gemcitabine hydrochloride

CHEBI:31647 ·resolve ·ANTIVIRAL ·EXACT SEEDED

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

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

Label unavailable CHEBI:36807
Label unavailable CHEBI:37143

Chemical structure

Computed structure properties
Molecular formula	H.C9H11F2N3O4.Cl
Charge	0
Average mass	299.661 Da
Monoisotopic mass	299.04844 Da
Source	ChEBI
InChIKey	OKKDEIYWILRZIA-OSZBKLCCSA-N

SMILES

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

InChI

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

Also called

2'-deoxy-2',2'-difluorocytidine hydrochloride (EXACT_SYNONYM)— chebi
2',2'-Difluorodeoxycytidine monohydrochloride (EXACT_SYNONYM)— chebi
2'-Deoxy-2',2'-difluorocytidine monohydrochloride (EXACT_SYNONYM)— chebi
Gemcitabine HCl (EXACT_SYNONYM)— chebi

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

beilstein:5386970
cas:122111-03-9

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

anticoronaviral agent CHEBI:149553
antiviral drug CHEBI:36044

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:31647`	gemcitabine hydrochloride	`antibioticmech:chebi-6f679a84e5`	2026-08-30

Mechanism summary

Clinical status: APPROVED

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-09-10 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record (YAML).

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