Pipemidic acid

Chemical compound

J01MB04 (WHO)

Identifiers

IUPAC name

8-Ethyl-5-oxo-2-piperazin-1-yl-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid

CAS Number

51940-44-4

PubChem CID

4831

ChemSpider

4665

UNII

LT12J5HVR8

KEGG

D08379

ChEBI

CHEBI:75250

ChEMBL

ChEMBL30116

CompTox Dashboard (EPA)

DTXSID3023479

ECHA InfoCard100.052.283

Chemical and physical dataFormulaC₁₄H₁₇N₅O₃Molar mass303.322 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

CCN1C=C(C(=O)C2=CN=C(N=C21)N3CCNCC3)C(=O)O

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)
Key:JOHZPMXAZQZXHR-UHFFFAOYSA-N

Pipemidic acid is a member of the pyridopyrimidine class of antibacterials, which display some overlap in mechanism of action with analogous pyridone-containing quinolones. It was introduced in 1979 and is active against gram negative and some gram positive bacteria. It was used for gastrointestinal, biliary, and urinary infections.^[1] The marketing authorization of pipemidic acid has been suspended throughout the EU.^[2]

References

^ "Pipemidic Acid - MeSH - NCBI". www.ncbi.nlm.nih.gov. Retrieved 2019-01-20.
^ "Disabling and potentially permanent side effects lead to suspension or restrictions of quinolone and fluoroquinolone antibiotics". European Medicines Agency. 11 March 2019.

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Brodimoprim
- Iclaprim^†
- Ormetoprim
- Pyrimethamine^#
- Tetroxoprim
- Trimethoprim^#

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Trimethoprim/sulfamethoxazole^#
Ormetoprim/sulfadimethoxine
Pyrimethamine/dapsone
Pyrimethamine/sulfadoxine

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Cinoxacin^‡
Flumequine^‡
Nalidixic acid^‡
Oxolinic acid^‡
Pipemidic acid^‡
Piromidic acid^‡
Rosoxacin^‡

Fluoroquinolones

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡/Levonadifloxacin/Alalevonadifloxacin Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡
3rd generation	Levofloxacin^# Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin^# Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin^‡

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Metronidazole^# Ornidazole Secnidazole Tinidazole
Nitrofuran derivatives	Furazolidone^‡ Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin^# Nitrofurazone