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Substance Name: Phenazopyridine hydrochloride [USAN:USP]
RN: 136-40-3
UNII: 0EWG668W17
InChIKey: QQBPIHBUCMDKFG-GEEYTBSJSA-N

Note

  • A local anesthetic that has been used in urinary tract disorders. Its use is limited by problems with toxicity (primarily blood disorders) and potential carcinogenicity.

Molecular Formula

  • C11-H11-N5.Cl-H

Molecular Weight

  • 249.7038
 

Classification Codes

Classification Codes

  • Analgesic (Urinary Tract)
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2B
  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Name of Substance

  • Phenazopyridine hydrochloride [USAN:USP]

Synonyms

  • 2,6-Diamino-3-(phenylazo)pyridine monohydrochloride
  • 2,6-Diamino-3-phenylazopyridine hydrochloride
  • 2,6-Pyridinediamine, 3-(phenylazo)-, monohydrochloride
  • 3-(Phenylazo)-2,6-pyridinediamine, hydrochloride
  • 3-Phenylazo-2,6-diaminopyridine hydrochloride
  • AI3-51273
  • Azo-Standard
  • Azodyne
  • Azomine
  • Azosulfisox
  • Bisteril
  • CCRIS 497
  • Di-Azo
  • Diridone
  • EINECS 205-243-8
  • Mallofeen
  • Mallophene
  • NC 150
  • NCI-C01672
  • Nefrecil
  • NSC 1879
  • Phenazodine
  • Phenazopyridine HCl
  • Phenazopyridine hydrochloride
  • Phenazopyridinium chloride
  • Phenyl-idium
  • Phenyl-idium 200
  • Phenylazo tablets
  • Phenylazo-alpha,alpha'-diaminopyridine monohydrochloride
  • Phenylazodiaminopyridine hydrochloride
  • Phenylazopyridine hydrochloride
  • Pirid
  • Pyrazodine
  • Pyridacil
  • Pyridiate
  • Pyridine, 2,6-diamino-3-(phenylazo)-, hydrochloride
  • Pyridium
  • Pyridivite
  • Pyripyridium
  • Pyrizin
  • Sedural
  • Suladyne
  • Thiosulfil-A forte
  • UNII-0EWG668W17
  • Urazium
  • Uridinal
  • Uriplex
  • Urodine
  • W 1655

Systematic Names

  • 2,6-Pyridinediamine, 3-(phenylazo)-, monohydrochloride
  • Pyridine, 2,6-diamino-3-(phenylazo)-, monohydrochloride

Superlist Names

  • 2,6-Pyridinediamine, 3-(phenylazo)-, monohydrochloride
  • Phenazopyridine hydrochloride

Mixture Names

  • Azo gantanol
  • Azo Gantrisin
  • Azo-Mandelamine
  • Azotrex
  • Dolonil
  • Pyridium plus
  • Thiosulfil-A

Registry Numbers

CAS Registry Number

  • 136-40-3

FDA UNII

  • 0EWG668W17

System Generated Number

  • 0000136403

Molecular Formulas

Molecular Formula

  • C11-H11-N5.Cl-H

Molecular Formula Fragments

  • C11-H11-N5
  • Cl-H
  • COMPONENT

Structure Descriptors

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+;

InChIKey

QQBPIHBUCMDKFG-GEEYTBSJSA-N

Smiles

c1ccc(cc1)/N=N/c2ccc(nc2N)N.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 35mg/kg (35mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

KIDNEY, URETER, AND BLADDER: HEMATURIA
American Journal of Diseases of Children. Vol. 117, Pg. 369, 1969.
child TDLo oral 125mg/kg (125mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Clinical Pediatrics Vol. 10, Pg. 537, 1971.
child TDLo oral 400mg/kg (400mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
American Journal of Diseases of Children. Vol. 110, Pg. 105, 1965.
man TDLo oral 86mg/kg/10D-I (86mg/kg) SPINAL CORD: INFLAMMATORY CHANGES Annals of Internal Medicine. Vol. 106, Pg. 164, 1987.
man TDLo oral 114mg/kg (114mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Human Toxicology. Vol. 2, Pg. 539, 1983.
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04014,
rat LD50 oral 472mg/kg (472mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 42, 1959.
rat LDLo intraperitoneal 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pharmacology and Experimental Therapeutics. Vol. 51, Pg. 200, 1934.
women TDLo oral 34mg/kg (34mg/kg)   Annals of Internal Medicine. Vol. 72, Pg. 89, 1970.
women TDLo oral 34mg/kg (34mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Annals of Internal Medicine. Vol. 72, Pg. 89, 1970.
women TDLo oral 140mg/kg (140mg/kg) BLOOD: NORMOCYTIC ANEMIA

GASTROINTESTINAL: NAUSEA OR VOMITING
Canadian Medical Association Journal. Vol. 91, Pg. 756, 1964.