Basic information
- CAS
19562-30-2- Standard SMILES
CCn1cc(C(=O)O)c(=O)c2cnc(N3CCCC3)nc21- InChIKey
RCIMBBZXSXFZBV-UHFFFAOYSA-N- Molecular formula
- C14H16N4O3
- Average molar mass
- 288.3 g/mol
- Monoisotopic mass
- 288.12224039
Overview
Piromidic acid is a pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid, substituted at position 2 by a pyrrolidin-1-yl group and at position 8 by an ethyl group. A synthetic antibacterial which is used for the treatment of urinary tract and intestinal infections. It has a role as an antibacterial drug and a DNA synthesis inhibitor. It is a monocarboxylic acid, a member of pyrrolidines, a pyridopyrimidine, a tertiary amino compound and a quinolone antibiotic.
Names & identifiers
- Preferred name
- Piromidic Acid
- IUPAC
- 8-ethyl-5-oxo-2-pyrrolidin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid
- English name
- Piromidic acid
- Molecular formula
- C14H16N4O3
- Molecular weight
- 288.3
Names & synonyms
piromidic acid19562-30-2BactramylPanacidReelonSepturalAcido piromidicoAcide piromidiqueActrun CGastrurolUropirAcidum piromidicum
Show more names
pd93PuriMpirodalenterolPirudallidinyl)-
PD-93PiromidateDTXSID40454243I12WH4EWFNSC-291120Pyrido(2,3-d)pyrimidine-6-carboxylic acid, 8-ethyl-5,8-dihydro-5-oxo-2-(1-pyrrolidinyl)-DTXCID2025424CHEBI:32019
Database identifiers
- CAS
19562-30-2- PubChem CID
- 4855
- DTXSID
DTXSID4045424- ChEMBL
CHEMBL311350- ChEBI
CHEBI:32019- UNII
- 3I12WH4EWF
- EC Number
- 243-161-4、419-730-1
- Nikkaji
- J3.146A
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 86.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 473
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Human DrugsPharmaceuticals
Collision Cross Section161.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 314 · 314-316°
- Boiling point
- 430.54 °C · 430.54°C (rough estimate)
- Density
- 1.1895 · 1.1895 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- 0 · 0-6°C
- solubility
- Chloroform (Slightly, Heated, Sonicated), Ethanol (Slightly, Heated)
- form
- Solid
- pka
- 4.14 · 4.14±0.20(Predicted)
- color
- 3 · Crystals from EtOH/CHCl3
- FDA UNII
- 3 I12WH4EWF · 3I12WH4EWF
- ATC code
- 1 MB03 · J01MB03
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
- Toxicity
- 50 in · LD50 in male, female mice, male, female rats (mg/kg): 287, 268, 177, 158 i.v.; all >4000 orally, s.c. and i.p. (Shimizu)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Regulatory InformationREACH registered substance: ENTEROL (EC: 419-730-1)
Hazard Classes and CategoriesNot Classified
Safety data
- Toxicity
- LD50 in male, female mice, male, female rats (mg/kg): 287, 268, 177, 158 i.v.; all >4000 orally, s.c. and i.p. (Shimizu)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Uses & manufacturing
Use ClassificationPharmaceuticals
Applications
DescriptionPiromidic acid is a quinolone antibiotic that is active against Gram-positive and Gram-negative bacteria including S. aureus and E. coli (MICs = 10 and 1 μg/ml, respectively). It inhibits growth of nalidixic acid-sensitive strains of E. coli in an in vitro model of bacterial cystitis when used at concentrations of 10 and 50 mg/L. Piromidic acid also has antimalarial properties and is active against chloroquine-sensitive and -resistant strains of P. falciparum in vitro (IC50s = 41.4 and 14.4 μg/ml, respectively) as well as against hepatic stages of P. yoelii yoelii (IC50 = 21.6 μg/ml).
UsesAntibacterial;Topoisomerase II inhibitor
UsesPiromidic acid is a quinolone antibacterial.
Upstream & downstream products
Upstream raw materials
Suppliers45 total
艾吉析科技（上海）有限公司17717235263 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
北京索莱宝科技有限公司010-50973130 17801761073 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
上海毕得医药科技股份有限公司400-164-7117 18317119277 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
艾吉析科技（上海）有限公司17717235263 17717235263 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
Target molecule Corp.857-239-0968 · [email protected]
上海泰坦科技股份有限公司13023226327 · [email protected]
Musechem+1-800-259-7612 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
北京沃凯生物科技有限公司010-62971590 18548936886 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
范德(北京)生物科技有限责任公司15911056312 · [email protected]
Aladdin Scientific[email protected]
Wuhan Topule Biopharmaceutical Co., Ltd+86-18327326525 · [email protected]
TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]
上海陌孚医药科技有限公司4000862158 18117107507 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海安谱实验科技股份有限公司18502138905 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
苏州致信生物科技有限公司0512-65118909 18100677375 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
上海鼓臣生物技术有限公司021-34675735 19147740836 · [email protected]
上海弘渠生物医药科技有限公司88888888888 · [email protected]
资川生化科技(苏州)有限公司0512-66317708 13372112871 · [email protected]
Additional notes
DefinitionChEBI: Piromidic acid is a pyridopyrimidine that is 5-oxo-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid, substituted at position 2 by a pyrrolidin-1-yl group and at position 8 by an ethyl group. A synthetic antibacterial which is used for the treatment of urinary tract and intestinal infections. It has a role as an antibacterial drug and a DNA synthesis inhibitor. It is a quinolone antibiotic, a member of pyrrolidines, a tertiary amino compound, a monocarboxylic acid and a pyridopyrimidine.
Related reactions
1 records
Compound notes
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