Identification
- Summary
Piflufolastat F 18 is a radiopharmaceutical diagnostic agent used with PET to image PSMA-positive lesions for the diagnosis of metastatic or recurrent prostate cancer.
- Brand Names
- Pylarify
- Generic Name
- Piflufolastat F 18
- DrugBank Accession Number
- DB14805
- Background
Prostate cancer is the most common non-cutaneous malignancy affecting men in North America2 - despite this, an ongoing challenge in prostate cancer therapy is the difficulty in imaging the extent and location of tumor metastases and recurrences.4 The images generated by positron emission tomography (PET) are less detailed than those obtained via MRI or CT, but are more sensitive and can reveal cancerous tissue in any area of the body provided the tissue is expressing the appropriate target protein. Prostate-specific membrane antigen (PSMA) is a transmembrane glycoprotein expressed in many tissues that plays a role in folate uptake and neurotransmitter release - it is expressed in the prostate at levels roughly 1000-fold greater than elsewhere in the body, and even higher in prostate cancer tissue.1 As such, it has become a desirable target for PET imaging of prostate cancer tissues.
Piflufolastat F18, also called [F-18]-DCFPyL, is a urea-based radiopharmaceutical that binds to PSMA and allows for the visualization of cancerous prostate tissue. It was first approved by the FDA in May 20215 under the brand name Pylarify and aims to allow for earlier and more accurate detection of suspected prostate cancer metastases or recurrences.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Piflufolastat F 18 (DB14805)
- Weight
- Average: 441.403
Monoisotopic: 441.152526384 - Chemical Formula
- C18H23FN4O8
- Synonyms
- (18F)DCFPyL
- [F-18]-DCFPyL
- 18F-DCFPyL
- DCFPyL F-18
- Piflufolastat F 18
- Piflufolastat F-18
- PyL
Pharmacology
- Indication
Piflufolastat F18 is indicated for positron emission tomography (PET) of prostate-specific membrane antigen (PSMA) positive lesions in men with prostate cancer who have suspected metastases and are candidates for initial definitive therapy and for men with a suspected recurrence of prostate cancer based on elevated prostate-specific antigen (PSA) levels.3
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- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Prostate-specific membrane antigen (PSMA) is a transmembrane glycoprotein that plays a role in dietary folate uptake and the release of neurotransmitters within the brain. While PSMA is expressed in many tissues, its expression levels in the prostate are roughly 1000-fold greater than elsewhere in the body and even higher in prostate cancer tissue.1
Piflufolastat F18 binds to PSMA and therefore, in combination with PET imaging, allows for the visualization of PSMA-positive lesions associated with prostate cancer.3
Target Actions Organism AGlutamate carboxypeptidase 2 binderHumans - Absorption
Not Available
- Volume of distribution
Within 60 minutes of intravenous administration, piflufolastat F18 distributes to the kidneys, liver, and lungs.3
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Piflufolastat F18 is eliminated via urinary excretion - within 8 hours of intravenous administration, approximately 50% of an administered dose is excreted in the urine.3
- Half-life
The half-life of distribution of piflufolastat F18 is 0.17 ± 0.044 hours and its elimination half-life is 3.47 ± 0.49 hours.3
- Clearance
Not Available
- Adverse Effects
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There are no data regarding the effects of overdosage with piflufolastat F18. In the event of overdose, the amount of absorbed radiation can be mitigated by administered fluids and encouraging frequent bladder voiding. The use of diuretics to encourage voiding may also be considered.3
- 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 softwareApalutamide Apalutamide may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent. Bicalutamide Bicalutamide may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent. Cyproterone acetate Cyproterone acetate may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent. Darolutamide Darolutamide may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent. Enzalutamide Enzalutamide may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent. Flutamide Flutamide may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent. Nilutamide Nilutamide may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent. Relugolix Relugolix may decrease effectiveness of Piflufolastat F 18 as a diagnostic agent. 
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- No interactions found.
Products
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- Pylarify (Lantheus Holdings, Inc.)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Pylarify Injection 80 mCi/1mL Intravenous Progenics Pharmaceuticals, Inc. 2021-05-26 Not applicable US 
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 3934EF02T7
- CAS number
- 1207181-29-0
- InChI Key
- OLWVRJUNLXQDSP-MVBOSPHXSA-N
- InChI
- InChI=1S/C18H23FN4O8/c19-13-6-4-10(9-21-13)15(26)20-8-2-1-3-11(16(27)28)22-18(31)23-12(17(29)30)5-7-14(24)25/h4,6,9,11-12H,1-3,5,7-8H2,(H,20,26)(H,24,25)(H,27,28)(H,29,30)(H2,22,23,31)/t11-,12-/m0/s1/i19-1
- IUPAC Name
- (2S)-2-({[(1S)-1-carboxy-5-{[6-(¹⁸F)fluoropyridin-3-yl]formamido}pentyl]carbamoyl}amino)pentanedioic acid
- SMILES
- OC(=O)CC[C@H](NC(=O)N[C@@H](CCCCNC(=O)C1=CC=C([18F])N=C1)C(O)=O)C(O)=O
References
- Synthesis Reference
Shan L: 2-(3-{1-Carboxy-5-[(6-[(18)F]fluoro-pyridine-3-carbonyl)-amino]-pentyl}-ureido)-p entanedioic acid. [PubMed:23256224]
- General References
- Shan L: 2-(3-{1-Carboxy-5-[(6-[(18)F]fluoro-pyridine-3-carbonyl)-amino]-pentyl}-ureido)-p entanedioic acid . [Article]
- Osborne JR, Akhtar NH, Vallabhajosula S, Anand A, Deh K, Tagawa ST: Prostate-specific membrane antigen-based imaging. Urol Oncol. 2013 Feb;31(2):144-54. doi: 10.1016/j.urolonc.2012.04.016. Epub 2012 May 31. [Article]
- FDA Approved Drug Products: Pylarify (piflufolastat F 18) injection for intravenous use [Link]
- American Cancer Society: Tests to Diagnose and Stage Prostate Cancer [Link]
- OncLive: FDA Approves Piflufolastat F18 PSMA PET Imaging Agent for Prostate Cancer [Link]
- External Links
- ChemSpider
- 32702072
- 2556616
- ChEMBL
- CHEMBL4297334
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Not Yet Recruiting Treatment Prostate Cancer 1 3 Completed Diagnostic Adenocarcinoma of Prostate / Metastatic Prostate Cancer / Prostate Cancer / Recurrent Prostate Cancer 1 2 Active Not Recruiting Diagnostic Prostate Cancer 1 2 Completed Diagnostic Prostate Cancer 2 2 Enrolling by Invitation Diagnostic Metastatic Prostate Cancer / Neoplasms of the Prostate / Prostate Cancer 2 2 Not Yet Recruiting Diagnostic Prostate Carcinoma 1 2 Not Yet Recruiting Treatment Adenocarcinoma of Prostate / Neoplasms of the Prostate / Prostate Cancer 1 2 Recruiting Diagnostic Breast Cancer / Human Epidermal Growth Factor 2 Negative Carcinoma of Breast / Metastatic Breast Cancer 1 2 Recruiting Diagnostic Castrate Sensitive Prostate Cancer 1 2 Recruiting Diagnostic Hepatocellular Carcinoma 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intravenous 80 mCi/1mL - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8778305 No 2014-07-15 2030-09-21 US US9861713 No 2018-01-09 2029-07-31 US US10947197 No 2021-03-16 2037-06-09 US US8487129 No 2013-07-16 2027-11-07 US
Properties
- State
- Liquid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.191 mg/mL ALOGPS logP -0.37 ALOGPS logP -0.32 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 2.99 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 195.02 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 101.38 m3·mol-1 Chemaxon Polarizability 42 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No 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
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Tetrahydrofolyl-poly(glutamate) polymer binding
- Specific Function
- Has both folate hydrolase and N-acetylated-alpha-linked-acidic dipeptidase (NAALADase) activity. Has a preference for tri-alpha-glutamate peptides. In the intestine, required for the uptake of fola...
- Gene Name
- FOLH1
- Uniprot ID
- Q04609
- Uniprot Name
- Glutamate carboxypeptidase 2
- Molecular Weight
- 84330.015 Da
References
Drug created at May 20, 2019 14:28 / Updated at June 02, 2021 20:04