Gemcitabine hydrochloride - Moligand™,10mM in Water , DNA polymerase (alpha/delta/epsilon) inhibitor, CAS No.122111-03-9, DNA polymerase (alpha/delta/epsilon) inhibitor

CAS: 122111-03-9 Cat. No.: G420950 Molecular Weight: 299.66 EC Number: 601-823-3

GRADE & PURITY Moligand™, 10mM in Water

Synonyms

dFdC | EX-A837 | Gemcitabine (as hydrochloride) | Gemcitabine HCL (Gemzar) | INFUGEM | NSC613327 | Gemcitabine hydrochloride [USAN] | LY 188011 hydrochloride | BG164501 | Gemzar (TN) | GEMCITABINE HYDROCHLORIDE [VANDF] | 4-amino-1-[(2R,4R,5R)-3,3-difluoro

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Gemcitabine Hydrochloride (LY 188011 Hydrochloride) is a pyrimidine nucleoside analog antimetabolite and an antineoplastic agent. Gemcitabine Hydrochloride inhibits DNA synthesis and repair, resulting in autophagyand apoptosis.This product is only used for scientific research.

Specifications

Synonyms

dFdC | EX-A837 | Gemcitabine (as hydrochloride) | Gemcitabine HCL (Gemzar) | INFUGEM | NSC613327 | Gemcitabine hydrochloride [USAN] | LY 188011 hydrochloride | BG164501 | Gemzar (TN) | GEMCITABINE HYDROCHLORIDE [VANDF] | 4-amino-1-[(2R, 4R, 5R)-3, 3-difluoro

Specifications & Purity

Moligand™, 10mM in Water

Biochemical and Physiological Mechanisms

Gemcitabine hydrochloride is used for treatment of non-small cell lung cancer, pancreatic cancer, mammary cancer, ovarian cancer, bladder cancer, nasopharyngeal carcinoma and non-Hodgkin's lymphoma.Deoxycytidine analog that inhibits DNA synthesis. Metabol

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

DNA polymerase (alpha/delta/epsilon) inhibitor

Names and Identifiers

• Canonical Smiles: Cl.NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)C2(F)F
• IUPAC Name: 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride
• InChIKey: OKKDEIYWILRZIA-OSZBKLCCSA-N
• INCHI: 1S/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-;/m1./s1
• Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F.Cl
• WGK Germany: 3
• RTECS: HA3840000
• Molecular Weight: 299.66
• Reaxy-Rn: 5386970
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=5386970&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Pyrimidine nucleosides
      • Subclass Pyrimidine 2'-deoxyribonucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Pyrimidine nucleosides
• Subclass: Pyrimidine 2'-deoxyribonucleosides
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrimidine 2'-deoxyribonucleosides
• Alternative Parents: Pyrimidones Aminopyrimidines and derivatives Hydropyrimidines Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Fluorohydrins Azacyclic compounds Oxacyclic compounds Organic oxides Hydrochlorides Hydrocarbon derivatives Organofluorides Organopnictogen compounds Primary alcohols Primary amines Alkyl fluorides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrimidine 2'-deoxyribonucleoside - Aminopyrimidine - Pyrimidone - Hydropyrimidine - Pyrimidine - Imidolactam - Heteroaromatic compound - Tetrahydrofuran - Fluorohydrin - Halohydrin - Secondary alcohol - Oxacycle - Organoheterocyclic compound - Azacycle - Hydrochloride - Organic oxide - Organopnictogen compound - Primary amine - Primary alcohol - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Organic oxygen compound - Alkyl fluoride - Alcohol - Organic nitrogen compound - Amine - Hydrocarbon derivative - Alkyl halide - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
• External Descriptors: hydrochloride - organofluorine compound

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MCF7 (126967 Activities)

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A549 (127892 Activities)

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HCT-116 (91556 Activities)

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NCI-H460 (60772 Activities)

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A2780 (11979 Activities)

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ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

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ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

Discover Target: ABCC4

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L02 (4864 Activities)

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Associated Targets(non-human)

TRAMP-C1A (16 Activities)

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C2D cell line (11 Activities)

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C2G cell line (11 Activities)

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TRAMP-C2H (17 Activities)

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Blood (6 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Heat & Light sensitive
• Refractive Index: 268
• Specific Rotation[α]: 48°C
• Melt Point(°C): 292°C
• Molecular Weight: 299.660 g/mol
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 299.048 Da
• Monoisotopic Mass: 299.048 Da
• Topological Polar Surface Area: 108.000 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 426.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Zhimei Wang, Yuehuan Zhang, Qing Chen, Xin Xiao, Carl Redshaw.  (2022)  Preparation of pelargonic acid vesicles and sustained drug release.  Canadian Journal of Chemistry,  101  (2):   [PMID:] [10.1139/cjc-2022-0075]

2. Yu Wang, Hongrui Fan, Qinjun Chen, Haolin Song, Xuwen Li, Boyu Su, Tao Sun, Leilei Cheng, Chen Jiang.  (2025)  Mitocytosis-inducing nanoparticles alleviate gemcitabine resistance via dual disruption of pyrimidine synthesis and redox homeostasis in pancreatic ductal adenocarcinoma.  BIOMATERIALS,      [PMID:40818322] [10.1016/j.biomaterials.2025.123630]

3. Zhe Zhang, Qitai Chen, Rujia Zheng, Zhenduo Shao, Xiaobao Wei, Xuanhao Gu, Yi Zang, Xishan Yang, Jiangchao Wu, Mengyao Dai, Wanyue Cao, Yangyang Wang, Yize Zhang, Chengyang Hu, Cao Chen, Linquan Wu, Tingbo Liang, Qi Zhang.  (2025)  Nano-enabled repurposing of Benproperine phosphate enhances pancreatic Cancer chemotherapy through lethal autophagy arrest and immune activation.  JOURNAL OF CONTROLLED RELEASE,      [PMID:40902670] [10.1016/j.jconrel.2025.114187]

4. Yadong Tang, Boxin Huang, Yuqin Dong, Wenlong Wang, Xi Zheng, Wei Zhou, Kun Zhang, Zhiyun Du.  (2017)  Three-dimensional prostate tumor model based on a hyaluronic acid-alginate hydrogel for evaluation of anti-cancer drug efficacy.  JOURNAL OF BIOMATERIALS SCIENCE-POLYMER EDITION,      [PMID:28583017] [10.1080/09205063.2017.1338502]

5. Yijing Zhang, Han Gao, Aiwen Tang, Haiwen Lyu, Zongmin Fan, Jiahui Guo, Yuzhi Wang, Hairong Yi, Qihao Pan, Haidan Luo, Baifu Qin, Boyu Zhang, Xiangqi Meng, Qingxin Liu, Mong-Hong Lee.  (2025)  CSN6 Promotes Pancreatic Cancer Progression and Gemcitabine Resistance via Antagonizing DCAF1-Mediated Ubiquitination of NPM1.  Advanced Science,      [PMID:41114465] [10.1002/advs.202510210]

6. Haitao Pan, Xue Pan, Zhenzhen Cao, Aoying Liu, Chunxia Li, Lijuan Guan, Yan Xing, Peng Zhang, Shixin Wang, Qian Lu.  (2026)  Self-expanding sodium alginate sulfate drug-loaded microspheres for stabilized arterial embolization.  CARBOHYDRATE POLYMERS,      [PMID:41832022] [10.1016/j.carbpol.2026.125119]