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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 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 Formula	C₂₁H₁₅F₄N₅O₂S
Molecular Weight	477.4 g/mol
XLogP3	3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	3
Exact Mass	477.08825856 g/mol
Monoisotopic Mass	477.08825856 g/mol
Topological Polar Surface Area	121 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	886
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

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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01

Dr Reddys Laboratories Ltd

India

CPHI Middle east

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Apalutamide

GDUFA

DMF Review : Complete

Rev. Date : 2020-10-28

Pay. Date : 2020-09-30

DMF Number : 34667

Submission : 2020-03-24

Status : Active

Type : II

02

Dr Reddys Laboratories Ltd

India

CPHI Middle east

Not Confirmed

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Apalutamide (amorphous)

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 35740

Submission : 2021-03-25

Status : Active

Type : II

03

Porton Pharma Solutions Ltd

China

CPHI Middle east

Not Confirmed

Porton Pharma Solutions: Value creation via innovation & discovery through technical platforms.

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China

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Apalutamide

GDUFA

DMF Review : N/A

Rev. Date :

Pay. Date :

DMF Number : 39029

Submission : 2023-11-02

Status : Active

Type : II

04

Alembic Pharmaceuticals Ltd

India

CPHI Middle east

Not Confirmed

05

Aurisco Pharmaceutical Co Ltd

China

CPHI Middle east

Not Confirmed

06

Apitoria Pharma Private Ltd

India

CPHI Middle east

Not Confirmed

07

Beijing Hope Pharmaceutical Co Ltd

China

India

CPHI Middle east

Not Confirmed

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ST20240707\/ST20240718-3\/ST20240707-2\/ST20240718-1)","address":"VILLAGE NAG KALAN,MAJITHA ROAD,MAJ","city":"AMRITSAR,PUNJAB","supplier":"M\/S. QUANZHOU FORTUNE BIOPHARMA CO.LTD","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"KWALITY PHARMACEUTICALS","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"4000","totalValueFC":"8068.8","currency":"USD","unitRateINR":"338400","date":"08-Aug-2024","totalValueINR":"676800","totalValueInUsd":"8068.8","indian_port":"Delhi Air","hs_no":"29339990","bill_no":"4936661","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"ADD:ROOM 2603 RONG TAI\\'AN BUILDINGNO.139 JINHUAI STREET FENGZE ROADFENGZE DISTRICT QUANZHOU CITY FUJIA CHINA","customerAddress":"VILLAGE NAG KALAN,MAJITHA ROAD,MAJ"}]

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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Drugs in Development

01 Kairos Pharma

U.S.A

CPHI Middle east

Not Confirmed

02 Kairos Pharma

U.S.A

CPHI Middle east

Not Confirmed

03 Kairos Pharma

U.S.A

U.S.A

CPHI Middle east

Not Confirmed

10 Veracyte

U.S.A

CPHI Middle east

Not Confirmed

Only 10 entries up to this point, click to access all

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INTERMEDIATES SUPPLIERS

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FDF Dossiers

01

Centocor

U.S.A

CPHI Middle east

Not Confirmed

Not Confirmed

06

Janssen-Cilag

Italy

CPHI Middle east

Not Confirmed

07

Johnson & Johnson Innovative Medici...

U.S.A

Gabon

CPHI Middle east

Not Confirmed

FULL SCREEN VIEW Click here to open all results in a new tab [this preview display 10 results]

FDA Orange Book

01

JANSSEN BIOTECH

U.S.A

Medlab Asia & Asia Health

Not Confirmed

02

JANSSEN BIOTECH

U.S.A

Medlab Asia & Asia Health

Not Confirmed

FULL SCREEN VIEW Click here to open all results in a new tab [this preview display 10 results]

Europe

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Canada

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Australia

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South Africa

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Listed Dossiers

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Related Excipient Companies

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Excipients by Applications

Click here to find the perfect excipient manufacturers by their capabilities

Fillers, Diluents & Binders

01

Gangwal Healthcare

India

CPHI Middle east

Not Confirmed

Gangwal Healthcare is powered by innovation, driving health, wellness & healing.

Dosage Form : Capsule, Tablet

Grade : Oral

Category : Co-Processed Excipients, Direct Compression, Disintegrants & Superdisintegrants, Fillers, Diluents & Binders, Lubricants & Glidants

Brand Name : ProBlend®

Application : Co-Processed Excipients, Direct Compression, Disintegrants & Superdisintegrants, Fillers, Diluents & Binders, Lubricants & Glidants

Excipient Details : ProBlend (Microcrystalline Cellulose) is used as a filler, binder, glidant, DC & co-processed excipient in tablets, capsules, and MUPS formulations.

Pharmacopoeia Ref : USP-NF

Technical Specs : NA

Ingredient(s) : Microcrystalline Cellulose

02

Gangwal Healthcare

India

CPHI Middle east

Not Confirmed

Gangwal Healthcare is powered by innovation, driving health, wellness & healing.

Dosage Form : Capsule, Tablet

Grade : Oral

Category : Co-Processed Excipients, Direct Compression, Fillers, Diluents & Binders

Brand Name : DiCOM-DC® PL009 P60

Application : Co-Processed Excipients, Direct Compression, Fillers, Diluents & Binders

Excipient Details : DiCOM-DC PL009 P60 is used as a filler, binder, directly compressible, and co-processed excipient in tablets and capsules.

Pharmacopoeia Ref : IH

Technical Specs : NA

Ingredient(s) : Maize Starch

03

Gangwal Healthcare

India

CPHI Middle east

Not Confirmed

Gangwal Healthcare is powered by innovation, driving health, wellness & healing.

Dosage Form : Capsule, Tablet

Grade : Oral

Category : Co-Processed Excipients, Direct Compression, Fillers, Diluents & Binders, Thickeners and Stabilizers

Brand Name : DiCOM-DC® SP204

Application : Co-Processed Excipients, Direct Compression, Fillers, Diluents & Binders, Thickeners and Stabilizers

Excipient Details : DiCOM-DC SP204 is used as a stabilizer, filler, binder, directly compressible, and co-processed excipient in tablets and capsules.

Pharmacopoeia Ref : In-house

Technical Specs : NA

Ingredient(s) : Corn Starch, Pregelatinized

04

Gangwal Healthcare

India

CPHI Middle east

Not Confirmed

Gangwal Healthcare is powered by innovation, driving health, wellness & healing.

Dosage Form : Capsule, Tablet

Grade : Oral

Category : Co-Processed Excipients, Direct Compression, Fillers, Diluents & Binders

Brand Name : Microlose™ M60 P60

Application : Co-Processed Excipients, Direct Compression, Fillers, Diluents & Binders

Excipient Details : Microlose M60 P60 is used as a filler, binder, directly compressible, and co-processed excipient in tablets and capsules.

Pharmacopoeia Ref : In-house

Technical Specs : Lactose Monohydrate – 40%, Microcrystalline cellulose – 60%

Ingredient(s) : Lactose Monohydrate

Excipients Web Link

India

CPHI Middle east

Not Confirmed

Only 10 entries up to this point, click to access all

Coating Systems & Additives

Thickeners and Stabilizers

Disintegrants & Superdisintegrants

Direct Compression

Controlled & Modified Release

01

Gangwal Healthcare

India

CPHI Middle east

Not Confirmed

Gangwal Healthcare is powered by innovation, driving health, wellness & healing.

Dosage Form : Capsule, Tablet

Grade : Oral

Category : Co-Processed Excipients, Controlled & Modified Release, Direct Compression

Brand Name : DiCOM-DC® SR300

Application : Co-Processed Excipients, Controlled & Modified Release, Direct Compression

Excipient Details : DiCOM-DC SR300 is used as a directly compressible, rate-controlling, and co-processed excipient in sustained-release tablets and capsules.

Pharmacopoeia Ref : In-house

Technical Specs : NA

Ingredient(s) : EthylCellulose

02

Nanjing Well Pharmaceutical

China

CPHI Middle east

Not Confirmed

Nanjing Well is focused on R&D, production & sales of Pharmaceutical Excipients & Synthetic Lubricating base oils.

Dosage Form : Cream / Lotion / Ointment, Gel, Injectable / Parenteral, Softgel Capsule, Softgels

Grade : Parenteral, Topical, Oral

Category : Fillers, Diluents & Binders, Film Formers & Plasticizers, Parenteral, Surfactant & Foaming Agents, Thickeners and Stabilizers, Topical

Brand Name : Polyethylene Glycol 400

Application : Fillers, Diluents & Binders, Film Formers & Plasticizers, Parenteral, Surfactant & Foaming Agents, Thickeners and Stabilizers, Topical

Excipient Details : PEG 400 is used as a suspending agent, stabilizer, plasticizer and filler in OSDs, liquids & semi-solids and as a solvent for parenteral formulations.

Pharmacopoeia Ref : ChP/USP/EP

Technical Specs : NA

Ingredient(s) : Polyethylene Glycol 400

03

Gangwal Healthcare

India

CPHI Middle east

Not Confirmed

Gangwal Healthcare is powered by innovation, driving health, wellness & healing.

Dosage Form : Capsule, Granule / Pellet, Tablet

Grade : Oral

Category : Controlled & Modified Release

Brand Name : Gellets-P®

Application : Controlled & Modified Release

Excipient Details : Gellets-P are Microcrystalline Cellulose based spheres for the manufacturing of pellets and modified release products.

Pharmacopoeia Ref : In-house

Technical Specs : NA

Ingredient(s) : Microcrystalline Cellulose

Excipients Web Link

U.S.A

CPHI Middle east

Not Confirmed

Only 10 entries up to this point, click to access all

Lubricants & Glidants

Co-Processed Excipients

Granulation

Topical

Film Formers & Plasticizers

Solubilizers

Emulsifying Agents

Parenteral

Taste Masking

Coloring Agents

Chewable & Orodispersible Aids

API Stability Enhancers

01

Gangwal Chemicals

India

CPHI Middle east

Not Confirmed

02

Ideal Cures Pvt Ltd

India

CPHI Middle east

Not Confirmed

Rheology Modifiers

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US Medicaid Prescriptions

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Finished Drug Prices

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Annual Reports

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Market Place

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APIs

Various APIs needed in Brazil [ENA12413]

A company that deals in the research, development & trading of health products is looking for suppliers of Various APIs for commercial purpose. The required quantity is MOQ for each. The suppliers must support this enquiry with ANVISA, DMF, PIC/s GMP & CoA. 1. Osimertinib API 2. Ruxolitinib API 3. Apalutamide API 4. Pembrolizumab API

14 Jan 2022

Various APIs needed in Brazil [ENA12002]

A large pharmaceutical manufacturing company that deals in portfolios like dermatological, cardiological, gynecological, gastric, oncology, respiratory & CNS is looking for suppliers of Various APIs for a new project. The suppliers must support this enquiry with USFDA, DMF, GMP & CoA. 1. EP/ BP/ USP Grade Apalutamide API 2. EP/ BP/ USP Grade Ruxolitinib Phosphate API

03 Dec 2021

Apalutamide API needed in India [ENA03003]

A multinational pharmaceutical company headquartered in Mumbai is looking for suppliers of Apalutamide API for domestic consumption.

20 Dec 2018

Apalutamide, Cabozantinib malate and other APIs needed in Bangladesh [ENA02773]

M.R Trading Corporation, Bangladesh is looking for suppliers of following APIs: 1. Apalutamide 2. Cabozantinib malate 3. Ruxolitinib Phosphate 4. Trabectedin INN 5. Venetoclax 6. Aflibercept Interested suppliers can contact Masud via Mob: +880 01725219963 or Email: info@mrtcbd.com.

28 Nov 2018

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FDF DOSSIERS

APALUTAMIDE

CPHI Middle east

Not Confirmed

Only 10 entries up to this point, click to access all

FULL SCREEN VIEW Click here to open all results in a new tab [this preview display 10 results]

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

28 API Suppliers

11 USDMF

4 EU WC

1 KDMF

7 NDC API

23 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

17 Drugs in Development

INTERMEDIATES

17 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

10 FDF Dossiers

2 FDA Orange Book

2 Europe

2 Canada

2 Australia

1 South Africa

1 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 SPI Pharma

2 Seqens

4 DKSH

2 Faran Shimi Pharmaceutical

7 Gangwal Healthcare

3 Actylis

1 Aeon Procare

5 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

9 BASF

5 Corel Pharma Chem

3 DFE Pharma

1 Finar

7 Gangwal Chemicals

3 Ideal Cures Pvt Ltd

1 Ingredion Pharma Solutions

6 Kerry

7 Microlex e.U

2 Nomisma Healthcare

1 Novo Excipients

1 Pharmatrans-Sanaq

2 Pluviaendo

3 Prachin Chemical

10 Roquette

3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

10 Sigachi Industries

3 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

22 Fillers, Diluents & Binders

20 Coating Systems & Additives

15 Thickeners and Stabilizers

15 Disintegrants & Superdisintegrants

14 Direct Compression

13 Controlled & Modified Release

13 Lubricants & Glidants

8 Co-Processed Excipients

8 Granulation

8 Topical

4 Film Formers & Plasticizers

4 Solubilizers

3 Emulsifying Agents

3 Parenteral

3 Taste Masking

3 Coloring Agents

2 Chewable & Orodispersible Aids

2 API Stability Enhancers

2 Rheology Modifiers

DIGITAL CONTENT

3 DATA COMPILATION #PharmaFlow

52 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions

2 Finished Drug Prices

4 Annual Reports

MARKET PLACE