シプロフロキサシン

1-シクロプロピル-1,4-ジヒドロ-6-フルオロ-4-オキソ-7-(1-ピペラジニル)-3-キノリンカルボン酸 · 1,4-ジヒドロ-1-シクロプロピル-6-フルオロ-4-オキソ-7-(1-ピペラジニル)キノリン-3-カルボン酸 · 1-シクロプロピル-6-フルオロ-1,4-ジヒドロ-4-オキソ-7-(1-ピペラジニル)キノリン-3-カルボン酸 · シフロキノン · 1-シクロプロピル-6-フルオロ-4-オキソ-7-(1-ピペラジニル)-1,4-ジヒドロキノリン-3-カルボン酸 · 1-シクロプロピル-6-フルオロ-4-オキソ-7-(1-ピペラジニル)-1,4-ジヒドロ-3-キノリンカルボン酸 · フロキシール · シフロサシン

https://huagongshe.com/ja/chemical/2764

識別子と物理属性

CAS No.	85721-33-1
分子式	C17H18FN3O3
平均分子量	331.34 g/mol
単同位体質量	331.13321966 g/mol
SMILES	O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O
InChIKey	MYSWGUAQZAJSOK-UHFFFAOYSA-N
PubChem CID	2764
ChEMBL	CHEMBL8
ChEBI	CHEBI:100241
EC No.	617-751-0
DTXSID	DTXSID8022824
現地名	シプロフロキサシン

化学・物理的性質

XLogP	-1.1
極性表面積	72.9
水素結合供与体数	2
水素結合受容体数	7
回転可能結合数	3
重原子数	24
形式電荷	0
複雑度	571
医薬品	Pharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Anti infectives for systemic use -> Antibacterials for systemic usePharmaceuticals -> Listed in ZINC15Pharmaceuticals -> AntibioticsPharmaceuticals -> Antibiotics (Quinolones)
pH	pH range for the 1.0% aqueous concentrates in vials is 3.3 to 3.9the pH range for the 0.2% ready-for-use infusion solutions is 3.5 to 4.6
LogP（分配係数）	log Kow = 0.28 (non-ionized)2.3
Color/Form	Faint to light yellow crystalline powder
溶解度	<1mg/mLWater Solubility: approx 36 mg/ml @ 25 °C /Ciprofloxacin hydrochloride/Soluble in dilute (0.1N) hydrochloric acidpractically insoluble in ethanolIn water, 30,000 mg/L at 20 °C1.35e+00 g/L25mg/mlで0.1N HClに可溶。 DMSOに難溶86mg/L(25℃)
Human Drugs	Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsQuinolonesFluoroquinolonesFDA approved drugs -> Active ingredientPharmaceuticalsEar, nose and throat medicines [c]
Decomposition	When heated to decomposition material emits toxic fumes of /nitrogen oxides and hydrogen fluoride/.
融点	255-257 °C225-257 °C, decomposes255 - 257 °C255-257°C
Physical Description	Solid
Stability/Shelf Life	Ciprofloxacin hydrochloride ophthalmic solution should be stored in tight, light-resistant containers at 2-25 °C. When stored as directed, the commercially available ophthalmic solution has an expiration date of 24 months following the date of manufacture. Ciprofloxacin hydrochloride ophthalmic ointment should be stored at 2-25 °C. Ciprofloxacin hydrochloride and hydrocortisone otic suspension should be stored in light-resistant containers below 25 °Cfreezing should be avoided. Ciprofloxacin hydrochloride and dexamethasone otic suspension should be stored at 15-30 °C and protected from lightfreezing should be avoided.Ciprofloxacin hydrochloride tablets should be stored in tight containers at a temperature <30 °C. The drug should be protected from intense uv light. Ciprofloxacin microcapsules for oral suspension & the diluent provided by the manufacturer should be stored at <25 °C & protected from freezing. Following mixture with the diluent, ciprofloxacin oral suspension should be stored at <30 °C & protected from freezing, & is stable for 14 days when stored at room temperature or in a refrigerator.The compatibility of 10 mg/ml ciprofloxacin injection in 0.9% sodium chloride and 5% dextrose soln were /mixed/ with other injectable drugs, including amikacin sulfate, aminophylline, clindiamycin phosphate, gentamicin phosphate, tobramycin sulfate and metronidazole ... soln ... were stored for up to 48 hr at room temperature and under refrigeration. Eight hr after amikacin was mixed with ciprofloxacin in sodium chloride soln and refrigerated, the drug concn was 89% of the original. Admixtures of the precipitate formed immediately whenever ciprofloxacin was mixed with aminophylline or clindamycin. /Results indicate/ that ciprofloxacin was incompatable with aminophylline and clindamycin, and that its compatibility with amikacin depended upon the vehicle and storage temperature.... The physical and chemical compatibilities of ciprofloxacin lactate infusion with other commonly used iv admin drugs /was investigated/ Ciprofloxacin lactate injection in a commercially available concn of 2 mg/ml was mixed with 15 iv drugs during a simulated Y-site injection. Of the 15 drugs /examined/ , only heparin, furosemide and teicoplanin were found to be incompatible with ciprofloxacin. ... /Ciprofloxacin lactate/
Ionization Efficiency	Positive3.12.7Agilent XCTElectrospray ionizationformic acid (5.3nM)
Dissociation Constants	6.168.626.256.09pKa = 6.09 (carboxylic acid group)pKa = 8.74 (nitrogen on piperazinyl ring)
沸点	581.8±50.0 °C(Predicted)
密度	1.461±0.06 g/cm3(Predicted)
貯蔵条件	Keep in dark place,Inert atmosphere,2-8°C
pKa（酸解離定数）	pKa 4.04 (Uncertain)
外観・状態	粉
色	White to Almost white
Merck	14,2314
BRN	3568352
主な用途	環境
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
SMILES	N1(C2CC2)C2=C(C=C(F)C(N3CCNCC3)=C2)C(=O)C(C(O)=O)=C1
CAS データベース	85721-33-1(CAS DataBase Reference)
EPAの化学物質情報	Ciprofloxacin (85721-33-1)

化学的特性

White Powder

安全性と法規制

消火手順
GHS 分類	This chemical does not meet GHS hazard criteria for 64.7% (66 of 102) of all reports.H412 (26.5%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P273, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 102 reports by companies from 11 notifications to the ECHA C&L Inventory.
火災の可能性	This material is assumed to be combustible.
FDA 要件	The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including ciprofloxacin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including ciprofloxacin hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Ciprofloxacin hydrochloride/
Special Reports	Extensive pharmacologic & clinical development of quinolone antimicrobial agents has resulted in improved antimicrobial activity, pharmacokinetic features, toxicity, & drug-drug interaction profiles. Nalidixic acid & other early quinolones had limited use due to poor pharmacokinetics, relatively narrow antimicrobial spectrum of activity, & frequent adverse effects. Beginning with the development of fluoroquinolones, such as norfloxacin & ciprofloxacin, in the 1980s, the agents assumed a greatly expanded clinical role because of their broad antimicrobial spectrum of action, improved pharmacokinetic properties, & more acceptable safety profile. Although the pharmacokinetics & efficacy of the drugs have improved significantly, a major area of continued emphasis is to further reduce the frequency & severity of adverse events & drug-drug interactions. Older agents such as ciprofloxacin & ofloxacin are still extensively prescribed, but the focus of this article is on the newer fluoroquinolones (levofloxacin & other drugs that have been approved or have been under investigation since approx 1997).[Fish DNPharmacotherapy 21 (10 Pt 2): 253S-272S (2001)]
Toxic Combustion Products	Emits toxic fumes under fire conditions.
Hazard Classes and Categories	Aquatic Chronic 3 (26.5%)

用途

解説

シプロフロキサシン，C17H18FN3O3(331.34)．キノロン系抗菌薬．7-クロロ-1-シクロプロピル-6-フルオロ-1,4-ジヒドロ-4-オキソキノリン-3-カルボン酸をピペラジンと縮合させると得られる．分解点255～257 ℃．幅広い抗菌スペクトルをもち，抗菌力も強い．細菌のDNAジャイレースに作用してDNAの合成を阻害する．2001年，アメリカでのバイオテロリズムでは，肺炭疽(そ)症の予防と治療に使用された．

用途

シプロフロキサシンは広域抗生物質であり、グラム陰性、グラム陽性のいずれのバクテリアにも活性である。デオキシリボ核酸二本鎖の切断再結合を行う酵素であるDNAジャイレース（DNAトポイソメラーゼの一種）に結合し、DNAの複製を阻害することで抗菌作用を示す。DNAの複製が阻害されることで、バクテリアは細胞分裂ができなくなる。

説明

Ciprofloxacin is a quinolone antibacterial related to recently marketed norfloxacin (10), ofloxacin (2), pefloxacin (2) and enoxacin. It has a broad spectrum of activity against gram-positive and gram-negative bacteria, and is useful in the treatment of urinary and upper respiratory tract infections.

来歴

Ciprofloxacin(original trade name:Cipro) is one of the world's most widely prescribed antibiotics for bacterial infections. Ciprofloxacin was discovered by scientists at Bayer Pharmaceuticals in the 1980s. In 1987, Bayer received US Food and Drug Administration approval for orally administered ciprofloxacin; the intravenous form was approved in 1991. It is on the World Health Organization's List of Essential Medicines.

使用

Ciprofloxacin is used in the treatment of infections from a wide range of aerobic gram-positive and aerobic gramnegative microorganisms. It has been shown to be effective against inhalational anthrax and reduce the incidence or progression of disease following exposure to aerosolized Bacillus anthracis. It is also used in select respiratory infections, urinary tract infections, typhoid fever, some sexually transmitted diseases, and septicemia. Infectious diarrhea may be caused by organisms found in food or water and transferred by person-to-person contact. This may have a devastating effect, globally, especially in immunocompromised individuals. Ciprofloxacin is effective against those organisms that may contribute to infectious diarrhea, such as Escherichia coli (enterotoxigenic strains), Campylobacter jejuni, and select strains of Shigella; and is utilized when antibacterial therapy is medically indicated. Ciprofloxacin has also been utilized as a secondary agent in the treatment of tuberculosis.