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Acalabrutinib

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ACTIVE PHARMA INGREDIENTS

17 API Suppliers, 8 USDMF, 1 EU WC, 1 KDMF, 5 NDC API, 12 Listed Suppliers, $ API Reference Price

17 API Suppliers
8 USDMF
1 EU WC
1 KDMF
5 NDC API
12 Listed Suppliers
$ API Reference Price

DEVELOPMENTS

25 Drugs in Development

25 Drugs in Development

INTERMEDIATES

16 Intermediates Suppliers

16 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

12 FDF Dossiers, 3 FDA Orange Book, 2 Europe, 1 Canada, 4 Australia, 1 South Africa, 1 Listed Dossiers

12 FDF Dossiers
3 FDA Orange Book
2 Europe
1 Canada
4 Australia
1 South Africa
1 Listed Dossiers

RELATED EXCIPIENT COMPANIES

4 SPI Pharma, 7 DKSH, 2 Faran Shimi Pharmaceutical, 10 Gangwal Healthcare, 4 ACG Worldwide, 5 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 3 DFE Pharma, 5 Gangwal Chemicals, 1 Ideal Cures Pvt Ltd, 3 Ingredion Pharma Solutions, 4 Kerry, 3 Lonza Capsugel, 7 Microlex e.U, 2 Pharmatrans-Sanaq, 2 Pluviaendo, 3 Prachin Chemical, 1 Qualicaps, 17 Roquette, 1 Seppic, 3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 9 Sigachi Industries, 3 Vasa Pharmachem

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excipientsByApplications
37 Fillers, Diluents & Binders
20 Direct Compression
18 Disintegrants & Superdisintegrants
17 Thickeners and Stabilizers
12 Lubricants & Glidants
11 Co-Processed Excipients
8 Empty Capsules
8 Coating Systems & Additives
7 Granulation
6 Taste Masking
5 Chewable & Orodispersible Aids
5 Controlled & Modified Release
3 Emulsifying Agents
3 Film Formers & Plasticizers
2 Coloring Agents
1 Rheology Modifiers
1 API Stability Enhancers

DIGITAL CONTENT

3 DATA COMPILATION #PharmaFlow, 71 NEWS #PharmaBuzz

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3 DATA COMPILATION #PharmaFlow
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GLOBAL SALES INFORMATION

2 US Medicaid Prescriptions, 2 Finished Drug Prices, 7 Annual Reports

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2 US Medicaid Prescriptions
2 Finished Drug Prices
7 Annual Reports

PATENTS & EXCLUSIVITIES

47 US Patents, 2 US Exclusivities

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47 US Patents
2 US Exclusivities

Synopsis

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US Patents

US Exclusivities

Health Canada Patents

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Annual Reports (USD Million)

6,560

Finished Drug Prices

99 RELATED EXCIPIENT COMPANIES

164EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 1420477-60-6, Acp-196, Calquence, Acalabrutinib (acp-196), Acalabrutinib [inn], I42748elqw

Molecular Formula

C₂₆H₂₃N₇O₂

Molecular Weight

465.5 g/mol

InChI Key

WDENQIQQYWYTPO-IBGZPJMESA-N

FDA UNII

I42748ELQW

Acalabrutinib is an orally available inhibitor of Bruton's tyrosine kinase (BTK) with potential antineoplastic activity. Upon administration, acalabrutinib inhibits the activity of BTK and prevents the activation of the B-cell antigen receptor (BCR) signaling pathway. This prevents both B-cell activation and BTK-mediated activation of downstream survival pathways. This leads to an inhibition of the growth of malignant B cells that overexpress BTK. BTK, a member of the src-related BTK/Tec family of cytoplasmic tyrosine kinases, is overexpressed in B-cell malignancies; it plays an important role in B lymphocyte development, activation, signaling, proliferation and survival.

Acalabrutinib is a Kinase Inhibitor. The mechanism of action of acalabrutinib is as a Tyrosine Kinase Inhibitor.

1 2D Structure

Acalabrutinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[8-amino-3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide

2.1.2 InChI

InChI=1S/C26H23N7O2/c1-2-6-21(34)32-15-5-7-19(32)25-31-22(23-24(27)29-14-16-33(23)25)17-9-11-18(12-10-17)26(35)30-20-8-3-4-13-28-20/h3-4,8-14,16,19H,5,7,15H2,1H3,(H2,27,29)(H,28,30,35)/t19-/m0/s1

2.1.3 InChI Key

WDENQIQQYWYTPO-IBGZPJMESA-N

2.1.4 Canonical SMILES

CC#CC(=O)N1CCCC1C2=NC(=C3N2C=CN=C3N)C4=CC=C(C=C4)C(=O)NC5=CC=CC=N5

2.1.5 Isomeric SMILES

CC#CC(=O)N1CCC[C@H]1C2=NC(=C3N2C=CN=C3N)C4=CC=C(C=C4)C(=O)NC5=CC=CC=N5

2.2 Other Identifiers

2.2.1 UNII

I42748ELQW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acp-196

2. Calquence

2.3.2 Depositor-Supplied Synonyms

1. 1420477-60-6

2. Acp-196

3. Calquence

4. Acalabrutinib (acp-196)

5. Acalabrutinib [inn]

6. I42748elqw

7. 4-[8-amino-3-[(2s)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-n-pyridin-2-ylbenzamide

8. Benzamide, 4-(8-amino-3-((2s)-1-(1-oxo-2-butyn-1-yl)-2-pyrrolidinyl)imidazo(1,5-a)pyrazin-1-yl)-n-2-pyridinyl-

9. (s)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-n-(pyridin-2-yl)benzamide

10. Acalabrutinib(acp196)

11. Acalabrutinib [usan:inn]

12. Acalabrutinibum

13. Unii-i42748elqw

14. Calquence (tn)

15. Benzamide, 4-[8-amino-3-[(2s)-1-(1-oxo-2-butyn-1-yl)-2-pyrrolidinyl]imidazo[1,5-a]pyrazin-1-yl]-n-2-pyridinyl-

16. Acp-196;acalabrutinib

17. Acalabrutinib [mi]

18. Acalabrutinib [jan]

19. Acalabrutinib [usan]

20. Acalabrutinib [who-dd]

21. Gtpl8912

22. Acalabrutinib (jan/usan/inn)

23. Chembl3707348

24. Schembl14637368

25. Acp 196

26. Amy5290

27. Ex-a881

28. Chebi:167707

29. Dtxsid401026209

30. Acalabrutinib [orange Book]

31. Bdbm50175583

32. Mfcd29472294

33. Nsc791164

34. Nsc800976

35. S8116

36. Zinc208774715

37. Ccg-269407

38. Cs-5356

39. Db11703

40. Ds-3326

41. Nsc-791164

42. Nsc-800976

43. Ncgc00479074-01

44. Hy-17600

45. Example 6 [us20140155385 A1]

46. D10893

47. A857446

48. J-690166

49. Q23668732

50. (s)-4-(8-amino-3-(1-(but-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-n-(pyridin-2-yl)benzamide;acalabrutinib

51. (s)-4-(8-amino-3-(1-but-2-ynoylpyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-n-(pyridin-2-yl)benzamide

52. 4-[8-amino-3-[(2s)-1-(1-oxo-2-butyn-1-yl)-2-pyrrolidinyl]imidazo[1,5-a]pyrazin-1-yl]-n-2-pyridinyl-benzamide

53. 4-[8-amino-3-[(2s)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-n-(2-pyridyl)benzamide

54. 4-{8-amino-3-[(2s)-1-(but-2-ynoyl)pyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl}-n-(pyridin-2-yl)benzamide

2.4 Create Date

2013-03-21

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₂₃N₇O₂
Molecular Weight	465.5 g/mol
XLogP3	3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	465.19132300 g/mol
Monoisotopic Mass	465.19132300 g/mol
Topological Polar Surface Area	119 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	845
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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 Information

1 of 1
Drug Name	CALQUENCE
Active Ingredient	ACALABRUTINIB
Company	ASTRAZENECA (Application Number: N210259. Patents: 9290504, 9758524, 9796721)

4.2 Drug Indication

Acalabrutinib is currently indicated for the treatment of adult patients with Mantle Cell Lymphoma (MCL) who have received at least one prior therapy. It has also been recently approved for chronic lymphocytic leukemia and small lymphocytic lymphoma.

FDA Label

Calquence as monotherapy or in combination with obinutuzumab is indicated for the treatment of adult patients with previously untreated chronic lymphocytic leukaemia (CLL).

Calquence as monotherapy is indicated for the treatment of adult patients with chronic lymphocytic leukaemia (CLL) who have received at least one prior therapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Acalabrutinib is a Bruton Tyrosine Kinase inhibitor that prevents the proliferation, trafficking, chemotaxis, and adhesion of B cells. It is taken every 12 hours and can cause other effects such as atrial fibrillation, other malignancies, cytopenia, hemorrhage, and infection.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ACALABRUTINIB

5.3.2 FDA UNII

I42748ELQW

5.3.3 Pharmacological Classes

Tyrosine Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]

5.4 ATC Code

L01XE51

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EL - Bruton's tyrosine kinase (btk) inhibitors

L01EL02 - Acalabrutinib

5.5 Absorption, Distribution and Excretion

Absorption

The geometric mean absolute bioavailability of acalabrutinib is 25% with a median time to peak plasma concentrations (Tmax) of 0.75 hours.

Route of Elimination

After administration of a single 100 mg radiolabelled acalabrutinib dose in healthy subjects, 84% of the dose was recovered in the feces and 12% of the dose was recovered in the urine. An irradiated dose of acalabrutinib was 34.7% recovered as the metabolite ACP-5862; 8.6% was recovered as unchanged acalabrutinub; 10.8 was recovered as a mixture of the M7, M8, M9, M10, and M11 metabolites; 5.9% was the M25 metabolite; 2.5% was recovered as the M3 metabolite.

Volume of Distribution

The mean steady-state volume of distribution is approximately 34 L.

Clearance

Acalabrutinib's mean apparent oral clearance (CL/F) is observed to be 159 L/hr with similar PK between patients and healthy subjects, based on population PK analysis.

5.6 Metabolism/Metabolites

Acalabrutinib is mainly metabolized by CYP3A enzymes. ACP-5862 is identified to be the major active metabolite in plasma with a geometric mean exposure (AUC) that is about 2-3 times greater than the exposure of acalabrutinib. ACP-5862 is about 50% less potent than acalabrutinib in regards to the inhibition of BTK.

5.7 Biological Half-Life

After administering a single oral dose of 100 mg acalabrutinib, the median terminal elimination half-life of the drug was found to be 0.9 (with a range of 0.6 to 2.8) hours. The half-life of the active metabolite, ACP-5862, is about 6.9 hours.

5.8 Mechanism of Action

Mantle Cell Lymphoma (MCL) is a rare yet aggressive type of B-cell non-Hodgkin lymphoma (NHL) with poor prognosis. Subsequently, relapse is common in MCL patients and ultimately represents disease progression. Lymphoma occurs when immune system lymphocytes grow and multiply uncontrollably. Such cancerous lymphocytes may travel to many parts of the body, including the lymph nodes, spleen, bone marrow, blood, and other organs where they can multiply and form a mass(es) called a tumor. One of the main kinds of lymphocytes that can develop into cancerous lymphomas are the body's own B-lymphocytes (B-cells). Bruton Tyrosine Kinase (BTK) is a signalling molecule of the B-cell antigen receptor and cytokine receptor pathways. Such BTK signaling causes the activation of pathways necessary for B-cell proliferation, trafficking, chemotaxis, and adhesion. Acalabrutinib is a small molecule inhibitor of BTK. Both acalabrutinib and its active metabolite, ACP-5862, act to form a covalent bond with a cysteine residue (Cys481) in the BTK active site, leading to inhibition of BTK enzymatic activity. As a result, acalabrutinib inhibits BTK-mediated activation of downstream signaling proteins CD86 and CD69, which ultimately inhibits malignant B-cell proliferation and survival Whereas ibrutinib is typically recognized as the first-in-class BTK inhibitor, acalabrutinib is considered a second generation BTK inhibitor primarily because it demonstrates highter selectivity and inhibition of the targeted activity of BTK while having a much greater IC50 or otherwise virtually no inhibition on the kinase activities of ITK, EGFR, ERBB2, ERBB4, JAK3, BLK, FGR, FYN, HCK, LCK, LYN, SRC, and YES1. In effect, acalabrutinib was rationally designed to be more potent and selective than ibrutinib, all the while demonstrating fewer adverse effects - in theory - because of the drug's minimized off target effects.

API SUPPLIERS

01

Dr. Reddy's Laboratories

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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Egis Pharmaceuticals PLC

Hungary

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

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Aarti Pharmalabs

India

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Sichuan Elixir Pharmaceuticals

China

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MSN Laboratories

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Natco Pharma

India

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Hangzhou Longshine Bio-Tech

China

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01

Aarti Pharmalabs Ltd

India

CPhI India 2024

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Benzyl(2s)-2-(8-amino-1-bromoimidazo[1,5-a]pyr...

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DMF Number : 35796

Submission : 2021-04-20

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Alembic Pharmaceuticals Ltd

India

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Cipla Ltd

India

India

CPhI India 2024

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API Reference Price

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Drugs in Development

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INTERMEDIATES SUPPLIERS

01

PMC Isochem

France

BMWS24

Not Confirmed

PMC Isochem is your partner for smart CDMOs of Intermediates, APIs, & excipients & a catalog of Intermediates & Generic APIs.

Z-Proline

CAS Number : 1148-11-4

End Use API : Acalabrutinib

Product Web Link

02

Aarti Pharmalabs

India

CPhI India 2024

Booth #2.F08

Aarti Pharmalabs is a partner of choice for APIs & Intermediates and the largest Indian manufacturer of Xanthine Derivatives.

(3-Chloropyrazin-2-yl) methanamine hydrochloride

CAS Number : 939412-86-9

End Use API : Acalabrutinib

03

Aarti Pharmalabs

India

CPhI India 2024

Booth #2.F08

Aarti Pharmalabs is a partner of choice for APIs & Intermediates and the largest Indian manufacturer of Xanthine Derivatives.

(2S)-2-(8-amino-1-bromoimidazo[1,5-a] pyrazin-3-yl...

CAS Number : 1420478-88-1

End Use API : Acalabrutinib

04

Aarti Pharmalabs

India

CPhI India 2024

Booth #2.F08

Aarti Pharmalabs is a partner of choice for APIs & Intermediates and the largest Indian manufacturer of Xanthine Derivatives.

4-(Pyridin-2-yl-aminocarbonyl) benzene boronic aci...

CAS Number : 850568-25-1

End Use API : Acalabrutinib

05

Aarti Pharmalabs

India

CPhI India 2024

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Aarti Pharmalabs is a partner of choice for APIs & Intermediates and the largest Indian manufacturer of Xanthine Derivatives.

N-(Benzyloxy carbonyl)-L-Proline

CAS Number : 1148-11-4

End Use API : Acalabrutinib

06

Aarti Pharmalabs

India

CPhI India 2024

Booth #2.F08

Aarti Pharmalabs is a partner of choice for APIs & Intermediates and the largest Indian manufacturer of Xanthine Derivatives.

(2S)-2-(8-amino-1-bromoimidazo[1,5-a] pyrazin-3-yl...

CAS Number : 503615-03-0

End Use API : Acalabrutinib

07

Aarti Pharmalabs

India

CPhI India 2024

Booth #2.F08

Aarti Pharmalabs is a partner of choice for APIs & Intermediates and the largest Indian manufacturer of Xanthine Derivatives.

5-Chloro-1-methyl-4-nitro imidazole

CAS Number : 4897-25-0

End Use API : Acalabrutinib

08

Hangzhou Longshine Bio-Tech Co.,LTD

China

BMWS24

Not Confirmed

09

Hangzhou Longshine Bio-Tech Co.,LTD

China

BMWS24

Not Confirmed

10

Hangzhou Longshine Bio-Tech Co.,LTD

China

BMWS24

Not Confirmed

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FDF Dossiers

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Europe

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Canada

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South Africa

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Listed Dossiers

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Fillers, Diluents & Binders

Direct Compression

Disintegrants & Superdisintegrants

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Lubricants & Glidants

Co-Processed Excipients

Empty Capsules

Coating Systems & Additives

Granulation

Taste Masking

Chewable & Orodispersible Aids

Controlled & Modified Release

Emulsifying Agents

Film Formers & Plasticizers

Coloring Agents

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Digital Content

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Global Sales Information

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US Medicaid Prescriptions

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Finished Drug Prices

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Annual Reports

ACALABRUTINIB MALEATE

CPhI India 2024

Not Confirmed

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US Exclusivities

01

ASTRAZENECA

ACALABRUTINIB

CPhI India 2024

Not Confirmed

02

ASTRAZENECA

ACALABRUTINIB

CPhI India 2024

Not Confirmed

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

17 API Suppliers

8 USDMF

1 EU WC

1 KDMF

5 NDC API

12 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

25 Drugs in Development

INTERMEDIATES

16 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

12 FDF Dossiers

3 FDA Orange Book

2 Europe

1 Canada

4 Australia

1 South Africa

1 Listed Dossiers

RELATED EXCIPIENT COMPANIES

4 SPI Pharma

7 DKSH

2 Faran Shimi Pharmaceutical

10 Gangwal Healthcare

4 ACG Worldwide

5 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

3 DFE Pharma

5 Gangwal Chemicals

1 Ideal Cures Pvt Ltd

3 Ingredion Pharma Solutions

4 Kerry

3 Lonza Capsugel

7 Microlex e.U

2 Pharmatrans-Sanaq

2 Pluviaendo

3 Prachin Chemical

1 Qualicaps

17 Roquette

1 Seppic

3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

9 Sigachi Industries

3 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

37 Fillers, Diluents & Binders

20 Direct Compression

18 Disintegrants & Superdisintegrants

17 Thickeners and Stabilizers

12 Lubricants & Glidants

11 Co-Processed Excipients

8 Empty Capsules

8 Coating Systems & Additives

7 Granulation

6 Taste Masking

5 Chewable & Orodispersible Aids

5 Controlled & Modified Release

3 Emulsifying Agents

3 Film Formers & Plasticizers

2 Coloring Agents

1 Rheology Modifiers

1 API Stability Enhancers

DIGITAL CONTENT

3 DATA COMPILATION #PharmaFlow

71 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

2 US Medicaid Prescriptions

2 Finished Drug Prices

7 Annual Reports

PATENTS & EXCLUSIVITIES

47 US Patents

2 US Exclusivities

ACTIVE PHARMA INGREDIENTS

API REF. PRICE (USD/KG)

$ 24,003

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