| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| October 5th, 2008 | 18 | Yes |
Popular Name: Gemcitabine Gemcitabine
Find On: PubMed — Wikipedia — Google
CAS Numbers: 122111-03-9 , 95058-81-4 , [122111-03-9] , [95058-81-4]
"Gemcitabine hydrochloride, 99%"
122111-03-9; D01155; Gemcitabine hydrochloride (JAN/USAN); Gemzar (TN)
2',2'-Difluoro-2'-deoxycytidine
2',2'-Difluoro-2'-deoxycytidine hydrochloride
2',2'-Difluoro-2'-deoxycytidine; DDFC
2'-Deoxy-.beta.-D-2',2'-difluorocytidine
2'-Deoxy-2',2'-difluoro-cytidine
2'-Deoxy-2',2'-difluorocytidine
2(1H)-Pyrimidinone, 4-amino-1-(2-deoxy-2,2-difluoro-D-erythro-pentofuranosyl)-
2?-Deoxy-2?,2?-difluorocytidine
2_-Deoxy-2_,2_-difluorocytidine
2`-Deoxy-2`,2`-difluorocytidine
4-Amino-1-((4R,5R)-3,3-difluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one
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
95058-81-4; C07650; Gemcitabine
95058-81-4; D02368; Gemcitabine (USAN/INN)
CPD000469146; GEMCITABINE HYDROCHLORIDE; SAM001246550
CPD000469146; GEMCITABINE HYDROCHLORIDE; SAM001246550; gemcitabine
Cytidine, 2'-deoxy-2',2'-difluoro-2'-Deoxy-.beta.-D-2',2'-difluorocytidine
Cytosine, 1-(2-deoxy-2,2-difluoro-beta-D-erythro-pentofuranosyl)-
GEMCITABIN HYDROCHLORIDE/Gemcitabine hydrochloride
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | -1.60 | -4.98 | -22.45 | 4 | 7 | 0 | 111 | 263.2 | 2 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| ALOGPS_SOLUBILITY | 2.23e+01 g/l | DrugBank-approved |
| MP | 292 | TCI |
| Purity | 95% | Fluorochem |
| Purity | 95+% | Matrix Scientific |
| Purity | 98% | Fluorochem |
| Indications | anticancer | KeyOrganics Bioactives |
| biological_use | Antimetabolite | IBScreen Bioactives |
| biological_use | Antineoplastic agent | IBScreen Bioactives ZereneX Building Blocks |
| biological_use | Antineoplastic agent for treatment of lung and pancreatic tumours | IBScreen Bioactives |
| biological_use | Antineoplastic agent | IBScreen Bioactives |
| biological_use | Antiviral agent | IBScreen Bioactives |
| Target | Autophagy,DNA/RNA Synthesis | Selleck Chemicals |
| UniProt Database Links | DCK_HUMAN; EST1_PIG; IEX1_HUMAN; IEX1_PANTR; NUPR1_HUMAN; S28A3_EPTST; S28A3_HUMAN; S28A3_MOUSE; S28A3_RAT | ChEBI |
| Target | DNA/RNA Synthesis | Selleck Chemicals |
| PUBCHEM_PATENT_ID | EP0272891A2; EP0630905A1; EP0630905B1; EP0688782A1; EP0688783A1; EP0712860A2; EP0719788A2; EP0719788A3; EP0719788B1; EP0727432A1; EP0735043A1; EP0735043B1; EP0750910A1; EP0970074A1; US4814438; US4954623; US4965374; US4994558; US5010176; US5223608; US54342 | IBM Patent Data |
| Warnings | IRRITANT | Matrix Scientific |
| Warnings | Irritant/Store in Freezer | Matrix Scientific |
| PUBCHEM_SUBSTANCE_COMMENT | NCC_SAMPLE_SUPPLIER : Sequoia Research Products Ltd.; NCC_SUPPLIER_STRUCTURE_ID : SRP01265g; 1 hydrogen chloride | NIH Clinical Collection via PubChem |
| mechanism | Nucleoside antimetabolite | ZereneX Building Blocks |
| biological_use | Nucleoside transporter substrate | IBScreen Bioactives |
| Target | Others | Selleck Chemicals |
| PUBCHEM_SUBSTANCE_COMMENT | SAMPLE_SUPPLIER: Sequoia Research Products Ltd.; SUPPLIER_STRUCTURE_ID: SRP01265g; SALT: 1 hydrogen chloride | NIH Clinical Collection via PubChem |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| Z100515-1-O | HPAC (Pancreatic Adenocarcinoma) (cluster #1 Of 2), Other | Other | 73 | 0.56 | Functional ≤ 10μM |
| Z100733-1-O | CT26 (Colon Carcinoma Cells) (cluster #1 Of 1), Other | Other | 6 | 0.64 | Functional ≤ 10μM |
| Z100757-1-O | SW1573 (Lung Carcinoma Cells) (cluster #1 Of 1), Other | Other | 8300 | 0.40 | Functional ≤ 10μM |
| Z103393-1-O | SK-N-AS (cluster #1 Of 1), Other | Other | 1100 | 0.46 | Functional ≤ 10μM |
| Z103407-1-O | SW1990 (cluster #1 Of 2), Other | Other | 1200 | 0.46 | Functional ≤ 10μM |
| Z80048-1-O | BXPC-3 (Pancreatic Adenocarcinoma Cells) (cluster #1 Of 1), Other | Other | 160 | 0.53 | Functional ≤ 10μM |
| Z80076-1-O | CEM-SS (T-cell Leukemia) (cluster #1 Of 5), Other | Other | 30 | 0.59 | Functional ≤ 10μM |
| Z80125-1-O | DU-145 (Prostate Carcinoma) (cluster #1 Of 9), Other | Other | 36 | 0.58 | Functional ≤ 10μM |
| Z80132-1-O | EL4 (Thymoma Cells) (cluster #1 Of 2), Other | Other | 7 | 0.63 | Functional ≤ 10μM |
| Z80156-2-O | HL-60 (Promyeloblast Leukemia Cells) (cluster #2 Of 12), Other | Other | 330 | 0.50 | Functional ≤ 10μM |
| Z80166-1-O | HT-29 (Colon Adenocarcinoma Cells) (cluster #1 Of 12), Other | Other | 43 | 0.57 | Functional ≤ 10μM |
| Z80186-1-O | K562 (Erythroleukemia Cells) (cluster #1 Of 11), Other | Other | 746 | 0.48 | Functional ≤ 10μM |
| Z80193-2-O | L1210 (Lymphocytic Leukemia Cells) (cluster #2 Of 12), Other | Other | 7 | 0.63 | Functional ≤ 10μM |
| Z80224-9-O | MCF7 (Breast Carcinoma Cells) (cluster #9 Of 14), Other | Other | 80 | 0.55 | Functional ≤ 10μM |
| Z80255-2-O | MES-SA/DxS (Uterine Sarcoma Cells) (cluster #2 Of 2), Other | Other | 9 | 0.63 | Functional ≤ 10μM |
| Z80390-1-O | PC-3 (Prostate Carcinoma Cells) (cluster #1 Of 10), Other | Other | 40 | 0.58 | Functional ≤ 10μM |
| Z80457-1-O | SCC-25 (cluster #1 Of 1), Other | Other | 47 | 0.57 | Functional ≤ 10μM |
| Z80466-1-O | SF268 (cluster #1 Of 4), Other | Other | 10 | 0.62 | Functional ≤ 10μM |
| Z80478-1-O | SK-LU-1 (cluster #1 Of 1), Other | Other | 55 | 0.56 | Functional ≤ 10μM |
| Z80482-2-O | SK-MEL-2 (Melanoma Cells) (cluster #2 Of 4), Other | Other | 7110 | 0.40 | Functional ≤ 10μM |
| Z80526-1-O | SW480 (Colon Adenocarcinoma Cells) (cluster #1 Of 6), Other | Other | 1700 | 0.45 | Functional ≤ 10μM |
| Z80561-1-O | U2OS (Osteosarcoma Cells) (cluster #1 Of 1), Other | Other | 91 | 0.55 | Functional ≤ 10μM |
| Z80563-1-O | U-373 MG ( Glioblastoma Cells) (cluster #1 Of 1), Other | Other | 130 | 0.54 | Functional ≤ 10μM |
| Z80682-1-O | A549 (Lung Carcinoma Cells) (cluster #1 Of 11), Other | Other | 90 | 0.55 | Functional ≤ 10μM |
| Z80702-1-O | BG-1 Cell Line (cluster #1 Of 1), Other | Other | 680 | 0.48 | Functional ≤ 10μM |
| Z80726-1-O | TRAMP-C1A (Prostate Carcinoma Cells) (cluster #1 Of 1), Other | Other | 9 | 0.63 | Functional ≤ 10μM |
| Z80730-1-O | C2D Cell Line (cluster #1 Of 1), Other | Other | 12 | 0.62 | Functional ≤ 10μM |
| Z80731-1-O | C2G Cell Line (cluster #1 Of 1), Other | Other | 4 | 0.65 | Functional ≤ 10μM |
| Z80732-1-O | TRAMP-C2H (Prostate Carcinoma Cells) (cluster #1 Of 1), Other | Other | 5 | 0.65 | Functional ≤ 10μM |
| Z80742-1-O | C6 (Glioma Cells) (cluster #1 Of 3), Other | Other | 504 | 0.49 | Functional ≤ 10μM |
| Z80874-1-O | CEM (T-cell Leukemia) (cluster #1 Of 7), Other | Other | 130 | 0.54 | Functional ≤ 10μM |
| Z80928-1-O | HCT-116 (Colon Carcinoma Cells) (cluster #1 Of 9), Other | Other | 10 | 0.62 | Functional ≤ 10μM |
| Z81024-1-O | NCI-H460 (Non-small Cell Lung Carcinoma) (cluster #1 Of 8), Other | Other | 8 | 0.63 | Functional ≤ 10μM |
| Z81034-1-O | A2780 (Ovarian Carcinoma Cells) (cluster #1 Of 10), Other | Other | 35 | 0.58 | Functional ≤ 10μM |
| Z81072-2-O | Jurkat (Acute Leukemic T-cells) (cluster #2 Of 10), Other | Other | 45 | 0.57 | Functional ≤ 10μM |
| Z81170-1-O | LNCaP (Prostate Carcinoma) (cluster #1 Of 5), Other | Other | 512 | 0.49 | Functional ≤ 10μM |
| Z81247-1-O | HeLa (Cervical Adenocarcinoma Cells) (cluster #1 Of 9), Other | Other | 8 | 0.63 | Functional ≤ 10μM |
| Z81252-3-O | MDA-MB-231 (Breast Adenocarcinoma Cells) (cluster #3 Of 11), Other | Other | 245 | 0.51 | Functional ≤ 10μM |
| Z81335-1-O | HCT-15 (Colon Adenocarcinoma Cells) (cluster #1 Of 5), Other | Other | 10 | 0.62 | Functional ≤ 10μM |
| Z80335-1-O | NHDF (cluster #1 Of 2), Other | Other | 22 | 0.60 | ADME/T ≤ 10μM |
| Z80704-1-O | BJ (Foreskin Fibroblast Cells) (cluster #1 Of 2), Other | Other | 9880 | 0.39 | ADME/T ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| Z81034 | Z81034 | A2780 (Ovarian Carcinoma Cells) | 1.5 | 0.69 | Functional ≤ 10μM |
| Z80682 | Z80682 | A549 (Lung Carcinoma Cells) | 14 | 0.61 | Functional ≤ 10μM |
| Z80702 | Z80702 | BG-1 Cell Line | 680 | 0.48 | Functional ≤ 10μM |
| Z80048 | Z80048 | BXPC-3 (Pancreatic Adenocarcinoma Cells) | 160 | 0.53 | Functional ≤ 10μM |
| Z80730 | Z80730 | C2D Cell Line | 11.9 | 0.62 | Functional ≤ 10μM |
| Z80731 | Z80731 | C2G Cell Line | 3.7 | 0.66 | Functional ≤ 10μM |
| Z80742 | Z80742 | C6 (Glioma Cells) | 504 | 0.49 | Functional ≤ 10μM |
| Z80874 | Z80874 | CEM (T-cell Leukemia) | 1000 | 0.47 | Functional ≤ 10μM |
| Z80076 | Z80076 | CEM-SS (T-cell Leukemia) | 30 | 0.59 | Functional ≤ 10μM |
| Z100733 | Z100733 | CT26 (Colon Carcinoma Cells) | 6 | 0.64 | Functional ≤ 10μM |
| Z80125 | Z80125 | DU-145 (Prostate Carcinoma) | 3.5 | 0.66 | Functional ≤ 10μM |
| Z80132 | Z80132 | EL4 (Thymoma Cells) | 7 | 0.63 | Functional ≤ 10μM |
| Z80928 | Z80928 | HCT-116 (Colon Carcinoma Cells) | 5 | 0.65 | Functional ≤ 10μM |
| Z81335 | Z81335 | HCT-15 (Colon Adenocarcinoma Cells) | 10 | 0.62 | Functional ≤ 10μM |
| Z81247 | Z81247 | HeLa (Cervical Adenocarcinoma Cells) | 4120 | 0.42 | Functional ≤ 10μM |
| Z80156 | Z80156 | HL-60 (Promyeloblast Leukemia Cells) | 330 | 0.50 | Functional ≤ 10μM |
| Z100515 | Z100515 | HPAC (Pancreatic Adenocarcinoma) | 73 | 0.56 | Functional ≤ 10μM |
| Z80166 | Z80166 | HT-29 (Colon Adenocarcinoma Cells) | 1530 | 0.45 | Functional ≤ 10μM |
| Z81072 | Z81072 | Jurkat (Acute Leukemic T-cells) | 30 | 0.59 | Functional ≤ 10μM |
| Z80186 | Z80186 | K562 (Erythroleukemia Cells) | 6 | 0.64 | Functional ≤ 10μM |
| Z80193 | Z80193 | L1210 (Lymphocytic Leukemia Cells) | 7 | 0.63 | Functional ≤ 10μM |
| Z81170 | Z81170 | LNCaP (Prostate Carcinoma) | 512 | 0.49 | Functional ≤ 10μM |
| Z80224 | Z80224 | MCF7 (Breast Carcinoma Cells) | 149 | 0.53 | Functional ≤ 10μM |
| Z81252 | Z81252 | MDA-MB-231 (Breast Adenocarcinoma Cells) | 11.4 | 0.62 | Functional ≤ 10μM |
| Z80255 | Z80255 | MES-SA/DxS (Uterine Sarcoma Cells) | 9.2 | 0.63 | Functional ≤ 10μM |
| Z81024 | Z81024 | NCI-H460 (Non-small Cell Lung Carcinoma) | 2.13 | 0.67 | Functional ≤ 10μM |
| Z80390 | Z80390 | PC-3 (Prostate Carcinoma Cells) | 2.6 | 0.67 | Functional ≤ 10μM |
| Z80457 | Z80457 | SCC-25 | 47 | 0.57 | Functional ≤ 10μM |
| Z80466 | Z80466 | SF268 | 10 | 0.62 | Functional ≤ 10μM |
| Z80478 | Z80478 | SK-LU-1 | 55 | 0.56 | Functional ≤ 10μM |
| Z80482 | Z80482 | SK-MEL-2 (Melanoma Cells) | 7110 | 0.40 | Functional ≤ 10μM |
| Z103393 | Z103393 | SK-N-AS | 1100 | 0.46 | Functional ≤ 10μM |
| Z100757 | Z100757 | SW1573 (Lung Carcinoma Cells) | 16 | 0.61 | Functional ≤ 10μM |
| Z103407 | Z103407 | SW1990 | 1200 | 0.46 | Functional ≤ 10μM |
| Z80526 | Z80526 | SW480 (Colon Adenocarcinoma Cells) | 13.6 | 0.61 | Functional ≤ 10μM |
| Z80726 | Z80726 | TRAMP-C1A (Prostate Carcinoma Cells) | 9 | 0.63 | Functional ≤ 10μM |
| Z80732 | Z80732 | TRAMP-C2H (Prostate Carcinoma Cells) | 4.7 | 0.65 | Functional ≤ 10μM |
| Z80563 | Z80563 | U-373 MG ( Glioblastoma Cells) | 130 | 0.54 | Functional ≤ 10μM |
| Z80561 | Z80561 | U2OS (Osteosarcoma Cells) | 180 | 0.52 | Functional ≤ 10μM |
| Z80704 | Z80704 | BJ (Foreskin Fibroblast Cells) | 9880 | 0.39 | ADME/T ≤ 10μM |
| Z80335 | Z80335 | NHDF | 20 | 0.60 | ADME/T ≤ 10μM |
