NORFLOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H18FN3O3
Molecular Weight	319.3308
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CCN1C=C(C(O)=O)C(=O)C2=CC(F)=C(C=C12)N3CCNCC3

InChI

InChIKey=OGJPXUAPXNRGGI-UHFFFAOYSA-N

InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)

HIDE SMILES / InChI

Molecular Formula	C16H18FN3O3
Molecular Weight	319.3308
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

Norfloxacin is an antibacterial agent, It inhibits inhibits DNA synthesis by inhibiting DNA gyrase enzyme. Norfloxacin was approved in 1986 for treatment of urinary tract infections, gynecological infections, prostatitis, gonorhhea and bladder infections. In ophtalmology, norfloxacin is used for treatment of conjunctivitus.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II beta 14	Inhibitor 8,297
Topoisomerase IV 62

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 205	Curative	Approved 8,429	NOROXIN
Gonorrhea 30	Curative	Approved 8,429	NOROXIN
Prostatitis 25	Curative	Approved 8,429	NOROXIN
Conjunctivitis 17	Curative	Approved 8,429	CHIBROXIN

C_max

Value	Dose	Co-administered	Analyte	Population
2.02 μg/mL	400 mg single, oral		NORFLOXACIN unknown	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
9.8 μg × h/mL	400 mg single, oral		NORFLOXACIN unknown	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
4 h	400 mg single, oral		NORFLOXACIN unknown	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
85%	400 mg single, oral		NORFLOXACIN unknown	Homo sapiens

Doses

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Dose	Population	Adverse events
1600 mg single, oral Studied dose	healthy, 24 ± 2 years n = 14
400 mg 2 times / day steady, oral Recommended	unhealthy, 32 years (range: 18-96 years) n = 357	Disc. AE: Nausea, Rash...
400 mg 2 times / day steady, oral Recommended	unhealthy, 46.0 years n = 190	Disc. AE: Abdominal cramps...

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AEs

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AE	Significance	Dose	Population
Nausea	1 patient Disc. AE	400 mg 2 times / day steady, oral Recommended	unhealthy, 32 years (range: 18-96 years) n = 357
Rash	2 patients Disc. AE	400 mg 2 times / day steady, oral Recommended	unhealthy, 32 years (range: 18-96 years) n = 357
Abdominal cramps	1 patient Disc. AE	400 mg 2 times / day steady, oral Recommended	unhealthy, 46.0 years n = 190

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587			inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 707 CYP3A2 10 CYP1A2 1,524

Drug as perpetrator

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Target	Modality	Activity
CYP3A4 1,925	inhibitor 3,277	likely
CYP2A6 739	inhibitor 3,277	no
CYP1A2 1,692	inhibitor 3,277	yes [Inhibition 500 uM]
CYP3A2 13	inhibitor 3,277	yes [Ki 2300 uM]

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:100246	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:100246
ChemicalBook	CB1711035	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1711035
MolPort	MolPort-001-738-625	https://www.molport.com/shop/molecule-link/MolPort-001-738-625
Selleck Chemicals	Norfloxacin(Norxacin)	http://www.selleckchem.com/products/Norfloxacin(Norxacin).html
ZINC	ZINC000000003742	http://zinc15.docking.org/substances/ZINC000000003742

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PubMed

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Title	Date	PubMed
Norfloxacin in the treatment of uncomplicated gonococcal infections.	1987 Jun 26	3300310
Norfloxacin-induced acute cholestatic hepatitis in a patient with alcoholic liver cirrhosis.	1999 Aug	10445586
Norfloxacin-induced eosinophilic necrotizing granulomatous hepatitis.	2000 Dec	11151924
Norfloxacin-induced hallucination--an unusual CNS toxicity of 4-fluoroquinolones.	2000 Sep	11198813
Profiles of hepatic and dysrhythmic cardiovascular events following use of fluoroquinolone antibacterials: experience from large cohorts from the Drug Safety Research Unit Prescription-Event Monitoring database.	2001	11772147

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Patents

Sample Use Guides

In Vivo Use Guide

Norfloxacin tablets is administered orally with a glass of water at least 1 hour before or at least 2 hours after a meal or dairy products (e.g., milk, yogurt). Patients receiving norfloxacin should be well hydrated and should be instructed to drink fluids liberally. The maximal oral dose is 400 mg. For treatment of conjunctivitus, norfloxacin should be instilled at 1 or 2 drops to the affected eye(s) 4 times daily for up to 7 days.

Route of Administration: Other

In Vitro Use Guide

Minimal inhibition concnetration of norfloxacin aganis S.aureus, E.coli and P.aeuginosa was determined using agar media by means of a standard twofold serial dilution method and comprised 0.39, 0.05 and 0.39 ug/mL correspondingly.