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Drug

D0259 | Ciprofloxacin

Molecular Formula C17H18FN3O3
Molecular Weight 331.34
Structure
State solid
Clearance The average renal clearance after a 250mg oral dose is 5.08mL/min\*kg.[A178858] Following a 100mg intravenous dose, the average total clearance is 9.62mL/min\*kg, average renal clearance is 4.42mL/min\*kg, and average non renal clearance is 5.21mL/min\*kg.[A178858]
Volume of distribution Cirpofloxacin follws a 3 compartment distribution model with a central compartment volume of 0.161L/kg[A178858] and a total volume of distribution of 2.00-3.04L/kg.[A178876]
Route of elimination 27% of an oral dose was recovered unmetabolized in urine compared to 46% of an intravenous dose.[A178858] Collection of radiolabelled ciprofloxacin resulted in 45% recovery in urine and 62% recovery in feces.[A178876]
Protein binding 20-40%.[Label,A178876]
Half life The average half life following a 250mg oral dose was 4.71 hours and 3.65 hours following a 100mg intravenous dose.[A178858] Generally the half life is reported as 4 hours.[Label,A178858]
Absorption A 250mg oral dose of ciprofloxacin reaches an average maximum concentration of 0.94mg/L in 0.81 hours with an average area under the curve of 1.013L/h\*kg.[A178858] The FDA reports an oral bioavailability of 70-80%[Label,A820] while other studies report it to be approximately 60%.[A178858] An early review of ciprofloxacin reported an oral bioavailability of 64-85% but recommends 70% for all practical uses.[A178876]

S

J

S03AA07 Ciprofloxacin


[S03AA] Antiinfectives


[S03A] ANTIINFECTIVES


[S03] OPHTHALMOLOGICAL AND OTOLOGICAL PREPARATIONS


[S] Sensory organs

S02AA15 Ciprofloxacin


[S02AA] Antiinfectives


[S02A] ANTIINFECTIVES


[S02] OTOLOGICALS


[S] Sensory organs

S01AE03 Ciprofloxacin


[S01AE] Fluoroquinolones


[S01A] ANTIINFECTIVES


[S01] OPHTHALMOLOGICALS


[S] Sensory organs

J01RA12 Ciprofloxacin and ornidazole


[J01RA] Combinations of antibacterials


[J01R] COMBINATIONS OF ANTIBACTERIALS


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J01RA11 Ciprofloxacin and tinidazole


[J01RA] Combinations of antibacterials


[J01R] COMBINATIONS OF ANTIBACTERIALS


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J01RA10 Ciprofloxacin and metronidazole


[J01RA] Combinations of antibacterials


[J01R] COMBINATIONS OF ANTIBACTERIALS


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

J01MA02 Ciprofloxacin


[J01MA] Fluoroquinolones


[J01M] QUINOLONE ANTIBACTERIALS


[J01] ANTIBACTERIALS FOR SYSTEMIC USE


[J] Antiinfectives for systemic use

Toxicity Dose Time Species Model Method Action Positive criterion Reference
MEMBRANE POTENTIAL > 400 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 195.0 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. increase EC20 36
RESPIRATION ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
RESPIRATION decrease 307
ELECTRON TRANSPORT CHAIN decrease 307
GENERATION OF LACTATE Increase 307
SWELLING > 400 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36
ROS PRODUCTION Increase 307
MITOCHONDRIAL DNA METABOLIC PROCESS decrease 307
MITOCHONDRIAL DNA METABOLIC PROCESS decrease 307

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase Inhibition 307
Succinate dehydrogenase ND 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. Negative EC20 36
Succinate dehydrogenase Inhibition 307
Cytochrome c oxidase Inhibition 307
Reactive oxygen species increase 307
Cytochrome c > 400 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Warning

Aggregated GHS information provided by 97 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


Reported as not meeting GHS hazard criteria by 56 of 97 companies. For more detailed information, please visit ECHA C&L website


Of the 9 notification(s) provided by 41 of 97 companies with hazard statement code(s):


H319 (14.63%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


H361 (21.95%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]


H412 (63.41%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


 P201, P202, P264, P273, P280, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
rat LD50 subcutaneous > 1gm/kg (1000mg/kg) Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992.
mouse LD50 intraperitoneal 1165mg/kg (1165mg/kg) Ensho. Japanese Journal of Inflammation. Vol. 11, Pg. 343, 1991.
mouse LD50 oral 5gm/kg (5000mg/kg) Journal of Medicinal Chemistry. Vol. 33, Pg. 1344, 1990.
women TDLo oral 40mg/kg/2D-I (40mg/kg) American Journal of Medicine. Vol. 87, Pg. 589, 1989.
mouse LD50 intravenous 122mg/kg (122mg/kg) 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 intravenous 207mg/kg (207mg/kg) Korean Journal of Toxicology. Vol. 8, Pg. 161, 1993.
man TDLo oral 21mg/kg/3D-I (21mg/kg) Annals of Pharmacotherpy. Vol. 29, Pg. 84, 1995.
women TDLo oral 10mg/kg (10mg/kg) Allergy. Vol. 50(Suppl,
women TDLo multiple routes 40mg/kg/6D-I (40mg/kg) Acta Clinica Belgica. Vol. 49, Pg. 173, 1994.
man TDLo oral 21429ug/kg/3D (21.429mg/kg) Annals of Pharmacotherpy. Vol. 26, Pg. 930, 1992.
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.
man TDLo oral 200mg/kg (200mg/kg) Annals of Pharmacotherpy. Vol. 28, Pg. 805, 1994.
man LDLo oral 5714ug/kg/2D- (5.714mg/kg) Lancet. Vol. 343, Pg. 738, 1994.
man TDLo oral 129mg/kg/6D-I (129mg/kg) behavioral: regidity Journal of Clinical Psychiatry. Vol. 54, Pg. 115, 1993.
women TDLo oral 280mg/kg/2W-I (280mg/kg) American Journal of Kidney Diseases. Vol. 22, Pg. 598, 1993.
mouse LD50 subcutaneous > 1gm/kg (1000mg/kg) Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 27, Pg. 297, 1992.

  • Abdominal infection

  • Acute sinusitis

  • Anthrax

  • Arthropathy

  • Back pain

  • Bacteraemia

  • Bacterial prostatitis

  • Bladder pain

  • Blepharitis

  • Body temperature increased

  • Bronchitis chronic

  • Cervicitis

  • Conjunctivitis

  • Conjunctivitis bacterial

  • Conjunctivitis infective

  • Convulsion

  • Cystic fibrosis

  • Cystitis noninfective

  • Drug interaction

  • Dysentery

  • Fasting

  • Gastroenteritis

  • Gastrointestinal infection

  • Glucose-galactose malabsorption

  • Gonorrhoea

  • Hepatic failure

  • Influenza

  • Liver disorder

  • Lower respiratory tract infection

  • Osteoarthritis

  • Osteomyelitis

  • Overgrowth bacterial

  • Paratyphoid fever

  • Peritonitis

  • Pneumonia anthrax

  • Pneumonia streptococcal

  • Prostatitis

  • Pseudomonas infection

  • Renal failure

  • Renal function test abnormal

  • Respiratory tract infection

  • Salpingo-oophoritis

  • Soft tissue infection

  • Tuberculosis

  • Typhoid fever

  • Ulcerative keratitis

  • Urethritis

  • Urethritis noninfective

  • Urinary tract infection

  • Agitation (0.011)

  • Vulvovaginal pruritus (0.01)

  • Dermatitis

  • Diarrhoea

  • Discomfort

  • Dizziness

  • Erythema

  • Fungal infection

  • Headache

  • Hyperaemia

  • Nausea

  • Pruritus

  • Rash

  • Sensation of foreign body

  • Vomiting

  • Vulvovaginal candidiasis

  • Vulvovaginal mycotic infection

    • 1-CYCLOPROPYL-6-FLUORO-4-OXO-7-PIPERAZIN-1-YL-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID 1-Cyclopropyl-6-fluoro-1,4-dihydro 4-oxo-7-[1-piperazinyl)-quinoline-3-carboxylic Acid 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7- (1-piperazinyl)-3-quinoline-carboxylic acid
    1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3- quinolinecarboxylic acid 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline-carboxylic acid 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid
    1-Cyclopropyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline carboxylic acid 1-Cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid 1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic acid
    1-Cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline -3-carboxylic acid 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinoline-3-carboxylic acid
    1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1piperazinyl)-3quinolinecarboxylic acid 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)-quinoline-3-carboxylic acid
    1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline-3-carboxylic acid hydrochloride 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-quinoline-3-carboxylic acid
    1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid 1-cyclopropyl-6-fluoro-4-oxo-7-piperazinylhydroquinoline-3-carboxylic acid 1-cyclopropyl-6-fluoro-7-(piperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
    1-cyclopropyl-6-fluoro-7-hexahydro-1-pyrazinyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid 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)-
    3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, hydrochloride 3-Quinolinecarboxylic acid,1,4-dihydro-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl) 3-Quinolinecarboxylicacid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-
    5E8K9I0O4U 721C331 85721-33-1
    A-8526 AB0011928 AB1009412
    AC-7613 AK163192 AKOS000269653
    ALBB-015909 ANHYDROUS CIPROFLOXACIN ARONIS020379
    Alcon Cilox AuriPro BAY q 3939
    BAY-Q-3939 BAY-o 9867 BAYQ3939
    BBL005612 BCP28586 BDBM21690
    BIDD:GT0205 BPBio1_000140 BRD-K04804440-311-02-3
    BRN 3568352 BSPBio_000126 BSPBio_003344
    Bacquinor Baflox Bay 09867
    Bay o 9867 Bay o 9867 (*Hydrochloride*) Bay-09867
    Bernoflox Bi-Cipro C05349
    C17H18FN3O3 CAS-93107-08-5 CBMicro_048498
    CCG-39345 CCRIS 5241 CHEBI:100241
    CHEMBL8 CIPRO IN DEXTROSE 5% IN PLASTIC CONTAINER CIPRO IN SODIUM CHLORIDE 0.9% IN PLASTIC CONTAINER
    CIPROFLOXACIN EXTENDED RELEASE CPD000471901 CPFX
    CS-2410 CTK3E8144 Certified Reference Material
    Cetraxal Ciflox Cifloxin
    Cilab Ciloxan (*Hydrochloride*) Ciplus
    Ciprecu Ciprine Ciprinol
    Cipro Cipro (*Hydrochloride*) Cipro (TN)
    Cipro IV Cipro XR Ciprobay
    Ciprobay Uro Ciprocinol Ciprodar
    Ciproflox Ciprofloxacin (Cipro) Ciprofloxacin (JP17/USP/INN)
    Ciprofloxacin Hydrchloride Ciprofloxacin [USAN:INN:BAN] Ciprofloxacin [USAN:USP:INN:BAN]
    Ciprofloxacin monohydrochloride Ciprofloxacin, 98% Ciprofloxacin, >=98.0% (HPLC)
    Ciprofloxacin, Antibiotic for Culture Media Use Only Ciprofloxacin, European Pharmacopoeia (EP) Reference Standard Ciprofloxacin, Pharmaceutical Secondary Standard
    Ciprofloxacin, United States Pharmacopeia (USP) Reference Standard Ciprofloxacin, VETRANAL(TM), analytical standard Ciprofloxacin,(S)
    Ciprofloxacina Ciprofloxacine Ciprofloxacine [INN-French]
    Ciprofloxacino Ciprofloxacino [INN-Spanish] Ciprofloxacinum
    Ciprofloxacinum [INN-Latin] Ciprogis Ciprolin
    Ciprolon Cipromycin Ciproquinol
    Ciprowin Ciproxan Ciproxin
    Ciproxina Ciproxine Ciriax
    Citopcin Cixan Corsacin
    Cycin Cyprobay D00186
    DB00537 DTXSID8022824 DivK1c_000095
    Eni FT-0601635 Fimoflox
    HMS1922E18 HMS2090O07 HMS2093I03
    HMS500E17 HSDB 6987 HY-B0356
    IDI1_000095 Ipiflox Italnik
    J10137 KBio1_000095 KBio2_000642
    KBio2_003210 KBio2_005778 KBio3_002846
    KBioGR_001567 KBioSS_000642 KS-000002BQ
    KS-00004C43 KS-5006 LS-141563
    Linhaliq Linhaliq [Liposomal Formulation] Loxan
    MCULE-8631780654 MFCD00185755 MLS001336035
    MLS006011837 MYSWGUAQZAJSOK-UHFFFAOYSA-N NCGC00016959-01
    NCGC00016959-02 NCGC00016959-03 NCGC00016959-04
    NCGC00016959-05 NCGC00016959-07 NCGC00095058-01
    NCGC00095058-02 NCGC00178128-01 NINDS_000095
    NSC-758467 NSC620634 NSC758467
    Oprea1_008239 Oprea1_313572 Otiprio
    Pharmakon1600-01503614 Prestwick0_000113 Prestwick1_000113
    Prestwick2_000113 Prestwick3_000113 Probiox
    Proflaxin Proflox Proksi 250
    Proksi 500 Q256602 Quinolid
    Quintor RKL10073 Rancif
    Roxytal SAM002264604 SBB012554
    SBI-0048462.P003 SC-17889 SCHEMBL2900
    SMP1_000125 SMR000471901 SPBio_001474
    SPBio_002065 SPECTRUM1503614 SR-05000001863
    SR-05000001863-1 SR-05000001863-3 ST024751
    ST24046329 STK021082 Septicide
    Sophixin Ofteno Spectrum2_001567 Spectrum3_001872
    Spectrum4_000874 Spectrum5_001089 Spectrum_000162
    Spitacin Superocin TX-017484
    UNII-5E8K9I0O4U Unex Velmonit
    Z56933707 ZINC20220 Zumaflox
    ciprofloxacin ciprofloxacin-cipro rubrum
    s2027

    DrugBank Name Ciprofloxacin
    DrugBank DB00537
    CAS Number 85721-33-1, 86393-32-0
    PubChem Compound 2764
    KEGG Compound ID C05349
    KEGG Drug D00186
    PubChem.Substance 46504733
    ChEBI 100241
    PharmGKB PA449009
    ChemSpider 2662
    BindingDB 21690.0
    TTD DAP001360
    Wikipedia Ciprofloxacin
    HET CPF
    DPD 93|8327