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Also known as: Gemcitabine hcl, 122111-03-9, Gemzar, Ly188011 hydrochloride, Gemcitabine (hydrochloride), 2'-deoxy-2',2'-difluorocytidine monohydrochloride
Molecular Formula
C9H12ClF2N3O4
Molecular Weight
299.66  g/mol
InChI Key
OKKDEIYWILRZIA-OSZBKLCCSA-N
FDA UNII
U347PV74IL

Gemcitabine
A deoxycytidine antimetabolite used as an antineoplastic agent.
1 2D Structure

Gemcitabine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride
2.1.2 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
2.1.3 InChI Key
OKKDEIYWILRZIA-OSZBKLCCSA-N
2.1.4 Canonical SMILES
C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)(F)F.Cl
2.1.5 Isomeric SMILES
C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F.Cl
2.2 Other Identifiers
2.2.1 UNII
U347PV74IL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 188011, Ly

2. 2' Deoxy 2' Difluorocytidine

3. 2' Deoxy 2',2'' Difluorocytidine 5' O Monophosphate

4. 2',2'-dfdc

5. 2',2'-difluoro-2'-deoxycytidine

6. 2',2'-difluorodeoxycytidine

7. 2'-deoxy-2',2''-difluorocytidine-5'-o-monophosphate

8. 2'-deoxy-2'-difluorocytidine

9. Dfdcyd

10. Gemcitabine

11. Gemcitabine, (alpha-d-threo-pentofuranosyl)-isomer

12. Gemcitabine, (beta-d-threo-pentafuranosyl)-isomer

13. Gemcitabine, (d-threo-pentafuranosyl)-isomer

14. Gemicitabine

15. Gemzar

16. Hydrochloride, Gemcitabine

17. Ly 188011

18. Ly-188011

2.3.2 Depositor-Supplied Synonyms

1. Gemcitabine Hcl

2. 122111-03-9

3. Gemzar

4. Ly188011 Hydrochloride

5. Gemcitabine (hydrochloride)

6. 2'-deoxy-2',2'-difluorocytidine Monohydrochloride

7. Cytidine, 2'-deoxy-2',2'-difluoro-, Monohydrochloride

8. Dfdc

9. 4-amino-1-((2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-one Hydrochloride

10. Gemcitabine (as Hydrochloride)

11. U347pv74il

12. Chebi:31647

13. 2',2'-difluoro-2'-deoxycytidine Hydrochloride

14. Ly-188011 Hydrochloride

15. Ly-188011

16. 122111-03-9 (hcl)

17. Dsstox_cid_27827

18. Dsstox_rid_82590

19. Dsstox_gsid_47849

20. 2'-deoxy-2',2'-difluorocytidine Hydrochloride

21. 4-amino-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride

22. Dizirconium Silicide

23. Cas-122111-03-9

24. Gemcitabine Hydrochloride [usan]

25. Gemcitabine Hcl (gemzar)

26. Ly 188011

27. Unii-u347pv74il

28. Mfcd01735988

29. Ncgc00168784-01

30. Gemzar (tn)

31. Infugem

32. Gemcitabine Hydrochloride [usan:usp]

33. Inno-d07001

34. Schembl4366

35. Chembl1637

36. Ly 188011 Hydrochloride

37. Mls003915643

38. Gemcitabine Hydrochloride,(s)

39. Dtxsid3047849

40. Ex-a837

41. 2'-deoxy-2',2'-difluorocytidine Monohydrochloride (beta-isomer)

42. Act06731

43. Hy-b0003

44. Ly-188011 . Hcl

45. Tox21_112644

46. Bdbm50247964

47. Gemcitabine Hydrochloride (jan/usp)

48. S1149

49. Gemcitabine Hydrochloride [mi]

50. Akos015999730

51. Tox21_112644_1

52. Ccg-267459

53. Cs-0755

54. Gemcitabine Hcl (gemzar,ly188011)

55. Gemcitabine Hydrochloride [jan]

56. 2'-deoxy-2',2'-difluorocytidine Hcl

57. Gemcitabine Hydrochloride [mart.]

58. Gemcitabine Hydrochloride [vandf]

59. Ncgc00168784-03

60. As-13656

61. Bg164501

62. Gemcitabine Hydrochloride [usp-rs]

63. Gemcitabine Hydrochloride [who-dd]

64. Smr000469146

65. Gemcitabine Hydrochloride, >=98% (hplc)

66. Gemcitabine Hydrochloride,gemzar, Ly-188011

67. D01155

68. Gemcitabine Hydrochloride [ep Monograph]

69. Gemcitabine Hydrochloride [orange Book]

70. 2'-deoxy-2',2'-difluorocytidine, Hydrochloride

71. Gemcitabine Hydrochloride [usp Monograph]

72. 111g039

73. W-60402

74. (+)-2'-deoxy-2',2'-difluorocytidine Hydrochloride

75. J-700175

76. Q27114559

77. 2'-deoxy-2',2'-difluorocytidine Monohydrochloride (.beta.-isomer)

78. Gemcitabine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

79. Gemcitabine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

80. (2'r,4'r,5'r)-4-amino-1-(3,3-difluoro-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyridin-2-one Hydrochloride

81. 4-amino-1-((2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)pyrimidin-2-one Hydrochloride

82. 4-amino-1-((2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1h)-onehydrochloride

2.3.3 Other Synonyms

1. Gemcitabine Free Base

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 299.66 g/mol
Molecular Formula C9H12ClF2N3O4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass299.0484399 g/mol
Monoisotopic Mass299.0484399 g/mol
Topological Polar Surface Area108 Ų
Heavy Atom Count19
Formal Charge0
Complexity426
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameGemcitabine hydrochloride
Drug LabelGemzar (gemcitabine for injection, USP) is a nucleoside metabolic inhibitor that exhibits antitumor activity. Gemcitabine HCl is 2-deoxy-2,2-difluorocytidine monohydrochloride (-isomer). The structural formula is as follows: The empirical...
Active IngredientGemcitabine hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 200mg base/vial; 1gm/26.3ml (38mg/ml); 2gm/52.6ml (38mg/ml); 200mg/5.26ml (38mg/ml); eq 1gm base/vial
Market StatusPrescription
CompanyHospira; Jiangsu Hansoh Pharm; Fresenius Kabi Oncol; Accord Hlthcare; Cipla; Sun Pharma Global; Actavis Elizabeth; Emcure Pharms; Teva Pharms; Fresenius Kabi Usa; Onco Therapies; Hameln Rds Gmbh; Luitpold; Sagent Pharms; Dr Reddys Labs

2 of 4  
Drug NameGemzar
PubMed HealthGemcitabine (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelGemzar (gemcitabine for injection, USP) is a nucleoside metabolic inhibitor that exhibits antitumor activity. Gemcitabine HCl is 2-deoxy-2,2-difluorocytidine monohydrochloride (-isomer). The structural formula is as follows: The empirical...
Active IngredientGemcitabine hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 200mg base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyLilly

3 of 4  
Drug NameGemcitabine hydrochloride
Drug LabelGemzar (gemcitabine for injection, USP) is a nucleoside metabolic inhibitor that exhibits antitumor activity. Gemcitabine HCl is 2-deoxy-2,2-difluorocytidine monohydrochloride (-isomer). The structural formula is as follows: The empirical...
Active IngredientGemcitabine hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 2gm base/vial; eq 200mg base/vial; 1gm/26.3ml (38mg/ml); 2gm/52.6ml (38mg/ml); 200mg/5.26ml (38mg/ml); eq 1gm base/vial
Market StatusPrescription
CompanyHospira; Jiangsu Hansoh Pharm; Fresenius Kabi Oncol; Accord Hlthcare; Cipla; Sun Pharma Global; Actavis Elizabeth; Emcure Pharms; Teva Pharms; Fresenius Kabi Usa; Onco Therapies; Hameln Rds Gmbh; Luitpold; Sagent Pharms; Dr Reddys Labs

4 of 4  
Drug NameGemzar
PubMed HealthGemcitabine (Injection)
Drug ClassesAntineoplastic Agent
Drug LabelGemzar (gemcitabine for injection, USP) is a nucleoside metabolic inhibitor that exhibits antitumor activity. Gemcitabine HCl is 2-deoxy-2,2-difluorocytidine monohydrochloride (-isomer). The structural formula is as follows: The empirical...
Active IngredientGemcitabine hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 200mg base/vial; eq 1gm base/vial
Market StatusPrescription
CompanyLilly

4.2 Drug Indication

Treatment of urothelial carcinoma


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antimetabolites, Antineoplastic

Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Nucleoside Metabolic Inhibitor [EPC]; Nucleic Acid Synthesis Inhibitors [MoA]

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LIFESCIENCES","customerCountry":"INDIA","quantity":"8.38","actualQuantity":"8.378","unit":"KGS","unitRateFc":"3258.8","totalValueFC":"27537","currency":"USD","unitRateINR":"275693.8","date":"02-Aug-2024","totalValueINR":"2309762.97","totalValueInUsd":"27537","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29335990","bill_no":"4837509","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"TAIPEI","supplierAddress":"No. 1, Nan-Ke-8th road SHAN HUA Tainan SDNF Taiwan","customerAddress":"PLOT NO. 3, PHARMEZ, SEZ, SARKEHJ"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1725301800,"product":"GEMCITABINE HYDROCHLORIDE BATCH NO.71801AA019","address":"PLOT NO. 3, PHARMEZ, SEZ, SARKEHJ","city":"TAL- SANAND, DIST- AHMEDABAD","supplier":"SCINOPHARM TAIWAN, LTD","supplierCountry":"TAIWAN","foreign_port":"TAIPEI","customer":"ZYDUS 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LIFESCIENCES","customerCountry":"INDIA","quantity":"71.70","actualQuantity":"71.695","unit":"KGS","unitRateFc":"3200","totalValueFC":"231610.8","currency":"USD","unitRateINR":"270720","date":"23-Sep-2024","totalValueINR":"19409270.4","totalValueInUsd":"231610.8","indian_port":"Ahmedabad-ZIPL-SEZ","hs_no":"29335990","bill_no":"5750478","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"TAIPEI","supplierAddress":"No. 1, Nan-Ke-8th road SHAN HUA SDNF Taiwan","customerAddress":"PLOT NO. 3, PHARMEZ, SEZ, SARKEHJ"}]
04-Jan-2021
30-Sep-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - INJECTABLE;INJECTION - EQ 1GM BASE/V...DOSAGE - INJECTABLE;INJECTION - EQ 1GM BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20509

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DOSAGE - INJECTABLE;INJECTION - EQ 200MG BASE...DOSAGE - INJECTABLE;INJECTION - EQ 200MG BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20509

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 1200MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1200MG BASE/120ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 1300MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1300MG BASE/130ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 1400MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1400MG BASE/140ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 1500MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1500MG BASE/150ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 1600MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1600MG BASE/160ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 1700MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1700MG BASE/170ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 1800MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1800MG BASE/180ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 1900MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 1900MG BASE/190ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 2000MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 2000MG BASE/200ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

read-more

DOSAGE - SOLUTION;INTRAVENOUS - EQ 2200MG BAS...DOSAGE - SOLUTION;INTRAVENOUS - EQ 2200MG BASE/220ML (EQ 10MG BASE/ML)

USFDA APPLICATION NUMBER - 208313

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Patents & EXCLUSIVITIES

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US Patents

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01

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

02

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

03

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

04

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

05

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

06

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

07

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

08

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

09

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

blank

10

arrow
PODD Partnership
Not Confirmed

SUN PHARM

India
arrow
PODD Partnership
Not Confirmed

GEMCITABINE HYDROCHLORIDE

US Patent Number : 9241948

Drug Substance Claim :

Drug Product Claim : Y

Application Number : 208313

Patent Use Code :

Delist Requested :

Patent Use Description :

Patent Expiration Date : 2033-07-01

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