Gemcitabine hydrochloride

Base Information

• Chemical Name: Gemcitabine hydrochloride
• CAS No.: 122111-03-9
• Molecular Formula: C9H11F2N3O4^.HCl
• Molecular Weight: 299.662
• Hs Code.: 29420000
• UNII: U347PV74IL
• DSSTox Substance ID: DTXSID3047849
• Wikidata: Q27114559
• NCI Thesaurus Code: C961
• RXCUI: 236234
• ChEMBL ID: CHEMBL1637
• Mol file: 122111-03-9.mol

Synonyms:188011, LY;2' Deoxy 2' Difluorocytidine;2' Deoxy 2',2'' Difluorocytidine 5' O Monophosphate;2',2'-DFDC;2',2'-difluoro-2'-deoxycytidine;2',2'-difluorodeoxycytidine;2'-deoxy-2',2''-difluorocytidine-5'-O-monophosphate;2'-deoxy-2'-difluorocytidine;dFdCyd;gemcitabine;gemcitabine hydrochloride;gemcitabine, (alpha-D-threo-pentofuranosyl)-isomer;gemcitabine, (beta-D-threo-pentafuranosyl)-isomer;gemcitabine, (D-threo-pentafuranosyl)-isomer;gemicitabine;Gemzar;Hydrochloride, Gemcitabine;LY 188011;LY-188011

Chemical Property of Gemcitabine hydrochloride

Chemical Property:

• Appearance/Colour: White crystalline granular, odorless
• Vapor Pressure: 2.41E-11mmHg at 25°C
• Melting Point: >250 °C dec
• Boiling Point: 482.7 °C at 760 mmHg
• Flash Point: 245.7 °C
• PSA: 110.60000
• Density: ==
• LogP: 0.09460
• Storage Temp.: Desiccate at +4°C
• Solubility.: H2O: ≥10mg/mL
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 299.0484399
• Heavy Atom Count: 19
• Complexity: 426

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Gemcitabine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 21-36/38-46-62-63
• Safety Statements: 25-26-36/37-53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)(F)F.Cl
• Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F.Cl
• Recent ClinicalTrials: Genetic Testing in Screening Patients With Stage IB-IIIA Non-small Cell Lung Cancer That Has Been or Will Be Removed by Surgery (The ALCHEMIST Screening Trial)
• Recent EU Clinical Trials: A Phase 3, Multicenter, Open-Label, Randomized Study of Nemvaleukin Alfa in Combination With Pembrolizumab Versus Investigator’s Choice Chemotherapy in Patients With Platinum-Resistant Epithelial Ovarian, Fallopian Tube, or Primary Peritoneal Cancer (ARTISTRY-7)
• Recent NIPH Clinical Trials: Examination of the safety and usefulness of preoperative chemotherapy and radiation therapy for locally advanced pancreatic cancer (Phase I / II)
• 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. An antineoplastic. An antineoplastic
• 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.

Technology Process of Gemcitabine hydrochloride

There total 26 articles about Gemcitabine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.4%

gemcitabine (95058-81-4,103882-85-5) → gemcitabine hydrochloride (122111-03-9)

Guidance literature:

With hydrogenchloride; In water; isopropyl alcohol; at 20 - 70 ℃;

Reference yield: 91.9%

β-2'-deoxy-2',2'-difluorocytidine hemihydrate → gemcitabine hydrochloride (122111-03-9)

Guidance literature:

With hydrogenchloride; In water; acetone; at 20 ℃; for 2h; Product distribution / selectivity;

Reference yield: 91.5%

β-2'-deoxy-2',2'-difluorocytidine dihydrate → gemcitabine hydrochloride (122111-03-9)

Guidance literature:

With hydrogenchloride; In water; acetone; at 20 ℃; for 2h; Product distribution / selectivity;

upstream raw materials:

3′,5′-O-bis(tert-butoxycarbonyl)-gemcitabine

α/β-1-(2-oxo-4-amino-1H-pyrimidin-1-yl)-2-desoxy-2,2'-difluororibose hydrochloride

2’-deoxy-2’,2’-difluoro-cytidine

gemcitabine

Downstream raw materials:

Deoxydifluorouridine

α-1-(2-oxo-4-amino-1,2-dihydropyrimidin-1-yl)-2-deoxy-2,2-difluororibose

N-(1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-2-propylpentanamide

dodecyl 2-((1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)carbamoyl)benzoate

Refernces

• 1、 Jiang, Xiangrui,Li, Jianfeng,Zhang, Rongxia,Zhu, Yi,Shen, Jingshan. "An improved preparation process for gemcitabine". . p. 888 - 891. Retrieved 2008.
• 2、 Liu, Tongchao,Tang, Jiadeng,Liang, Jianpeng,Chen, Yabin,Wang, Xiaowen,Shen, Jingkang,Zhao, Dongmei,Xiong, Bing,Cen, Jun-Da,Chen, Yue-Lei. "Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine". . p. 1203 - 1213. Retrieved 2019/01/29.
• 3、 -. "Novel preparation method for gemcitabine hydrochloride". . . Retrieved 2018/04/21.