Name: Pipemidic acid
SKU: 51940-44-4

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Basic Information

Molecular Structure:
CAS No.:	51940-44-4
Name:	Pipemidic acid
Article Data:	9

Formula:	C₁₄H₁₇N₅O₃
Molecular Weight:	303.321
Synonyms:	1489RB;8-Ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido[2,3-d]pyrimidine-6-carboxylicacid;Deblaston;Dolcol;Filtrax;Memento 400;Palin;Pi-Coli;Pipeacid;Pipedac;Pipemid;Pipurin;Tractur;Uromidin;Uropimid;Urosten;Uroval;
EINECS:	257-530-2
Density:	1.38 g/cm³
Melting Point:	251-255℃
Boiling Point:	534.9 °C at 760 mmHg
Flash Point:	277.3 °C
Solubility:	Soluble in 1N sodium hydroxide or in DMSO. Insoluble in water
Appearance:	white to off-white powder
Hazard Symbols:	Xi
Risk Codes:	42/43
Safety:	22-36/37-45
PSA:	100.35000
LogP:	0.31300

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Chemistry

IUPAC Name: 8-Ethyl-5-oxo-2-piperazin-1-ylpyrido[2,3-d]pyrimidine-6-carboxylic acid
Synonyms: 8-Ethyl-5,8-dihydro-5-oxo-2-[1-piperazinyl]pyrido[2,3-d]-pyrimidine-6-carboxylic acid ; Labotest-bb lt00772244 ; Pipemidic acid ; 1489RB ; 5,8-Dihydro-8-ethyl-5-oxo-2-(1-piperazinyl)pyrido(2,3-d)pyrimidine-6-carboxy ; Acideethyl-8oxo-5piperazinyl-2dihydro-5,8pyrido(2,3-d)pyrimidine-6carbo ; Acidopipemidico ; Deblaston
Molecular Structure :
Molecular Formula : C₁₄H₁₇N₅O₃
Molecular Weight: 303.32
CAS NO: 51940-44-4
EINECS : 257-530-2
Index of Refraction: 1.617
Surface Tension: 65.5 dyne/cm
Density: 1.38 g/cm³
Flash Point: 277.3 °C
Enthalpy of Vaporization: 85.38 kJ/mol
Boiling Point: 534.9 °C at 760 mmHg
Vapour Pressure: 2.86E-12 mmHg at 25°C
Appearance: Pipram (CAS NO.51940-44-4) is light yellow crystalline powder.
Melting point :251-255 °C (decomposition)
Solubility: Pipram (CAS NO.51940-44-4) is soluble in glacial acetic acid, insoluble in methanol, acetone, DMF, very difficult to dissolve in water, ethanol, chloroform, insoluble in benzene, soluble in dilute alkali or acid solution. Odorless, bitter taste.

Uses

Pipram (CAS NO.51940-44-4) is anti-bacterial drugs, Pseudomonas aeruginosa,have a stronger antibacterial effect on Escherichia coli, Shigella and other Gram-negative bacteria , mainly for the treatment of acute urinary tract infections and other diseases.

Production

The 2,4 - dichloro-pyrimidine -5 - carboxylic acid ethyl ester and β-amino propionate ,condensated, cyclized into 2 - Chloro--5 - hydroxy -7,8 - dihydro -8 - ethyl - pyridine [2,3-d] pyrimidine -6 - carboxylic acid ester. Then, after bromination, piperazine condensation, hydrolysis, and neutralization ,derive Pipram (CAS NO.51940-44-4) .

Toxicity Data With Reference

1.	dnd-rat-orl 152 mg/kg	MUTAEX Mutagenesis. 3 (1988),397.
2.	orl-rat LD50:16 g/kg	PHINDQ Pharmacy International. 1 (1980),108.
3.	scu-rat LD50:1438 mg/kg	YKYUA6 Yakkyoku. Pharmacy. 29 (1978),1231.
4.	ivn-rat LD50:529 mg/kg	YKYUA6 Yakkyoku. Pharmacy. 29 (1978),1231.
5.	scu-mus LD50:2200 mg/kg	37ASAA Kirk-Othmer Encyclopedia of Chemical Technology. 2 (1978),782.
6.	ivn-mus LD50:300 mg/kg	37ASAA Kirk-Othmer Encyclopedia of Chemical Technology. 2 (1978),782.
7.	skn-rbt LD50:4000 mg/kg	37ASAA Kirk-Othmer Encyclopedia of Chemical Technology. 2 (1978),782.

Safety Profile

Poison by intravenous route. Moderately toxic by skin contact and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x. Used as an antibacterial agent.