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Crizotinib

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3 USDMF
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$ API Reference Price

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5 FDA Orange Book
8 Europe
2 Canada
4 Australia
2 South Africa
2 Listed Dossiers

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1 SPI Pharma, 8 DKSH, 1 Faran Shimi Pharmaceutical, 6 Gangwal Healthcare, 1 Nanjing Well Pharmaceutical, 4 ACG Worldwide, 3 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 1 BASF, 2 DFE Pharma, 1 Finar, 6 Gangwal Chemicals, 1 Ideal Cures Pvt Ltd, 3 Kerry, 3 Lonza Capsugel, 7 Microlex e.U, 1 Pharmatrans-Sanaq, 1 Pluviaendo, 2 Prachin Chemical, 1 Qualicaps, 9 Roquette, 1 Seppic, 2 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 8 Sigachi Industries, 1 Valens Pharmachem, 2 Vasa Pharmachem

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1 US Medicaid Prescriptions, 6 Finished Drug Prices, 10 Annual Reports

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1 US Medicaid Prescriptions
6 Finished Drug Prices
10 Annual Reports

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5 APIs, 1 FDF Dossiers

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PATENTS & EXCLUSIVITIES

35 US Patents, 14 US Exclusivities, 8 Health Canada Patents

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35 US Patents
14 US Exclusivities
8 Health Canada Patents

Synopsis

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FDF Dossiers

FDA Orange Book

Europe

Canada

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Listed Dossiers

12DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

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US Patents

US Exclusivities

Health Canada Patents

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113

News #PharmaBuzz

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US Medicaid (USD)

58,588,555

Annual Reports (USD Million)

4,578

Finished Drug Prices

76 RELATED EXCIPIENT COMPANIES

129EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 877399-52-5, Xalkori, Pf-02341066, (r)-crizotinib, Pf-2341066, Pf 2341066

Molecular Formula

C₂₁H₂₂Cl₂FN₅O

Molecular Weight

450.3 g/mol

InChI Key

KTEIFNKAUNYNJU-GFCCVEGCSA-N

FDA UNII

53AH36668S

A piperidine and aminopyridine derivative that acts as an inhibitor of RECEPTOR PROTEIN-TYROSINE KINASES, including ANAPLASTIC LYMPHOMA KINASE (ALK) and HEPATOCYTE GROWTH FACTOR RECEPTOR (HGFR; c-Met). It is used in the treatment of NON-SMALL CELL LUNG CANCER.

Crizotinib is a Kinase Inhibitor. The mechanism of action of crizotinib is as a Cytochrome P450 3A Inhibitor, and Receptor Tyrosine Kinase Inhibitor, and Cytochrome P450 2B6 Inhibitor, and P-Glycoprotein Inhibitor, and Organic Cation Transporter 1 Inhibitor, and Organic Cation Transporter 2 Inhibitor.

1 2D Structure

Crizotinib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine

2.1.2 InChI

InChI=1S/C21H22Cl2FN5O/c1-12(19-16(22)2-3-17(24)20(19)23)30-18-8-13(9-27-21(18)25)14-10-28-29(11-14)15-4-6-26-7-5-15/h2-3,8-12,15,26H,4-7H2,1H3,(H2,25,27)/t12-/m1/s1

2.1.3 InChI Key

KTEIFNKAUNYNJU-GFCCVEGCSA-N

2.1.4 Canonical SMILES

CC(C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N

2.1.5 Isomeric SMILES

C[C@H](C1=C(C=CC(=C1Cl)F)Cl)OC2=C(N=CC(=C2)C3=CN(N=C3)C4CCNCC4)N

2.2 Other Identifiers

2.2.1 UNII

53AH36668S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Pf 02341066

2. Pf 2341066

3. Pf-02341066

4. Pf-2341066

5. Pf02341066

6. Pf2341066

7. Xalkori

2.3.2 Depositor-Supplied Synonyms

1. 877399-52-5

2. Xalkori

3. Pf-02341066

4. (r)-crizotinib

5. Pf-2341066

6. Pf 2341066

7. Crizotinib (pf-02341066)

8. (r)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1h-pyrazol-4-yl)pyridin-2-amine

9. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1h-pyrazol-4-yl]-2-pyridinamine

10. Pf 02341066

11. Pf2341066

12. Chembl601719

13. Crizotinib (pf-2341066)

14. Chebi:64310

15. 877399-52-5 (free Base)

16. 53ah36668s

17. Nsc-756645

18. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(piperidin-4-yl)-1h-pyrazol-4-yl]pyridin-2-amine

19. 2-pyridinamine, 3-((1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(4-piperidinyl)-1h-pyrazol-4-yl)-

20. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-yl-1h-pyrazol-4-yl)pyridin-2-amine

21. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine

22. 3-[(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]-5-[1-(4-piperidinyl)-1h-pyrazol-4-yl]pyridin-2-amine

23. (r)-3-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1h-pyrazol-4-yl)-pyridin-2-ylamine

24. Xalkori (tn)

25. Crizotinib [usan]

26. Crizotinib [usan:inn]

27. Crizotinibum

28. Unii-53ah36668s

29. 3-((1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1h-pyrazol-4-yl)pyridin-2-amine

30. Vgh

31. Crizotinib- Bio-x

32. Crizotinib [mi]

33. Crizotinib [inn]

34. Crizotinib [jan]

35. Pf02341066

36. Crizotinib [vandf]

37. Crizotinib [mart.]

38. Crizotinib [who-dd]

39. Schembl93829

40. Pf-2341066,crizotinib

41. Crizotinib (jan/usan/inn)

42. Gtpl4903

43. Crizotinib [orange Book]

44. Crizotinib, >=98% (hplc)

45. Pf-2341066 - Crizotinib

46. Ex-a096

47. Bcpp000116

48. Dtxsid701009329

49. Amy10313

50. Bdbm50306682

51. Mfcd12407409

52. Nsc749005

53. Nsc749769

54. Nsc800080

55. Zinc35902489

56. Akos015901233

57. Akos015995207

58. Ccg-264803

59. Db08865

60. Gs-6178

61. Nsc 756645

62. Nsc-749005

63. Nsc-749769

64. Nsc-800080

65. Ncgc00250400-01

66. Ncgc00250400-02

67. Ncgc00250400-09

68. Ncgc00250400-12

69. Bc164334

70. Hy-50878

71. Bb 0261738

72. Sw202555-3

73. D09731

74. 399p525

75. J-510370

76. Q5186964

77. Brd-k78431006-001-01-1

78. Brd-k78431006-001-03-7

79. 877399-52-5, 877399-53-6 (acetate)

80. 3-(2,6-dichloro-3-fluorobenzyloxy)-5-(1-(piperidin-4-yl)-1h-pyrazol-4-yl)pyridin-2-amine

81. (r)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(1-(piperidin-4-yl)-1h-pyrazol-4-yl)pyridin-2-am Ine

82. 3-(1r)-1-(2,6-dichloro-3-fluorophenyl)ethoxy-5-1-(4-piperidinyl)-1h-pyrazol-4-yl-2-pyridinamine

83. 3-[(r)-1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-5-(1-piperidin-4-yl-1h-pyrazol-4-yl)-pyridin-2-ylamine

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₂Cl₂FN₅O
Molecular Weight	450.3 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	449.1185439 g/mol
Monoisotopic Mass	449.1185439 g/mol
Topological Polar Surface Area	78 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	558
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 2
Drug Name	Xalkori
PubMed Health	Crizotinib (By mouth)
Drug Classes	Antineoplastic Agent
Drug Label	XALKORI (crizotinib) is an oral receptor tyrosine kinase inhibitor. The molecular formula for crizotinib is C21H22Cl2FN5O. The molecular weight is 450.34 Daltons. Crizotinib is described chemically as (R)-3-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[...
Active Ingredient	Crizotinib
Dosage Form	Capsule
Route	Oral
Strength	200mg; 250mg
Market Status	Prescription
Company	Pf Prism Cv

2 of 2
Drug Name	Xalkori
PubMed Health	Crizotinib (By mouth)
Drug Classes	Antineoplastic Agent
Drug Label	XALKORI (crizotinib) is an oral receptor tyrosine kinase inhibitor. The molecular formula for crizotinib is C21H22Cl2FN5O. The molecular weight is 450.34 Daltons. Crizotinib is described chemically as (R)-3-[1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-5-[...
Active Ingredient	Crizotinib
Dosage Form	Capsule
Route	Oral
Strength	200mg; 250mg
Market Status	Prescription
Company	Pf Prism Cv

4.2 Drug Indication

Crizotinib is used for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC) that is anaplastic-lymphoma kinase (ALK)-positive as detected by a FDA-approved test.

FDA Label

Xalkori is indicated for the first-line treatment of adults with anaplastic lymphoma kinase (ALK) positive advanced non-small cell lung cancer (NSCLC).

Xalkori is indicated for the treatment of adults with previously treated anaplastic lymphoma kinase (ALK) positive advanced non-small cell lung cancer (NSCLC).

Treatment of lung malignant neoplasms

Treatment of anaplastic large cell lymphoma, Treatment of inflammatory myofibroblastic tumours

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents

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

Protein Kinase Inhibitors

Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

CRIZOTINIB

5.2.2 FDA UNII

53AH36668S

5.2.3 Pharmacological Classes

Cytochrome P450 3A Inhibitors [MoA]; Kinase Inhibitor [EPC]; Organic Cation Transporter 1 Inhibitors [MoA]; Organic Cation Transporter 2 Inhibitors [MoA]; P-Glycoprotein Inhibitors [MoA]; Receptor Tyrosine Kinase Inhibitors [MoA]; Cytochrome P450 2B6 Inhibitors [MoA]

5.3 ATC Code

L01ED01

L01XE16

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01ED - Anaplastic lymphoma kinase (alk) inhibitors

L01ED01 - Crizotinib

5.4 Absorption, Distribution and Excretion

Absorption

The peak serum concentration was reached in 4 to 6 hours following an oral single-dose administration. Steady state was reached within 15 days when a dose of 250 mg twice daily was administered. The mean absolute bioavailability was 43% (range of 32% to 66%) following a single 250 mg oral dose. When taken with high-fat meal, AUC and Cmax were reduced.

Route of Elimination

Following the administration of a single 250 mg radiolabeled crizotinib dose to healthy subjects, 63% and 22% of the administered dose was recovered in feces and urine, respectively. Unchanged crizotinib represented approximately 53% and 2.3% of the administered dose in feces and urine, respectively.

Volume of Distribution

Mean volume of distribution (Vss) is 1772 L following intravenous administration of a 50 mg dose. This high volume of distribution suggest extensive distribution into tissue from plasma.

Clearance

The mean apparent clearance (CL/F) of crizotinib was lower at steady state (60 L/hr) after 250 mg twice daily than that after a single 250 mg oral dose (100 L/hr), which was likely due to autoinhibition of CYP3A by crizotinib after multiple dosing.

5.5 Metabolism/Metabolites

Crizotinib is metabolized by CYP3A4 and CYP3A5 in which these enzymes mediates the O-dealkylation of the drug.

5.6 Biological Half-Life

Plasma terminal half-life, patients = 42 hours

5.7 Mechanism of Action

Crizotinib is a tyrosine kinase receptor inhibitor. More specifically, it inhibits anaplastic lymphoma kinase (ALK), hepatocyte growth factor receptor (HGFR, c-MET), and Recepteur d'Origine Nantais (RON). Abnormalities in the ALK gene caused by mutations or translocations may lead to expression of oncogenic fusion proteins. In patients with NSCLC, they have the EML4-ALK gene. Crizotinib inhibits ALK tyrosine kinase which ultimately results in decreased proliferation of cells that carry the genetic mutation and tumour survivability.

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CHETTY ROAD,T.NAGAR"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1716143400,"product":"CRIZOTINIB (TEST & ANALYSIS) (FREE OF CHARGE SAMPLE) (100%EOU)","address":"PLOT NO.B3,B4&B5 PT SIPCOT,INDUSTR","city":"SRIPERUMPUDUR,TAMIL NADU","supplier":"PFIZER MANUFACTURING DEUTSCHLAND GMBH","supplierCountry":"GERMANY","foreign_port":"FRANKFURT\/MAIN INT\\'L","customer":"PFIZER INC","customerCountry":"INDIA","quantity":"0.02","actualQuantity":"15","unit":"GMS","unitRateFc":"7.5","totalValueFC":"127","currency":"EUR","unitRateINR":"705.7","date":"20-May-2024","totalValueINR":"10585.99","totalValueInUsd":"127","indian_port":"Madras Air","hs_no":"29339990","bill_no":"3575292","productDescription":"API","marketType":"REGULATED MARKET","country":"GERMANY","selfForZScoreResived":"Pharma Grade","supplierPort":"FRANKFURT\/MAIN INT\\'L","supplierAddress":"MOOSWALDALLEE 1 79108 FREIBURG \/ GERMANY , , , , GERMANYSDNF GERMANY","customerAddress":"PLOT NO.B3,B4&B5 PT SIPCOT,INDUSTR"}]

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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Finished Drug Prices

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Brand Name : Xalkori

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Medlab Asia & Asia Health

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ACTIVE PHARMA INGREDIENTS

19 API Suppliers

3 USDMF

1 EU WC

3 NDC API

16 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

12 Drugs in Development

INTERMEDIATES

14 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

23 FDF Dossiers

5 FDA Orange Book

8 Europe

2 Canada

4 Australia

2 South Africa

2 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 SPI Pharma

8 DKSH

1 Faran Shimi Pharmaceutical

6 Gangwal Healthcare

1 Nanjing Well Pharmaceutical

4 ACG Worldwide

3 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

1 BASF

2 DFE Pharma

1 Finar

6 Gangwal Chemicals

1 Ideal Cures Pvt Ltd

3 Kerry

3 Lonza Capsugel

7 Microlex e.U

1 Pharmatrans-Sanaq

1 Pluviaendo

2 Prachin Chemical

1 Qualicaps

9 Roquette

1 Seppic

2 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

8 Sigachi Industries

1 Valens Pharmachem

2 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

25 Fillers, Diluents & Binders

16 Thickeners and Stabilizers

14 Direct Compression

11 Lubricants & Glidants

8 Empty Capsules

8 Coating Systems & Additives

8 Co-Processed Excipients

5 Film Formers & Plasticizers

5 Granulation

5 Disintegrants & Superdisintegrants

4 Emulsifying Agents

4 Controlled & Modified Release

3 Taste Masking

3 Coloring Agents

3 Topical

2 Solubilizers

2 Chewable & Orodispersible Aids

1 API Stability Enhancers

1 Rheology Modifiers

1 Parenteral

DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow

113 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions

6 Finished Drug Prices

10 Annual Reports

MARKET PLACE

5 APIs