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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
    30-Aug-2023
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    ABOUT THIS PAGE

    Netupitant Manufacturers

    A Netupitant manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Netupitant, including repackagers and relabelers. The FDA regulates Netupitant manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Netupitant API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Netupitant manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Netupitant Suppliers

    A Netupitant supplier is an individual or a company that provides Netupitant active pharmaceutical ingredient (API) or Netupitant finished formulations upon request. The Netupitant suppliers may include Netupitant API manufacturers, exporters, distributors and traders.

    click here to find a list of Netupitant suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Netupitant USDMF

    A Netupitant DMF (Drug Master File) is a document detailing the whole manufacturing process of Netupitant active pharmaceutical ingredient (API) in detail. Different forms of Netupitant DMFs exist exist since differing nations have different regulations, such as Netupitant USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Netupitant DMF submitted to regulatory agencies in the US is known as a USDMF. Netupitant USDMF includes data on Netupitant's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Netupitant USDMF is kept confidential to protect the manufacturer’s intellectual property.

    click here to find a list of Netupitant suppliers with USDMF on PharmaCompass.

    Netupitant KDMF

    In Korea, the Ministry of Food and Drug Safety (MFDS) is in charge of regulating pharmaceutical products and services.

    Pharmaceutical companies submit a Netupitant Drug Master File in Korea (Netupitant KDMF) to the MFDS, which includes comprehensive information about the production, processing, facilities, materials, packaging, and testing of Netupitant. The MFDS reviews the Netupitant KDMF as part of the drug registration process and uses the information provided in the Netupitant KDMF to evaluate the safety and efficacy of the drug.

    After submitting a Netupitant KDMF to the MFDS, the registered manufacturer can provide importers or distributors with the registration number without revealing confidential information to Korean business partners. Applicants seeking to register their Netupitant API can apply through the Korea Drug Master File (KDMF).

    click here to find a list of Netupitant suppliers with KDMF on PharmaCompass.

    Netupitant WC

    A Netupitant written confirmation (Netupitant WC) is an official document issued by a regulatory agency to a Netupitant manufacturer, verifying that the manufacturing facility of a Netupitant active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Netupitant APIs or Netupitant finished pharmaceutical products to another nation, regulatory agencies frequently require a Netupitant WC (written confirmation) as part of the regulatory process.

    click here to find a list of Netupitant suppliers with Written Confirmation (WC) on PharmaCompass.

    Netupitant NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Netupitant as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Netupitant API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Netupitant as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Netupitant and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Netupitant NDC to their finished compounded human drug products, they may choose to do so.

    click here to find a list of Netupitant suppliers with NDC on PharmaCompass.

    Netupitant GMP

    Netupitant Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Netupitant GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Netupitant GMP manufacturer or Netupitant GMP API supplier for your needs.

    Netupitant CoA

    A Netupitant CoA (Certificate of Analysis) is a formal document that attests to Netupitant's compliance with Netupitant specifications and serves as a tool for batch-level quality control.

    Netupitant CoA mostly includes findings from lab analyses of a specific batch. For each Netupitant CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Netupitant may be tested according to a variety of international standards, such as European Pharmacopoeia (Netupitant EP), Netupitant JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Netupitant USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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