatocellular injury 64.76 49.66 34 8304 4021 2345726
Troponin increased 64.55 49.66 23 8315 1051 2348696
Tumour lysis syndrome 64.53 49.66 23 8315 1052 2348695
Biliary tract infection 64.30 49.66 13 8325 57 2349690
Jaundice cholestatic 64.07 49.66 20 8318 603 2349144
Gamma-glutamyltransferase increased 62.48 49.66 37 8301 5525 2344222
Enterocolitis 62.12 49.66 21 8317 819 2348928
Gastric ulcer 61.99 49.66 30 8308 2986 2346761
Erysipelas 61.83 49.66 22 8316 1001 2348746
Peripheral sensory neuropathy 61.69 49.66 22 8316 1008 2348739
Left ventricular dysfunction 61.33 49.66 23 8315 1217 2348530
Transaminases increased 60.83 49.66 34 8304 4553 2345194
Acute myocardial infarction 60.40 49.66 35 8303 5020 2344727
Mental status changes 59.75 49.66 36 8302 5546 2344201
Microangiopathic haemolytic anaemia 59.65 49.66 14 8324 136 2349611
Thrombosis 59.01 49.66 43 8295 9101 2340646
Hyperglycaemia 58.83 49.66 34 8304 4851 2344896
Pain in extremity 58.75 49.66 87 8251 42453 2307294
Cardiac failure congestive 58.12 49.66 54 8284 16047 2333700
Post thrombotic syndrome 57.87 49.66 13 8325 102 2349645
Platelet count increased 57.58 49.66 26 8312 2211 2347536
Pseudocellulitis 57.06 49.66 9 8329 3 2349744
Blood urea increased 56.92 49.66 30 8308 3575 2346172
Breast cancer recurrent 56.22 49.66 19 8319 740 2349007
Haematemesis 56.16 49.66 31 8307 4051 2345696
Extremity necrosis 55.85 49.66 15 8323 261 2349486
Dizziness 55.35 49.66 101 8237 58564 2291183
Disease recurrence 55.29 49.66 29 8309 3422 2346325
Renal impairment 55.22 49.66 43 8295 10049 2339698
Desmoplastic small round cell tumour 55.05 49.66 9 8329 6 2349741
Hypovolaemia 54.75 49.66 21 8317 1182 2348565
Respiratory distress 54.70 49.66 33 8305 5096 2344651
Lethargy 53.95 49.66 40 8298 8690 2341057
Muscular weakness 53.84 49.66 50 8288 14847 2334900
Hydronephrosis 53.69 49.66 21 8317 1246 2348501
Enteritis 53.18 49.66 20 8318 1066 2348681
International normalised ratio increased 53.09 49.66 37 8301 7299 2342448
Left ventricular failure 53.09 49.66 18 8320 708 2349039
Neutrophil count abnormal 52.97 49.66 16 8322 431 2349316
Seizure 52.27 49.66 62 8276 24404 2325343
Paraesthesia 52.26 49.66 59 8279 22029 2327718
Abdominal distension 51.91 49.66 42 8296 10369 2339378
Hypertransaminasaemia 51.50 49.66 17 8321 615 2349132
Lymphadenopathy 51.50 49.66 33 8305 5665 2344082
Drug resistance 50.63 49.66 25 8313 2599 2347148
Vasculitis 50.50 49.66 24 8314 2294 2347453
Liver function test abnormal 50.09 49.66 36 8302 7454 2342293
Haemoglobin abnormal 49.92 49.66 17 8321 678 2349069

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Thrombocytopenia 1991.03 51.00 732 8480 20517 1717052
Malignant neoplasm progression 1350.93 51.00 496 8716 13662 1723907
Pyrexia 1291.42 51.00 681 8531 45719 1691850
Anaemia 1277.91 51.00 586 8626 28871 1708698
Neutropenia 1118.22 51.00 464 8748 17796 1719773
Febrile neutropenia 832.55 51.00 327 8885 10773 1726796
Interstitial lung disease 799.22 51.00 306 8906 9390 1728179
Nausea 715.59 51.00 484 8728 50712 1686857
Disease progression 699.63 51.00 329 8883 16934 1720635
Pneumonia 699.05 51.00 459 8753 45723 1691846
Platelet count decreased 697.73 51.00 324 8888 16199 1721370
Cholangitis 675.63 51.00 166 9046 1023 1736546
Thrombotic microangiopathy 666.54 51.00 167 9045 1128 1736441
Pancytopenia 643.90 51.00 274 8938 11083 1726486
Dehydration 622.64 51.00 306 8906 17352 1720217
Pleural effusion 590.03 51.00 256 8956 10854 1726715
Sepsis 588.99 51.00 304 8908 19134 1718435
Vomiting 576.60 51.00 380 8832 37935 1699634
Dyspnoea 570.91 51.00 425 8787 51634 1685935
General physical health deterioration 543.02 51.00 254 8958 12864 1724705
Haemolytic uraemic syndrome 503.79 51.00 109 9103 338 1737231
Leukopenia 491.41 51.00 208 9004 8272 1729297
Pulmonary embolism 464.66 51.00 228 8984 12831 1724738
Decreased appetite 464.17 51.00 279 8933 23592 1713977
Abdominal pain 451.22 51.00 264 8948 21226 1716343
Neoplasm progression 449.45 51.00 151 9061 3116 1734453
Bone marrow failure 437.80 51.00 167 9045 5033 1732536
Oedema peripheral 424.20 51.00 227 8985 15323 1722246
White blood cell count decreased 421.73 51.00 214 8998 12935 1724634
Asthenia 421.60 51.00 302 8910 34368 1703201
Acute kidney injury 417.16 51.00 301 8911 34643 1702926
Diarrhoea 412.86 51.00 357 8855 53495 1684074
Pneumonitis 403.85 51.00 146 9066 3769 1733800
Haemoglobin decreased 387.54 51.00 221 8991 16893 1720676
Deep vein thrombosis 385.18 51.00 184 9028 9736 1727833
Neutrophil count decreased 371.53 51.00 155 9057 5926 1731643
Fatigue 363.49 51.00 324 8888 50457 1687112
Ascites 339.90 51.00 142 9070 5444 1732125
Neutropenic sepsis 333.95 51.00 100 9112 1392 1736177
Pancreatic carcinoma 315.24 51.00 99 9113 1630 1735939
Neuropathy peripheral 309.24 51.00 155 9057 9098 1728471
Pancreatic carcinoma metastatic 300.36 51.00 76 9136 534 1737035
Renal failure 293.45 51.00 196 9016 19821 1717748
Off label use 289.15 51.00 253 8959 38318 1699251
Respiratory failure 282.38 51.00 170 9042 14335 1723234
Metastases to liver 258.00 51.00 91 9121 2176 1735393
Disseminated intravascular coagulation 233.65 51.00 96 9116 3518 1734051
Infection 233.07 51.00 142 9070 12218 1725351
Chills 227.38 51.00 137 9075 11550 1726019
Mucosal inflammation 220.42 51.00 96 9116 4073 1733496
Peripheral ischaemia 193.39 51.00 58 9154 810 1736759
Thrombocytosis 193.07 51.00 54 9158 579 1736990
Haematotoxicity 191.98 51.00 59 9153 899 1736670
Constipation 184.49 51.00 132 9080 14868 1722701
Epistaxis 176.16 51.00 103 9109 8203 1729366
Recall phenomenon 173.57 51.00 37 9175 104 1737465
Bacteraemia 171.07 51.00 64 9148 1816 1735753
Lung disorder 168.58 51.00 85 9127 5034 1732535
Pulmonary toxicity 165.27 51.00 51 9161 788 1736781
Blood alkaline phosphatase increased 164.48 51.00 84 9128 5111 1732458
Hypoxia 159.14 51.00 86 9126 5877 1731692
Pseudocellulitis 157.29 51.00 27 9185 6 1737563
Device occlusion 156.41 51.00 50 9162 872 1736697
Cardiac failure 152.83 51.00 110 9102 12492 1725077
Death 150.69 51.00 274 8938 87169 1650400
Tumour lysis syndrome 149.85 51.00 57 9155 1694 1735875
Septic shock 149.72 51.00 92 9120 8017 1729552
Generalised oedema 149.60 51.00 57 9155 1702 1735867
Hyponatraemia 145.84 51.00 94 9118 8906 1728663
Blood creatinine increased 145.06 51.00 111 9101 13835 1723734
Pain 141.93 51.00 145 9067 26512 1711057
C-reactive protein increased 140.86 51.00 79 9133 5806 1731763
Haemoptysis 140.44 51.00 74 9138 4802 1732767
Liver abscess 139.84 51.00 42 9170 589 1736980
Urinary tract infection 137.88 51.00 95 9117 10058 1727511
Pneumocystis jirovecii pneumonia 134.47 51.00 58 9154 2398 1735171
Alanine aminotransferase increased 132.69 51.00 100 9112 12178 1725391
Hypotension 132.56 51.00 147 9065 29507 1708062
Jaundice cholestatic 126.85 51.00 42 9170 822 1736747
Blood bilirubin increased 126.33 51.00 75 9137 6135 1731434
Cerebral infarction 124.85 51.00 70 9142 5139 1732430
Atrial fibrillation 124.63 51.00 105 9107 15006 1722563
Metastases to lung 124.29 51.00 48 9164 1487 1736082
Cytopenia 123.55 51.00 42 9170 894 1736675
Alopecia 122.60 51.00 62 9150 3691 1733878
Capillary leak syndrome 120.63 51.00 32 9180 276 1737293
Rash 119.44 51.00 159 9053 38534 1699035
Aspartate aminotransferase increased 117.07 51.00 88 9124 10668 1726901
Acute respiratory distress syndrome 116.98 51.00 59 9153 3492 1734077
Gastrointestinal haemorrhage 115.30 51.00 98 9114 14169 1723400
Colitis 113.48 51.00 61 9151 4119 1733450
Cellulitis 113.32 51.00 71 9141 6397 1731172
Chest pain 112.63 51.00 112 9100 19802 1717767
Myositis 111.81 51.00 45 9167 1558 1736011
Blood lactate dehydrogenase increased 109.30 51.00 57 9155 3618 1733951
Product use in unapproved indication 109.06 51.00 80 9132 9342 1728227
Confusional state 108.20 51.00 113 9099 21165 1716404
Weight decreased 107.16 51.00 116 9096 22637 1714932
Oedema 106.22 51.00 70 9142 6878 1730691
Jaundice 104.83 51.00 66 9146 5996 1731573
Bile duct obstruction 104.39 51.00 31 9181 417 1737152
Extremity necrosis 102.20 51.00 28 9184 276 1737293
Hypophagia 97.63 51.00 52 9160 3445 1734124
Atelectasis 97.17 51.00 43 9169 1891 1735678
Device related infection 96.44 51.00 45 9167 2241 1735328
Pericardial effusion 96.31 51.00 51 9161 3339 1734230
Renal impairment 96.24 51.00 83 9129 12231 1725338
Pulmonary oedema 95.00 51.00 64 9148 6522 1731047
Platelet count increased 94.39 51.00 40 9172 1581 1735988
Malaise 93.44 51.00 123 9089 29442 1708127
Non-small cell lung cancer 92.47 51.00 31 9181 631 1736938
Erythema 91.86 51.00 86 9126 14102 1723467
Stomatitis 91.34 51.00 58 9154 5346 1732223
Pulmonary fibrosis 89.54 51.00 44 9168 2460 1735109
Performance status decreased 89.01 51.00 31 9181 711 1736858
Malignant ascites 88.51 51.00 21 9191 108 1737461
Biliary tract infection 84.58 51.00 19 9193 73 1737496
Drug ineffective 82.88 51.00 178 9034 63623 1673946
White blood cell count increased 82.14 51.00 61 9151 7251 1730318
Hepatic failure 81.88 51.00 56 9156 5847 1731722
Lung infiltration 80.38 51.00 39 9173 2120 1735449
Haematocrit decreased 80.13 51.00 49 9163 4224 1733345
Gamma-glutamyltransferase increased 79.45 51.00 52 9160 5046 1732523
Hepatocellular injury 78.97 51.00 44 9168 3187 1734382
Hypertransaminasaemia 78.50 51.00 26 9186 509 1737060
Hyperbilirubinaemia 78.25 51.00 39 9173 2248 1735321
Pneumothorax 77.60 51.00 41 9171 2671 1734898
Neurotoxicity 76.67 51.00 37 9175 1987 1735582
Carbohydrate antigen 19-9 increased 76.37 51.00 17 9195 62 1737507
Transaminases increased 76.23 51.00 46 9166 3871 1733698
Multiple organ dysfunction syndrome 75.66 51.00 64 9148 9178 1728391
Aortic thrombosis 75.22 51.00 20 9192 174 1737395
Hepatic function abnormal 74.98 51.00 57 9155 7017 1730552
Toxicity to various agents 73.75 51.00 109 9103 29032 1708537
Acute myeloid leukaemia 73.20 51.00 41 9171 3000 1734569
Intestinal obstruction 72.97 51.00 43 9169 3464 1734105
Thrombosis 71.88 51.00 57 9155 7464 1730105
Back pain 71.74 51.00 81 9131 16532 1721037
Syncope 71.50 51.00 75 9137 14094 1723475
Treatment failure 71.30 51.00 46 9166 4355 1733214
Failure to thrive 70.14 51.00 29 9183 1076 1736493
Metastases to central nervous system 70.12 51.00 32 9180 1513 1736056
Condition aggravated 69.87 51.00 90 9122 21060 1716509
Dyspnoea exertional 68.66 51.00 44 9168 4117 1733452
Hypoalbuminaemia 68.66 51.00 31 9181 1429 1736140
Red blood cell count decreased 68.42 51.00 42 9170 3644 1733925
Upper gastrointestinal haemorrhage 68.31 51.00 39 9173 2960 1734609
Palmar-plantar erythrodysaesthesia syndrome 67.76 51.00 41 9171 3466 1734103
Lymphangiosis carcinomatosa 67.46 51.00 19 9193 209 1737360
Bone marrow toxicity 67.28 51.00 21 9191 337 1737232
Cough 67.06 51.00 84 9128 19113 1718456
Enteritis 66.62 51.00 27 9185 951 1736618
Pneumonia aspiration 66.11 51.00 47 9165 5219 1732350
Urosepsis 65.43 51.00 30 9182 1434 1736135
Biliary sepsis 65.22 51.00 16 9196 97 1737472
Hodgkin's disease 65.15 51.00 25 9187 760 1736809
Thrombotic thrombocytopenic purpura 63.71 51.00 24 9188 693 1736876
Alveolitis 63.34 51.00 20 9192 334 1737235
Peripheral sensory neuropathy 62.91 51.00 25 9187 836 1736733
Adenocarcinoma pancreas 62.88 51.00 19 9193 272 1737297
Leukocytosis 62.39 51.00 39 9173 3494 1734075
Abdominal pain upper 62.34 51.00 62 9150 10939 1726630
Blood urea increased 61.35 51.00 43 9169 4668 1732901
Gastrointestinal toxicity 61.18 51.00 20 9192 375 1737194
Therapy non-responder 60.97 51.00 48 9164 6218 1731351
Tubulointerstitial nephritis 60.83 51.00 36 9176 2922 1734647
Blood sodium decreased 60.77 51.00 33 9179 2271 1735298
Polyneuropathy 60.24 51.00 30 9182 1725 1735844
Pain in extremity 60.05 51.00 78 9134 18394 1719175
Blood albumin decreased 59.03 51.00 29 9183 1619 1735950
Febrile bone marrow aplasia 58.99 51.00 24 9188 854 1736715
Splenic infarction 58.28 51.00 19 9193 353 1737216
Cardiomyopathy 57.92 51.00 34 9178 2718 1734851
Neoplasm malignant 57.42 51.00 40 9172 4299 1733270
Cerebral ischaemia 57.04 51.00 25 9187 1073 1736496
Skin necrosis 56.99 51.00 23 9189 801 1736768
Venous thrombosis 56.74 51.00 22 9190 688 1736881
End stage renal disease 56.25 51.00 21 9191 591 1736978
Livedo reticularis 56.11 51.00 18 9194 317 1737252
Hypokalaemia 56.01 51.00 46 9166 6328 1731241
Metastases to spleen 54.93 51.00 13 9199 66 1737503
Metastases to muscle 54.21 51.00 11 9201 22 1737547
Platelet count abnormal 54.04 51.00 20 9192 549 1737020
Acute myocardial infarction 53.52 51.00 51 9161 8536 1729033
Haematuria 53.11 51.00 48 9164 7512 1730057
Peritonitis 52.85 51.00 32 9180 2707 1734862
Post thrombotic syndrome 52.64 51.00 12 9200 50 1737519
Bacterial infection 52.28 51.00 28 9184 1874 1735695
Obstruction gastric 51.91 51.00 15 9197 182 1737387
Organising pneumonia 51.74 51.00 22 9190 876 1736693
Microangiopathic haemolytic anaemia 51.65 51.00 14 9198 132 1737437
Mental status changes 51.62 51.00 43 9169 6032 1731537
Autoimmune haemolytic anaemia 51.49 51.00 21 9191 752 1736817
Muscular weakness 51.23 51.00 54 9158 10195 1727374
Hyperglycaemia 51.18 51.00 40 9172 5125 1732444

Pharmacologic Action:

SourceCodeDescription
ATC L01BC05 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
ANTIMETABOLITES
Pyrimidine analogues
CHEBI has role CHEBI:47868 photosensitizing agent
CHEBI has role CHEBI:132992 radiosensitizing agent
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:36044 antiviral drug
CHEBI has role CHEBI:35705 immunosuppressive agent
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000963 Antimetabolites
MeSH PA D000964 Antimetabolites, Antineoplastic
MeSH PA D000970 Antineoplastic Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D007155 Immunologic Factors
MeSH PA D007166 Immunosuppressive Agents
MeSH PA D009676 Noxae
MeSH PA D011838 Radiation-Sensitizing Agents
FDA MoA N0000000233 Nucleic Acid Synthesis Inhibitors
FDA EPC N0000175595 Nucleoside Metabolic Inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Non-small cell lung cancer indication 254637007 DOID:3908
Malignant tumor of ovary indication 363443007 DOID:2394
Adenocarcinoma of pancreas indication 700423003 DOID:4074
Metastatic Breast Carcinoma indication
Ewing's sarcoma off-label use 76909002 DOID:3369
Small cell carcinoma of lung off-label use 254632001 DOID:5409
Malignant tumor of head and/or neck off-label use 255056009
Malignant tumor of testis off-label use 363449006 DOID:2998
Malignant tumor of urinary bladder off-label use 399326009 DOID:11054
Biliary Tract Malignancy off-label use
Refractory Osteosarcoma off-label use
Infectious disease contraindication 40733004
Interstitial pneumonia contraindication 64667001
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Hemolytic uremic syndrome contraindication 111407006 DOID:12554
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.69 acidic
pKa2 12.86 acidic
pKa3 3.97 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA polymerase (alpha/delta/epsilon) Enzyme INHIBITOR CHEMBL CHEMBL
Ribonucleoside-diphosphate reductase subunit M2 Enzyme INHIBITOR WOMBAT-PK CHEMBL
Ribonucleoside-diphosphate reductase large subunit Enzyme INHIBITOR WOMBAT-PK CHEMBL
UMP-CMP kinase Kinase WOMBAT-PK
Thymidylate synthase Enzyme WOMBAT-PK
Deoxycytidine kinase Kinase WOMBAT-PK

External reference:

IDSource
4024031 VUID
N0000022036 NUI
C0045093 UMLSCUI
D01155 KEGG_DRUG
108811008 SNOMEDCT_US
4024031 VANDF
130312 MMSL
005472 NDDF
d04010 MMSL
4777 MMSL
12574 RXNORM
386920008 SNOMEDCT_US
B76N6SBZ8R UNII
6515 INN_ID
CHEBI:175901 CHEBI
CHEMBL888 ChEMBL_ID
DB00441 DRUGBANK_ID
CHEMBL1637 ChEMBL_ID
122111-03-9 SECONDARY_CAS_RN
GEO PDB_CHEM_ID
60750 PUBCHEM_CID
C056507 MESH_SUPPLEMENTAL_RECORD_UI
4793 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Gemzar HUMAN PRESCRIPTION DRUG LABEL 1 0002-7501 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 200 mg INTRAVENOUS NDA 17 sections
Gemzar HUMAN PRESCRIPTION DRUG LABEL 1 0002-7502 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS NDA 17 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 0409-0181 INJECTION, SOLUTION 38 mg INTRAVENOUS NDA 18 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 0409-0182 INJECTION, SOLUTION 38 mg INTRAVENOUS NDA 18 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 0409-0183 INJECTION, SOLUTION 38 mg INTRAVENOUS NDA 18 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 0409-0185 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 38 mg INTRAVENOUS ANDA 18 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 0409-0186 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 38 mg INTRAVENOUS ANDA 18 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 0409-0187 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 38 mg INTRAVENOUS ANDA 18 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16714-909 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 200 mg INTRAVENOUS ANDA 17 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16714-930 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
GEMCITABINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16729-092 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 200 mg INTRAVENOUS ANDA 17 sections
GEMCITABINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16729-117 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
GEMCITABINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16729-118 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16729-391 INJECTION, SOLUTION 100 mg INTRAVENOUS NDA 18 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16729-419 INJECTION, SOLUTION 100 mg INTRAVENOUS NDA 18 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16729-423 INJECTION, SOLUTION 100 mg INTRAVENOUS NDA 18 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 16729-426 INJECTION, SOLUTION 100 mg INTRAVENOUS NDA 18 sections
Gemcitabine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-213 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 200 mg INTRAVENOUS ANDA 17 sections
Gemcitabine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-214 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 25021-234 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 200 mg INTRAVENOUS ANDA 17 sections
gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 25021-235 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 25021-239 INJECTION, SOLUTION 38 mg INTRAVENOUS ANDA 16 sections
gemcitabine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 45963-612 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 200 mg INTRAVENOUS ANDA 17 sections
gemcitabine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 45963-619 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 17 sections
gemcitabine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 45963-620 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 2 g INTRAVENOUS ANDA 17 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 45963-623 INJECTION 38 mg INTRAVENOUS ANDA 17 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 45963-624 INJECTION 38 mg INTRAVENOUS ANDA 17 sections
Gemcitabine HUMAN PRESCRIPTION DRUG LABEL 1 45963-636 INJECTION 38 mg INTRAVENOUS ANDA 17 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 50742-496 INJECTION, SOLUTION 38 mg INTRAVENOUS ANDA 17 sections
GEMCITABINE HUMAN PRESCRIPTION DRUG LABEL 1 50742-497 INJECTION, SOLUTION 38 mg INTRAVENOUS ANDA 17 sections