Basic information
- Standard SMILES
CCn1cc(C(=O)O)c(=O)c2cnc(N3CCNCC3)nc21- InChIKey
JOHZPMXAZQZXHR-UHFFFAOYSA-N- Molecular formula
- C14H17N5O3
- Average molar mass
- 303.32 g/mol
- Monoisotopic mass
- 303.1331394
Overview
Pipemidic acid is a pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid substituted at position 2 by a piperazin-1-yl group and at position 8 by an ethyl group. A synthetic broad-spectrum antibacterial, it is used for treatment of gastrointestinal, biliary, and urinary infections. It has a role as an antibacterial drug and a DNA synthesis inhibitor. It is a monocarboxylic acid, an amino acid, a pyridopyrimidine, a N-arylpiperazine and a quinolone antibiotic.
Names & identifiers
- Preferred name
- Pipemidic Acid
- IUPAC
- 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid
Names & synonyms
pipemidic acid51940-44-4PipedacPipemidAcido pipemidicoAcide pipemidiqueAcidum pipemidicumpipeaciduropimidFiltraxPipemidatePipurin
Show more names
TracturUrostenUrovalNurilPi-coli8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acidMemento 400PIPEMIDIC ACID ANHYDROUS
Database identifiers
- CAS
51940-44-4- PubChem CID
- 4831
- DTXSID
DTXSID3023479- ChEMBL
CHEMBL30116- ChEBI
CHEBI:75250- UNII
- LT12J5HVR8
- EC Number
- 257-530-2
- Nikkaji
- J10.405A
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 98.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 3
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 489
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
LogP-2.15
Solubility0.322 mg/mL at 25 °C
Human DrugsPharmaceuticals
Melting Point253 - 255 °C
Physical DescriptionSolid
Collision Cross Section
185.6 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with Waters Major Mix]
171 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
172.63 Ų [M+H]+
Safety & regulation
GHS classification
GHS Classification
Danger
H317 (97.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Pyrido[2,3-d]pyrimidine-6-carboxylic acid, 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-: Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (97.6%)
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Mechanism of ActionPipemidic acid is a quinolone antibacterial, which acts by inhibiting the bacterial DNA gyrase DNA topoisomerase IV.
MeSH Pharmacological Classification
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that inhibit the growth or reproduction of BACTERIA.
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals
Related reactions
33 records
Linked notes
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