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85721-33-1 molecular structure
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1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid

ChemBase ID: 419
Molecular Formular: C17H18FN3O3
Molecular Mass: 331.3415232
Monoisotopic Mass: 331.13321967
SMILES and InChIs

SMILES:
Fc1c(N2CCNCC2)cc2n(C3CC3)cc(c(=O)c2c1)C(=O)O
Canonical SMILES:
Fc1cc2c(cc1N1CCNCC1)n(cc(c2=O)C(=O)O)C1CC1
InChI:
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)
InChIKey:
MYSWGUAQZAJSOK-UHFFFAOYSA-N

Cite this record

CBID:419 http://www.chembase.cn/molecule-419.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
IUPAC Traditional name
ciprofloxacin
1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
Brand Name
Bacquinor
Baycip
Bernoflox
Ciflox
Cifloxin
Ciloxan
Ciprinol
Cipro
Cipro I.V.
Cipro XL
Cipro XR
Ciprobay
Ciprocinol
Ciprodar
Cipromycin
Ciproquinol
Ciproxan
Ciproxin
Flociprin
Floxin
Ocuflox
Proquin XR
Septicide
Velomonit
Synonyms
Ciprofloxacin monohydrochloride
Ciprofloxacin hydrochloride
Ciprofloxacin HCl
Ciprofloxacin dihydrochloride
Ciprofloxacina
ciprofloxacin
Ciprofloxacin
Ciprofloxacin (Cipro)
Ciprobay
Ciprofloxacin
Cipro
Ciproxan
1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperzinyl)-3-quinolinecarboxylic acid HCl H2O
CIPROFLOXACIN HYDROCHLORIDE
Baycip
Belmacina
Catex
Ceprimax
Cetraxal
Ciflox
Cilox
Ciloxan
Ciprok
Ciproxin
Ciproxine
Cunesin
Estecina
Flociprin
Rigoran
Septocipro
Uniflox
Velmonit
1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic Acid
Bay q 3939
Ciflafin
Ciprine
Cipro IV
Ciprobay 100
Ciprofloxacillin
西普乐
环丙沙星
CAS Number
85721-33-1
86393-32-0
MDL Number
MFCD00185755
Beilstein Number
3568352
PubChem SID
24860222
46504733
160963882
24850750
PubChem CID
2764

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 5.7555547  H Acceptors
H Donor LogD (pH = 5.5) -1.1448648 
LogD (pH = 7.4) -0.8145325  Log P -0.81459606 
Molar Refractivity 87.9394 cm3 Polarizability 32.267574 Å3
Polar Surface Area 72.88 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.57  LOG S -2.39 
Solubility (Water) 1.35e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1.1 mg/L expand Show data source
dilute aqueous acid: soluble expand Show data source
Hot DMSO expand Show data source
Hot Methanol expand Show data source
Apperance
White Powder expand Show data source
Melting Point
253-255°C expand Show data source
314-318°C expand Show data source
Density
0.2-0.7 g/ml expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
2-8°C expand Show data source
RTECS
VB1993800 expand Show data source
VB1994000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Target
Others expand Show data source
Gene Information
human ... CYP1A2(1544), KCNH1(3756)rat ... Gabra1(29705) expand Show data source
Mechanism of Action
DNA gyrase (type II topoisomerase) and topoisomerase IV inhibitor expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
suitable for 1694 per US EPA expand Show data source
Application(s)
Broad spectrum antibacterial agent (used in treatment of Legionnaire's disease) expand Show data source
Provides postexposure protection against exp. inhalation anthrax ( Bacillus anthracis ) expand Show data source
Empirical Formula (Hill Notation)
C17H18FN3O3 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02199020 external link
Hydrochloride
Anti-bacterial Agent
DrugBank - DB00537 external link
Item Information
Drug Groups approved; investigational
Description A broad-spectrum antimicrobial carboxyfluoroquinoline. [PubChem]
Indication For the treatment of the following infections caused by susceptible organisms: urinary tract infections, acute uncomplicated cystitis, chronic bacterial prostatitis, lower respiratory tract infections, acute sinusitis, skin and skin structure infections, bone and joint infections, complicated intra-abdominal infections (used in combination with metronidazole), infectious diarrhea, typhoid fever (enteric fever), uncomplicated cervical and urethral gonorrhea, and inhalational anthrax (post-exposure).
Pharmacology Ciprofloxacin is a broad-spectrum antiinfective agent of the fluoroquinolone class. Ciprofloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. The mechanism of action of quinolones, including ciprofloxacin, is different from that of other antimicrobial agents such as beta-lactams, macrolides, tetracyclines, or aminoglycosides; therefore, organisms resistant to these drugs may be susceptible to ciprofloxacin. There is no known cross-resistance between ciprofloxacin and other classes of antimicrobials. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian.
Toxicity The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic. Four metabolites have been identified in human urine which together account for approximately 15% of an oral dose. The metabolites have antimicrobial activity, but are less active than unchanged ciprofloxacin.
Absorption Rapidly and well absorbed from the gastrointestinal tract after oral administration. The absolute bioavailability is approximately 70% with no substantial loss by first pass metabolism.
Half Life 4 hours
Protein Binding 20 to 40%
Elimination Approximately 40 to 50% of an orally administered dose is excreted in the urine as unchanged drug.
Clearance * Renal cl=300 mL/min
References
Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J: Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother. 1986 Sep;30(3):444-6. [Pubmed]
Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF: A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69. [Pubmed]
Spivey JM, Cummings DM, Pierson NR: Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy. 1996 Mar-Apr;16(2):314-6. [Pubmed]
Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Sigma Aldrich - 17850 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Sigma Aldrich - 33434 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - C482500 external link
Fluorinated quinolone antibacterial.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Hilliard JJ, Krause HM, Bernstein JI, Fernandez JA, Nguyen V, Ohemeng KA, Barrett JF: A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv Exp Med Biol. 1995;390:59-69. Pubmed
  • • Spivey JM, Cummings DM, Pierson NR: Failure of prostatitis treatment secondary to probable ciprofloxacin-sucralfate drug interaction. Pharmacotherapy. 1996 Mar-Apr;16(2):314-6. Pubmed
  • • Drusano GL, Standiford HC, Plaisance K, Forrest A, Leslie J, Caldwell J: Absolute oral bioavailability of ciprofloxacin. Antimicrob Agents Chemother. 1986 Sep;30(3):444-6. Pubmed
  • • Brouwers JR: Drug interactions with quinolone antibacterials. Drug Saf. 1992 Jul-Aug;7(4):268-81. Pubmed
  • • Hoffken, G., et al.: Antimicrob. Ag. Chemother., 27, 375 (1985)
  • • Scully, B.E., et al.: Lancet, 1, 819 (1986)
  • • Ger. Pat., 1983, Bayer, 3 142 854; CA, 99, 53790h, (synth, pharmacol)
  • • Chin, N.X. et al., Antimicrob. Agents Chemother., 1984, 25, 319, (pharmacol)
  • • Curr. Clin. Pract. Ser., (Eds. Neu, H.C. et al), Excerpta Medica, 1986, (book)
  • • Ball, P., J. Antimicrob. Chemother., Suppl. D, 1986, 18, 187, (tox)
  • • Ciprofloxacin Product Information Monograph, M. Dekker, 1988, (book)
  • • Campoli-Richards, D.M. et al., Drugs, 1988, 35, 373, (rev)
  • • Vance-Bryan, K. et al., Clin. Pharmacokinet., 1990, 19, 434, (rev, pharmacokinet)
  • • New Gener. Quinolones, 1990, (Eds. Siporin, C. et al), M. Dekker (see Infect. Dis. Ther. v5 1990), 1990, (book)
  • • Textbook of Adverse Drug Reactions, 4th edn., (ed. Davies, D.M.), Oxford University Press, 1991, (tox)
  • • Mehta, A.C. et al., J. Clin. Pharm. Ther., 1992, 17, 117, (hplc)
  • • Friedlander, A.M. et al., J. Infect. Dis., 1993, 167, 1239-1243, (use)
  • • Wiseman, L.R. et al., Drugs Aging, 1994, 4, 145, (rev)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5748, (synonyms)
  • • Davis, R. et al., Drugs, 1996, 51, 1019, (rev, pharmacol)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 185
  • • Hay, A.M. et al., Synthesis, 1999, 1979-1985, (synth, uv, pmr)
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PATENTS

PATENTS

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INTERNET

INTERNET

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