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
Structure for Piritrexim (DB03695)
- Weight
- Average: 325.3651
Monoisotopic: 325.153874877 - Chemical Formula
- C17H19N5O2
- Synonyms
- Piritrexim
- External IDs
- BW 301U
- BW-301U
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDihydrofolate reductase Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The therapeutic efficacy of Piritrexim can be increased when used in combination with Acetazolamide. Ambroxol The risk or severity of methemoglobinemia can be increased when Piritrexim is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Piritrexim is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Piritrexim is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Piritrexim is combined with Benzyl alcohol. - Food Interactions
- Not Available
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 Piritrexim isethionate V77I71FH72 79483-69-5 IOEMETRLOWNXGW-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 show 2 more
- 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
- External Links
- 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
Phase Status Purpose Conditions Count 2 Completed Treatment Bladder Cancer / Cancer of the Urethra / Transitional Cell Cancer of the Renal Pelvis and Ureter 1
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
Property Value Source Water Solubility 0.064 mg/mL ALOGPS logP 2.23 ALOGPS logP 2.44 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 16.06 Chemaxon pKa (Strongest Basic) 2.66 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 109.17 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 95.58 m3·mol-1 Chemaxon Polarizability 34.37 Å3 Chemaxon Number of Rings 3 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
Property Value Probability Human Intestinal Absorption + 0.9946 Blood Brain Barrier + 0.9531 Caco-2 permeable + 0.6964 P-glycoprotein substrate Non-substrate 0.5083 P-glycoprotein inhibitor I Non-inhibitor 0.6491 P-glycoprotein inhibitor II Inhibitor 0.5249 Renal organic cation transporter Non-inhibitor 0.7951 CYP450 2C9 substrate Non-substrate 0.8532 CYP450 2D6 substrate Non-substrate 0.8253 CYP450 3A4 substrate Substrate 0.5169 CYP450 1A2 substrate Inhibitor 0.5058 CYP450 2C9 inhibitor Non-inhibitor 0.6163 CYP450 2D6 inhibitor Non-inhibitor 0.6833 CYP450 2C19 inhibitor Non-inhibitor 0.7365 CYP450 3A4 inhibitor Non-inhibitor 0.6194 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5758 Ames test AMES toxic 0.588 Carcinogenicity Non-carcinogens 0.9373 Biodegradation Not ready biodegradable 0.9956 Rat acute toxicity 2.4764 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8309 hERG inhibition (predictor II) Non-inhibitor 0.6007
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0009000000-058aea1a458de311bc27 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-0019000000-b511ab2eac4e3d4bcf5d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004l-0339000000-d8d25bcf89c83b833b22 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05bo-1694000000-cea8acfef002640b3c14 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-074j-0391000000-1160aa06f677d7e095e8 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-4190000000-357576d5764695503a20 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.6858033 predictedDarkChem Lite v0.1.0 [M-H]- 184.67589 predictedDeepCCS 1.0 (2019) [M+H]+ 190.8013033 predictedDarkChem Lite v0.1.0 [M+H]+ 187.03392 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.4073033 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.08838 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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 at June 13, 2005 13:24 / Updated at February 21, 2021 18:51