3-[(E)-2-phenyldiazen-1-yl]pyridine-2,6-diamine

• ChemBase ID: 1245
• Molecular Formular: C11H11N5
• Molecular Mass: 213.23854
• Monoisotopic Mass: 213.10144538
• SMILES: n1c(N)c(/N=N/c2ccccc2)ccc1N
• Canonical SMILES: Nc1ccc(c(n1)N)/N=N/c1ccccc1
• InChI: 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+
• InChIKey: QPFYXYFORQJZEC-FOCLMDBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(E)-2-phenyldiazen-1-yl]pyridine-2,6-diamine
• IUPAC Traditional name: phenazopyridine
• Brand Name: Azo-Standard; Baridium; Phenazodine; Prodium; Pyridiate; Pyridium; Sedural; Uristat; Urodine; Urogesic; Suladyne; Viridium; Pyrazodine; Phenylazo
• Synonyms: 3-(2-Phenyldiazenyl)-2,6-pyridinediamine Hydrochloride; 3-(Phenylazo)-2,6-pyridinediamine; 2,6-Diamino-3-phenylazopyridine; Gastracid; Gastrotest; NSC 145895; PhenazopyridineSee P313750; Pyridacil; PAP; PDP; Phenazopyridine

Database IDs

• CAS Number: 94-78-0
• PubChem SID: 46507962; 160964705
• PubChem CID: 4756

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.848724
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.4064969
• LogD (pH = 7.4): 2.5843492
• Log P: 2.6925302
• Molar Refractivity: 68.2479 cm^3
• Polarizability: 22.945698 Å^3
• Polar Surface Area: 89.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.31
• LOG S: -3.02
• Solubility (Water): 2.02e-01 g/l

DETAILS

DrugBank - DB01438

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: For the symptomatic relief of pain, burning, urgency, frequency, and other discomforts arising from irritation of the lower urinary tract mucosa caused by infection, trauma, surgery, endoscopic procedures, or the passage of sounds or catheters.
• Pharmacology: Phenazopyridine is 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.
• Toxicity: Methemoglobinemia generally follows a massive, acute overdose.
• Affected Organisms: Humans and other mammals
• Biotransformation: Likely hepatic but also in other tissues. One of the metabolites is acetaminophen.
• Half Life: 7.35 hours
• Elimination: 40% hepatic
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - P313751

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

REFERENCES

• Becker, B.A., et al.: Toxicol. Appl. Pharmacol., 1, 42 (1959)
• Blessel, K.W., et al.: Anal. Profiles Drug. Subs., 3, 465 (1959)
• Shang, E., et al.: Anal. Bioanal. Chem., 382, 216 (1959)