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Chemistry

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Also known as: 1442472-39-0, Dcc-2618, N-{4-bromo-5-[1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3- yl]-2-fluorophenyl}-n'-phenylurea, Urea, n-[4-bromo-5-[1-ethyl-1,2-dihydro-7-(methylamino)-2-oxo-1,6- naphthyridin-3-yl]-2-fluorophenyl]-n'-phenyl-39-0, Ripretinib free base, Ripretinib [usan]
Molecular Formula
C24H21BrFN5O2
Molecular Weight
510.4  g/mol
InChI Key
CEFJVGZHQAGLHS-UHFFFAOYSA-N
FDA UNII
9XW757O13D

Ripretinib
Ripretinib is an orally bioavailable switch pocket control inhibitor of wild-type and mutated forms of the tumor-associated antigens (TAA) mast/stem cell factor receptor (SCFR) KIT and platelet-derived growth factor receptor alpha (PDGFR-alpha; PDGFRa), with potential antineoplastic activity. Upon oral administration, ripretinib targets and binds to both wild-type and mutant forms of KIT and PDGFRa specifically at their switch pocket binding sites, thereby preventing the switch from inactive to active conformations of these kinases and inactivating their wild-type and mutant forms. This abrogates KIT/PDGFRa-mediated tumor cell signaling and prevents proliferation in KIT/PDGFRa-driven cancers. DCC-2618 also inhibits several other kinases, including vascular endothelial growth factor receptor type 2 (VEGFR2; KDR), angiopoietin-1 receptor (TIE2; TEK), PDGFR-beta and macrophage colony-stimulating factor 1 receptor (FMS; CSF1R), thereby further inhibiting tumor cell growth. KIT and PDGFRa are tyrosine kinase receptors that are upregulated or mutated in a variety of cancer cell types; mutated forms play a key role in the regulation of tumor cell proliferation and resistance to chemotherapy.
Ripretinib is a Kinase Inhibitor. The mechanism of action of ripretinib is as a Stem Cell Factor (KIT) Receptor Inhibitor, and Platelet-derived Growth Factor alpha Receptor Inhibitor, and Cytochrome P450 2C8 Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor.
1 2D Structure

Ripretinib

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[4-bromo-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-phenylurea
2.1.2 InChI
InChI=1S/C24H21BrFN5O2/c1-3-31-21-12-22(27-2)28-13-14(21)9-17(23(31)32)16-10-20(19(26)11-18(16)25)30-24(33)29-15-7-5-4-6-8-15/h4-13H,3H2,1-2H3,(H,27,28)(H2,29,30,33)
2.1.3 InChI Key
CEFJVGZHQAGLHS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN1C2=CC(=NC=C2C=C(C1=O)C3=CC(=C(C=C3Br)F)NC(=O)NC4=CC=CC=C4)NC
2.2 Other Identifiers
2.2.1 UNII
9XW757O13D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea

2. Urea, N-(4-bromo-5-(1-ethyl-1,2-dihydro-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl)-2-fluorophenyl)-n'-phenyl-

2.3.2 Depositor-Supplied Synonyms

1. 1442472-39-0

2. Dcc-2618

3. N-{4-bromo-5-[1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3- Yl]-2-fluorophenyl}-n'-phenylurea

4. Urea, N-[4-bromo-5-[1-ethyl-1,2-dihydro-7-(methylamino)-2-oxo-1,6- Naphthyridin-3-yl]-2-fluorophenyl]-n'-phenyl-39-0

5. Ripretinib Free Base

6. Ripretinib [usan]

7. Ripretinib (dcc-2618)

8. 9xw757o13d

9. Ripretinib (usan)

10. 1442472-39-0 (free Base)

11. 1-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea

12. Qinlock

13. 1-[4-bromo-5-[1-ethyl-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl]-2-fluorophenyl]-3-phenylurea

14. N-(4-bromo-5-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-n'-phenylurea

15. Urea, N-(4-bromo-5-(1-ethyl-1,2-dihydro-7-(methylamino)-2-oxo-1,6-naphthyridin-3-yl)-2-fluorophenyl)-n'-phenyl-

16. Quinlock

17. Qinlock (tn)

18. Ripretinib [mi]

19. Ripretinib [inn]

20. Ripretinib [who-dd]

21. Unii-9xw757o13d

22. Gtpl9175

23. Chembl4216467

24. Ripretinib [orange Book]

25. Schembl14999718

26. Dcc2618

27. Dtxsid201027956

28. Bcp29218

29. Ex-a4883

30. S8757

31. At18473

32. Db14840

33. Ac-36722

34. Hy-112306

35. Cs-0044835

36. D11353

37. Dcc 2618;dcc2618;kit/pdgfr Inhibitor;ripretinib

2.4 Create Date
2013-07-08
3 Chemical and Physical Properties
Molecular Weight 510.4 g/mol
Molecular Formula C24H21BrFN5O2
XLogP34.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass509.08627 g/mol
Monoisotopic Mass509.08627 g/mol
Topological Polar Surface Area86.4 Ų
Heavy Atom Count33
Formal Charge0
Complexity746
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

Ripretinib is indicated to treat adults diagnosed with advanced gastrointestinal stromal tumor (GIST) who have had prior therapy with at least 3 kinase inhibitors, including with [imatinib].


FDA Label


Qinlock is indicated for the treatment of adult patients with advanced gastrointestinal stromal tumour (GIST) who have received prior treatment with three or more kinase inhibitors, including imatinib.


5 Pharmacology and Biochemistry
5.1 Pharmacology

As a broad-spectrum kinase inhibitor, ripretinib inhibits various gene mutations, increasing progression-free survival in patients with advanced gastrointestinal stromal tumors (GIST). It is effective in treating mutations that are resistant to chemotherapy with other kinase inhibitors, such as imatinib. Ripretinib has the propensity to cause cardiac dysfunction and new primary cutaneous malignancy. It is important to measure cardiac ejection fraction before and during treatment as well as to perform regular dermatological assessments.


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
RIPRETINIB
5.2.2 FDA UNII
9XW757O13D
5.2.3 Pharmacological Classes
Cytochrome P450 2C8 Inhibitors [MoA]; Kinase Inhibitor [EPC]; P-Glycoprotein Inhibitors [MoA]; Platelet-derived Growth Factor alpha Receptor Inhibitors [MoA]; Stem Cell Factor (KIT) Receptor Inhibitors [MoA]; Breast Cancer Resistance Protein Inhibitors [MoA]
5.3 ATC Code

L01


L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EX - Other protein kinase inhibitors

L01EX19 - Ripretinib


5.4 Absorption, Distribution and Excretion

Absorption

Ripretinib is absorbed in the gastrointestinal tract and Tmax is achieved in 4 hours, with steady-state concentrations reached within 14 days.


Route of Elimination

Ripretinib is 34% excreted in the feces and 0.2% excreted in the urine.


Volume of Distribution

The mean volume of distribution of ripretinib is 307 L.


Clearance

The mean apparent clearance of ripretinib is 15.3 L/hour.


5.5 Metabolism/Metabolites

Ripretinib is metabolized by the CYP3A subfamily of enzymes with contributions from CYP2D6 and CYP2E1 to its active metabolite, DP-5439.


5.6 Biological Half-Life

The average half-life of ripretinib is 14.8 hours.


5.7 Mechanism of Action

Protein kinases play important roles in cellular function, and their dysregulation can lead to carcinogenesis. Ripretinib inhibits protein kinases including wild type and mutant platelet-derived growth factor receptor A (PDGFRA) and KIT that cause the majority of gastrointestinal stromal tumor (GIST). In vitro, ripretinib has been shown to inhibit PDGFRB, BRAF, VEGF, and TIE2 genes. Ripretinib binds to KIT and PDGFRA receptors with mutations on the exons 9, 11, 13, 14, 17 and 18 (for KIT mutations), and exons 12, 14 and 18 (for PDGFRA mutations). The switch pocket of a protein kinase is normally bound to the activation loop, acting as an on-off switch of a kinase. Ripretinib boasts a unique dual mechanism of action of binding to the kinase switch pocket as well as the activation loop, thereby turning off the kinase and its ability to cause dysregulated cell growth.


API SUPPLIERS

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Dr. Reddy's Laboratories

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TAPI Technology & API Services

Israel

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Cambrex Corporation

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Cambrex Corporation

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Cambrex Corporation

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Cambrex Corporation

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Cambrex Corporation

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Cambrex Corporation

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Cambrex Corporation

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Beijing Sjar Technology Developmen...

China

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DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 39508

Submission : 2024-02-23

Status : Active

Type : II

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Ripretinib

About the Company : Founded in 1984, DRL is well-known for its generic APIs and its track record in drug product development. It is one of the earliest pharma API manufacturers with a diverse portfoli...

Founded in 1984, DRL is well-known for its generic APIs and its track record in drug product development. It is one of the earliest pharma API manufacturers with a diverse portfolio that provides high-quality, low-cost APIs to leading pharma companies in 80+ countries. It has 8 USFDA-inspected facilities – 6 in India & 1 each in Mexico & the UK & are inspected by international regulatory authorities on a regular basis. Its facilities are supplemented by formulation facilities that provide a wide range of dosage forms. Product(s) under patent(s) are offered only for R&D purposes U/S 107A of the Patent Act and not for commercial sale
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Ripretinib

About the Company : Founded in 1935, TAPI Technology & API Services has a long-standing tradition of advancing health through innovation and dedication. Today, we proudly build upon this legacy, drivi...

Founded in 1935, TAPI Technology & API Services has a long-standing tradition of advancing health through innovation and dedication. Today, we proudly build upon this legacy, driving progress in the pharmaceutical industry. Leveraging our extensive experience and world-class expertise, we deliver one of the most comprehensive API portfolios in the industry with over 350 Products portfolio. Additionally, we provide tailored CDMO services, harnessing our proficiency in diverse technologies to meet our partners' unique needs, ensuring flexibility and excellence in every project.
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Ripretinib

About the Company : Beijing Sjar Technology Development Co., Ltd. founded in 2014, it is a high-tech enterprise which specialized in the research and development of active pharmaceutical ingredients a...

Beijing Sjar Technology Development Co., Ltd. founded in 2014, it is a high-tech enterprise which specialized in the research and development of active pharmaceutical ingredients and their intermediates, electronic chemical materials and intermediates, large-scale production, sales and services, and provide customized synthetic services according to customer requirements. Sjar-Tech locates in Beijing Economic and Technological Development Zone, has its own R&D and development laboratory. Sjar-Tech has set up a R&D team with rich experience and strong technical strength, most of the practitioners have more than ten years' experience.
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PharmaCompass offers a list of Ripretinib API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Ripretinib manufacturer or Ripretinib supplier for your needs.

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API | Excipient name

Ripretinib

Synonyms

1442472-39-0, Dcc-2618, N-{4-bromo-5-[1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3- yl]-2-fluorophenyl}-n'-phenylurea, Urea, n-[4-bromo-5-[1-ethyl-1,2-dihydro-7-(methylamino)-2-oxo-1,6- naphthyridin-3-yl]-2-fluorophenyl]-n'-phenyl-39-0, Ripretinib free base, Ripretinib [usan]

Cas Number

1442472-39-0

Unique Ingredient Identifier (UNII)

9XW757O13D

About Ripretinib

Ripretinib is an orally bioavailable switch pocket control inhibitor of wild-type and mutated forms of the tumor-associated antigens (TAA) mast/stem cell factor receptor (SCFR) KIT and platelet-derived growth factor receptor alpha (PDGFR-alpha; PDGFRa), with potential antineoplastic activity. Upon oral administration, ripretinib targets and binds to both wild-type and mutant forms of KIT and PDGFRa specifically at their switch pocket binding sites, thereby preventing the switch from inactive to active conformations of these kinases and inactivating their wild-type and mutant forms. This abrogates KIT/PDGFRa-mediated tumor cell signaling and prevents proliferation in KIT/PDGFRa-driven cancers. DCC-2618 also inhibits several other kinases, including vascular endothelial growth factor receptor type 2 (VEGFR2; KDR), angiopoietin-1 receptor (TIE2; TEK), PDGFR-beta and macrophage colony-stimulating factor 1 receptor (FMS; CSF1R), thereby further inhibiting tumor cell growth. KIT and PDGFRa are tyrosine kinase receptors that are upregulated or mutated in a variety of cancer cell types; mutated forms play a key role in the regulation of tumor cell proliferation and resistance to chemotherapy.

Ripretinib Manufacturers

A Ripretinib manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Ripretinib, including repackagers and relabelers. The FDA regulates Ripretinib manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Ripretinib 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 Ripretinib manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Ripretinib Suppliers

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

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Ripretinib USDMF

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

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

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Ripretinib 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 Ripretinib as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Ripretinib 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 Ripretinib 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 Ripretinib and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Ripretinib NDC to their finished compounded human drug products, they may choose to do so.

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Ripretinib GMP

Ripretinib 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 Ripretinib 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 Ripretinib GMP manufacturer or Ripretinib GMP API supplier for your needs.

Ripretinib CoA

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

Ripretinib CoA mostly includes findings from lab analyses of a specific batch. For each Ripretinib 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.

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