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Details

Stereochemistry ACHIRAL
Molecular Formula C11H11N5.ClH
Molecular Weight 249.699
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PHENAZOPYRIDINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=QQBPIHBUCMDKFG-GEEYTBSJSA-N
InChI=1S/C11H11N5.ClH/c12-10-7-6-9(11(13)14-10)16-15-8-4-2-1-3-5-8;/h1-7H,(H4,12,13,14);1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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 Although in the early 1930s the medical and scientific communities rescinded the claim that phenazopyridine is bactericidal, a specific mechanism of action has not been identified subsequently.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

ConditionModalityTargetsHighest PhaseProduct
Primary
SULFAMETHOXAZOLE AND TRIMETHOPRIM AND PENAZOPYRIDINE HYDROCHLORIDE
Primary
PHENAZOPYRIDINE

PubMed

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
Substance Class Chemical
Record UNII
0EWG668W17
Record Status Validated (UNII)
Record Version