Chemical substance record

Gemcitabine

95058-81-4C₉H₁₁F₂N₃O₄263.2 g/mol

Organic/Inorganic Small MoleculeChEBI source record

A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	95058-81-4	ChEBI ↗
Molecular formula	C₉H₁₁F₂N₃O₄	ChEBI ↗
Molar mass	263.2 g/mol	ChEBI ↗
Monoisotopic mass	263.07176 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:175901	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	263.20 g/mol	PubChem ↗
Exact mass	263.07176216 Da	PubChem ↗
Computed XLogP	-1.5	PubChem ↗
Topological polar surface area (Å²)	108	PubChem ↗
H-bond donors	3	PubChem ↗
H-bond acceptors	6	PubChem ↗
Rotatable bonds	2	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

gemcitabine

IUPAC name

2'-deoxy-2',2'-difluorocytidine

InChIKey

SDUQYLNIPVEERB-QPPQHZFASA-N

SMILES

Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1

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

Names & synonyms

2'-deoxy-2',2'-difluorocytidinegemcitabinagemcitabinum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

pyrimidine 2'-deoxyribonucleosideChEBI parent class · 19255 ↗organofluorine compoundChEBI parent class · 37143 ↗

nucleoside organofluorine compound organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

radiosensitizing agentantimetaboliteanxiolytic drugantineoplastic agentxenobioticimmunosuppressive agentantiviral drugphotosensitizing agentprodrugDNA synthesis inhibitor

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00379939 mol

Uses 263.2 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 9 atoms

41.07%

O

Oxygen · 4 atoms

24.31%

N

Nitrogen · 3 atoms

15.97%

F

Fluorine · 2 atoms

14.44%

H

Hydrogen · 11 atoms

4.21%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Pharmacokinetics of gemcitabine and 2',2'-difluorodeoxyuridine in a patient with ascites. ↗Pharmacotherapy · 2000 Oct · PMID 11034044

Phase II trial of gemcitabine in patients with previously untreated metastatic cancer of the esophagus or gastroesophageal junction. ↗Annals of oncology : official journal of the European Society for Medical Oncology · 2000 Sep · PMID 11061612

EP1939198 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

EP2108368 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

EP2275135 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:175901

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 60750 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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