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Details

Stereochemistry ACHIRAL
Molecular Formula C17H18FN3O3
Molecular Weight 331.3415
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIPROFLOXACIN

SMILES

OC(=O)C1=CN(C2CC2)C3=C(C=C(F)C(=C3)N4CCNCC4)C1=O

InChI

InChIKey=MYSWGUAQZAJSOK-UHFFFAOYSA-N
InChI=1S/C17H18FN3O3/c18-13-7-11-14(8-15(13)20-5-3-19-4-6-20)21(10-1-2-10)9-12(16(11)22)17(23)24/h7-10,19H,1-6H2,(H,23,24)

HIDE SMILES / InChI

Description

Ciprofloxacin (1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid) is the synthetic antimicrobial agent for oral or intravenous administration. Ciprofloxacin is a member of the fluoroquinolone class of antibacterial agents. The bactericidal action of ciprofloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV (both Type II topoisomerases), which are required for bacterial DNA replication, transcription, repair, and recombination. Ciprofloxacin is used to treat a wide variety of infections, including infections of bones and joints, endocarditis, gastroenteritis, malignant otitis externa, respiratory tract infections, cellulitis, urinary tract infections, prostatitis, anthrax, and chancroid. In the United States, ciprofloxacin is pregnancy category C. This category includes drugs for which no adequate and well-controlled studies in human pregnancy exist, and for which animal studies have suggested the potential for harm to the fetus, but potential benefits may warrant use of the drug in pregnant women despite potential risks. Fluoroquinolones have been reported as present in a mother's milk and thus passed on to the nursing child. Oral and intravenous ciprofloxacin is approved by the FDA for use in children for only two indications due to the risk of permanent injury to the musculoskeletal system: Inhalational anthrax (postexposure) and Complicated urinary tract infections and pyelonephritis due to Escherichia coli.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.
2000 Oct
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.
2000 Oct
Bacteriologic and clinical efficacy of ofloxacin 0.3% versus ciprofloxacin 0.3% ophthalmic solutions in the treatment of patients with culture-positive bacterial keratitis.
2001 Mar
Ciprofloxacin resistance in gonococci.
2001 Mar 10
What have we learned from pharmacokinetic and pharmacodynamic theories?
2001 Mar 15
Patents

Sample Use Guides

In Vivo Use Guide
Skin and Skin Structure 500 -750 mg every 12 hours 7 to 14 days Bone and Joint 500-750 mg every 12 hours 4 to 8 weeks Complicated Intra-Abdominal 500 mg every 12 hours 7 to 14 days Infectious Diarrhea 500 mg every 12 hours 5 to 7 days Typhoid Fever 500 mg every 12 hours 10 days Uncomplicated Gonorrhea 250 mg single dose single dose Inhalational anthrax (pos-exposure) 500 mg every 12 hours 60 days Plague 500–750 mg every 12 hours 14 days Chronic Bacterial Prostatitis 500 mg every 12 hours 28 days Lower Respiratory Tract 500 -750 mg every 12 hours 7 to 14 days Urinary Tract 250-500 mg every 12 hours 7 to 14 days Acute Uncomplicated Cystitis 250 mg every 12 hours 3 days Acute Sinusitis 500 mg every 12 hours 10 days
Route of Administration: Oral
In Vitro Use Guide
Eight hospital isolates of methicillin-resistant and two standard strains of S. epidermidis (ATCC 12228, ATCC 35984) were cultured overnight in Tryptone Soy Broth supplemented with 0.5% glucose. The solution of tested compounds in TSB-glucose medium were mixed (1:1) with the bacterial inoculums (10^7 CFU/mL) in sterile 96-well polystyrene microtiter plates (Karell - Medlab, Italy) and incubated at 37 C for 24 h. Ciprofloxacin was used as the reference antimicrobial compound; its final concentration ranged from 0.125 to 8 mkg/ml.
Name Type Language
CIPROFLOXACIN
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
CIPROFLOXACIN [MART.]
Common Name English
CIPROFLOXACIN [MI]
Common Name English
ENROFLOXACIN FOR VETERINARY USE SPECIFIED IMPURITY B [EP]
Common Name English
BAY-Q-3939
Code English
CIPROFLOXACIN [WHO-IP]
Common Name English
CIPROFLOXACINUM [WHO-IP LATIN]
Common Name English
CIPROFLOXACIN [USAN]
Common Name English
3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-
Systematic Name English
BAY Q 3939
Code English
CIPROFLOXACIN [JAN]
Common Name English
CIPROFLOXACIN [INN]
Common Name English
CIPRODEX COMPONENT CIPROFLOXACIN
Common Name English
ENROFLOXACIN FOR VETERINARY USE IMPURITY B [EP]
Common Name English
CIPROFLOXACIN [USP-RS]
Common Name English
BAY O 9867 FREE BASE
Code English
1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)-3-QUINOLINE-CARBOXYLIC ACID
Systematic Name English
CIPROFLOXACIN [EP]
Common Name English
CIPROFLOXACIN [VANDF]
Common Name English
BAY-O-9867 FREE BASE
Code English
CIPROFLOXACIN [WHO-DD]
Common Name English
CIPROFLOXACIN COMPONENT OF CIPRODEX
Common Name English
CIPROFLOXACIN [HSDB]
Common Name English
OTIPRIO
Brand Name English
BAYQ3939
Code English
CIPROFLOXACIN [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01MA02
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
NDF-RT N0000175937
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
NDF-RT N0000007606
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
FDA ORPHAN DRUG 216905
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ATC S01AE03
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
EU-Orphan Drug EU/3/07/469
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ATC S02AA15
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ATC S03AA07
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
FDA ORPHAN DRUG 297209
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-VATC QS01AE03
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
NCI_THESAURUS C280
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
FDA ORPHAN DRUG 230806
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
FDA ORPHAN DRUG 339911
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.2
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
NCI_THESAURUS C795
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ATC S01AX13
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ATC J01MA02
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ATC J01RA12
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ATC J01RA10
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-VATC QS03AA07
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-VATC QS02AA15
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
FDA ORPHAN DRUG 422314
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
LIVERTOX 210
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ATC J01RA11
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 28
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
FDA ORPHAN DRUG 369812
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
Code System Code Type Description
MESH
D002939
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
DRUG BANK
DB00537
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
WIKIPEDIA
CIPROFLOXACIN
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
LactMed
85721-33-1
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
ChEMBL
CHEMBL8
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
RXCUI
2551
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
CIPROFLOXACIN
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY Description: A white to pale yellow, crystalline powder.Solubility: Practically insoluble in water; very slightly soluble in ethanol (~750 g/l) TS and dichloromethane R.Category: Antibacterial.Storage: Ciprofloxacin should be kept in a well-closed container, protected from light.Additional information: Ciprofloxacin exists in different polymorphic forms.
CAS
85721-33-1
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
NCI_THESAURUS
C375
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
MERCK INDEX
M3583
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY Merck Index
EPA CompTox
85721-33-1
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
HSDB
85721-33-1
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
EVMPD
SUB07470MIG
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY
INN
5446
Created by admin on Mon Oct 21 19:50:00 UTC 2019 , Edited by admin on Mon Oct 21 19:50:00 UTC 2019
PRIMARY