NAV

PR-104

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
PR-104
DrugBank Accession Number
DB05968
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 579.27
Monoisotopic: 577.971943
Chemical Formula
C14H20BrN4O12PS
Synonyms
Not Available
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Pharmacology

Indication

Investigated for use/treatment in cancer/tumors (unspecified) and solid tumors.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

PR-104 is a novel hypoxia-activated DNA cross-linking agent with marked activity against human tumor xenografts, both as monotherapy and combined with radiotherapy and chemotherapy. Upon intravenous administration, PR-104 is converted by systemic phosphatases to the alcohol intermediate PR-104A, which is reduced to form the active DNA-crosslinking mustard species hydroxylamine PR-104H intracellularly under hypoxic conditions. PR-104H specifically crosslinks hypoxic tumor cell DNA, resulting in the inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis in susceptible hypoxic tumor cell populations while sparing normoxic tissues.

TargetActionsOrganism
UTumor necrosis factorNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
V16D2ZT7DT
CAS number
851627-62-8
InChI Key
GZSOKPMDWVRVMG-UHFFFAOYSA-N
InChI
InChI=1S/C14H20BrN4O12PS/c1-33(28,29)31-7-5-17(4-2-15)13-11(14(20)16-3-6-30-32(25,26)27)8-10(18(21)22)9-12(13)19(23)24/h8-9H,2-7H2,1H3,(H,16,20)(H2,25,26,27)
IUPAC Name
[2-({2-[(2-bromoethyl)[2-(methanesulfonyloxy)ethyl]amino]-3,5-dinitrophenyl}formamido)ethoxy]phosphonic acid
SMILES
CS(=O)(=O)OCCN(CCBr)C1=C(C=C(C=C1[N+]([O-])=O)[N+]([O-])=O)C(=O)NCCOP(O)(O)=O

References

General References
  1. Patterson AV, Ferry DM, Edmunds SJ, Gu Y, Singleton RS, Patel K, Pullen SM, Hicks KO, Syddall SP, Atwell GJ, Yang S, Denny WA, Wilson WR: Mechanism of action and preclinical antitumor activity of the novel hypoxia-activated DNA cross-linking agent PR-104. Clin Cancer Res. 2007 Jul 1;13(13):3922-32. [Article]
ChemSpider
9630821
ZINC
ZINC000043131754
Wikipedia
PR-104

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentLung Cancer1
1CompletedTreatmentUnspecified Adult Solid Tumor, Protocol Specific3
1, 2TerminatedTreatmentHepatocellular Carcinoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0342 mg/mLALOGPS
logP0.43ALOGPS
logP0.32Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)1.54Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count11Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area228.75 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity115.64 m3·mol-1Chemaxon
Polarizability46.98 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.73405
predicted
DeepCCS 1.0 (2019)
[M+H]+197.01402
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.07008
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Tumor necrosis factor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da

Drug created at November 18, 2007 18:29 / Updated at June 12, 2020 16:52