Compound: pipemidic acid
SMILES: O=c1c(C(=O)O)cn(CC)c2c1cnc(n2)N3CCNCC3
InChIKey: JOHZPMXAZQZXHR-UHFFFAOYSA-N
Synonyms: pipemidic acid, 51940-44-4, Pipedac, Pipemid, Acido pipemidico, Acide pipemidique, Acidum pipemidicum, pipeacid, uropimid, Filtrax, Pipemidate, Pipurin, Tractur, Urosten, Uroval, Nuril, Pi-coli, 8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acid, Memento 400, PIPEMIDIC ACID ANHYDROUS, LT12J5HVR8, NSC-758160, DTXSID3023479, CHEBI:75250, 5,8-Dihydro-8-ethyl-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxylic acid, piperamic acid, Pyrido(2,3-d)pyrimidine-6-carboxylic acid, 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-, DTXCID803479, 8-ethyl-5-oxo-2-(piperazin-1-yl)-5H,8H-pyrido[2,3-d]pyrimidine-6-carboxylic acid, Acid, Pipemidic, Acid, Piperamic, 8-ethyl-5-oxo-2-piperazin-1-ylpyrido(6,5-d)pyrimidine-6-carboxylic acid, 8-ethyl-5-oxo-2-piperazin-1-ylpyrido[6,5-d]pyrimidine-6-carboxylic acid, 8-ethyl-5-oxo-2-(piperazin-1-yl)-5H,8H-pyrido(2,3-d)pyrimidine-6-carboxylic acid, RefChem:174379, J01MB04, 257-530-2, Pipram, Dolcol, Pipemidic acid hydrate, MLS000028608, Uromidin, Palin, 8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid, Pyrido[2,3-d]pyrimidine-6-carboxylicacid, 8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)-, NCGC00016866-01, Pipemidic acid (INN), SMR000058711, CAS-51940-44-4, 8-ethyl-5-oxo-2-piperazin-1-yl-pyrido[2,3-d]pyrimidine-6-carboxylic acid, PIPEMIDIC ACID [INN], Pipemidicacid, Acido pipemidico [Spanish], 8-ethyl-5-oxo-2-piperazinyl-8-hydropyridino[2,3-d]pyrimidine-6-carboxylic acid, 1489 RB, RB 1489, Acide pipemidique [INN-French], Acido pipemidico [INN-Spanish], Acidum pipemidicum [INN-Latin], SR-01000000245, EINECS 257-530-2, UNII-LT12J5HVR8, BRN 0626575, Pipemidic, pipemidic-acid, CCRIS 8517, Pipemidic acid [INN:BAN:DCF], MFCD00057291, Nuril (TN), Spectrum_001387, Opera_ID_1142, Prestwick0_000897, Prestwick1_000897, Prestwick2_000897, Prestwick3_000897, Spectrum2_001185, Spectrum3_001487, Spectrum4_000155, Spectrum5_001214, Epitope ID:613452, Acide ethyl-8 oxo-5 piperazinyl-2 dihydro-5,8 pyrido(2,3-d)pyrimidine-6 carboxylique [French], PIPEMIDIC ACID [MI], BSPBio_000714, BSPBio_003073, KBioGR_000630, KBioSS_001867, PIPEMIDIC ACID [JAN], BIDD:GT0126, CHEMBL30116, DivK1c_000651, SCHEMBL135557, SPECTRUM1502024, SPBio_001229, SPBio_002923, BPBio1_000786, orb1310652, orb3025188, PIPEMIDIC ACID [MART.], PIPEMIDIC ACID [WHO-DD], SCHEMBL29351712, GTPL12774, HMS502A13, KBio1_000651, KBio2_001867, KBio2_004435, KBio2_007003, KBio3_002573, MSK5762, NINDS_000651, GLXC-21416, HMS1570D16, HMS1921F04, HMS2097D16, HMS3714D16, Pharmakon1600-01502024, HY-B1210, Tox21_110655, NSC758160, s5051, SBB012523, STK686262, AKOS005599752, Tox21_110655_1, CCG-220897, CS-4838, DB13823, FP52512, NSC 758160, Acide ethyl-8 oxo-5 piperazinyl-2 dihydro-5,8 pyrido(2,3-d)pyrimidine-6 carboxylique, IDI1_000651, Pyrido(2,3-d)pyrimidine-6-carboxylic acid, 5,8-dihydro-8-ethyl-5-oxo-2-(1-piperazinyl)-, SMP1_000242, NCGC00016866-02, NCGC00016866-03, NCGC00016866-04, NCGC00016866-05, NCGC00016866-06, NCGC00016866-07, NCGC00016866-08, NCGC00016866-11, NCGC00023999-03, NCGC00023999-04, NCGC00178314-01, NCGC00178314-02, AS-47690, DA-76909, ST072200, SBI-0051703.P002, AB00490004, NS00000503, D08379, F15437, AB00052258_14, Q754986, SR-01000000245-2, SR-01000000245-3, SR-01000000245-4, BRD-K08999871-001-05-5, BRD-K08999871-001-13-9, BRD-K08999871-213-01-5, -ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid, 2-(1-piperazinyl)-5,8-dihydro-8-ethyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid, 2-(1-piperazinyl)-8-ethyl-5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid, 5,8-Dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido-[2,3-d]pyrimidine-6-carboxylic acid, 5,8-dihydro-8-ethyl-2-(1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid, 7-(1-Piperazinyl)-1-ethyl-4-oxo-1,4-dihydro-6,8-diazaquinoline-3-carboxylic acid, 8-ethyl-5-oxo-2-piperazin-1-yl-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid, 8-ETHYL-5-OXO-2-PIPERAZINO-5,8-DIHYDROPYRIDO[2,3-D]PYRIMIDINE-6-CARBOXYLIC ACID, 8-Ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido- [2,3-d]pyrimidine-6-carboxylic acid trihydrate
Theoretical properties:
molecular_formula: C14H17N5O3
molecular_weight: 303.32 g/mol
exact_mass: 303.13313942 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 3
heavy_atom_count: 22
topological_polar_surface_area: 98.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 253 - 255 °C
solubility: 0.322 mg/mL at 25 °C
Descriptions:
pubchem: 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.
chebi: A pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-<em>d</em>]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.
chembl: PIPEMIDIC ACID is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 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. The marketing authorization of pipemidic acid has been suspended throughout the EU.