Gemcitabine Hydrochloride
GEMCITABINE HCL · gemzar · Gecitabine · 2',2'-DIFLUORO-2'-DEOXYCYTIDINE · 4-amino-1-[3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1h-pyrimidin-2-one hydrochloride · DFDC · DDFC · DFDCYD
Identifiers & Physical Properties
| CAS No. | 122111-03-9 |
|---|---|
| Molecular formula | C9H12ClF2N3O4 |
| Average molar mass | 299.66 g/mol |
| Monoisotopic mass | 299.04843998 g/mol |
| SMILES | Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1 |
| InChIKey | OKKDEIYWILRZIA-OSZBKLCCSA-N |
| PubChem CID | 60749 |
| ChEMBL | CHEMBL1637 |
| EC No. | 601-823-3 |
| DTXSID | DTXSID3047849 |
Chemical & Physical Properties
| Topological polar surface area | 108 |
|---|---|
| Hydrogen bond donors | 4 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 2 |
| Heavy atoms | 19 |
| Formal charge | 0 |
| Complexity | 426 |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Melting point | >250°C dec. |
| alpha | D +48°365 +257.9° (c = 1.0 in deuterated water) |
| Storage conditions | 2-8°C |
| Solubility | H2O: ≥10mg/mLwater: 25mg/mL |
| Physical state | White powder |
| pKa (acidity coefficient) | 3.58 (acidic) |
| Color | White |
| λmax | 268nm(H2O)(lit.) |
| Merck | 14,4386 |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month. |
| InChI | InChI=1/C9H11F2N3O4.ClH/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)1H/t4-,6-,7-/s3 |
| InChIKey | OKKDEIYWILRZIA-LJAFHONQNA-N |
| SMILES | [C@H]1(O[C@@H]([C@@H](O)C1(F)F)CO)N1C=CC(N)=NC1=O.Cl |&1:0,2,3,r| |
| CAS DataBase Reference | 122111-03-9(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| NCI Dictionary of Cancer Terms | gemcitabine hydrochlorideGemzar |
| FDA UNII | U347PV74IL |
| NCI Drug Dictionary | gemcitabine hydrochloride |
| UNSPSC Code | 41116107 |
| NACRES | NA.77 |
| GHS pictogram | GHS08 |
| Signal word | Danger |
| GHS hazard statements | H360 |
| GHS precautionary statements | P201-P202-P280-P308+P313-P405-P501 |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 21-36/38-46-62-63 |
| Safety statements (S) | 25-26-36/37-53 |
| Water hazard class (WGK) | 3 |
| RTECS number | HA3840000 |
| Customs code | 29420000 |
| Storage class | 6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazard class | Repr. 1B |
Safety & Regulations
| GHS classification | DangerH302 (11.3%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P317, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (11.3%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Gemcitabine hydrochloridevMost-DILI-concern8Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Water hazard class (WGK) | 3 |
| RTECS number | HA3840000 |
| Customs code | 29420000 |
| Risk statements (R) | 21-36/38-46-62-63 |
| Signal word | Danger |
| GHS pictogram | GHS08 |
| Hazard symbols | Xn,Xi |
| Safety statements (S) | 25-26-36/37-53 |
| Storage class | 6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| GHS hazard statements | H360 |
| Hazard class | Repr. 1B |
| GHS precautionary statements | P201-P202-P280-P308+P313-P405-P501 |
Applications & Uses
Uses
Suitable for the treatment of inoperable advanced or metastatic pancreatic cancer and the treatment of locally advanced or metastatic non-small cell lung cancer, and the treatment for mid-term and advanced non-small cell lung cancer, non-small cell lung cancer, pancreatic cancer, bladder cancer, breast cancer and other solid tumors.
Description
Gemcitabine is a novel nucleoside analog that was launched in 1995 in the Netherlands for the treatment of non-small cell lung cancer (nsclc) and in Sweden for pancreatic cancer. Gemcitabine is a prodrug which is phosphorylated intracellularly by deoxycytadine kinase to its active forms, the di- and triphosphates which bind to DNA competitively. This insertion inhibits processes required for DNA synthesis and metabolism, the essential function for both cell replication and repair. Furthermore, gemcitabine displays an extraordinary array of self-potentiating mechanisms that increase the concentration and prolong the retention of its active nucleotides in tumor cells. The title compound has shown activity against a wide spectrum of human solid tumors including colon, mammary, breast, bladder cancers. Synergistic activity of gemcitabine with other anticancer agents such as cisplatin has been reported.
Uses
An antineoplastic.