Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00063
|
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| Drug Name |
Gemcitabine
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| Synonyms |
2',2'-DiF-dC; 2',2'-Difluoro-2'-deoxycytidine; 2',2'-Difluorodeoxycytidine; 2'-Deoxy-.beta.-D-2',2'-difluorocytidine; 2'-Deoxy-2',2'-difluorocytidine; 4-Amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one; 4-Amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl) tetrahydrofuran-2-yl]-1H-pyrimidin-2-one; 4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one; Cytidine, 2'-deoxy-2',2'-difluoro-2'-Deoxy-.beta.-D-2',2'-difluorocytidine; DDFC; DFdC; DFdCyd; Folfugem; GEO; Gamcitabine; GemLip; Gemcel; Gemcin; Gemcitabina; Gemcitabina [INN-Spanish]; Gemcitabine (USAN/INN); Gemcitabine HCl; Gemcitabine stereoisomer; Gemcitabinum; Gemcitabinum [INN-Latin]; Gemtro; Gemzar; Gemzar (TN); Gemzar (hydrochloride); Inno-D07001; LY 188011; LY-188011; LY188011; Zefei
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| Drug Type |
Small molecular drug
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| Indication | Pancreatic cancer [ICD11:2C10] | Approved | [1] | |||
| Cholangiocarcinoma [ICD11:2C12.10] | Approved | [1] | ||||
| Therapeutic Class |
Anticancer Agents
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| Structure |
|
 |
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| 3D MOL | 2D MOL | |||||
| Formula |
C9H11F2N3O4
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| Canonical SMILES |
C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)(F)F
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| 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
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| InChIKey |
SDUQYLNIPVEERB-QPPQHZFASA-N
|
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| CAS Number |
CAS 95058-81-4
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| Pharmaceutical Properties | Molecular Weight | 263.2 | Topological Polar Surface Area | 108 | ||
| Heavy Atom Count | 18 | Rotatable Bond Count | 2 | |||
| Hydrogen Bond Donor Count | 3 | Hydrogen Bond Acceptor Count | 6 | |||
| XLogP |
-1.5
|
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| PubChem CID | ||||||
| PubChem SID |
103233471
,104321551
,117682518
,121264498
,124893555
,127340623
,127340624
,129221764
,134338484
,135022769
,135684653
,136367931
,136369166
,137001852
,142312486
,143493338
,144116012
,15197115
,152059722
,15221618
,152240379
,152258737
,24769903
,24875076
,43118104
,46506425
,49684285
,49835789
,49960194
,50298729
,53787881
,56311575
,56312523
,56312627
,56312648
,56313191
,56313205
,56313872
,57304498
,57314089
,597200
,60815357
,7849427
,7887820
,7979381
,8187035
,829253
,87322653
,92308986
,9852
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| ChEBI ID |
ChEBI:175901
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | CNT1 | Transporter Info | Concentrative nucleoside transporter 1 | Substrate | [2] | |
| MRP5 | Transporter Info | Multidrug resistance-associated protein 5 | Substrate | [3] | ||
| P-GP | Transporter Info | P-glycoprotein 1 | Substrate | [4] | ||
| References | ||||||
| 1 | Gemcitabine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019) | |||||
| 2 | Pancreatic Cancer Chemoresistance to Gemcitabine. Cancers (Basel). 2017 Nov 16;9(11). | |||||
| 3 | Interdependence of gemcitabine treatment, transporter expression, and resistance in human pancreatic carcinoma cells. Neoplasia. 2010 Sep;12(9):740-7. | |||||
| 4 | Increased sensitivity to gemcitabine of P-glycoprotein and multidrug resistance-associated protein-overexpressing human cancer cell lines. Br J Cancer. 2003 Jun 16;88(12):1963-70. | |||||
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