Niraparib

Identification

Summary

Niraparib is a poly-ADP ribose polymerase inhibitor used to treat recurrent epithelial ovarian, fallopian tube, or primary peritoneal cancer responding to platinum based chemotherapy.

Brand Names

Zejula

Generic Name

Niraparib

DrugBank Accession Number

DB11793

Background

Niraparib is an orally active poly (ADP-ribose) polymerase (PARP) inhibitor. By blocking the enzymes responsible for DNA repair, niraparib induces cytotoxicity in cancer cells.⁶ Niraparib is selective towards PARP-1 and PARP-2.² First approved by the FDA on March 27, 2017,³ niraparib is used to treat epithelial ovarian, fallopian tube, or primary peritoneal cancer.⁶ Niraparib was approved by the European Commission on November 16, 2017 ⁷ and by Health Canada on June 27, 2019.⁸

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Niraparib (DB11793)

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Weight

Average: 320.396
Monoisotopic: 320.16371128

Chemical Formula

C₁₉H₂₀N₄O

Synonyms

• Niraparib

External IDs

• MK 4827
• MK-4827
• MK-4827 FREE BASE
• MK4827

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Pharmacology

Indication

Niraparib is indicated for the maintenance treatment of adult patients with advanced or recurrent epithelial ovarian, fallopian tube, or primary peritoneal cancer who are in complete or partial response to first-line platinum-based chemotherapy.^6,7,8

In Canada and the US, niraparib is also available in a combination product with abiraterone, which is indicated with prednisone for the treatment of adults with deleterious or suspected deleterious BRCA-mutated (BRCAm) metastatic castration-resistant prostate cancer (mCRPC).^9,10 In Canada, this combination product is also used with prednisolone and is reserved for patients who are asymptomatic or mildly symptomatic, and in whom chemotherapy is not clinically indicated.⁹

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Advanced epithelial ovarian cancer		••••••••••••	•••••	•••••••••• •• •••••••••••••• ••••••••••••
Treatment of	Advanced primary peritoneal carcinoma		••••••••••••	•••••	•••••••••• •• •••••••••••••• ••••••••••••
Used in combination to treat	Metastatic castration-resistant prostate cancer (mcrpc)	Regimen in combination with: Prednisone (DB00635), Abiraterone (DB05812)	••••••••••••	•••••		••••••
Used in combination to treat	Metastatic castration-resistant prostate cancer (mcrpc)	Combination Product in combination with: Abiraterone (DB05812)	••••••••••••	•••••	••••••••••••• •••••••••••• ••• •••••••••• •••••••••	••••••
Used in combination to treat	Metastatic castration-resistant prostate cancer (mcrpc)	Combination Product in combination with: Abiraterone (DB05812)	••••••••••••	•••••	•••• •••••••• ••••••••• •••••••••••• ••• •••••••••• •••••••••	••••••

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Associated Therapies

• Maintenance therapy

Contraindications & Blackbox Warnings

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Pharmacodynamics

Niraparib mediated cytotoxic effects in tumour cell lines with or without deficiencies in BRCA1/2. Decreased tumour growth was observed in both mouse xenograft models of human cancer cell lines with deficiencies in BRCA1/2 and human patient-derived xenograft tumour models with homologous recombination deficiency (HRD) that had either mutated or wild-type BRCA1/2.⁶

In vitro studies suggest that niraparib inhibits dopamine, norepinephrine, and serotonin transporters, which may explain its off-target cardiovascular effects such as increased pulse rate and blood pressure.²

Mechanism of action

Niraparib is a potent and selective inhibitor of poly(ADP-ribose) polymerase (PARP) enzymes, PARP-1 and PARP-2.^7,8 PARPs play an important role in DNA repair. They recognize and repair cellular DNA damage, such as single-strand breaks (SSBs) and double-strand breaks (DSBs). Different DNA repair pathways exist to repair these DNA damages, including the base excision repair (BER) pathway for SSBs and BRCA-dependent homologous recombination for DSBs.⁴ If BER is impaired, SSBs accumulate and become DSBs, forcing cells to rely on other repair pathways, mainly the homologous recombination (HR) and the nonhomologous end joining, to repair DNA damages.¹ However, some cells can have defective or deficient HR resulting from specific mutations in DNA repair genes, such as BRCA1 and 2.² Inhibiting PARPs in the presence of HR deficiency leads to a phenomenon called 'synthetic lethality,' whereby the PARP inhibitor impedes BER, leading to genetic instability and cell death.^1,2

Selectivity towards PARP-1 and PARP-2 is 100-fold higher than for other PARP family members.² Niraparib-induced cytotoxicity may involve inhibition of PARP enzymatic activity and increased formation of PARP-DNA complexes resulting in DNA damage, apoptosis, and cell death.^6,7,8

Target	Actions	Organism
APoly [ADP-ribose] polymerase 1	inhibitor	Humans
APoly [ADP-ribose] polymerase 2	inhibitor	Humans

Absorption

Following a single-dose administration of 300 mg niraparib, the mean (±SD) peak plasma concentration (C_max) was 804 (±403) ng/mL. The exposure (C_max and AUC) of niraparib increased in a dose-proportional manner with daily doses ranging from 30 mg (0.1 times the approved recommended dose) to 400 mg (1.3 times the approved recommended dose). The accumulation ratio of niraparib exposure following 21 days of repeated daily doses was approximately 2-fold for doses ranging from 30 to 400 mg. The Tmax is about three hours.⁶

The absolute bioavailability of niraparib is approximately 73%. Food does not appear to affect drug exposure.⁶

Volume of distribution

The average (±SD) apparent volume of distribution (Vd/F) was 1,220 (±1,114) L. In a population pharmacokinetic analysis, the Vd/F of niraparib was 1,074 L in patients with cancer.⁶

Protein binding

Niraparib is 83% bound to human plasma proteins.⁶

Metabolism

Niraparib is primarily metabolized by carboxylesterases (CEs) to form M1, which is a major inactive metabolite. The M1 metabolite can subsequently undergo glucuronidation mediated by UDP-glucuronosyltransferases (UGTs) to form the M10 metabolite.⁶ In a mass balance study, M1 and M10 were the major circulating metabolites.⁷ The M1 metabolite can also undergo methylation, monooxygenation, and hydrogenation to form other minor metabolites.⁵

Hover over products below to view reaction partners

• Niraparib
  • Niraparib M1 metabolite
    • Niraparib M10 metabolite

Route of elimination

Niraparib is eliminated via multiple pathways, including liver metabolism, hepatobiliary excretion, and renal elimination.⁸ Following administration of a single oral 300-mg dose of radio-labeled niraparib, the average percent recovery of the administered dose over 21 days was 47.5% (range: 33.4% to 60.2%) in urine and 38.8% (range: 28.3% to 47.0%) in feces. In pooled samples collected over 6 days, unchanged niraparib accounted for 11% and 19% of the administered dose recovered in urine and feces, respectively.⁶

Half-life

Following multiple daily doses of 300 mg of niraparib, the mean half-life (t_1/2) is 36 hours.⁶

Clearance

In a population pharmacokinetic analysis, the apparent total clearance (CL/F) of niraparib was 16.2 L/h in patients with cancer.⁶

Adverse Effects

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Toxicity

There is limited information available regarding the acute toxicity profile and overdosage of niraparib.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Ambroxol	The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Ambroxol.
Articaine	The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Articaine.
Benzocaine	The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Benzocaine.
Benzyl alcohol	The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Benzyl alcohol.
Bupivacaine	The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Bupivacaine.

Food Interactions

• Take at the same time every day.
• Take with or without food. Food does not affect the absorption of niraparib.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Niraparib hydrochloride	L4JFC1PHCI	1038915-64-8	YXYDNYFWAFBCAN-PFEQFJNWSA-N
Niraparib tosylate	75KE12AY9U	1038915-73-9	LCPFHXWLJMNKNC-PFEQFJNWSA-N
Niraparib tosylate monohydrate	195Q483UZD	1613220-15-7	ACNPUCQQZDAPJH-FMOMHUKBSA-N

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Zejula	Tablet, film coated	100 mg	Oral	Glaxo Smith Kline (Ireland) Limited	2023-11-14	Not applicable
Zejula	Capsule	100 mg	Oral	Glaxo Smith Kline (Ireland) Limited	2020-12-16	Not applicable
Zejula	Tablet, film coated	200 mg/1	Oral	GlaxoSmithKline LLC	2023-06-27	Not applicable
Zejula	Capsule	100 mg	Oral	Glaxosmithkline Inc	2020-01-09	Not applicable
Zejula	Tablet, film coated	100 mg	Oral	Glaxo Smith Kline (Ireland) Limited	2023-11-14	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Akeega	Niraparib (50 mg) + Abiraterone acetate (500 mg)	Tablet, film coated	Oral	Janssen Cilag International Nv	2023-06-09	Not applicable
Akeega	Niraparib tosylate (100 mg) + Abiraterone acetate (500 mg)	Tablet	Oral	Janssen Pharmaceuticals	2023-08-14	Not applicable
Akeega	Niraparib tosylate monohydrate (50 mg/1) + Abiraterone acetate (500 mg/1)	Tablet, film coated	Oral	Janssen Biotech, Inc.	2023-08-11	Not applicable
Akeega	Niraparib tosylate (50 mg) + Abiraterone acetate (500 mg)	Tablet	Oral	Janssen Pharmaceuticals	2023-08-14	Not applicable
Akeega	Niraparib (100 mg) + Abiraterone acetate (500 mg)	Tablet, film coated	Oral	Janssen Cilag International Nv	2023-06-09	Not applicable

Categories

ATC Codes

L01XK02 — Niraparib

• L01XK — Poly (ADP-ribose) polymerase (PARP) inhibitors
• L01X — OTHER ANTINEOPLASTIC AGENTS
• L01 — ANTINEOPLASTIC AGENTS
• L — ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Drug Categories

• Antineoplastic Agents
• Antineoplastic and Immunomodulating Agents
• BCRP/ABCG2 Inhibitors
• BCRP/ABCG2 Substrates
• Cytochrome P-450 CYP1A2 Inducers
• Cytochrome P-450 CYP1A2 Inducers (weak)
• Cytochrome P-450 Enzyme Inducers
• Enzyme Inhibitors
• Heterocyclic Compounds, Fused-Ring
• MATE 1 Inhibitors
• MATE 1 Substrates
• MATE 1 Substrates with a Narrow Therapeutic Index
• MATE 2 Inhibitors
• MATE 2 Substrates
• MATE 2 Substrates with a Narrow Therapeutic Index
• MATE inhibitors
• MATE substrates
• Narrow Therapeutic Index Drugs
• P-glycoprotein substrates
• P-glycoprotein substrates with a Narrow Therapeutic Index
• Poly (ADP-ribose) polymerase (PARP) inhibitors
• Poly(ADP-ribose) Polymerase Inhibitors
• Pyrazoles

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Phenylpyrazoles / Indazoles / Aralkylamines / Benzene and substituted derivatives / Heteroaromatic compounds / Primary carboxylic acid amides / Amino acids and derivatives / Dialkylamines / Azacyclic compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives

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Substituents

Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzopyrazole / Carboxamide group / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Indazole / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Phenylpiperidine / Phenylpyrazole / Primary carboxylic acid amide / Pyrazole / Secondary aliphatic amine / Secondary amine

show 15 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

HMC2H89N35

CAS number

1038915-60-4

InChI Key

PCHKPVIQAHNQLW-CQSZACIVSA-N

InChI

InChI=1S/C19H20N4O/c20-19(24)17-5-1-3-15-12-23(22-18(15)17)16-8-6-13(7-9-16)14-4-2-10-21-11-14/h1,3,5-9,12,14,21H,2,4,10-11H2,(H2,20,24)/t14-/m1/s1

IUPAC Name

2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide

SMILES

NC(=O)C1=CC=CC2=CN(N=C12)C1=CC=C(C=C1)[C@@H]1CCCNC1

References

General References

1. Chen A: PARP inhibitors: its role in treatment of cancer. Chin J Cancer. 2011 Jul;30(7):463-71. doi: 10.5732/cjc.011.10111. [Article]
2. Heo YA, Duggan ST: Niraparib: A Review in Ovarian Cancer. Target Oncol. 2018 Aug;13(4):533-539. doi: 10.1007/s11523-018-0582-1. [Article]
3. Ison G, Howie LJ, Amiri-Kordestani L, Zhang L, Tang S, Sridhara R, Pierre V, Charlab R, Ramamoorthy A, Song P, Li F, Yu J, Manheng W, Palmby TR, Ghosh S, Horne HN, Lee EY, Philip R, Dave K, Chen XH, Kelly SL, Janoria KG, Banerjee A, Eradiri O, Dinin J, Goldberg KB, Pierce WF, Ibrahim A, Kluetz PG, Blumenthal GM, Beaver JA, Pazdur R: FDA Approval Summary: Niraparib for the Maintenance Treatment of Patients with Recurrent Ovarian Cancer in Response to Platinum-Based Chemotherapy. Clin Cancer Res. 2018 Sep 1;24(17):4066-4071. doi: 10.1158/1078-0432.CCR-18-0042. Epub 2018 Apr 12. [Article]
4. Bochum S, Berger S, Martens UM: Olaparib. Recent Results Cancer Res. 2018;211:217-233. doi: 10.1007/978-3-319-91442-8_15. [Article]
5. van Andel L, Zhang Z, Lu S, Kansra V, Agarwal S, Hughes L, Tibben MM, Gebretensae A, Lucas L, Hillebrand MJX, Rosing H, Schellens JHM, Beijnen JH: Human mass balance study and metabolite profiling of (14)C-niraparib, a novel poly(ADP-Ribose) polymerase (PARP)-1 and PARP-2 inhibitor, in patients with advanced cancer. Invest New Drugs. 2017 Dec;35(6):751-765. doi: 10.1007/s10637-017-0451-2. Epub 2017 Mar 16. [Article]
6. FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
7. EMA Approved Drug Products: Zejula (niraparib) Oral Capsules [Link]
8. Health Canada Approved Drug Products: ZEJULA (niraparib) Oral Capsules or Tablets [Link]
9. Health Canada Approved Drug Proucts: AKEEGA (Niraparib and abiraterone acetate) tablets for oral use [Link]
10. FDA Approved Drug Products: AKEEGA (niraparib and abiraterone acetate) tablets, for oral use [Link]

External Links

PubChem Compound

24958200

PubChem Substance

347828142

ChemSpider

24531930

BindingDB

50316226

RxNav

1918231

ChEBI

176844

ChEMBL

CHEMBL1094636

ZINC

ZINC000043206370

PharmGKB

PA166131610

PDBe Ligand

3JD

Wikipedia

Niraparib

PDB Entries

4r6e / 7f43 / 7kk5 / 7kkp / 8i2m

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Ovarian Cancer	1
4	Not Yet Recruiting	Treatment	Epithelial Ovarian Cancer / Ovarian Cancer / Stage III Ovarian Cancer / Stage IV Ovarian Cancer	1
4	Recruiting	Prevention	Adult Patients With Platinum-sensitive, Relapsed, High Grade Serous Epithelial Ovarian Cancer	1
3	Active Not Recruiting	Treatment	Breast Neoplasms	1
3	Active Not Recruiting	Treatment	Castration Resistant Prostate Cancer	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet, film coated	Oral
Capsule	Oral	100 mg
Capsule	Oral	100 mg/1
Tablet	Oral	100 mg
Tablet, film coated	Oral	100 mg
Tablet, film coated	Oral	100 mg/1
Tablet, film coated	Oral	200 mg/1
Tablet, film coated	Oral	300 mg/1

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8859562	No	2014-10-14	2031-08-04
US8143241	No	2012-03-27	2027-08-12
US8071579	No	2011-12-06	2027-08-12
US8071623	No	2011-12-06	2030-03-22
US8436185	No	2013-05-07	2029-04-24
US11091459	No	2021-08-17	2038-03-27
US11673877	No	2018-03-27	2038-03-27
US11207311	No	2021-12-28	2037-07-28
US11730725	No	2019-01-04	2039-01-04

Properties

State

Solid

Experimental Properties

Property	Value	Source
boiling point (°C)	463	https://file.medchemexpress.com/batch_PDF/HY-10619/Niraparib-SDS-MedChemExpress.pdf

Predicted Properties

Property	Value	Source
Water Solubility	0.0149 mg/mL	ALOGPS
logP	2.45	ALOGPS
logP	2.47	Chemaxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.03	Chemaxon
pKa (Strongest Basic)	10.08	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	72.94 Å2	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	94.92 m3·mol-1	Chemaxon
Polarizability	36.4 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0fk9-0009000000-0c70995be19b18915530
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-0019000000-1388e4a12d215f990898
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-0009000000-5c85ca7c860bb4d24ba6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0ukd-0896000000-f65ad9bda964f9894915
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0019000000-eeb821d574d7bde1221c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00kf-2592000000-8fb7f4c5972faed3a84c
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	197.5784799	predicted	DarkChem Lite v0.1.0
[M-H]-	174.91042	predicted	DeepCCS 1.0 (2019)
[M+H]+	197.2974799	predicted	DarkChem Lite v0.1.0
[M+H]+	177.44865	predicted	DeepCCS 1.0 (2019)
[M+Na]+	197.3550799	predicted	DarkChem Lite v0.1.0
[M+Na]+	184.7957	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. Poly [ADP-ribose] polymerase 1

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Zinc ion binding

Specific Function

Involved in the base excision repair (BER) pathway, by catalyzing the poly(ADP-ribosyl)ation of a limited number of acceptor proteins involved in chromatin architecture and in DNA metabolism. This ...

Gene Name

PARP1

Uniprot ID

P09874

Uniprot Name

Poly [ADP-ribose] polymerase 1

Molecular Weight

113082.945 Da

References

1. Heo YA, Duggan ST: Niraparib: A Review in Ovarian Cancer. Target Oncol. 2018 Aug;13(4):533-539. doi: 10.1007/s11523-018-0582-1. [Article]
2. FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
3. EMA Approved Drug Products: Zejula (niraparib) Oral Capsules [Link]
4. Health Canada Approved Drug Products: ZEJULA (niraparib) Oral Capsules or Tablets [Link]

Details2. Poly [ADP-ribose] polymerase 2

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Inhibitor

General Function

Nad+ adp-ribosyltransferase activity

Specific Function

Involved in the base excision repair (BER) pathway, by catalyzing the poly(ADP-ribosyl)ation of a limited number of acceptor proteins involved in chromatin architecture and in DNA metabolism. This ...

Gene Name

PARP2

Uniprot ID

Q9UGN5

Uniprot Name

Poly [ADP-ribose] polymerase 2

Molecular Weight

66205.31 Da

References

1. Heo YA, Duggan ST: Niraparib: A Review in Ovarian Cancer. Target Oncol. 2018 Aug;13(4):533-539. doi: 10.1007/s11523-018-0582-1. [Article]
2. FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
3. EMA Approved Drug Products: Zejula (niraparib) Oral Capsules [Link]
4. Health Canada Approved Drug Products: ZEJULA (niraparib) Oral Capsules or Tablets [Link]

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Drug created at October 20, 2016 20:48 / Updated at February 20, 2024 23:54