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Substance Name: Gemcitabine hydrochloride [USAN:USP]
RN: 122111-03-9
UNII: U347PV74IL
InChIKey: OKKDEIYWILRZIA-OSZBKLCCSA-N

Note

  • NCI: Gemcitabine hydrochloride is approved by the Food and Drug Administration (FDA) to be used by itself to treat pancreatic cancer that is advanced or has metastasized (spread to other parts of the body). It is used in patients who cannot be treated with surgery and have already been treated with other chemotherapy.[National Cancer Institute]

Molecular Formula

  • C9-H11-F2-N3-O4.Cl-H

Molecular Weight

  • 299.6598
 

Classification Codes

  • Anti-Infective Agents
  • Antimetabolites
  • Antimetabolites, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Antiviral Agents
  • Enzyme Inhibitors
  • Immunologic Factors
  • Immunosuppressive Agents
  • Noxae
  • Radiation-Sensitizing Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Gemcitabine hydrochloride [USAN:USP]

Synonyms

  • 2',2'-Difluorodeoxycytidine monohydrochloride
  • 2'-Deoxy-2',2'-difluorocytidine monohydrochloride
  • 2'-Deoxy-2',2'-difluorocytidine monohydrochloride (beta-isomer)
  • Gemcitabine HCl
  • Gemcitabine hydrochloride
  • Gemzar
  • LY188011 hydrochloride
  • UNII-U347PV74IL

Systematic Name

  • Cytidine, 2'-deoxy-2',2'-difluoro-, monohydrochloride

Registry Numbers

CAS Registry Number

  • 122111-03-9

FDA UNII

  • U347PV74IL

Related Registry Numbers

  • 103882-84-4
  • 95058-81-4

System Generated Number

  • 0122111039

Molecular Formulas

Molecular Formula

  • C9-H11-F2-N3-O4.Cl-H

Molecular Formula Fragments

  • C9-H11-F2-N3-O4
  • Cl-H
  • COMPONENT

Structure Descriptors

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

InChIKey

OKKDEIYWILRZIA-OSZBKLCCSA-N

Smiles

n1([C@H]2C([C@H](O)[C@H](O2)CO)(F)F)c(nc(N)cc1)=O.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 500mg/kg (500mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 391, 2000.
rat LD50 intravenous 236mg/kg (236mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 42, Pg. 391, 2000.
women TDLo parenteral 300mg/kg/12W- (300mg/kg) LUNGS, THORAX, OR RESPIRATION: "FIBROSIS, FOCAL (PNEUMOCONIOSIS)"

LUNGS, THORAX, OR RESPIRATION: CONSOLIDATION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Cancer Vol. 80, Pg. 286, 1997.