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
- Weight
- Average: 320.396
Monoisotopic: 320.16371128 - Chemical Formula
- C19H20N4O
- Synonyms
- Niraparib
- External IDs
- MK 4827
- MK-4827
- MK-4827 FREE BASE
- MK4827
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 a complete or partial response to first-line platinum-based chemotherapy.6,7,8
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- Associated Therapies
- 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 inhibitorHumans APoly [ADP-ribose] polymerase 2 inhibitorHumans - Absorption
Following a single-dose administration of 300 mg niraparib, the mean (±SD) peak plasma concentration (Cmax) was 804 (±403) ng/mL. The exposure (Cmax 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
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- 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 (t1/2) 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
- Not Available
Interactions
- Drug Interactions
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol 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. Butacaine The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Butacaine. Butamben The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Butamben. Capsaicin The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Capsaicin. Chloroprocaine The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Chloroprocaine. Cinchocaine The risk or severity of methemoglobinemia can be increased when Niraparib is combined with Cinchocaine. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take at the same time every day.
- Take with or without food. Food does not affect the absorption of niraparib.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- 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 Capsule 100 mg Oral Glaxosmithkline Inc 2020-01-09 Not applicable Canada Zejula Capsule 100 mg Oral Glaxo Smith Kline (Ireland) Limited 2020-12-16 Not applicable EU Zejula Capsule 100 mg Oral Glaxo Smith Kline (Ireland) Limited 2020-12-16 Not applicable EU Zejula Capsule 100 mg/1 Oral GlaxoSmithKline LLC 2017-03-27 Not applicable US Zejula Tablet 100 mg Oral Glaxosmithkline Inc Not applicable Not applicable Canada Zejula Capsule 100 mg Oral Glaxo Smith Kline (Ireland) Limited 2020-12-16 Not applicable EU
Categories
- ATC Codes
- L01XK02 — Niraparib
- 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 show 2 more
- Substituents
- Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzopyrazole / Carboxamide group / Carboxylic acid derivative 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
- 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]
- 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]
- 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]
- 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]
- 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]
- FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
- EMA Approved Drug Products: Zejula (niraparib) Oral Capsules [Link]
- Health Canada Approved Drug Products: ZEJULA (niraparib) Oral Capsules or Tablets [Link]
- External Links
- PubChem Compound
- 24958200
- PubChem Substance
- 347828142
- ChemSpider
- 24531930
- BindingDB
- 50316226
- 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
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 Castration Resistant Prostate Cancer 1 3 Active Not Recruiting Treatment Neoplasm 1 3 Active Not Recruiting Treatment Non-Small Cell Lung Cancer (NSCLC) 1 3 Active Not Recruiting Treatment Ovarian Neoplasms 1 3 Active Not Recruiting Treatment Ovarian Neoplasms / Ovarian, Fallopian Tube and Primary Peritoneal Carcinoma 1 3 Active Not Recruiting Treatment Recurrent Ovarian Carcinoma 1 3 Completed Treatment Ovarian Neoplasms / Platinum Sensitive Ovarian Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 100 mg Capsule Oral 100 mg/1 Tablet Oral 100 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8859562 No 2014-10-14 2031-08-04 US US8143241 No 2012-03-27 2027-08-12 US US8071579 No 2011-12-06 2027-08-12 US US8071623 No 2011-12-06 2030-03-22 US US8436185 No 2013-05-07 2029-04-24 US US11091459 No 2021-08-17 2038-03-27 US
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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

- 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
- 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]
- FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
- EMA Approved Drug Products: Zejula (niraparib) Oral Capsules [Link]
- Health Canada Approved Drug Products: ZEJULA (niraparib) Oral Capsules or Tablets [Link]
- 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
- 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]
- FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
- EMA Approved Drug Products: Zejula (niraparib) Oral Capsules [Link]
- Health Canada Approved Drug Products: ZEJULA (niraparib) Oral Capsules or Tablets [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Carboxylic ester hydrolase activity
- Specific Function
- Not Available
- Gene Name
- CES1A1a
- Uniprot ID
- Q6LAP9
- Uniprot Name
- Carboxylesterase
- Molecular Weight
- 1908.25 Da
References
- FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inducer
- Curator comments
- Niraparib weakly induces CYP1A2 in vitro.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Health Canada Approved Drug Products: ZEJULA (niraparib) Oral Capsules or Tablets [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- Curator comments
- Niraparib inhibits MATE1 with IC50 of 0.18 microM. Niraparib M1 metabolite is a substrate of MATE1.
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- Curator comments
- Niraparib inhibits MATE2 with IC50 of ≤0.14 microM. Niraparib M1 metabolite is a substrate of MATE2.
- General Function
- Drug transmembrane transporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
- Gene Name
- SLC47A2
- Uniprot ID
- Q86VL8
- Uniprot Name
- Multidrug and toxin extrusion protein 2
- Molecular Weight
- 65083.915 Da
References
- FDA Approved Drug Products: ZEJULA (niraparib) capsules, for oral use (September 2022) [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
Drug created at October 20, 2016 20:48 / Updated at May 26, 2023 16:43