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148 US Patents
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Axplora Olaparib

Synopsis

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148

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Health Canada Patents

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224EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 763113-22-0, Lynparza, Azd2281, Azd-2281, Ku-0059436, Azd 2281

Molecular Formula

C₂₄H₂₃FN₄O₃

Molecular Weight

434.5 g/mol

InChI Key

FDLYAMZZIXQODN-UHFFFAOYSA-N

FDA UNII

WOH1JD9AR8

Olaparib is a small molecule inhibitor of the nuclear enzyme poly(ADP-ribose) polymerase (PARP) with potential chemosensitizing, radiosensitizing, and antineoplastic activities. Olaparib selectively binds to and inhibits PARP, inhibiting PARP-mediated repair of single strand DNA breaks; PARP inhibition may enhance the cytotoxicity of DNA-damaging agents and may reverse tumor cell chemoresistance and radioresistance. PARP catalyzes post-translational ADP-ribosylation of nuclear proteins and can be activated by single-stranded DNA breaks.

Olaparib is a Poly(ADP-Ribose) Polymerase Inhibitor. The mechanism of action of olaparib is as a Poly(ADP-Ribose) Polymerase Inhibitor.

1 2D Structure

Olaparib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2H-phthalazin-1-one

2.1.2 InChI

InChI=1S/C24H23FN4O3/c25-20-8-5-15(14-21-17-3-1-2-4-18(17)22(30)27-26-21)13-19(20)24(32)29-11-9-28(10-12-29)23(31)16-6-7-16/h1-5,8,13,16H,6-7,9-12,14H2,(H,27,30)

2.1.3 InChI Key

FDLYAMZZIXQODN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CC1C(=O)N2CCN(CC2)C(=O)C3=C(C=CC(=C3)CC4=NNC(=O)C5=CC=CC=C54)F

2.2 Other Identifiers

2.2.1 UNII

WOH1JD9AR8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Azd 2281

2. Azd-2281

3. Azd221

4. Azd2281

5. Lynparza

2.3.2 Depositor-Supplied Synonyms

1. 763113-22-0

2. Lynparza

3. Azd2281

4. Azd-2281

5. Ku-0059436

6. Azd 2281

7. 1-(cyclopropylcarbonyl)-4-[5-[(3,4-dihydro-4-oxo-1-phthalazinyl)methyl]-2-fluorobenzoyl]piperazine

8. Olaparib (azd-2281)

9. 4-(3-(4-(cyclopropanecarbonyl)piperazine-1-carbonyl)-4-fluorobenzyl)phthalazin-1(2h)-one

10. Ku-59436

11. Olaparib (azd2281, Ku-0059436)

12. 4-[[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]-4-fluorophenyl]methyl]-2h-phthalazin-1-one

13. Az2281

14. Mfcd13185161

15. Woh1jd9ar8

16. Nsc-747856

17. C24h23fn4o3

18. Chebi:83766

19. 4-(3-{[4-(cyclopropylcarbonyl)piperazin-1-yl]carbonyl}-4-fluorobenzyl)phthalazin-1(2h)-one

20. 4-[3-(4-cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro-benzyl]-2h-phthalazin-1-one

21. Az-2281

22. Keylynk-010 Component Olaparib

23. Ku59436

24. Olaparib Component Of Keylynk-010

25. Olaparib [inn]

26. Olaparib Cpd

27. Olaparib (azd2281; Ku-0059436)

28. Olaparib [usan:inn]

29. Unii-woh1jd9ar8

30. Olaparib (azd2281)

31. Acylpiperazine Analogue, 47

32. Olaparibum

33. Azd221

34. 4-[3-[4-(cyclopropanecarbonyl)piperazine-1-carbonyl]-4-fluorobenzyl]phthalazin-1(2h)-one

35. Olaparib- Bio-x

36. Lynparza (tn)

37. 09l

38. 4-((3-((4-(cyclopropylcarbonyl)piperazin-1-yl)carbonyl)-4-fluorophenyl)methyl)phthalazin-1(2h)-one

39. 4-((3-{(4-(cyclopropylcarbonyl)piperazin-1-yl)carbonyl}-4-fluorophenyl)methyl)phthalazin-1(2h)-one

40. 4-[(3-{[4-(cyclopropylcarbonyl)piperazin-1-yl]carbonyl}-4-fluorophenyl)methyl]phthalazin-1(2h)-one

41. Ku 59436

42. Olaparib [usan]

43. Olaparib [jan]

44. Ku0059436

45. Olaparib [mi]

46. Olaparib [vandf]

47. Olaparib - Azd2281

48. Olaparib [mart.]

49. Olaparib [who-dd]

50. Azd-2281 (olaparib)

51. Olaparib (jan/usan/inn)

52. Mls006010185

53. Schembl426568

54. Olaparib [orange Book]

55. Chembl521686

56. Gtpl7519

57. Bdbm27566

58. Dtxsid60917988

59. Ex-a002

60. Bcpp000360

61. Hms3295i09

62. Hms3426c03

63. Hms3654g13

64. Hms3746k07

65. Hms3870h03

66. Amy10295

67. Bcp01872

68. 763113-22-0, Lynparza,

69. Nsc747856

70. Nsc753686

71. S1060

72. Zinc40430143

73. Akos005145764

74. Ac-7939

75. Bcp9000363

76. Ccg-264799

77. Cs-0075

78. Db09074

79. Ex-7210

80. Nsc 747856

81. Nsc-753686

82. Sb14617

83. Ss-4573

84. Azd2281,olaparib, Ku-0059436

85. Ncgc00238451-01

86. Ncgc00238451-02

87. Ncgc00238451-08

88. Ncgc00238451-09

89. Ncgc00238451-11

90. 4-[(3-{[4-cyclopropylcarbonyl)piperazin-4-yl]carbonyl}-4-fluorophenyl)methyl]phtalazin-1(2h)-one

91. 4-[[3-[[4-(cyclopropylcarbonyl)-1-piperazinyl]carbonyl]-4-fluorophenyl]methyl]-1(2h)-phthalazinone

92. Bo164169

93. Hy-10162

94. Smr004701291

95. Sy040527

96. Olaparib(azd2281,kudosku-0059436)

97. A9666

98. Bb 0260909

99. Ft-0651458

100. Ku 0059436

101. Sw218142-2

102. Ec-000.2324

103. D09730

104. J-503540

105. Q7083106

106. Brd-k02113016-001-08-9

107. Brd-k02113016-001-09-7

108. 1-(cyclopropylcarbonyl)-4-[5-[(3,4-dihydro-4-oxo-1-phthalazine

109. 4-(3-(1-(cyclopropanecarbonyl)piperazine-4-carbonyl)-4-fluorobenzyl)phthalazin-1(2h)-one

110. (2h)-phthalazinone, 4-((3-((4-(cyclopropylcarbonyl)-1-piperazinyl)carbonyl)-4-fluorophenyl)methyl)-

111. 1(2h)-phthalazinone, 4-((3-((4-(cyclopropylcarbonyl)-1-piperazinyl)carbonyl)-4-fluorophenyl)methyl)-

112. 1021843-02-6

113. 4-({3-[(4-cyclopropanecarbonylpiperazin-1-yl)carbonyl]-4-fluorophenyl}methyl)-1,2-dihydrophthalazin-1-one

114. Piperazine, 1-(cyclopropylcarbonyl)-4-(5-((3,4-dihydro-4-oxo-1-phthalazinyl)methyl)-2-fluorobenzoyl)-

2.4 Create Date

2008-02-11

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₃FN₄O₃
Molecular Weight	434.5 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	434.17541877 g/mol
Monoisotopic Mass	434.17541877 g/mol
Topological Polar Surface Area	82.1 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	790
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

Olaparib is a poly (ADP-ribose) polymerase (PARP) inhibitor indicated for the treatment of: - Ovarian cancer, in which the medication is intended for [a] the maintenance treatment of adult patients with recurrent epithelial ovarian, fallopian tube or primary peritoneal cancer, who are in complete or partial response to platinum-based chemotherapy, or [b] for the treatment of adult patients with deleterious or suspected deleterious germline BRCA-mutated (gBRCAm) advanced ovarian cancer who have been treated with three or more prior lines of chemotherapy. Select patients for therapy based on an FDA-approved companion diagnostic for olaparib. - Breast cancer, in which the medication is intended for use in patients with deleterious or suspected deleterious gBRCAm, human epidermal growth factor receptor 2 (HER2)-negative metastatic breast cancer who have previously been treated with chemotherapy in the neoadjuvant, adjuvant or metastatic setting. Patients with hormone receptor (HR)-positive breast cancer should have been treated with a prior endocrine therapy or be considered inappropriate for endocrine treatment. Select patients for therapy based on an FDA-approved companion diagnostic for olaparib.

FDA Label

* Ovarian cancer :

Lynparza is indicated as monotherapy for the:

- maintenance treatment of adult patients with advanced (FIGO stages III and IV) BRCA1/2-mutated (germline and/or somatic) high-grade epithelial ovarian, fallopian tube or primary peritoneal cancer who are in response (complete or partial) following completion of first-line platinum-based chemotherapy.

- maintenance treatment of adult patients with platinum sensitive relapsed high grade epithelial ovarian, fallopian tube, or primary peritoneal cancer who are in response (complete or partial) to platinum based chemotherapy.

Lynparza in combination with bevacizumab is indicated for the:

- maintenance treatment of adult patients with advanced (FIGO stages III and IV) high-grade epithelial ovarian, fallopian tube or primary peritoneal cancer who are in response (complete or partial) following completion of first-line platinum-based chemotherapy in combination with bevacizumab and whose cancer is associated with homologous recombination deficiency (HRD) positive status defined by either a BRCA1/2 mutation and/or genomic instability (see section 5. 1).

* Breast cancer :

Lynparza is indicated as monotherapy for the treatment of adult patients with germline BRCA1/2-mutations, who have HER2 negative locally advanced or metastatic breast cancer . Patients should have previously been treated with an anthracycline and a taxane in the (neo)adjuvant or metastatic setting unless patients were not suitable for these treatments (see section 5. 1).

Patients with hormone receptor (HR)-positive breast cancer should also have progressed on or after prior endocrine therapy, or be considered unsuitable for endocrine therapy.

* Adenocarcinoma of the pancreas:

Lynparza is indicated as monotherapy for the maintenance treatment of adult patients with germline BRCA1/2-mutations who have metastatic adenocarcinoma of the pancreas and have not progressed after a minimum of 16 weeks of platinum treatment within a first-line chemotherapy regimen.

* Prostate cancer :

Lynparza is indicated as monotherapy for the treatment of adult patients with metastatic castration-resistant prostate cancer and BRCA1/2-mutations (germline and/or somatic) who have progressed following prior therapy that included a new hormonal agent.

Lynparza is indicated as monotherapy for the maintenance treatment of adult patients with platinum sensitive relapsed BRCA mutated (germline and/or somatic) high grade serous epithelial ovarian, fallopian tube, or primary peritoneal cancer who are in response (complete response or partial response) to platinum based chemotherapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

The effect of olaparib on cardiac repolarization was assessed in 119 patients following a single dose of 300 mg and in 109 patients following multiple dosing of 300 mg twice daily. No clinically relevant effect of olaparib on QT interval was observed.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents

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

Poly(ADP-ribose) Polymerase Inhibitors

Chemicals and drugs that inhibit the action of POLY(ADP-RIBOSE)POLYMERASES. (See all compounds classified as Poly(ADP-ribose) Polymerase Inhibitors.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

OLAPARIB

5.3.2 FDA UNII

WOH1JD9AR8

5.3.3 Pharmacological Classes

Poly(ADP-Ribose) Polymerase Inhibitors [MoA]; Poly(ADP-Ribose) Polymerase Inhibitor [EPC]

5.4 ATC Code

L01XK01

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XK - Poly (adp-ribose) polymerase (parp) inhibitors

L01XK01 - Olaparib

5.5 Absorption, Distribution and Excretion

Absorption

Following oral administration, the absorption of olaparib is very rapid and can reach a peak concentration ranging between 4.7 and 9.1 mcg/ml after 1-3 hours. The reported AUC of olaparib after a dose of 200 mg is of 25.8 mcg.h/L and this AUC can be increased by 26% with constant administration. The consumption of a high-fat diet with olaparib can only decrease the tmax but do not have an effect in the peak concentration.

Route of Elimination

From the administered dose, approximately 86% of the administered dose is recovered after 7 days from which 44% is found in the urine and 42% is obtained in feces.

Volume of Distribution

After administration of a dose of 100 mg/kg, the reported volume of distribution was of 40.3 L.

Clearance

The total clearance of olaparib was reported to be 4.6 L/h.

5.6 Metabolism/Metabolites

Olaparib is extensively metabolized in the liver by the action of CYP3A isoenzymes. From the administered dose, the unchanged form of olaparib accounted for 70% of the circulating dose and it was considered the major component in urine and feces. The metabolic pathway of olaparib is mainly attributable to oxidation reactions with subsequent glucuronide and sulfate conjugation. However, the over 20 metabolites found in plasma, urine, and feces represented a minor portion of the administered dose. The major circulating metabolites were represented by the mono-oxygenated form and the piperazin-3-ol form.

5.7 Biological Half-Life

The reported elimination half-life ranges between 5 to 11 hours.

5.8 Mechanism of Action

Olaparib is an inhibitor of poly (ADP-ribose) polymerase (PARP) enzymes, including PARP1, PARP2, and PARP3. PARP enzymes are involved in normal cellular homeostasis, such as DNA transcription, cell cycle regulation, and DNA repair. Olaparib has been shown to inhibit growth of select tumor cell lines in vitro and decrease tumor growth in mouse xenograft models of human cancer both as monotherapy or following platinum-based chemotherapy. Increased cytotoxicity and anti-tumor activity following treatment with olaparib were noted in cell lines and mouse tumor models with deficiencies in BRCA. In vitro studies have shown that olaparib-induced cytotoxicity may involve inhibition of PARP enzymatic activity and increased formation of PARP-DNA complex, resulting in disruption of cellular homeostasis and cell death.

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