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Purity: ≥98%
Ciprofloxacin Hydrochloride hydrate (also known as Bay-09867) is a broad-spectrum, carboxyfluoroquinolone antibiotic/antimicrobial interfering with the bacterial DNA gyrase, inhibiting the DNA synthesis, and preventing bacterial cell growth. It shows MIC90 (minimal inhibitory concentrations for 90%) of between 0.008 and 2 μg/ml for Enterobacteriaceae, Pseudomonas aeruginosa, Haemophilus influenzae, Neisseria gonorrhoeae, streptococci, Staphylococcus aureus, and Bacteroidesfragilis strains. Ciprofloxacin inhibits topoisomerase IV as a primary topoisomerase target and gyrase as a secondary target.
| ln Vitro |
In tendon cells, ciprofloxacin (Bay-09867) hydrochloride monohydrate (5–50 μg/mL; 0–24 h) suppresses cell growth and induces cell cycle arrest at the G2/M phase[1]. With MIC90s of 0.03 μg/mL and 0.12 μg/mL, respectively, ciprofloxacin (Bay-09867) hydrochloride monohydrate exhibits strong action against Y. pestis and B. anthracis[2].
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| ln Vivo |
Y is protected from by ciprofloxacin (Bay-09867) hydrochloride monohydrate (30 mg/kg; ip; for 24 hours; BALB/c mice). pestis in the pneumonic plague model in mice[3]. By lowering LOX levels and raising MMP levels and activity in the aorta wall, ciprofloxacin (Bay-09867) hydrochloride monohydrate (100 mg/kg; ig; daily, for 4 weeks; C57BL/6J mice) accelerates aortic root expansion and raises the incidence of aortic dissection and rupture[4]. Ciprofloxacin (Bay-09867) hydrochloride monohydrate (100 mg/kg; ig; daily, for 4 weeks; C57BL/6J mice) causes mitochondrial dysfunction, cytosolic DNA sensor signaling activation, and DNA damage and release into the cytosol. Apoptosis and necroptosis in the aortic wall are increased by ciprofloxacin lactate[4].
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| Cell Assay |
Cell Viability Assay[1]
Cell Types: Tendon cells Tested Concentrations: 5, 10, 20 and 50 μg /mL Incubation Duration: 24 hrs (hours) Experimental Results: diminished the cellularity of tendon cells. Cell Cycle Analysis[1] Cell Types: Tendon cells Tested Concentrations: 50 μg/mL Incubation Duration: 24 hrs (hours) Experimental Results: Arrested cell cycle at the G2/M phase and inhibited cell division in tendon cells. Western Blot Analysis[1] Cell Types: Tendon cells Tested Concentrations: 50 μg/mL Incubation Duration: 0, 6, 12, 17 and 24 hrs (hours) Experimental Results: Down-regulated the expression of CDK-1 and cyclin B protein and mRNA. Up-regulated the expression of PLK-1 protein. |
| Animal Protocol |
Animal/Disease Models: balb/c (Bagg ALBino) mouse[3]
Doses: 30 mg/kg Route of Administration: intraperitoneal (ip)injection; for 24 hrs (hours) Experimental Results: decreased the lung bacterial load in murine model of pneumonic plague. Animal/Disease Models: C57BL/6J mice[4] Doses: 100 mg/kg Route of Administration: po (oral gavage); daily, for 4 weeks Experimental Results: Had aortic destruction that was accompanied by diminished LOX expression and increased MMP expression and activity. Animal/Disease Models: C57BL/ 6J mice[4] Doses: 100 mg/kg Route of Administration: po (oral gavage); daily, for 4 weeks Experimental Results: Caused mitochondrial DNA and nuclear DNA damage, leading to mitochondrial dysfunction and ROS production. Increased apoptosis and necroptosis in the aortic wall. |
| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation Amounts of ciprofloxacin in breastmilk are low. Fluoroquinolones such as ciprofloxacin have traditionally not been used in infants because of concern about adverse effects on the infants' developing joints. However, studies indicate little risk. The calcium in milk might decrease absorption of the small amounts of fluoroquinolones in milk, but insufficient data exist to prove or disprove this assertion. Use of ciprofloxacin is acceptable in nursing mothers with monitoring of the infant for possible effects on the gastrointestinal flora, such as diarrhea or candidiasis (thrush, diaper rash). Avoiding breastfeeding for 3 to 4 hours after a dose should decrease the exposure of the infant to ciprofloxacin in breastmilk. Maternal use of an ear drop or eye drop that contains ciprofloxacin presents negligible risk for the nursing infant. To substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue. ◉ Effects in Breastfed Infants A case of pseudomembranous colitis in a 2-month-old breastfed infant with a history of necrotizing enterocolitis was probably caused by maternal self-treatment with ciprofloxacin. Ciprofloxacin was used as part of multi-drug regimens to treat three pregnant women with multidrug-resistant tuberculosis throughout pregnancy and postpartum. Their three infants were breastfed (extent and duration not stated). At age 1.25, 1.8 and 3.9 years, the children were developing normally except for one who had failure to thrive, possibly due to tuberculosis contracted after birth. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. |
| References |
[1]. Tsai WC, et, al. Ciprofloxacin-mediated cell proliferation inhibition and G2/M cell cycle arrest in rat tendon cells. Arthritis Rheum. 2008 Jun;58(6):1657-63.
[2]. Steenbergen J, et, al. In Vitro and In Vivo Activity of Omadacycline against Two Biothreat Pathogens, Bacillus anthracis and Yersinia pestis. Antimicrob Agents Chemother. 2017 Apr 24;61(5):e02434-16. [3]. Hamblin KA, et, al. Inhaled Liposomal Ciprofloxacin Protects against a Lethal Infection in a Murine Model of Pneumonic Plague. Front Microbiol. 2017 Feb 6;8:91. [4]. LeMaire SA, et, al. Effect of Ciprofloxacin on Susceptibility to Aortic Dissection and Rupture in Mice. JAMA Surg. 2018 Sep 1;153(9):e181804. |
| Additional Infomation |
Ciprofloxacin hydrochloride hydrate is the monohydrate form of ciprofloxacin monohydrochloride. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an antibacterial drug, a topoisomerase IV inhibitor and an antiinfective agent. It contains a ciprofloxacin hydrochloride (anhydrous).
Ciprofloxacin is an antibacterial prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment and prevention of several infections caused by certain types of bacteria, for example, certain urinary tract infections, lower respiratory tract infections, and skin infections. Some bacterial infections can be opportunistic infections (OIs) of HIV. An OI is an infection that occurs more frequently or is more severe in people with weakened immune systems—such as people with HIV—than in people with healthy immune systems. Ciprofloxacin Hydrochloride is the hydrochloride salt form of ciprofloxacin, a fluoroquinolone related to nalidixic acid with antibacterial activity. Ciprofloxacin hydrochloride exerts its bactericidal effect by interfering with the bacterial DNA gyrase, thereby inhibiting the DNA synthesis and preventing bacterial cell growth. A broad-spectrum antimicrobial carboxyfluoroquinoline. See also: Ciprofloxacin (has active moiety); Ciprofloxacin; Ciprofloxacin Hydrochloride (component of); Ciprofloxacin hydrochloride; hydrocortisone (component of) ... View More ... Drug Indication Treatment of chronic pulmonary infections caused by Pseudomonas aeruginosa |
| Molecular Formula |
C17H21CLFN3O4MOLECULARWEIGHT
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|---|---|
| Molecular Weight |
385.8177
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| Exact Mass |
385.12
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| CAS # |
86393-32-0
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| Related CAS # |
Ciprofloxacin;85721-33-1;Ciprofloxacin monohydrochloride;93107-08-5;Ciprofloxacin-d8 hydrochloride monohydrate
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| PubChem CID |
62998
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| Appearance |
Typically exists as solid at room temperature
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| Boiling Point |
581.8ºC at 760 mmHg
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| Melting Point |
318-320 °C
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| Flash Point |
305.6ºC
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| LogP |
2.714
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
26
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| Complexity |
571
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Cl.O=C(C1C(=O)C2C(=CC(N3CCNCC3)=C(C=2)F)N(C2CC2)C=1)O.O
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| InChi Key |
ARPUHYJMCVWYCZ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C17H18FN3O3.ClH.H2O/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);1H;1H2
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| Chemical Name |
1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrate;hydrochloride
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~5 mg/mL (~12.96 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.5 mg/mL (1.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.5 mg/mL (1.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 5.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 0.5 mg/mL (1.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5919 mL | 12.9594 mL | 25.9188 mL | |
| 5 mM | 0.5184 mL | 2.5919 mL | 5.1838 mL | |
| 10 mM | 0.2592 mL | 1.2959 mL | 2.5919 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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