Pipemidic acid

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Pipemidic acid
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	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 InfoCard	100.052.283
Chemical and physical data
Formula	C₁₄H₁₇N₅O₃
Molar mass	303.322 g·mol⁻¹
3D 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

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

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

Other DHPS inhibitors

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

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ 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)

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

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin^# Rifapentine^# Rifaximin Rifalazil^§
Lipiarmycins	Fidaxomicin

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