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    AR 101

    ACTIVE PHARMA INGREDIENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 192314-93-5, Ar-100, Mersarex, 5-[(2-cyclopropyl-7,8-dimethoxy-2h-chromen-5-yl)methyl]pyrimidine-2,4-diamine, Ro-48-2622, 5-((2-cyclopropyl-7,8-dimethoxy-2h-chromen-5-yl)methyl)pyrimidine-2,4-diamine
    Molecular Formula
    C19H22N4O3
    Molecular Weight
    354.4  g/mol
    InChI Key
    HWJPWWYTGBZDEG-UHFFFAOYSA-N
    FDA UNII
    42445HUU0O
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[(2-cyclopropyl-7,8-dimethoxy-2H-chromen-5-yl)methyl]pyrimidine-2,4-diamine
    2.1.2 InChI
    InChI=1S/C19H22N4O3/c1-24-15-8-11(7-12-9-22-19(21)23-18(12)20)13-5-6-14(10-3-4-10)26-16(13)17(15)25-2/h5-6,8-10,14H,3-4,7H2,1-2H3,(H4,20,21,22,23)
    2.1.3 InChI Key
    HWJPWWYTGBZDEG-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    COC1=C(C2=C(C=CC(O2)C3CC3)C(=C1)CC4=CN=C(N=C4N)N)OC
    2.2 Other Identifiers
    2.2.1 UNII
    42445HUU0O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ar 100

    2. Ar-100

    2.3.2 Depositor-Supplied Synonyms

    1. 192314-93-5

    2. Ar-100

    3. Mersarex

    4. 5-[(2-cyclopropyl-7,8-dimethoxy-2h-chromen-5-yl)methyl]pyrimidine-2,4-diamine

    5. Ro-48-2622

    6. 5-((2-cyclopropyl-7,8-dimethoxy-2h-chromen-5-yl)methyl)pyrimidine-2,4-diamine

    7. 42445huu0o

    8. Ro-482622

    9. Ar-100.001

    10. Ro 63-9141;bal 9141

    11. Ro 48-2622

    12. Iclaprim [inn]

    13. Ar-101

    14. 2,4-pyrimidinediamine, 5-((2-cyclopropyl-7,8-dimethoxy-2h-1-benzopyran-5-yl)methyl)-

    15. 2,4-pyrimidinediamine, 5-[(2-cyclopropyl-7,8-dimethoxy-2h-1-benzopyran-5-yl)methyl]-

    16. Iclaprim [usan]

    17. Iclaprim (usan/inn)

    18. Iclaprim [usan:inn]

    19. Unii-42445huu0o

    20. Ar 100

    21. Iclaprim [mi]

    22. Iclaprim [mart.]

    23. Iclaprim [who-dd]

    24. 5-(2-cyclopropyl-7,8-dimethoxy-2h-chromen-5-ylmethyl)-pyrimidine-2,4-diamine (iclaprim]

    25. Schembl379386

    26. Chembl134561

    27. Schembl12899446

    28. Bdbm18070

    29. Gtpl10820

    30. Dtxsid70870191

    31. Chebi:131751

    32. Hms3749a21

    33. Bcp04499

    34. Ar-100ar-100

    35. Mfcd09837803

    36. Cs-7873

    37. Db06358

    38. Sb17354

    39. 5-((2rs)-2-cyclopropyl-7,8-dimethoxy-2h-chromen-5-ylmethyl)pyrimidine-2,4-diamine

    40. As-74032

    41. Da-38934

    42. Hy-101479

    43. Ft-0670271

    44. Ft-0670272

    45. D08337

    46. W16646

    47. Q907480

    48. J-012427

    49. 5-(2-cyclopropyl-7,8-dimethoxy-2h-1-benzopyran-5-ylmethyl)pyrimidine-2,4-diamine

    50. 5-[(2-cyclopropyl-7,8-dimethoxy-2h-1-benzopyran-5-yl)methyl]-2,4-pyrimidine- Diamine

    51. 5-[(2-cyclopropyl-7,8-dimethoxy-2h-1-benzopyran-5-yl)methyl]pyrimidine-2,4-diamine

    52. 5-[(2-cyclopropyl-7,8-dimethoxy-2h-chromen-5-yl)methyl]pyrimidine-2,4- Diamine

    53. 5-(((2rs)-2-cyclopropyl-7,8-dimethoxy-2h-1-benzopyran-5-yl)methyl)pyrimidine-2,4-diamine

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 354.4 g/mol
    Molecular Formula C19H22N4O3
    XLogP32.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count5
    Exact Mass354.16919058 g/mol
    Monoisotopic Mass354.16919058 g/mol
    Topological Polar Surface Area106 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity515
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in bacterial infection, skin infections/disorders, obesity, liver disease, kidney disease, and pneumonia.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Folic Acid Antagonists

    Inhibitors of the enzyme, dihydrofolate reductase (TETRAHYDROFOLATE DEHYDROGENASE), which converts dihydrofolate (FH2) to tetrahydrofolate (FH4). They are frequently used in cancer chemotherapy. (From AMA, Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Folic Acid Antagonists.)

    5.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01E - Sulfonamides and trimethoprim

    J01EA - Trimethoprim and derivatives

    J01EA03 - Iclaprim

    5.3 Mechanism of Action

    Iclaprim is a novel diaminopyrimidine, and an inhibitor of dihydrofolate reductase, which has shown potent, extended-spectrum in vitro activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus, vancomycin-intermediate and vancomycin-resistant S. aureus and macrolide-, quinolone- and trimethoprim-resistant strains. In addition, iclaprim has demonstrated activity against Streptococcus pneumoniae including penicillin-, erythromycin-, levofloxacin- and trimethoprim/sulfamethoxazole-resistant strains.