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4 Europe
1 Canada
1 South Africa
1 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 Minakem, 1 Rochem International Inc, 4 SPI Pharma, 7 DKSH, 2 Jai Radhe Sales, 2 Faran Shimi Pharmaceutical, 3 Boai NKY Pharmaceuticals Ltd, 1 Chynops Pharma, 9 Gangwal Healthcare, 2 Nanjing Well Pharmaceutical, 4 ACG Worldwide, 2 Actylis, 1 Alcedo Pharmachem, 6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 3 DFE Pharma, 5 Gangwal Chemicals, 1 Ideal Cures Pvt Ltd, 1 Ingredion Pharma Solutions, 4 Kerry, 3 Lonza Capsugel, 7 Microlex e.U, 1 NEWEDGE Overseas, 2 Pharmatrans-Sanaq, 3 Pluviaendo, 4 Prachin Chemical, 1 Qualicaps, 19 Roquette, 4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 1 Shanghai Welltone Material Technology Co., Ltd, 1 Shijiazhuang Huaxu Pharmaceutical, 9 Sigachi Industries, 1 Ulanqab Kema New Material, 3 Vasa Pharmachem, 1 Zhejiang Huakang Pharmaceutical

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Synopsis

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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 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 Formula	C₃₀H₃₂F₆N₄O
Molecular Weight	578.6 g/mol
XLogP3	6.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	5
Exact Mass	578.24803063 g/mol
Monoisotopic Mass	578.24803063 g/mol
Topological Polar Surface Area	39.7 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	865
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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 SUPPLIERS

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USDMF

01

Has Healthcare Advanced Synthesis Sa

Switzerland

American Pharma Summit

Not Confirmed

02

Msn Laboratories Private Ltd

India

American Pharma Summit

Not Confirmed

03

Tianish Laboratories Private Ltd

U.S.A

American Pharma Summit

Not Confirmed

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EU WC

01

MSN Laboratories

India

Pharma Manufacturing 2024

Not Confirmed

02

MSN Laboratories

India

Pharma Manufacturing 2024

Not Confirmed

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Listed Suppliers

01

Metrochem API Private Limited

India

Pharmtech & Ingredients

Exhibiting

Metrochem has been delivering customized volume & quality products to customers across the world, taking utmost care of their needs.

Contact Supplier

India

Virtual Booth

Digital Content

Netupitant

About the Company :

Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product ...

Established in 2004, Metrochem API is one of the fastest-growing APIs, pellets & intermediates manufacturers. It has 6 dedicated manufacturing facilities for its 3 core product groups and has been approved by ISO 9001-2015, USFDA, WHO GMP, Cofepris & Japanese authorities. Metrochem’s in-depth industry knowledge, & hi-tech & advanced infrastructure, helps it provide quality products to its customers. Note: None of the products will be supplied to the countries where this could conflict with existing patents. Further, any products under patent will be offered for R&D purposes only. However, the final responsibility lies with the buyer

02

Guangzhou Tosun Pharmaceutical

China

American Pharma Summit

Not Confirmed

03

Viatris

U.S.A

American Pharma Summit

Not Confirmed

04

Zhejiang Tiantai Pharmaceutical

China

American Pharma Summit

Not Confirmed

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API Reference Price

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Number of Transactions

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01

HUNAN OUYA BIOLOGICAL CO.,LTD

China

American Pharma Summit

Not Confirmed

02

HUNAN OUYA BIOLOGICAL CO.,LTD

China

American Pharma Summit

Not Confirmed

03

Vio Chemicals

Switzerland

American Pharma Summit

Not Confirmed

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ACTIVE PHARMA INGREDIENTS

7 API Suppliers

3 USDMF

2 EU WC

1 KDMF

2 NDC API

4 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

5 Drugs in Development

INTERMEDIATES

3 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

8 FDF Dossiers

1 FDA Orange Book

4 Europe

1 Canada

1 South Africa

1 Listed Dossiers

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EXCIPIENTS BY APPLICATIONS

34 Fillers, Diluents & Binders

18 Lubricants & Glidants

17 Disintegrants & Superdisintegrants

16 Thickeners and Stabilizers

16 Direct Compression

11 Coating Systems & Additives

11 Co-Processed Excipients

11 Film Formers & Plasticizers

8 Empty Capsules

7 Granulation

7 Taste Masking

6 Chewable & Orodispersible Aids

5 Parenteral

5 Controlled & Modified Release

3 Emulsifying Agents

2 API Stability Enhancers

2 Solubilizers

2 Coloring Agents

2 Rheology Modifiers

1 Soft Gelatin