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    Technical details about Gemcitabine, learn more about the structure, uses, toxicity, action, side effects and more

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    Gemcitabine

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

    2D Structure

    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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