GEMCITABINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H11F2N3O4.ClH
Molecular Weight	299.659
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)C2(F)F

InChI

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

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C9H11F2N3O4
Molecular Weight	263.1981
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB00441
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020509s075lbl.pdf

Gemcitabine is a nucleoside analog used as chemotherapy. It is marketed as Gemzar® by Eli Lilly and Company. Gemcitabine inhibits thymidylate synthetase, leading to inhibition of DNA synthesis and cell death. Gemcitabine is a prodrug so activity occurs as a result of intracellular conversion to two active metabolites, gemcitabine diphosphate and gemcitabine triphosphate by deoxycitidine kinase. Gemcitabine diphosphate also inhibits ribonucleotide reductase, the enzyme responsible for catalyzing synthesis of deoxynucleoside triphosphates required for DNA synthesis. Finally, Gemcitabine triphosphate (diflurorodeoxycytidine triphosphate) competes with endogenous deoxynucleoside triphosphates for incorporation into DNA. Gemcitabine is indicated for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum-based therapy; metastatic ovarian cancer; inoperable, locally advanced (Stage IIIA or IIIB), or metastatic (Stage IV) non-small cell lung cancer; and locally advanced (nonresectable Stage II or Stage III) or metastatic (Stage IV) adenocarcinoma of the pancreas.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Ribonucleoside-diphosphate reductase M1 chain 4 Target ID: CHEMBL1830 Sources: http://www.drugbank.ca/drugs/DB00441	Inhibitor 8504
DNA 282 Target ID: DNA Sources: http://www.drugbank.ca/drugs/DB00441	Inhibitor 8504
T-24 2 Target ID: CHEMBL614774 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833690	Inhibitor 8504	3.0 nM [IC50]
CAKI-1 3 Target ID: CHEMBL614067 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25833690	Inhibitor 8504	30.0 nM [IC50]
PANC-1 5 Target ID: CHEMBL614139 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25517919	Inhibitor 8504	10.0 nM [IC50]
MIA PaCa-2 2 Target ID: CHEMBL614725 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25517919	Inhibitor 8504	7.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Advanced ovarian cancer 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020509s075lbl.pdf	Primary	Approved 8583	Gemzar Approved Use Gemzar is a nucleoside metabolic inhibitor indicated: • in combination with carboplatin, for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum- based therapy. • in combination with paclitaxel, for first-line treatment of metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated. • in combination with cisplatin for the treatment of non-small cell lung cancer. • as a single agent for the treatment of pancreatic cancer. Launch Date 1996
Metastatic breast cancer 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020509s075lbl.pdf	Primary	Approved 8583	Gemzar Approved Use Gemzar is a nucleoside metabolic inhibitor indicated: • in combination with carboplatin, for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum- based therapy. • in combination with paclitaxel, for first-line treatment of metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated. • in combination with cisplatin for the treatment of non-small cell lung cancer. • as a single agent for the treatment of pancreatic cancer. Launch Date 1996
Pancreatic cancer 98 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020509s075lbl.pdf	Primary	Approved 8583	Gemzar Approved Use Gemzar is a nucleoside metabolic inhibitor indicated: • in combination with carboplatin, for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum- based therapy. • in combination with paclitaxel, for first-line treatment of metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated. • in combination with cisplatin for the treatment of non-small cell lung cancer. • as a single agent for the treatment of pancreatic cancer. Launch Date 1996
Non-small cell lung cancer 211 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020509s075lbl.pdf	Primary	Approved 8583	Gemzar Approved Use Gemzar is a nucleoside metabolic inhibitor indicated: • in combination with carboplatin, for the treatment of advanced ovarian cancer that has relapsed at least 6 months after completion of platinum- based therapy. • in combination with paclitaxel, for first-line treatment of metastatic breast cancer after failure of prior anthracycline-containing adjuvant chemotherapy, unless anthracyclines were clinically contraindicated. • in combination with cisplatin for the treatment of non-small cell lung cancer. • as a single agent for the treatment of pancreatic cancer. Launch Date 1996

C_max

Value	Dose	Analyte	Population
229 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19556122	75 mg/m² 1 times / week multiple, intravenous dose: 75 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	GEMCITABINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
263.6 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19556122	135 mg/m² 1 times / week multiple, intravenous dose: 135 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	GEMCITABINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
292.5 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19556122	180 mg/m² 1 times / week multiple, intravenous dose: 180 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	GEMCITABINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
3526.4 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19556122	75 mg/m² 1 times / week multiple, intravenous dose: 75 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	GEMCITABINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4818.5 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19556122	135 mg/m² 1 times / week multiple, intravenous dose: 135 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	GEMCITABINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4863.4 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19556122	180 mg/m² 1 times / week multiple, intravenous dose: 180 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered:	GEMCITABINE blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
5700 mg/m2 1 times / 2 weeks multiple, intravenous MTD Dose: 5700 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 5700 mg/m2, 1 times / 2 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf https://pubmed.ncbi.nlm.nih.gov/17434832	unhealthy, 55 years (range: 34-71 years) Health Status: unhealthy Age Group: 55 years (range: 34-71 years) Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf https://pubmed.ncbi.nlm.nih.gov/17434832	Other AEs: Myelosuppression, Paresthesia... Other AEs: Myelosuppression Paresthesia Rash (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf https://pubmed.ncbi.nlm.nih.gov/17434832
2200 mg/m2 3 times / 4 weeks multiple, intravenous MTD Dose: 2200 mg/m2, 3 times / 4 weeks Route: intravenous Route: multiple Dose: 2200 mg/m2, 3 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/8996158	unhealthy, 58 years (range: 40-77 years) Health Status: unhealthy Age Group: 58 years (range: 40-77 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8996158	Other AEs: Neutropenia, AST increased... Other AEs: Neutropenia (grade 2, 1 patient) AST increased (grade 2, 1 patient) ALT increased (grade 2, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8996158
2800 mg/m2 3 times / 4 weeks multiple, intravenous Dose: 2800 mg/m2, 3 times / 4 weeks Route: intravenous Route: multiple Dose: 2800 mg/m2, 3 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/8996158	unhealthy, 58 years (range: 40-77 years) Health Status: unhealthy Age Group: 58 years (range: 40-77 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8996158	DLT: Hepatotoxicity, Neutropenic infection... Dose limiting toxicities: Hepatotoxicity (grade 3, 2 patients) Neutropenic infection (grade 4, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/8996158
1000 mg/m2 3 times / 4 weeks multiple, intravenous Recommended Dose: 1000 mg/m2, 3 times / 4 weeks Route: intravenous Route: multiple Dose: 1000 mg/m2, 3 times / 4 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/30397477	unhealthy, 74 years Health Status: unhealthy Age Group: 74 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/30397477	Disc. AE: Necrosis skin... AEs leading to discontinuation/dose reduction: Necrosis skin (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/30397477
800 mg/m2 3 times / 4 weeks multiple, intravenous Dose: 800 mg/m2, 3 times / 4 weeks Route: intravenous Route: multiple Dose: 800 mg/m2, 3 times / 4 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf	Disc. AE: Myocardial infarction, Cerebrovascular accident... AEs leading to discontinuation/dose reduction: Myocardial infarction (2%) Cerebrovascular accident (2%) Arrhythmia (2%) Hypertension (2%) Anemia (<1%) Thrombocytopenia (<1%) Hepatic dysfunction NOS (<1%) Kidney dysfunction (<1%) Nausea (<1%) Vomiting (<1%) Fever (<1%) Rash (<1%) Dyspnea (<1%) Hemorrhage (<1%) Infection (<1%) Stomatitis (<1%) Somnolence (<1%) Flu syndrome (<1%) Edema (<1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/020509s082lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	TK2 3 hCNT1 2 hCNT2 2 hCNT3 2 MRP5 41

Drug as victim

Target	Modality	Activity
MRP5 41	substrate 4014 Sources: https://www.nature.com/articles/6601011/ Page: -	yes
TK2 3	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0923753419381785 Page: -	yes
hCNT1 2	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0923753419381785 Page: -	yes
hCNT2 2	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0923753419381785 Page: -	yes
hCNT3 2	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0923753419381785 Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:175901	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:175901
ChemicalBook	CB4438054	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4438054
MolPort	MolPort-003-987-478	https://www.molport.com/shop/molecule-link/MolPort-003-987-478
Selleck Chemicals	Gemcitabine(Gemzar)	http://www.selleckchem.com/products/Gemcitabine(Gemzar).html
ZINC	ZINC000018279854	http://zinc15.docking.org/substances/ZINC000018279854

PubMed

Title	Date	PubMed
Akt, MAPK (Erk1/2), and p38 act in concert to promote apoptosis in response to ErbB receptor family inhibition.	2001-05-04	11278435
Gemcitabine following radiotherapy with concurrent 5-fluorouracil for nonmetastatic adenocarcinoma of the pancreas.	2001-04-20	11291097
Combined use of gemcitabine and radiation in mice.	2001-04-13	11299753
Neoadjuvant, adjuvant, and palliative treatment of pancreatic cancer.	2001-04	11276380
2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentofuranosylcytosine: a novel anticancer nucleoside analog that causes both DNA strand breaks and G(2) arrest.	2001-04	11259616
Cotton-wool spots associated with pancreatic carcinoma.	2001-03-26	11309222
Steroids affect collateral sensitivity to gemcitabine of multidrug-resistant human lung cancer cells.	2001-03-23	11282108
Phase I study of stealth liposomal doxorubicin in combination with gemcitabine in the treatment of patients with metastatic breast cancer.	2001-03-15	11251001
Novel approaches in the treatment of non-small-cell lung cancer.	2001-03	11301850
Treatment of elderly patients with non-small-cell lung cancer.	2001-03	11301849
Optimizing chemoradiation in locally advanced non-small-cell lung cancer.	2001-03	11301848
Gemcitabine and cisplatin combination in early-stage non-small-cell lung cancer.	2001-03	11301847
Gemcitabine for the treatment of non-small-cell lung cancer.	2001-03	11301846
Triplet combination chemotherapy and targeted therapy regimens.	2001-03	11301845
Gemcitabine and nonplatinum combinations in non-small-cell lung cancer.	2001-03	11301844
Gemcitabine in combination with new platinum compounds: an update.	2001-03	11301843
Irinotecan/gemcitabine combination chemotherapy in pancreatic cancer.	2001-03	11301841
Unexpected severe myelotoxicity of gemcitabine in pretreated breast cancer patients.	2001-03	11290868
Gemcitabine and vinorelbine as first-line chemotherapy for advanced non-small cell lung cancer: a phase II trial.	2001-03	11290433
Latent hematopoietic stem cell toxicity associated with protracted drug administration.	2001-03	11274755
[A case of primary malignant hemangiopericytoma of the lung with marked response to combination chemotherapy with cisplatin, ifosfamide and gemcitabine].	2001-03	11265407
Neoadjuvant chemoradiotherapy for adenocarcinoma of the pancreas: treatment variables and survival duration.	2001-03	11258776
End-joining deficiency and radiosensitization induced by gemcitabine.	2001-02-15	11245469
P53 modulates the effect of loss of DNA mismatch repair on the sensitivity of human colon cancer cells to the cytotoxic and mutagenic effects of cisplatin.	2001-02-15	11245458
Phase II trial of two-weekly gemcitabine in patients with advanced biliary tract cancer.	2001-02	11300321
[Medical treatment of pulmonary neoplasms].	2001-02	11294106
Challenging the platinum combinations: docetaxel (Taxotere) combined with gemcitabine or vinorelbine in non-small cell lung cancer.	2001-02	11284620
[Palliative therapy of pancreatic adenocarcinoma].	2001-02	11253511
Biweekly gemcitabine, doxorubicin, and paclitaxel as first-line treatment in metastatic breast cancer. Final results from a phase II trial.	2001-02	11252890
The gemcitabine/epirubicin/paclitaxel trials in advanced breast cancer.	2001-02	11252889
Gemcitabine, paclitaxel, and trastuzumab in metastatic breast cancer.	2001-02	11252888
Gemcitabine and Pemetrexed disodium in treating breast cancer.	2001-02	11252887
Gemcitabine plus cisplatin in breast cancer.	2001-02	11252886
Gemcitabine and paclitaxel as salvage therapy in metastatic breast cancer.	2001-02	11252885
Docetaxel/gemcitabine: salvage chemotherapy in anthracycline-pretreated patients with advanced breast cancer.	2001-02	11252884
Treatment of advanced breast cancer with gemcitabine and vinorelbine.	2001-02	11252883
Gemcitabine as single-agent therapy in the management of advanced breast cancer.	2001-02	11252882
Chemotherapy agents in transitional cell carcinoma: the old and the new.	2001-02	11246730
Effects of gemcitabine on cisplatin-induced nephrotoxicity in rats: schedule-dependent study.	2001-02	11243722
Gemcitabine-associated posterior reversible encephalopathy syndrome: MR imaging and MR spectroscopy findings.	2001-01	11295355
Phase I trial of gemcitabine in patients with advanced pancreatic cancer.	2001-01	11256843
Second-line chemotherapy for non-small-cell lung cancer with monthly docetaxel and weekly gemcitabine: a phase II trial.	2001-01	11249055
High-dose thiotepa and melphalan with hemopoietic progenitor support following induction therapy with epirubicin-paclitaxel-containing regimens in metastatic breast cancer (MBC).	2001-01	11249051
Treatment of pancreatic cancer with a combination of docetaxel, gemcitabine and granulocyte colony-stimulating factor: a phase II study of the Greek Cooperative Group for Pancreatic Cancer.	2001-01	11249034
Treatment of classical Kaposi's sarcoma with gemcitabine.	2001	11306832
Noncardiogenic pulmonary edema: an unusual and serious complication of anticancer therapy.	2001	11306727
Chemotherapy of metastatic breast cancer: what to expect in 2001 and beyond.	2001	11306725
Excellent response to gemcitabine in a massively pre-treated woman with extensive cutaneous involvement after recurrence of breast cancer.	2001	11291839
Achievement of complete remission in refractory Hodgkin's disease with prolonged infusion of gemcitabine.	2001	11291828
Recent advances in bladder cancer chemotherapy.	2001	11291559

Patents

Sample Use Guides

In Vivo Use Guide

For intravenous use only. • Ovarian Cancer: 1000 mg/m2 over 30 minutes on Days 1 and 8 of each 21-day cycle. (2.1) • Breast Cancer: 1250 mg/m2 over 30 minutes on Days 1 and 8 of each 21-day cycle. (2.2) • Non-Small Cell Lung Cancer: 1000 mg/m2 over 30 minutes on Days 1, 8, and 15 of each 28-day cycle or 1250 mg/m2 over 30 minutes on Days 1 and 8 of each 21-day cycle. (2.3) • Pancreatic Cancer: 1000 mg/m2 over 30 minutes once weekly for the first 7 weeks, then one week rest, then once weekly for 3 weeks of each 28-day cycle

Route of Administration: Intravenous

In Vitro Use Guide

Treatment of PANC-1 cells with gemcitabine (10 nM) increased the percentage of cells in S phase to 60.1±6.0% and reduced the percentage in the G0/G1 phase to 28.7±4.2%

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:50:15 GMT 2025` Edited by `admin` on `Mon Mar 31 17:50:15 GMT 2025`
Record UNII	U347PV74IL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INFUGEM

Preferred Name

English

GEMCITABINE HYDROCHLORIDE

Official Name

English

GEMCITABINE HYDROCHLORIDE [MI]

Common Name

English

GEMCITABINE HYDROCHLORIDE [VANDF]

Common Name

English

GEMCITABINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

Gemcitabine hydrochloride [WHO-DD]

Common Name

English

4-AMINO-1-((2R,4R,5R)-3,3-DIFLUORO-4-HYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL)PYRIMIDIN-2-ONE HYDROCHLORIDE

Systematic Name

English

GEMCITABINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

GEMCITABINE HYDROCHLORIDE [USP-RS]

Common Name

English

GEMCITABINE HYDROCHLORIDE [MART.]

Common Name

English

GEMCITABINE HYDROCHLORIDE [JAN]

Common Name

English

LY-188011 HYDROCHLORIDE

Code

English

GEMZAR

Brand Name

English

CYTIDINE, 2'-DEOXY-2',2'-DIFLUORO-, MONOHYDROCHLORIDE

Common Name

English

2'-DEOXY-2',2'-DIFLUOROCYTIDINE MONOHYDROCHLORIDE (.BETA.-ISOMER)

Common Name

English

GEMCITABINE HYDROCHLORIDE [USAN]

Common Name

English

LY188011 HYDROCHLORIDE

Code

English

GEMCITABINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

GEMCITABINE HCL

Common Name

English

GEMCITABINE (AS HYDROCHLORIDE)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557