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Substance Name: Ciprofloxacin [USAN:USP:INN:BAN]
RN: 85721-33-1
UNII: 5E8K9I0O4U
InChIKey: MYSWGUAQZAJSOK-UHFFFAOYSA-N

Note

  • A broad-spectrum antimicrobial carboxyfluoroquinoline.

Molecular Formula

  • C17-H18-F-N3-O3

Molecular Weight

  • 331.3452
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antineoplastic Agents
  • Cytochrome P-450 CYP1A2 Inhibitors
  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Nucleic Acid Synthesis Inhibitors
  • Topoisomerase II Inhibitors
  • Topoisomerase Inhibitors

Names and Synonyms

Name of Substance

  • Ciprofloxacin
  • Ciprofloxacin [USAN:USP:INN:BAN]

MeSH Heading

  • Ciprofloxacin

Synonyms

  • 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
  • 1-Cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid
  • Alcon Cilox
  • AuriPro
  • Bacquinor
  • Baflox
  • Bay o 9867
  • Bay q 3939
  • BAYQ3939
  • Bernoflox
  • Bi-Cipro
  • BRN 3568352
  • CCRIS 5241
  • Cetraxal
  • Cifloxin
  • Cilab
  • Ciplus
  • Ciprecu
  • Cipro
  • Cipro in dextrose 5% in plastic container
  • Cipro in sodium chloride 0.9% in plastic container
  • Cipro IV
  • Cipro XR
  • Ciprobay
  • Ciprobay Uro
  • Ciprocinol
  • Ciprodar
  • Ciproflox
  • Ciprofloxacin
  • Ciprofloxacina
  • Ciprofloxacine
  • Ciprofloxacine [INN-French]
  • Ciprofloxacino
  • Ciprofloxacino [INN-Spanish]
  • Ciprofloxacinum
  • Ciprofloxacinum [INN-Latin]
  • Ciprogis
  • Ciprolin
  • Ciprolon
  • Cipromycin
  • Ciproquinol
  • Ciprowin
  • Ciproxan
  • Ciproxina
  • Ciproxine
  • Ciriax
  • Citopcin
  • Cixan
  • Corsacin
  • Cycin
  • Cyprobay
  • Eni
  • Fimoflox
  • HSDB 6987
  • Ipiflox
  • Italnik
  • Linhaliq
  • Linhaliq [Liposomal Formulation]
  • Loxan
  • Otiprio
  • Probiox
  • Proflaxin
  • Proflox
  • Proksi 250
  • Proksi 500
  • Quinolid
  • Quintor
  • Rancif
  • Roxytal
  • Septicide
  • Sophixin Ofteno
  • Spitacin
  • Superocin
  • Unex
  • UNII-5E8K9I0O4U
  • Zumaflox

Systematic Names

  • 3-Quinolinecarboxylic acid, 1,4-dihydro-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-
  • 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-
  • Ciprofloxacin

Mixture Name

  • Ciprofloxacin Extended Release

Registry Numbers

CAS Registry Number

  • 85721-33-1

FDA UNII

  • 5E8K9I0O4U

System Generated Number

  • 0085721331

Structure Descriptors

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

Smiles

OC(=O)C1=CN(C2CC2)c3cc(N4CCNCC4)c(F)cc3C1=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo oral 5714ug/kg/2D- (5.714mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

BEHAVIORAL: COMA

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Lancet. Vol. 343, Pg. 738, 1994.
man TDLo oral 21mg/kg/3D-I (21mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

KIDNEY, URETER, AND BLADDER: PROTEINURIS
Annals of Pharmacotherpy. Vol. 29, Pg. 84, 1995.
man TDLo oral 21429ug/kg/3D (21.429mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Annals of Pharmacotherpy. Vol. 26, Pg. 930, 1992.
man TDLo oral 129mg/kg/6D-I (129mg/kg) BEHAVIORAL: REGIDITY Journal of Clinical Psychiatry. Vol. 54, Pg. 115, 1993.
man TDLo oral 200mg/kg (200mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: TREMOR

GASTROINTESTINAL: OTHER CHANGES
Annals of Pharmacotherpy. Vol. 28, Pg. 805, 1994.
mouse LD50 intraperitoneal 1165mg/kg (1165mg/kg)   Ensho. Japanese Journal of Inflammation. Vol. 11, Pg. 343, 1991.
mouse LD50 intravenous 122mg/kg (122mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Korean Journal of Toxicology. Vol. 8, Pg. 161, 1993.
mouse LD50 oral 5gm/kg (5000mg/kg)   Journal of Medicinal Chemistry. Vol. 33, Pg. 1344, 1990.
mouse LD50 subcutaneous > 1gm/kg (1000mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992.
rat LD50 intravenous 207mg/kg (207mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Korean Journal of Toxicology. Vol. 8, Pg. 161, 1993.
rat LD50 oral > 2gm/kg (2000mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992.
rat LD50 subcutaneous > 1gm/kg (1000mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992.
women TDLo multiple routes 40mg/kg/6D-I (40mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
Acta Clinica Belgica. Vol. 49, Pg. 173, 1994.
women TDLo oral 10mg/kg (10mg/kg)   Allergy. Vol. 50(Suppl,
women TDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

GASTROINTESTINAL: NAUSEA OR VOMITING
Allergy. Vol. 50(Suppl,
women TDLo oral 40mg/kg/2D-I (40mg/kg)   American Journal of Medicine. Vol. 87, Pg. 589, 1989.
women TDLo oral 40mg/kg/2D-I (40mg/kg) BLOOD: EOSINOPHILIA

BEHAVIORAL: HEADACHE
American Journal of Medicine. Vol. 87, Pg. 589, 1989.
women TDLo oral 135mg/kg/3D-I (135mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Archives of Internal Medicine. Vol. 153, Pg. 1258, 1993.
women TDLo oral 280mg/kg/2W-I (280mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
American Journal of Kidney Diseases. Vol. 22, Pg. 598, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 6.09 (none)   EXP
log P (octanol-water) 0.28 (none)   EXP
Water Solubility 3.00E+04 mg/L 20 EXP
Vapor Pressure 1.65E-12 mm Hg 25 EST
Henry's Law Constant 5.09E-19 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.13E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.