ChemicalBook > CAS DataBase List > PIROMIDIC ACID

PIROMIDIC ACID

Product Name: PIROMIDIC ACID
CAS No.: 19562-30-2
Chemical Name: PIROMIDIC ACID
Synonyms: pd93;PuriM;reelon;uropir;pirodal;enterol;Pirudal;panacid;septural;lidinyl)-
CBNumber: CB3690633
Molecular Formula: C14H16N4O3
Formula Weight: 288.3
MOL File: 19562-30-2.mol

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PIROMIDIC ACID Property

Melting point:: 314-316°
Boiling point:: 430.54°C (rough estimate)
Density: 1.1895 (rough estimate)
refractive index: 1.6000 (estimate)
storage temp.: 0-6°C
solubility: Chloroform (Slightly, Heated, Sonicated), Ethanol (Slightly, Heated)
form: Solid
pka: 4.14±0.20(Predicted)
color: Crystals from EtOH/CHCl3

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Safety

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)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 19255
Product name: Piromidic Acid
Purity: ≥95%
Packaging: 100mg
Price: $43
Updated: 2024/03/01

Cayman Chemical

Product number: 19255
Product name: Piromidic Acid
Purity: ≥95%
Packaging: 500mg
Price: $187
Updated: 2024/03/01

Cayman Chemical

Product number: 19255
Product name: Piromidic Acid
Purity: ≥95%
Packaging: 1g
Price: $332
Updated: 2024/03/01

TRC

Product number: P509500
Product name: PiromidicAcid
Packaging: 100mg
Price: $1555
Updated: 2021/12/16

TRC

Product number: P509500
Product name: PiromidicAcid
Packaging: 10mg
Price: $195
Updated: 2021/12/16

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PIROMIDIC ACID Chemical Properties,Usage,Production

Description

Piromidic 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).

Originator

Panacid, Dainippon, Japan ,1972

Uses

Antibacterial;Topoisomerase II inhibitor

Uses

Piromidic acid is a quinolone antibacterial.

Definition

ChEBI: 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.

Manufacturing Process

150 mg of 6-carboxy-5,8-dihydro-8-ethyl-2-methylthio-5-oxopyrido[2,3d]pyrimidine was added to 30 ml of absolute ethanol containing 1.1 g of dissolved pyrrolidine, and the mixture was reacted for 5 hours at 95°C in a sealed tube. The solvent was removed by distillation, and the residue was recrystallized from methanol-chloroform. There were obtained 111 mg of 6carboxy-5,8-dihydro-8-ethyl-5-oxo-2-pyrrolidino-pyrido[2,3-d]pyrimidine having a MP of 314° to 316°C.
The starting material is produced by reacting 6-amino-2-methylthiopyrimidine with ethoxymethylene malonic acid diethyl ester. That intermediate is thermally treated in diphenyl ether to give 6-ethoxycarbonyl-2-methylthio-5oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine. The ethoxy group is hydrolyzed off with sodium hydroxide and one nitrogen is ethylated with diethyl sulfate to give the starting material. These are the same initial steps as used in the pipemidic acid syntheses earlier in this volume.

Therapeutic Function

Antibacterial (urinary)

Pharmaceutical Applications

A pyrimidopyrimidine derivative with a C7-pyrrolidinyl ring, allowing a slight increase in activities against Gram-positive cocci. Its main antibacterial activity is close to that of nalidixic acid and there have been reports of renal toxicity. It is available in only a few countries.

Safety Profile

Poison by subcutaneous and intravenous routes. Moderately toxic by skin contact and intraperitoneal routes. An antibacterial agent. When heated to decomposition it emits toxic fumes of NOx.

References

[1] S. MINAMI J M T Shono. Pyrido [2, 3- d ] pyrimidine Antibacterial Agents. II. Piromidic Acid and Related Compounds[J]. Chemical & pharmaceutical bulletin, 1971, 45 1: 1426-1432. DOI: 10.1248/cpb.19.1426
[2] GREENWOOD D. The assessment of antimicrobial activity in an in-vitro model of the treatment of bacterial cystitis.[J]. Journal of Antimicrobial Chemotherapy, 1984, 13 Suppl B: 43-48. DOI: 10.1093/jac/13.suppl_b.43
[3] NASSIRA MAHMOUDI. In vitro activities of 25 quinolones and fluoroquinolones against liver and blood stage Plasmodium spp.[J]. Antimicrobial Agents and Chemotherapy, 2003, 47 8: 2636-2639. DOI: 10.1128/aac.47.8.2636-2639.2003

PIROMIDIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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19562-30-2, PIROMIDIC ACIDRelated Search:

PINOSYLVIN 2-Amino-5-pyrimidinecarboxyaldehyde 2-Pyrrolidin-1-ylpyrimidine-5-carboxaldehyde 97% PIROMIDIC ACID 1-(5-Pyrimidinyl)ethanone 2,4-DIAMINO-PYRIMIDINE-5-CARBALDEHYDE 2-Pyrimidinamine, 5-methyl- (9CI) 5-ETHYL-2-PYRIMIDINAMINE 3-DIMETHYLAMINO-2-METHYL-2-PROPENAL 2-DIMETHYLAMINO-PYRIMIDINE-5-CARBALDEHYDE 2,4-BIS(DIMETHYLAMINO)-PYRIMIDINE Ethanone,1-(2-amino-5-pyrimidinyl)- 5-Pyrimidinecarboxaldehyde, 2-(ethylamino)- (9CI) 5-PROPYL-2-PYRIMIDINAMINE N2,N4-DIMETHYLPYRIMIDINE-2,4-DIAMINE 5-Pyrimidinecarboxaldehyde, 4-amino- (8CI,9CI) 2-(PROPYLAMINO)PYRIMIDINE-5-CARBALDEHYDE ethyl 8-ethyl-5,8-dihydro-5-oxo-2-(pyrrolidinyl)pyrido[2,3-d]pyrimidine-6-carboxylate

enterol

gastrurol

lidinyl)-

panacid

pd93

pirodal

5,8-Dihydro-8-ethyl-5-oxo-2-pyrrolidinopyrido[2,3-d]pyriMidine-6-carboxylic Acid

NSC 291120

Pirudal

PuriM

PyroMidic Acid

pyrido(2,3-d)pyrimidine-6-carboxylicacid,5,8-dihydro-8-ethyl-5-oxo-2-(1-pyrro

PIROMIDIC ACID

8-ethyl-5-oxo-2-(1-pyrrolidinyl)-5,8-dihydropyrido(2,3-d)pyrimidine-6-carbox

bactramyl

reelon

septural

uropir

8-Ethyl-5,8-dihydro-5-oxo-2-(1-pyrrolidinyl)pyrido[2,3-d]pyrimidine-6-carboxylic acid

Piromidic acid standard

Pyrido[2,3-d]pyrimidine-6-carboxylic acid, 8-ethyl-5,8-dihydro-5-oxo-2-(1-pyrrolidinyl)-

PiromidicAci

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

inhibit,Piromidic acid,Antibiotic,Inhibitor,Bacterial

8-ethyl-5-oxo-2-pyrrolidin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid

Piromidic acid in MeOH with 0.04M NaOH

Piromidic acid in Acetonitrile

19562-30-2

Inhibitors

Aromatics

Heterocycles

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