Phenazopyridine hydrochloride Chemical Properties

Melting point:

139°C

Boiling point:

394.6°C (rough estimate)

Density 

1.2645 (rough estimate)

refractive index 

1.6110 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO (Slightly, Heated), Methanol (Slightly, Heated)

form 

Liquid

color 

Clear to hazy colorless to yellow

Water Solubility 

0.01-0.1 g/100 mL at 20 ºC

Merck 

14,7210

Stability:

Light Sensitive

InChIKey

QQBPIHBUCMDKFG-GEEYTBSJSA-N

CAS DataBase Reference

136-40-3(CAS DataBase Reference)

IARC

2B (Vol. 24, Sup 7) 1987

EPA Substance Registry System

Phenazopyridine hydrochloride (136-40-3)

Safety Information

Hazard Codes 

Xn,C

Risk Statements 

22-36/37/38-40-34-42/43

Safety Statements 

26-36/37-45-36/37/39-27-22

RIDADR 

2811

WGK Germany 

3

RTECS 

US7875000

HS Code 

29333990

Toxicity

LD50 orally in rats: 403 mg/kg (Becker, Swift)

MSDS

• Language:English Provider:2,6-Diamino-3-phenylazopyridine hydrochloride
• Language:English Provider:ALFA

Phenazopyridine hydrochloride Usage And Synthesis

Description

Phenazopyridine is an azo dye with analgesic properties. It decreases the bladder distension-induced firing rate of afferent bladder Aγ-fibers, but not C-fibers, in anesthetized rats when administered at a doses of 0.3, 1, and 3 mg/kg. Formulations containing phenazopyridine have been used as analgesics in the treatment of urinary tract infections.

Chemical Properties

Brick-Red Crystals

Originator

Phenazopyridine ,AroKor Holdings Inc.

Uses

Phenazopyridine hydrochloride has been used for 50 years as an analgesic drug either alone or in combination with other drugs to reduce pain associated with urinary tract infection. An azo dye used in urinary tract infections. Also used as a local anesthetic. Exposure to phenazopyridine hydrochloride occurs during manufacture and formulation.

Uses

An azo dye used in treatment of urinary tract infections. Used as an analgesic (urinary tract).

Uses

anticonvulsant, antieleptic

Uses

therapeutic for urinary tract infections

Definition

ChEBI: A hydrochloride obtained by combining phenazopyridine with one equivalent of hydrochloric acid. A local anesthetic that has topical analgesic effect on mucosa lining of the urinary tract. Its use is limited by problems with toxicity (primarily blood disord rs) and potential carcinogenicity.

Manufacturing Process

Phenyldiazene chloride reacted with 2,6-diaminopyridine and in the result 2,6diamino-3-(phenylazo)pyridine was obtained.
In practice it is usually used as monohydrochloride.

brand name

Pyridium (Parke-Davis).

Therapeutic Function

Urinary analgesic, Antiseptic, Diagnostic aid

General Description

Brick-red microcrystals with a slight violet luster or a purple powder. Aqueous solutions are yellow to brick-red and slightly acidic; they may be stabilized by the addition of 10% glucose. Slightly bitter taste.

Air & Water Reactions

Dust can be explosive when suspended in air at specific concentrations. Phenazopyridine hydrochloride may be sensitive to air and light. . Very slightly water soluble.

Reactivity Profile

Phenazopyridine hydrochloride is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Fire Hazard

Flash point data for Phenazopyridine hydrochloride are not available. Phenazopyridine hydrochloride is probably combustible.

Clinical Use

Phenazopyridine hydrochloride, 2,6-diamino-3-(phenylazopyridinehydrochloride (Pyridium), is a brick-red, finecrystalline powder. It is slightly soluble in alcohol, in chloroform,and in water.Phenazopyridine hydrochloride was formerly used asa urinary antiseptic. Although it is active in vitro againststaphylococci, streptococci, gonococci, and E. coli, it has nouseful antibacterial activity in the urine. Thus, its presentutility lies in its local analgesic effect on the mucosa of theurinary tract.
Usually, phenazopyridine is given in combination withurinary antiseptics. For example, it is available as Azo-Gantrisin, a fixed-dose combination with the sulfonamide antibacterialsulfisoxazole, and as Urobiotic, a combination withthe antibiotic oxytetracycline and the sulfonamide sulfamethizole. The drug is rapidly excreted in the urine, towhich it gives an orange-red color. Stains in fabrics may beremoved by soaking in a 0.25% solution of sodium dithionite.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion. Human systemic effects by ingestion: somnolence, cyanosis, dlarrhea, nausea or vomiting, anuria or decreased urine volume, normocytic anemia, methemoglobinemiacarboxyhemoglobinemia, dehydration, changes in blood sodium levels. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl

Carcinogenicity

Phenazopyridine hydrochloride is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity fromstudies in experimental animals.

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