Piritrexim

Identification

Generic Name
Piritrexim
DrugBank Accession Number
DB03695
Background

Piritrexim has been used in trials studying the treatment of Bladder Cancer, Urethral Cancer, and Transitional Cell Cancer of the Renal Pelvis and Ureter.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 325.3651
Monoisotopic: 325.153874877
Chemical Formula
C17H19N5O2
Synonyms
  • Piritrexim
External IDs
  • BW 301U
  • BW-301U

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot 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
Adverseeffects
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Toxicity

Not Available

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.
DrugInteraction
AcetazolamideThe therapeutic efficacy of Piritrexim can be increased when used in combination with Acetazolamide.
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Piritrexim.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Piritrexim.
Folic acidThe therapeutic efficacy of Piritrexim can be decreased when used in combination with Folic acid.
LeucovorinThe therapeutic efficacy of Piritrexim can be decreased when used in combination with Leucovorin.
LevoleucovorinThe therapeutic efficacy of Piritrexim can be decreased when used in combination with Levoleucovorin.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Piritrexim.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Piritrexim.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Piritrexim isethionateV77I71FH7279483-69-5IOEMETRLOWNXGW-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrido[2,3-d]pyrimidines. These are compounds containing the pyrido[2,3-d]pyrimidine ring system, which is a pyridopyrimidine isomer with three ring nitrogen atoms at the 1-, 3-, and 8- position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridopyrimidines
Sub Class
Pyrido[2,3-d]pyrimidines
Direct Parent
Pyrido[2,3-d]pyrimidines
Alternative Parents
Dimethoxybenzenes / Phenoxy compounds / Anisoles / Methylpyridines / Aminopyrimidines and derivatives / Alkyl aryl ethers / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines
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Substituents
Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Dimethoxybenzene / Ether / Heteroaromatic compound
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
MK2A783ZUT
CAS number
72732-56-0
InChI Key
VJXSSYDSOJBUAV-UHFFFAOYSA-N
InChI
InChI=1S/C17H19N5O2/c1-9-11(6-10-7-12(23-2)4-5-13(10)24-3)8-20-16-14(9)15(18)21-17(19)22-16/h4-5,7-8H,6H2,1-3H3,(H4,18,19,20,21,22)
IUPAC Name
6-[(2,5-dimethoxyphenyl)methyl]-5-methylpyrido[2,3-d]pyrimidine-2,4-diamine
SMILES
COC1=CC(CC2=C(C)C3=C(N=C2)N=C(N)N=C3N)=C(OC)C=C1

References

General References
Not Available
PubChem Compound
54369
PubChem Substance
46506046
ChemSpider
49108
BindingDB
18224
ChEMBL
CHEMBL7492
ZINC
ZINC000000000640
PDBe Ligand
MXA
PDB Entries
1dlr / 1u71

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentBladder Cancer, Cancer / Transitional Cell Cancer of the Renal Pelvis and Ureter / Urethral Cancer1

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 Solubility0.064 mg/mLALOGPS
logP2.23ALOGPS
logP2.44ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)16.06ChemAxon
pKa (Strongest Basic)3.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.17 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.58 m3·mol-1ChemAxon
Polarizability34.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9946
Blood Brain Barrier+0.9531
Caco-2 permeable+0.6964
P-glycoprotein substrateNon-substrate0.5083
P-glycoprotein inhibitor INon-inhibitor0.6491
P-glycoprotein inhibitor IIInhibitor0.5249
Renal organic cation transporterNon-inhibitor0.7951
CYP450 2C9 substrateNon-substrate0.8532
CYP450 2D6 substrateNon-substrate0.8253
CYP450 3A4 substrateSubstrate0.5169
CYP450 1A2 substrateInhibitor0.5058
CYP450 2C9 inhibitorNon-inhibitor0.6163
CYP450 2D6 inhibitorNon-inhibitor0.6833
CYP450 2C19 inhibitorNon-inhibitor0.7365
CYP450 3A4 inhibitorNon-inhibitor0.6194
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5758
Ames testAMES toxic0.588
CarcinogenicityNon-carcinogens0.9373
BiodegradationNot ready biodegradable0.9956
Rat acute toxicity2.4764 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8309
hERG inhibition (predictor II)Non-inhibitor0.6007
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Details
1. Dihydrofolate reductase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nadph binding
Specific Function
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA pre...
Gene Name
DHFR
Uniprot ID
P00374
Uniprot Name
Dihydrofolate reductase
Molecular Weight
21452.61 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created on June 13, 2005 13:24 / Updated on February 21, 2021 18:51