8-ethyl-5-oxo-2-(piperazin-1-yl)-5H,8H-pyrido[2,3-d]pyrimidine-6-carboxylic acid

• ChemBase ID: 104529
• Molecular Formular: C14H17N5O3
• Molecular Mass: 303.31648
• Monoisotopic Mass: 303.13313943
• SMILES: CCn1cc(C(=O)O)c(=O)c2cnc(nc12)N1CCNCC1
• Canonical SMILES: CCn1cc(C(=O)O)c(=O)c2c1nc(nc2)N1CCNCC1
• InChI: InChI=1S/C14H17N5O3/c1-2-18-8-10(13(21)22)11(20)9-7-16-14(17-12(9)18)19-5-3-15-4-6-19/h7-8,15H,2-6H2,1H3,(H,21,22)
• InChIKey: JOHZPMXAZQZXHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-ethyl-5-oxo-2-(piperazin-1-yl)-5H,8H-pyrido[2,3-d]pyrimidine-6-carboxylic acid
• IUPAC Traditional name: pipemidic acid
• Synonyms: 8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acid; Pipemidic acid; 8-Ethyl-5,8-dihydro-5-oxo-2-[1-piperazinyl]pyrido[2,3-d]-pyrimidine-6-carboxylic acid; PIPEMIDIC ACID; 8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylic Acid Trihydrate; Pipemidic Acid Trihydrate

Database IDs

• CAS Number: 72571-82-5; 51940-44-4
• EC Number: 257-530-2
• MDL Number: MFCD00057291
• PubChem SID: 24898889; 162092749
• PubChem CID: 4831

CALCULATED PROPERTIES

• Acid pKa: 5.3060255
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.9307057
• LogD (pH = 7.4): -1.7834423
• Log P: -1.7723289
• Molar Refractivity: 82.1842 cm^3
• Polarizability: 29.709658 Å^3
• Polar Surface Area: 98.66 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSo
• Apperance: White Solid
• Melting Point: 253-255°C (dec.)

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Desiccate
• RTECS: UV1153800
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)

DETAILS

MP Biomedicals - 02156266

(8-Ethyl-5,8-dihydro-5-oxo-2-
[1-piperazinyl]pyrido[2,3-d]-
pyrimidine-6-carboxylic acid)

Sigma Aldrich - P7903

Application
Pipemidic acid is used to study DNA damage and mutagenic activity1. It has been used to induce articular lesions in the neonatal mouse2 and is used to study human lymphocyte blastogenesis and γ-interferon production 3.
Biochem/physiol Actions
Pipemidic acid modulates (inhibits) bacterial DNA gyrase-dependent processes such as DNA polymerization, (ATP-dependent) DNA supercoiling, and chromosome fragmentation. Pipemidic acid has been shown to induce inhibition of lymphocyte DNA synthesis3.
Pipemidic acid modulates (inhibits) bacterial DNA gyrase-dependent processes such as DNA polymerization, (ATP-dependent) DNA supercoiling, and chromosome fragmentation.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P7903.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - P479800

An antibacterial agent that is effective againts garam negative bacteria such as Pseudomonas Aeruginosa as well as some gram positive bacteria.

REFERENCES

• Massano, S. et al.: Antimicrob. Agents Chemother., 8, 132 (1975)
• Falagas, M.E. et al.: J. Antimicrob, Chemother., 65, 1863 (1975)