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    Pradaxa

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    2D Structure
    Also known as: Dabigatran etexilate mesylate, 872728-81-9, Pradaxa, Ethyl 3-[[2-[[4-[(z)-n'-hexoxycarbonylcarbamimidoyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate;methanesulfonic acid, Dtxsid20236248, Ex-a1966
    Molecular Formula
    C35H45N7O8S
    Molecular Weight
    723.8  g/mol
    InChI Key
    XETBXHPXHHOLOE-UHFFFAOYSA-N
    A THROMBIN inhibitor which acts by binding and blocking thrombogenic activity and the prevention of thrombus formation. It is used to reduce the risk of stroke and systemic EMBOLISM in patients with nonvalvular atrial fibrillation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    ethyl 3-[[2-[[4-[(Z)-N'-hexoxycarbonylcarbamimidoyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate;methanesulfonic acid
    2.1.2 InChI
    InChI=1S/C34H41N7O5.CH4O3S/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29;1-5(2,3)4/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44);1H3,(H,2,3,4)
    2.1.3 InChI Key
    XETBXHPXHHOLOE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCCCOC(=O)N=C(C1=CC=C(C=C1)NCC2=NC3=C(N2C)C=CC(=C3)C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)N.CS(=O)(=O)O
    2.1.5 Isomeric SMILES
    CCCCCCOC(=O)/N=C(/C1=CC=C(C=C1)NCC2=NC3=C(N2C)C=CC(=C3)C(=O)N(CCC(=O)OCC)C4=CC=CC=N4)\N.CS(=O)(=O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Bibr 1048

    2. Dabigatran

    3. Dabigatran Etexilate

    4. Dabigatran Etexilate Mesylate

    5. Etexilate Mesylate, Dabigatran

    6. Etexilate, Dabigatran

    7. Mesylate, Dabigatran Etexilate

    8. N-((2-(((4-(aminoiminomethyl)phenyl)amino)methyl)-1-methyl-1h-benzimidazol-5-yl)carbonyl)-n-2-pyridinyl-beta-alanine

    9. Pradaxa

    2.2.2 Depositor-Supplied Synonyms

    1. Dabigatran Etexilate Mesylate

    2. 872728-81-9

    3. Pradaxa

    4. Ethyl 3-[[2-[[4-[(z)-n'-hexoxycarbonylcarbamimidoyl]anilino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate;methanesulfonic Acid

    5. Dtxsid20236248

    6. Ex-a1966

    7. Mfcd25424070

    8. S5960

    9. Ccg-213236

    10. Cs-w004358

    11. (z)-ethyl 3-(2-(((4-(n'-((hexyloxy)carbonyl)carbamimidoyl)phenyl)amino)methyl)-1-methyl-n-(pyridin-2-yl)-1h-benzo[d]imidazole-5-carboxamido)propanoate Methanesulfonate

    12. 728p819

    2.3 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 723.8 g/mol
    Molecular Formula C35H45N7O8S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count17
    Exact Mass723.30503259 g/mol
    Monoisotopic Mass723.30503259 g/mol
    Topological Polar Surface Area217 Ų
    Heavy Atom Count51
    Formal Charge0
    Complexity1100
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NamePradaxa
    PubMed HealthDabigatran (By mouth)
    Drug ClassesAnticoagulant
    Drug LabelThe chemical name for dabigatran etexilate mesylate, a direct thrombin inhibitor, is -Alanine, N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl] phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-,ethyl ester, methanesulfo...
    Active IngredientDabigatran etexilate mesylate
    Dosage FormCapsule
    RouteOral
    Strengtheq 150mg base; eq 75mg base
    Market StatusPrescription
    CompanyBoehringer Ingelheim

    2 of 2  
    Drug NamePradaxa
    PubMed HealthDabigatran (By mouth)
    Drug ClassesAnticoagulant
    Drug LabelThe chemical name for dabigatran etexilate mesylate, a direct thrombin inhibitor, is -Alanine, N-[[2-[[[4-[[[(hexyloxy)carbonyl]amino]iminomethyl] phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-2-pyridinyl-,ethyl ester, methanesulfo...
    Active IngredientDabigatran etexilate mesylate
    Dosage FormCapsule
    RouteOral
    Strengtheq 150mg base; eq 75mg base
    Market StatusPrescription
    CompanyBoehringer Ingelheim

    4.2 Drug Indication

    Pradaxa 75 mg

    - Primary prevention of venous thromboembolic events in adult patients who have undergone elective total hip replacement surgery or total knee replacement surgery.

    Pradaxa 110 mg

    - Primary prevention of venous thromboembolic events in adult patients who have undergone elective total hip replacement surgery or total knee replacement surgery.

    - Prevention of stroke and systemic embolism in adult patients with non-valvular atrial fibrillation (NVAF), with one or more risk factors, such as prior stroke or transient ischemic attack (TIA); age 75 years; heart failure (NYHA Class II); diabetes mellitus; hypertension.

    - Treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE), and prevention of recurrent DVT and PE in adults.

    Pradaxa 150 mg

    - Prevention of stroke and systemic embolism in adult patients with non-valvular atrial fibrillation (NVAF), with one or more risk factors, such as prior stroke or transient ischemic attack (TIA); age 75 years; heart failure (NYHA Class II); diabetes mellitus; hypertension.

    - Treatment of deep vein thrombosis (DVT) and pulmonary embolism (PE), and prevention of recurrent DVT and PE in adults.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antithrombins

    Endogenous factors and drugs that directly inhibit the action of THROMBIN, usually by blocking its enzymatic activity. They are distinguished from INDIRECT THROMBIN INHIBITORS, such as HEPARIN, which act by enhancing the inhibitory effects of antithrombins. (See all compounds classified as Antithrombins.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Thrombin Inhibitors [MoA]; Direct Thrombin Inhibitor [EPC]
    5.3 ATC Code

    B01AE07