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    Chemistry

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    Also known as: 290297-26-6, 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide, 2-(3,5-bis(trifluoromethyl)phenyl)-n,2-dimethyl-n-(6-(4-methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)propanamide, Ro-67-3189, Ro-673189000, Ro 67-3189/000
    Molecular Formula
    C30H32F6N4O
    Molecular Weight
    578.6  g/mol
    InChI Key
    WAXQNWCZJDTGBU-UHFFFAOYSA-N
    FDA UNII
    7732P08TIR
    Netupitant
    Netupitant is a selective neurokinin 1 (NK1) receptor antagonist with potential antiemetic activity. Netupitant competitively binds to and blocks the activity of the human substance P/NK1 receptors in the central nervous system (CNS), thereby inhibiting NK1-receptor binding of the endogenous tachykinin neuropeptide substance P (SP), which may result in the prevention of chemotherapy-induced nausea and vomiting (CINV). SP is found in neurons of vagal afferent fibers innervating the brain-stem nucleus tractus solitarii and the area postrema, which contains the chemoreceptor trigger zone (CTZ), and may be elevated in response to chemotherapy. The NK-receptor is a G-protein receptor coupled to the inositol phosphate signal-transduction pathway and is found in both the nucleus tractus solitarii and the area postrema.
    Netupitant is a Substance P/Neurokinin-1 Receptor Antagonist. The mechanism of action of netupitant is as a Neurokinin 1 Antagonist, and Cytochrome P450 3A4 Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor.
    1 2D Structure

    Netupitant

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[3,5-bis(trifluoromethyl)phenyl]-N,2-dimethyl-N-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide
    2.1.2 InChI
    InChI=1S/C30H32F6N4O/c1-19-8-6-7-9-23(19)24-17-26(40-12-10-38(4)11-13-40)37-18-25(24)39(5)27(41)28(2,3)20-14-21(29(31,32)33)16-22(15-20)30(34,35)36/h6-9,14-18H,10-13H2,1-5H3
    2.1.3 InChI Key
    WAXQNWCZJDTGBU-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=CC=C1C2=CC(=NC=C2N(C)C(=O)C(C)(C)C3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N4CCN(CC4)C
    2.2 Other Identifiers
    2.2.1 UNII
    7732P08TIR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(3,5-bis(trifluoromethyl)phenyl)-n,2-dimethyl-n-(4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl)propanamide

    2. 2-(3,5-bis(trifluoromethyl)phenyl)-n-methyl-n-(4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl)-2-methylpropanamide

    3. Benzeneacetamide, N, Alpha, Alpha-trimethyl-n-(4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl)-3,5-bis(trifluoromethyl)-

    4. Benzeneacetamide, N, Alpha,alpha-trimethyl-n-(4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl)-3,5-bis(trifluoromethyl)-, Hydrochloride (1:2)

    5. Netupitant Dihydrochloride

    6. Netupitant Hydrochloride

    7. Ro 67-3189 000

    8. Ro 673189000

    9. Ro-67-3189

    10. Ro-67-3189 000

    11. Ro-673189000

    2.3.2 Depositor-Supplied Synonyms

    1. 290297-26-6

    2. 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide

    3. 2-(3,5-bis(trifluoromethyl)phenyl)-n,2-dimethyl-n-(6-(4-methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)propanamide

    4. Ro-67-3189

    5. Ro-673189000

    6. Ro 67-3189/000

    7. Chembl206253

    8. Chebi:85155

    9. 7732p08tir

    10. Cid 6451149

    11. Ro 67-31898/000

    12. Benzeneacetamide, N,alpha,alpha-trimethyl-n-[4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl]-3,5-bis(trifluoromethyl)-

    13. 2-(3,5-bis(trifluoromethyl)phenyl)-n,2-dimethyl-n-(4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl)propanamide

    14. 2-(3,5-bis(trifluoromethyl)phenyl)-n,2-dimethyl-n-(6-(4-methylpiperazin-1-yl)-4-o-tolylpyridin-3-yl)propanamide

    15. 2-[3,5-bis(trifluoromethyl)phenyl]-~{n},2-dimethyl-~{n}-[4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl]propanamide

    16. Netupitant [usan]

    17. Netupitant [usan:inn]

    18. Unii-7732p08tir

    19. Benzeneacetamide, N,alpha,alpha-trimethyl-n-(4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl)-3,5-bis(trifluoromethyl)-

    20. Cid6451149

    21. Netupitant [mi]

    22. Netupitant [inn]

    23. Netupitant (usan/inn)

    24. Netupitant [vandf]

    25. Netupitant [who-dd]

    26. Schembl445804

    27. Gtpl5742

    28. Netupitant(cid-6451149)

    29. Netupitant [orange Book]

    30. Dtxsid50183271

    31. Glxc-15009

    32. Hms3887e19

    33. Bcp08751

    34. Ex-a2747

    35. Bdbm50178574

    36. Mfcd25976831

    37. S4654

    38. Zinc11681563

    39. Akos027251056

    40. Ccg-270121

    41. Cs-3337

    42. Db09048

    43. Sb18973

    44. Cid-6451149

    45. Ncgc00390569-01

    46. 2-(3,5-bis(trifluoromethyl)phenyl)-n-methyl-n-(4-(2-methylphenyl)-6-(4-methylpiperazin-1-yl)pyridin-3-yl)-2-methylpropanamide

    47. Ac-29232

    48. As-10239

    49. Hy-16346

    50. Ro 67-31898

    51. Akynzeo Capsule Component Netupitant

    52. Netupitant Component Akynzeo Capsule

    53. Ft-0699740

    54. A14428

    55. D05152

    56. Ro-67-3189/000

    57. Q19598139

    58. 2-(3,5-bis(trifluoromethyl)phenyl)-n,2-dimethyl-n-(6-(4-methylpiperazin-1-yl)-4-o-tolylpyridin-3-yl)propanamide, Aldrichcpr

    59. 2-(3,5-bis(trifluoromethyl)phenyl)-n,2-dimethyl-n-(6-(4-methylpiperazin-1yl)-4-(o-tolyl)pyridin-3yl)propanamide

    60. 2-(3,5-bis-trifluoromethyl-phenyl)-n-methyl-n-[6-(4-methyl-piperazin-1-yl)-4-o-tolyl-pyridin-3-yl]-isobutyramide

    61. 2-[3,5-bis(trifluoromethyl)phenyl]-n,2-dimethyl-n-[4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl]propanamide

    62. Benzeneacetamide, N,.alpha.,.alpha.-trimethyl-n-(4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl)-3,5-bis(trifluoromethyl)-

    63. Gaw

    64. N,alpha,alpha-trimethyl-n-[4-(2-methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinyl]-3,5-bis(trifluoromethyl)-benzeneacetamide

    2.4 Create Date
    2006-04-29
    3 Chemical and Physical Properties
    Molecular Weight 578.6 g/mol
    Molecular Formula C30H32F6N4O
    XLogP36.8
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count5
    Exact Mass578.24803063 g/mol
    Monoisotopic Mass578.24803063 g/mol
    Topological Polar Surface Area39.7 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity865
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Netupitant is an antiemitic drug approved by the FDA in October 2014 for use in combination with palonosetron for the prevention of acute and delayed vomiting and nausea associated with cancer chemotherapy including highly emetogenic chemotherapy.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 FDA Pharmacological Classification
    5.1.1 Active Moiety
    NETUPITANT
    5.1.2 FDA UNII
    7732P08TIR
    5.1.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors
    5.2 Absorption, Distribution and Excretion

    Absorption

    Upon oral administration of a single dose of netupitant, netupitant started to be measurable in plasma between 15 minutes and 3 hours after dosing. Plasma concentrations reached Cmax in approximately 5 hours. There was a greater than dose-proportional increase in the systemic exposure with the dose increase from 10 mg to 300 mg and a dose-proportional increase in systemic exposure with a dose increase from 300 mg to 450 mg.

    Route of Elimination

    Primarily fecal.

    Volume of Distribution

    In cancer patients, Vz/F: 1982 906 L (mean SD).

    Clearance

    Estimated systemic clearance of 20.3 9.2 L/h (mean SD).

    5.3 Metabolism/Metabolites

    Once absorbed, netupitant is extensively metabolized to form three major metabolites: desmethyl derivative, M1; N-oxide derivative, M2; and OH-methyl derivative, M3. Metabolism is mediated primarily by CYP3A4 and to a lesser extent by CYP2C9 and CYP2D6. Metabolites M1, M2 and M3 were shown to bind to the substance P/neurokinin 1 (NK1) receptor.

    5.4 Biological Half-Life

    96 hours with CV% of 61.

    5.5 Mechanism of Action

    Delayed emesis (vomiting) has been largely associated with the activation of tachykinin family neurokinin 1 (NK1) receptors (broadly distributed in the central and peripheral nervous systems) by substance P. As shown in in vitro and in vivo studies, netupitant inhibits substance P mediated responses.

    API Reference Price

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    18-Nov-2021
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