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    Chemistry

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    Also known as: 120685-11-2, Pkc-412, Pkc412, Cgp 41251, 4'-n-benzoylstaurosporine, Pkc 412
    Molecular Formula
    C35H30N4O4
    Molecular Weight
    570.6  g/mol
    InChI Key
    BMGQWWVMWDBQGC-IIFHNQTCSA-N
    FDA UNII
    ID912S5VON
    Midostaurin
    Midostaurin is a synthetic indolocarbazole multikinase inhibitor with potential antiangiogenic and antineoplastic activities. Midostaurin inhibits protein kinase C alpha (PKCalpha), vascular endothelial growth factor receptor 2 (VEGFR2), c-kit, platelet-derived growth factor receptor (PDGFR) and FMS-like tyrosine kinase 3 (FLT3) tyrosine kinases, which may result in disruption of the cell cycle, inhibition of proliferation, apoptosis, and inhibition of angiogenesis in susceptible tumors.
    Midostaurin is a Kinase Inhibitor. The mechanism of action of midostaurin is as a Receptor Tyrosine Kinase Inhibitor.
    1 2D Structure

    Midostaurin

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[(2S,3R,4R,6R)-3-methoxy-2-methyl-16-oxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-4-yl]-N-methylbenzamide
    2.1.2 InChI
    InChI=1S/C35H30N4O4/c1-35-32(42-3)25(37(2)34(41)19-11-5-4-6-12-19)17-26(43-35)38-23-15-9-7-13-20(23)28-29-22(18-36-33(29)40)27-21-14-8-10-16-24(21)39(35)31(27)30(28)38/h4-16,25-26,32H,17-18H2,1-3H3,(H,36,40)/t25-,26-,32-,35+/m1/s1
    2.1.3 InChI Key
    BMGQWWVMWDBQGC-IIFHNQTCSA-N
    2.1.4 Canonical SMILES
    CC12C(C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)N(C)C(=O)C9=CC=CC=C9)OC
    2.1.5 Isomeric SMILES
    C[C@@]12[C@@H]([C@@H](C[C@@H](O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)N(C)C(=O)C9=CC=CC=C9)OC
    2.2 Other Identifiers
    2.2.1 UNII
    ID912S5VON
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4'-n-benzoyl Staurosporine

    2. 4'-n-benzoylstaurosporine

    3. Benzamide, N-(2,3,9,10,11,12-hexahydro-9-methoxy-8-methyl-1-oxo-8,12-epoxy-1h,8h-2,7b,12a-triazadibenzo(a,g)cyclonona(cde)trinden-10-yl)-n-methyl-, (8alpha,9beta,10beta,12alpha)-

    4. Benzoylstaurosporine

    5. Cgp 41 251

    6. Cgp 41251

    7. Cgp-41251

    8. N-((9s,10r,11r,13r)-10-methoxy-9-methyl-1-oxo-2,3,10,11,12,13-hexahydro-9,13-epoxy-1h,9h-diindolo(1,2,3-gh:3',2',1'-lm)pyrrolo(3,4-j)(1,7)benzodiazonin-11-yl)-n-methylbenzamide

    9. Pkc 412

    10. Pkc-412

    11. Pkc412

    12. Rydapt

    2.3.2 Depositor-Supplied Synonyms

    1. 120685-11-2

    2. Pkc-412

    3. Pkc412

    4. Cgp 41251

    5. 4'-n-benzoylstaurosporine

    6. Pkc 412

    7. Rydapt

    8. Cgp-41251

    9. Benzoylstaurosporine

    10. N-benzoylstaurosporine

    11. Id912s5von

    12. Nvp-pkc412

    13. Chembl608533

    14. Chebi:63452

    15. Nsc-656576

    16. N-((9s,10r,11r,13r)-10-methoxy-9-methyl-1-oxo-2,3,10,11,12,13-hexahydro-9,13-epoxy-1h,9h-diindolo(1,2,3-gh:3',2',1'-lm)pyrrolo(3,4-j)(1,7)benzodiazonin-11-yl)-n-methylbenzamide

    17. N-[(5s,6r,7r,9r)-6-methoxy-5-methyl-14-oxo-6,7,8,9,15,16-hexahydro-5h,14h-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacen-7-yl]-n-methylbenzamide

    18. Midostaurin [inn]

    19. Cgp 41 251

    20. Midostaurin [usan:inn]

    21. Unii-id912s5von

    22. Cgp41251

    23. Cgp 41231

    24. Rydapt (tn)

    25. Midostaurin(pkc412)

    26. 4-n-benzoylstaurosporine

    27. Midostaurin [mi]

    28. Staurosporine, N-benzoyl

    29. Midostaurin [jan]

    30. Midostaurin [usan]

    31. Midostaurin [mart.]

    32. Midostaurin [who-dd]

    33. Midostaurin (jan/usan/inn)

    34. Gtpl5702

    35. Schembl8295379

    36. Midostaurin [orange Book]

    37. Hms3229k17

    38. Ex-a1741

    39. Bdbm50326053

    40. Cgp-41521

    41. Mfcd00871372

    42. Nsc800791

    43. S8064

    44. Akos024457372

    45. Zinc100013130

    46. Ccg-101288

    47. Cs-3331

    48. Db06595

    49. Nsc 656576

    50. Nsc-800791

    51. Ncgc00241102-01

    52. Ncgc00241102-02

    53. Ncgc00241102-05

    54. Ncgc00484987-03

    55. Ac-31929

    56. Benzamide, N-(2,3,9,10,11,12-hexahydro-9-methoxy-8-methyl-1-oxo-8,12-epoxy-1h,8h-2,7b,12a-triazadibenzo(a,g)cyclonona(cde)trinden-10-yl)-n-methyl-, (8alpha,9beta,10beta,12alpha)-

    57. Hy-10230

    58. C71714

    59. D05029

    60. J-004379

    61. Q6842945

    62. Brd-k13646352-001-01-2

    63. [9s-(9?,10?,11?,13?)]-n-(2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-1-oxo-9,13-epoxy-1h,9h-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl)-n-methylbenzamide

    64. Benzamide, N-((9s,10r,11r,13r)-2,3,9,10,11,12-hexahydro-10-methoxy-9-methyl-1-oxo-9,13-epoxy-1h,9h-diindolo(1,2,3-gh:3',2',1'-lm)pyrrolo(3,4-j)(1,7)benzodiazonin-11-yl)-n-methyl-

    65. N-[(2s,3r,4r,6r)-3-methoxy-2-methyl-16-oxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8,10,12,14(28),15(19),20(27),21,23,25-nonaen-4-yl]-n-methylbenzamide

    66. N-[(2s,3r,4r,6r)-3-methoxy-2-methyl-16-oxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8(13),9,11,14,19,21(26),22,24,27-nonaen-4-yl]-n-methyl-benzamide

    67. N-[(2s,3r,4r,6r)-3-methoxy-2-methyl-16-oxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14,19,21,23,25,27-nonaen-4-yl]-n-methylbenzamide

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 570.6 g/mol
    Molecular Formula C35H30N4O4
    XLogP34.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass570.22670545 g/mol
    Monoisotopic Mass570.22670545 g/mol
    Topological Polar Surface Area77.7 Ų
    Heavy Atom Count43
    Formal Charge0
    Complexity1140
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 1  
    Drug NameRYDAPT
    Active IngredientMIDOSTAURIN
    CompanyNOVARTIS PHARMS CORP (Application Number: N207997. Patents: 7973031, 8222244, 8575146)

    4.2 Drug Indication

    Investigated for use/treatment in adult patients with high-risk acute myeloid leukemia (AML) who are FLT3 mutation-positive, agressive systemic mastocytosis (ASM), systemic mastocytosis with associated hematological neoplasm (SM-AHN), or mast cell leukemia (MCL).

    FDA Label

    Rydapt is indicated:

    - in combination with standard daunorubicin and cytarabine induction and high dose cytarabine consolidation chemotherapy, and for patients in complete response followed by Rydapt single agent maintenance therapy, for adult patients with newly diagnosed acute myeloid leukaemia (AML) who are FLT3 mutation positive (see section 4. 2);

    - as monotherapy for the treatment of adult patients with aggressive systemic mastocytosis (ASM), systemic mastocytosis with associated haematological neoplasm (SM AHN), or mast cell leukaemia (MCL).

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    It targets multiple WT and mutated kinases that, when activated, constitutively stimulate aberrant signalling cascades that lead to malignancies such as AML and ASM. Alternative pharmacodynamic effect of midostaurin in prolonging QTc intervals was not clinically significant in patients with advanced SM or AML when compared to placebo. Midostaurin is therapeutically beneficial as a combination therapy for patients undergoing chemotherapy.

    5.2 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    Protein Kinase Inhibitors

    Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    MIDOSTAURIN
    5.3.2 FDA UNII
    ID912S5VON
    5.3.3 Pharmacological Classes
    Receptor Tyrosine Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]
    5.4 ATC Code

    L01XE

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01E - Protein kinase inhibitors

    L01EX - Other protein kinase inhibitors

    L01EX10 - Midostaurin

    5.5 Absorption, Distribution and Excretion

    Absorption

    The time to reach maximum concentration ranges from 1-3 hrs in fasting patients. The maximum concentration and the time it takes to reach this concentration is reduced up to 20% in presence of a standard meal.

    Route of Elimination

    Accounting for 95% of recovered dose eliminated through fecal excretion, 91% was determined as metabolites and 4% as unchanged parent drug. Remaining 5% of the recovered dose is eliminated via renal excretion.

    Volume of Distribution

    The Vd of midostaurin is 95.2L. The parent drug and its main metabolites (CGP62221, CGP52421) are distributed in plasma in vitro.

    Clearance

    The clearance values of during the initial formation of metabolites are 1.47 L/h for CGP62221 metabolite and 0.501 L/h for CGP52421. 28 days following the oral administration of midostaurin, the clearance of CGP52421 may increase up to 5.2 fold in a recommended dose of 25 mg, resulting in a 2.1- to 2.5-fold increase in total clearance of midostaurin.

    5.6 Metabolism/Metabolites

    Midostaurin is primarily metabolized into CGP62221 and CGP52421 via hepatic CYP3A4 enzymatic activity. The metabolism of CGP62221 takes place initially in a linear relationship whereas CGP52421 formation is an inducible process.

    5.7 Biological Half-Life

    Elimination half life is approximately 21 hrs for midostaurin, 32 hrs for CGP62221 and 482 hrs for CGP52421.

    5.8 Mechanism of Action

    It potently inhibits multiple receptor tyrosine kinases. Midostaurin and its major active metabolites CGP62221 and CGP52421 inhibit the activity of protein kinase C alpha (PKCalpha), VEGFR2, KIT, PDGFR and WT and/or mutant FLT3 tyrosine kinases. Inhibition of FLT3 receptor signalling cascades induces apoptosis of target leukemia cells expressing target receptors and mast cells, in addition to its antiproliferative activity toward multiple cancer cell lines. Midostaurin also interacts with organic anion transporter (OATP) 1A1 and multidrug resistance protein (MRP)-2 according to preliminary in vitro studies.

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