Gemcitabine Hydrochloride

Gemcitabine hydrochloride was first approved in ZA on Jan 10, 1995, then approved by the U.S. Food and Drug Administration (FDA) on May 15, 1996, and approved by Pharmaceuticals and Medicals Devices Agency of Japan (PMDA) on Aug 31, 2001. It was developed and marketed as Gemzar® by Eli Lilly.

Gemcitabine hydrochloride is a nucleoside metabolic inhibitor. It kills cells undergoing DNA synthesis and blocks the progression of cells through the G1/S-phase boundary. It is indicated 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, and it is also indicated in combination with cisplatin for the treatment of non-small cell lung cancer, and treated as a single agent for the treatment of pancreatic cancer.

Gemzar® is available as injection of lyophilized powder for intravenous use, containing 200 mg or 1000 mg of free Gemcitabine per vial. The recommended initial dosage is 1000 mg/m2 over 30 minutes on days 1 and 8 of each 21 day cycle for ovarian cancer, 1250 mg/m2 over 30 minutes on days 1 and 8 of each 21 day cycle for breast 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 for non-small cell lung cancer, and 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 for pancreatic cancer.

Index：

General Information

Update Date：2016-04-13

Drug Name：
Gemcitabine Hydrochloride
Research Code：
LY-188011; NSC-613327
Trade Name：
Gemzar®
MOA：
Nucleoside metabolic inhibitor
Indication：
Relapsed or refractory malignant lymphoma; Non small cell lung cancer (NSCLC); Urothelial cancer; Advanced ovarian cancer; Breast cancer; Advanced breast cancer; Ovarian cancer; Biliary cancer; Pancreatic cancer
Status：
Approved
Company：
Lilly (Originator)
Sales：
$147 Million (Y2015);
$153 Million (Y2014);;
$193 Million (Y2013);;
$290 Million (Y2012);;
$452 Million (Y2011);
ATC Code：
L01BC05
Approved Countries or Area

Update Date：2015-07-29

Approval Date Approval Type Trade Name Indication Dosage Form Strength Company Review Classification
1996-05-15 First approval Gemzar Ovarian cancer,Breast cancer,Non small cell lung cancer (NSCLC),Pancreatic cancer Injection, Lyophilized powder, For solution Eq. 200 mg/1000 mg Gemcitabine/vial Lilly Priority
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Approval Date Approval Type Trade Name Indication Dosage Form Strength Company Review Classification
2013-02-01 New indication Gemzar Relapsed or refractory malignant lymphoma Injection, Lyophilized powder, For solution 200 mg; 1 g Lilly
2011-02-23 New indication Gemzar Advanced ovarian cancer Injection, Lyophilized powder, For solution 200 mg; 1 g Lilly
2010-02-05 New indication Gemzar Advanced breast cancer Injection, Lyophilized powder, For solution 200 mg; 1 g Lilly
2008-11-25 New indication Gemzar Urothelial cancer Injection, Lyophilized powder, For solution 200 mg; 1 g Lilly
2006-06-15 New indication Gemzar Biliary cancer Injection, Lyophilized powder, For solution 200 mg; 1 g Lilly
2001-08-31 First approval Gemzar Pancreatic cancer,Non small cell lung cancer (NSCLC) Injection, Lyophilized powder, For suspension 200 mg; 1 g Lilly
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Approval Date Approval Type Trade Name Indication Dosage Form Strength Company Review Classification
2014-04-15 Marketing approval Ovarian cancer,Breast cancer,Non small cell lung cancer (NSCLC),Pancreatic cancer Injection Eq. 1000 mg Gemcitabine per vial 湖北一半天制药
2014-04-15 Marketing approval Ovarian cancer,Breast cancer,Non small cell lung cancer (NSCLC),Pancreatic cancer Injection Eq. 200 mg Gemcitabine per vial 湖北一半天制药 6类
2014-04-08 Marketing approval Ovarian cancer,Breast cancer,Non small cell lung cancer (NSCLC),Pancreatic cancer Injection Eq.1000 mg Gemcitabine per vial 南京正大天晴制药 6类
2011-12-02 Marketing approval 健择/Gemzar Ovarian cancer,Breast cancer,Non small cell lung cancer (NSCLC),Pancreatic cancer Injection Eq. 200 mg/1000 mg Gemcitabine per vial Lilly
2010-08-31 Marketing approval Ovarian cancer,Breast cancer,Non small cell lung cancer (NSCLC),Pancreatic cancer Injection 1000 mg/200 mg 北京协和药厂 6类
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Approval Date Approval Type Trade Name Indication Dosage Form Strength Company Review Classification
1995-01-10 First approval Gemzar Ovarian cancer,Breast cancer,Non small cell lung cancer (NSCLC),Pancreatic cancer Injection, Lyophilized powder, For solution Eq. 200 mg/1000 mg Gemcitabine per vial Lilly
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Chemical Structure

Update Date：2015-08-27

Molecular Weight 299.66
Formula C9H11F2N3O4 • HCl
CAS No. 95058-81-4 (Gemcitabine);
122111-03-9 (Gemcitabine HCl);
Chemical Name Cytidine, 2'-deoxy-2',2'-difluoro-, hydrochloride (1:1)
Gemcitabine （Free Acid/Base）Parameters：
MW HD HA FRB* PSA* cLogP*
263.20 4 7 4 108 -2.216±0.487
*：Calculated by ACD/Labs software V11.02.
Synthesis & Impurities

Update Date：2015-10-09


1. J. Org. Chem. 1988, 53, 2406-2409.

2. US4808614A.


1. CN102417533A.


1. Nucleosides, Nucleotides and Nucleic Acids 2010, 29, 113-122.


1. CN102617677A.


1. CN103012527A.

1
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Gemicitabine Hydrochloride Impurity F C23H19F2N3O6 471.41 134790-40-2
2
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Gemicitabine Hydrochloride Impurity G C23H19F2N3O6 471.41 1268237-46-2
3
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Gemicitabine Hydrochloride Impurity H C23H19F2N3O6 471.41
4
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Gemicitabine Hydrochloride Impurity A C9H11F2N3O4 263.2 95058-85-8
5
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Gemicitabine Hydrochloride Impurity B C4H5N3O 111.1 71-30-7
6
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Gemicitabine Hydrochloride Impurity C C9H11F2N3O4 263.2 103882-85-5
7
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Gemicitabine Hydrochloride Impurity D C9H11F2N3O4.HCl 299.66 122111-05-1
8
Impurity Name: Molecular Formula: Molecular Weight: CAS No.:
Gemicitabine Hydrochloride Impurity E C17H17F2N3O6 397.33 138685-83-3