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Chemistry

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Also known as: Arn-509, 956104-40-8, Erleada, Jnj-56021927, Arn 509, Apalutamide [inn]
Molecular Formula
C21H15F4N5O2S
Molecular Weight
477.4  g/mol
InChI Key
HJBWBFZLDZWPHF-UHFFFAOYSA-N
FDA UNII
4T36H88UA7

Apalutamide
Apalutamide is a small molecule and androgen receptor (AR) antagonist with potential antineoplastic activity. Apalutamide binds to AR in target tissues thereby preventing androgen-induced receptor activation and facilitating the formation of inactive complexes that cannot be translocated to the nucleus. This prevents binding to and transcription of AR-responsive genes. This ultimately inhibits the expression of genes that regulate prostate cancer cell proliferation and may lead to an inhibition of cell growth in AR-expressing tumor cells.
1 2D Structure

Apalutamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-N-methylbenzamide
2.1.2 InChI
InChI=1S/C21H15F4N5O2S/c1-27-17(31)13-4-3-11(8-15(13)22)30-19(33)29(18(32)20(30)5-2-6-20)12-7-14(21(23,24)25)16(9-26)28-10-12/h3-4,7-8,10H,2,5-6H2,1H3,(H,27,31)
2.1.3 InChI Key
HJBWBFZLDZWPHF-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CNC(=O)C1=C(C=C(C=C1)N2C(=S)N(C(=O)C23CCC3)C4=CC(=C(N=C4)C#N)C(F)(F)F)F
2.2 Other Identifiers
2.2.1 UNII
4T36H88UA7
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Arn-509

2. Erleada

2.3.2 Depositor-Supplied Synonyms

1. Arn-509

2. 956104-40-8

3. Erleada

4. Jnj-56021927

5. Arn 509

6. Apalutamide [inn]

7. Arn509

8. Apalutamide (arn-509)

9. 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro[3.4]octan-5-yl)-2-fluoro-n-methylbenzamide

10. 4t36h88ua7

11. 956104-40-8 (free Base)

12. 4-[7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl]-2-fluoro-n-methylbenzamide

13. 4-{7-[6-cyano-5-(trifluoromethyl)pyridin-3-yl]-8-oxo-6-sulfanylidene-5,7-diazaspiro[3.4]octan-5-yl}-2-fluoro-n-methylbenzamide

14. 4-(7-(6-cyano-5-(trifluoromethyl)pyridin-3-yl)-8-oxo-6-thioxo-5,7-diazaspiro(3.4)octan-5-yl)-2-fluoro-n-methylbenzamide

15. Unii-4t36h88ua7

16. Ar509

17. Apalutamidearn509

18. Erleada (tn)

19. Jnj 56021927

20. Apalutamide (jan/inn)

21. Apalutamide [mi]

22. Apalutamide [jan]

23. Apalutamide [who-dd]

24. Mls006011109

25. Schembl909297

26. Gtpl9043

27. Chembl3183409

28. Apalutamide [orange Book]

29. Dtxsid40241899

30. Ex-a089

31. Hms3656n12

32. Amy24182

33. Bcp05829

34. Ar509/ar-509

35. Bdbm50094975

36. Mfcd22380626

37. Nsc771649

38. Nsc794776

39. S2840

40. Zinc43174901

41. Akos025401932

42. Ccg-264760

43. Cs-0885

44. Db11901

45. Nsc-771649

46. Nsc-794776

47. Pb27306

48. Ncgc00346725-01

49. Ncgc00346725-02

50. Ncgc00346725-06

51. Ac-27403

52. As-35181

53. Hy-16060

54. Smr004702891

55. Sw220300-1

56. 24872560, Erleada, C21h15f4n5o2s

57. D11040

58. J-519596

59. Q21098975

60. Benzamide, 4-(7-(6-cyano-5-(trifluoromethyl)-3-pyridinyl)-8-oxo-6-thioxo-5,7-diazaspiro(3.4)oct-5-yl)-2-fluoro-n-methyl-

2.4 Create Date
2008-08-18
3 Chemical and Physical Properties
Molecular Weight 477.4 g/mol
Molecular Formula C21H15F4N5O2S
XLogP33
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count3
Exact Mass477.08825856 g/mol
Monoisotopic Mass477.08825856 g/mol
Topological Polar Surface Area121 Ų
Heavy Atom Count33
Formal Charge0
Complexity886
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

Indicated for the treatment of patients with non-metastatic, castration-resistant prostate cancer (NM-CRPC).


FDA Label


Erleada is indicated:

in adult men for the treatment of non metastatic castration resistant prostate cancer (nmCRPC) who are at high risk of developing metastatic disease. in adult men for the treatment of metastatic hormone-sensitive prostate cancer (mHSPC) in combination with androgen deprivation therapy (ADT).


5 Pharmacology and Biochemistry
5.1 Pharmacology

In an open-label, uncontrolled, multi-center, single-arm dedicated QT study in 45 patients with CRPC, an exposure-QT analysis suggested a concentration-dependent increase in QTcF for apalutamide and its active metabolite. Apalutamide demonstrated an antitumor activity in the mouse xenograft models of prostate cancer, where it decreased tumor cell proliferation and reduced tumor volume.


5.2 ATC Code

L02BB05


L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02B - Hormone antagonists and related agents

L02BB - Anti-androgens

L02BB05 - Apalutamide


5.3 Absorption, Distribution and Excretion

Absorption

Mean absolute oral bioavailability was approximately 100%. Median time to achieve peak plasma concentration (tmax) was 2 hours (range: 1 to 5 hours). Median tmax may be increased with a high-fat meal. Administration of oral apalutamide at recommended dosages resulted in a steady state within 4 weeks with a maximum peak concentration (Cmax) and AUC of 6.0 mcg/mL and 100 mcgh/mL, respectively. Cmax and AUC of apalutamide is expected to increase in a dose-proportional manner. The mean mean peak-to-trough ratio was 1.63 indicating low daily fluctuations in the plasma concentrations of the drug. The major active metabolite N-desmethyl apalutamide Cmax was 5.9 mcg/mL (1.0) and AUC was 124 mcgh/mL (23) at steady-state after the recommended dosage.


Route of Elimination

Apalutamide and its main active metabolite are subject to both renal and focal elimination. Up to 70 days following a single oral administration of radiolabeled apalutamide, 65% of the dose was recovered in urine (1.2% of dose as unchanged apalutamide and 2.7% as N-desmethyl apalutamide) and 24% was recovered in feces (1.5% of dose as unchanged apalutamide and 2% as N-desmethyl apalutamide).


Volume of Distribution

The mean apparent volume of distribution at steady-state of apalutamide was approximately 276 L.


Clearance

The CL/F of apalutamide was 1.3 L/h after single dosing and increased to 2.0 L/h at steady-state after once-daily dosing. An increase in apparent clearance (CL/F) was observed with repeat dosing, likely due to induction of apalutamides own metabolism. The auto-induction effect likely reached its maximum at the recommended dosage because exposure of apalutamide across the dose range of 30 to 480 mg is dose-proportional.


5.4 Metabolism/Metabolites

Apalutamide primarily undergoes CYP2C8 and CYP3A4-mediated metabolism to its pharmacologically active metabolite, N-desmethyl apalutamide. The contribution of CYP2C8 and CYP3A4 in the total metabolism of apalutamide is approximately 58% and and 13% following single dose but changes to 40% and 37%, respectively at steady-state. The auto-induction of CYP3A4-mediated metabolism by apalutamide may explain the increase in CYP3A4 enzymatic activity at steady-state. Based on systemic exposure, relative potency, and pharmacokinetic properties, N-desmethyl apalutamide likely contributed to the clinical activity of apalutamide.


5.5 Biological Half-Life

The mean effective half-life for apalutamide in patients with NM-CRPC was approximately 3 days at steady-state.


5.6 Mechanism of Action

Persistent androgen receptor (AR) signaling is a common feature of castration-resistant prostate cancer (CRPC), attributed to AR gene-amplification, AR gene mutation, increased AR expression or increased androgen biosynthesis in prostate tumors. Apalutamide is an antagonist of AR that to the binding-site in the ligand-binding domain of the receptor with the IC50 of 16 nM. Upon binding, apalutamide disrupts AR signalling, inhibits DNA binding, and impedes AR-mediated gene transcription. Apalutamide impairs the translocation of AR from the cytoplasm to the nucleus thus reduces the concentrations of AR available to interact with the androgen response-elements (AREs). Upon treatment with apalutamide, AR was not recruited to the DNA promoter-regions. Its main metabolite, N-desmethyl apalutamide, is a less potent inhibitor of AR, and exhibited one-third the activity of apalutamide in an in vitro transcriptional reporter assay.


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Apalutamide IH

Date of Issue : 2022-07-28

Valid Till : 2025-11-30

Written Confirmation Number : WC-0390

Address of the Firm : CTO-SEZ-Process Unit-01, Sector No 28 to 34, 36 to 37, 40, 50 to 53 & 03, Survey...

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Date of Issue : 2022-06-17

Valid Till : 2025-07-02

Written Confirmation Number : WC-0082

Address of the Firm : API Division Kharakhadi, Plot No. 842-843, Kharakhadi, Padra Vadodara-391 450, G...

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Apalutamide IH

Date of Issue : 2022-09-02

Valid Till : 2025-05-05

Written Confirmation Number : WC-0349

Address of the Firm : MIs. MSN Laboratories Private Limited, Unit-II, sv. No, 50, Kardanur (Village), ...

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Apalutamide IH

Date of Issue : 2021-04-23

Valid Till : 2022-05-05

Written Confirmation Number : WC-0349A12

Address of the Firm : Unit-||, Sy. No. 50, Kardanur Village, Patti/Post Patancheru Mandal,Medak Distri...

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20-Jan-2021
24-Apr-2025
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ABOUT THIS PAGE

Looking for 956104-40-8 / Apalutamide API manufacturers, exporters & distributors?

Apalutamide manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Apalutamide 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 Apalutamide manufacturer or Apalutamide supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Apalutamide manufacturer or Apalutamide supplier.

PharmaCompass also assists you with knowing the Apalutamide API Price utilized in the formulation of products. Apalutamide API Price is not always fixed or binding as the Apalutamide Price is obtained through a variety of data sources. The Apalutamide Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Apalutamide

Synonyms

Arn-509, 956104-40-8, Erleada, Jnj-56021927, Arn 509, Apalutamide [inn]

Cas Number

956104-40-8

Unique Ingredient Identifier (UNII)

4T36H88UA7

About Apalutamide

Apalutamide is a small molecule and androgen receptor (AR) antagonist with potential antineoplastic activity. Apalutamide binds to AR in target tissues thereby preventing androgen-induced receptor activation and facilitating the formation of inactive complexes that cannot be translocated to the nucleus. This prevents binding to and transcription of AR-responsive genes. This ultimately inhibits the expression of genes that regulate prostate cancer cell proliferation and may lead to an inhibition of cell growth in AR-expressing tumor cells.

Apalutamide Manufacturers

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

Apalutamide Suppliers

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

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

Apalutamide USDMF

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

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

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

Apalutamide KDMF

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

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

After submitting a Apalutamide 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 Apalutamide API can apply through the Korea Drug Master File (KDMF).

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

Apalutamide WC

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

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

Apalutamide 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 Apalutamide as an active pharmaceutical ingredient (API).

Finished drug products

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

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

Apalutamide GMP

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

Apalutamide CoA

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

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

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