PHENAZOPYRIDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H11N5
Molecular Weight	213.2385
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

NC1=NC(N)=C(C=C1)\N=N\C2=CC=CC=C2

InChI

InChIKey=QPFYXYFORQJZEC-FOCLMDBBSA-N

InChI=1S/C11H11N5/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8/h1-7H,(H4,12,13,14)/b16-15+

HIDE SMILES / InChI

Molecular Formula	C11H11N5
Molecular Weight	213.2385
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description

Phenazopyridine hydrochloride, an azo dye first synthesized in 1914, became widely prescribed for the treatment of urinary tract infections (UTIs). With the assumption that the drug possessed antiseptic properties, phenazopyridine was recommended for UTIs caused by Staphylococcus, Streptococcus, and Escherichia coli. Although in the early 1930s the medical and scientific communities rescinded the claim that phenazopyridine is bactericidal, a specific mechanism of action has not been identified subsequently. Currently, phenazopyridine is classified as a urinary analgesic that relieves burning, urgency, frequency, and pain associated with UTI, trauma, or surgery.

Approval Year

Conditions

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205	Primary		Approved 8,429	SULFAMETHOXAZOLE AND TRIMETHOPRIM AND PENAZOPYRIDINE HYDROCHLORIDE
Urinary tract infections 205	Primary		Approved 8,429	PHENAZOPYRIDINE

PubMed

Show entries

Title	Date	PubMed
Heinz body hemolytic animea. "Bite cells" -a clue to diagnosis.	1976 Feb	1247346
Phenazopyridine-induced hepatitis.	1976 Oct 9	990717
Rapid increase in calculous size: a possible hazard of phenazopyridine hydrochloride therapy in the presence of already formed stones.	1978 Feb	633496
Phenylazopyridine (Pyridium) and acute renal failure.	1979 Mar	426430
[Sedural toxicity].	1991 Mar 15	1879765

Showing 1 to 5 of 48 entries

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Patents

Sample Use Guides

In Vivo Use Guide

200 mg 3 times daily after meals. When used concomitantly with an antibacterial agent for the treatment of a urinary tract infection, the administration of phenazopyridine should not exceed 2 days. If symptoms persist, the patient should be re-evaluated.

Route of Administration: Oral

In Vitro Use Guide

3 uM phenazopyridine enhances neuronal differentiation of human embryonic stem cells cells and allows the generation of a monolayer of synchronized neural progenitors