U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H12BNO4.ClH
Molecular Weight 245.468
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BORONOPHENYLALANINE HYDROCHLORIDE

SMILES

Cl.N[C@@H](CC1=CC=C(C=C1)B(O)O)C(O)=O

InChI

InChIKey=ITAYDCRFNXQNBL-QRPNPIFTSA-N
InChI=1S/C9H12BNO4.ClH/c11-8(9(12)13)5-6-1-3-7(4-2-6)10(14)15;/h1-4,8,14-15H,5,11H2,(H,12,13);1H/t8-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H12BNO4
Molecular Weight 209.007
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Boron neutron capture therapy induces apoptosis of glioma cells through Bcl-2/Bax.
2010-12-02
Aryl boronic acid inhibition of synthetic melanin polymerization.
2010-08-01
Early effect of boron neutron capture therapy mediated by boronophenylalanine (BPA-BNCT) on mast cells in premalignant tissue and tumors of the hamster cheek pouch.
2010-05
Role of p53 mutation in the effect of boron neutron capture therapy on oral squamous cell carcinoma.
2009-12-11
Convection enhanced delivery of boronated EGF as a molecular targeting agent for neutron capture therapy of brain tumors.
2009-12
Boron neutron capture therapy of EGFR or EGFRvIII positive gliomas using either boronated monoclonal antibodies or epidermal growth factor as molecular targeting agents.
2009-07
Boron neutron capture therapy at the crossroads: challenges and opportunities.
2009-07
Synthesis and evaluation of a novel liposome containing BPA-peptide conjugate for BNCT.
2009-07
In vitro neutron irradiation of glioma and endothelial cultured cells.
2009-07
Calculations of dose distributions in the lungs of a rat model irradiated in the thermal column of the TRIGA reactor in Pavia.
2009-07
Selective uptake of p-boronophenylalanine by osteosarcoma cells for boron neutron capture therapy.
2009-07
Feasibility of boron neutron capture therapy for malignant spinal tumors.
2009-07
Boron neutron capture therapy (BNCT) inhibits tumor development from precancerous tissue: an experimental study that supports a potential new application of BNCT.
2009-07
Boronophenylalanine uptake in C6 glioma model is dramatically increased by L-DOPA preloading.
2009-07
Metabolically stable bradykinin B2 receptor agonists enhance transvascular drug delivery into malignant brain tumors by increasing drug half-life.
2009-05-13
Insight into the mechanisms underlying tumor response to boron neutron capture therapy in the hamster cheek pouch oral cancer model.
2009-05
Planned fractionated boron neutron capture therapy using epithermal neutrons for a patient with recurrent squamous cell carcinoma in the temporal bone: a case report.
2009-03
Boron neutron capture therapy for newly diagnosed glioblastoma.
2009-01
An international dosimetry exchange for BNCT part II: computational dosimetry normalizations.
2008-12
Comments to article: Henriksson R et al., Boron neutron capture therapy (BNCT) for glioblastoma multiforme: a phase II study evaluating a prolonged high-dose of boronophenylalanine (BPA) Radiother Oncol (2008).
2008-08
Boron neutron capture therapy (BNCT) for glioblastoma multiforme: a phase II study evaluating a prolonged high-dose of boronophenylalanine (BPA).
2008-08
Application of drug delivery system to boron neutron capture therapy for cancer.
2008-04
Effect of Boron Neutron Capture Therapy (BNCT) on normal liver regeneration: towards a novel therapy for liver metastases.
2007-10
Therapeutic effect of boron neutron capture therapy (BNCT) on field cancerized tissue: inhibition of DNA synthesis and lag in the development of second primary tumors in precancerous tissue around treated tumors in DMBA-induced carcinogenesis in the hamster cheek pouch oral cancer model.
2007-03
Molecular targeting and treatment of an epidermal growth factor receptor-positive glioma using boronated cetuximab.
2007-02-15
Early effects of boron neutron capture therapy on rat glioma models.
2007
Impact of intra-arterial administration of boron compounds on dose-volume histograms in boron neutron capture therapy for recurrent head-and-neck tumors.
2006-12-01
Homogeneous boron targeting of heterogeneous tumors for boron neutron capture therapy (BNCT): chemical analyses in the hamster cheek pouch oral cancer model.
2006-10
Therapeutic success of boron neutron capture therapy (BNCT) mediated by a chemically non-selective boron agent in an experimental model of oral cancer: a new paradigm in BNCT radiobiology.
2006-08
Pharmacokinetic study of BSH and BPA in simultaneous use for BNCT.
2006-07
Molecular targeting and treatment of EGFRvIII-positive gliomas using boronated monoclonal antibody L8A4.
2006-06-15
Boron containing macromolecules and nanovehicles as delivery agents for neutron capture therapy.
2006-03
Histopathological changes of testes and eyes by neutron irradiation with boron compounds in mice.
2006-03
Capillary electrophoresis-electrospray mass spectrometry and HR-ICP-MS for the detection and quantification of 10B-boronophenylalanine (10B-BPA) used in boron neutron capture therapy.
2006-02
Modified boron neutron capture therapy for malignant gliomas performed using epithermal neutron and two boron compounds with different accumulation mechanisms: an efficacy study based on findings on neuroimages.
2005-12
Noninvasive quantitative in vivo mapping and metabolism of boronophenylalanine (BPA) by nuclear magnetic resonance (NMR) spectroscopy and imaging.
2005-11
Boron neutron capture therapy of cancer: current status and future prospects.
2005-06-01
Optimized 1H MRS and MRSI methods for the in vivo detection of boronophenylalanine.
2005-05
Boron neutron capture therapy for glioblastoma multiforme.
2005-04
Effectiveness of BNCT for recurrent head and neck malignancies.
2004-11
Boronated epidermal growth factor as a delivery agent for neutron capture therapy of EGF receptor positive gliomas.
2004-11
Radiobiology of BNCT mediated by GB-10 and GB-10+BPA in experimental oral cancer.
2004-11
The effect of dexamethasone on the uptake of p-boronophenylalanine in the rat brain and intracranial 9L gliosarcoma.
2004-11
Neutron capture therapy of epidermal growth factor (+) gliomas using boronated cetuximab (IMC-C225) as a delivery agent.
2004-11
MicroPET-based pharmacokinetic analysis of the radiolabeled boron compound [18F]FBPA-F in rats with F98 glioma.
2004-11
Boron-containing nucleosides as potential delivery agents for neutron capture therapy of brain tumors.
2004-09-01
Synchrotron radiation-based experimental determination of the optimal energy for cell radiotoxicity enhancement following photoelectric effect on stable iodinated compounds.
2004-08-02
Accumulation of boron in human malignant glioma cells in vitro is cell type dependent.
2004-07
Delivery of (10)boron to oral squamous cell carcinoma using boronophenylalanine and borocaptate sodium for boron neutron capture therapy.
2004-05
A microdosimetric approach to the thermal neutron fluence prescription for clinical BNCT.
2004
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:44:46 GMT 2025
Edited
by admin
on Mon Mar 31 20:44:46 GMT 2025
Record UNII
O37300B3AP
Record Status Validated (UNII)
Record Version
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Name Type Language
BORONOPHENYLALANINE HYDROCHLORIDE
Systematic Name English
BPA-HCL
Preferred Name English
L-PHENYLALANINE, 4-BORONO-, HYDROCHLORIDE
Systematic Name English
L-PHENYLALANINE, 4-BORONO-, HYDROCHLORIDE, (-)-
Systematic Name English
BOROFALAN HYDROCHLORIDE
Common Name English
Code System Code Type Description
FDA UNII
O37300B3AP
Created by admin on Mon Mar 31 20:44:46 GMT 2025 , Edited by admin on Mon Mar 31 20:44:46 GMT 2025
PRIMARY
PUBCHEM
71423166
Created by admin on Mon Mar 31 20:44:46 GMT 2025 , Edited by admin on Mon Mar 31 20:44:46 GMT 2025
PRIMARY
EPA CompTox
DTXSID30227243
Created by admin on Mon Mar 31 20:44:46 GMT 2025 , Edited by admin on Mon Mar 31 20:44:46 GMT 2025
PRIMARY
CAS
76410-59-8
Created by admin on Mon Mar 31 20:44:46 GMT 2025 , Edited by admin on Mon Mar 31 20:44:46 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE