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Cinoxacin

pharmaceutical raw materials
Cinoxacin structure

Cinoxacin 

structure
  • CAS No:

    28657-80-9

  • Formula:

    C12H10N2O5

  • Chemical Name:

    Cinoxacin

  • Synonyms:

    [1,3]Dioxolo[4,5-g]cinnoline-3-carboxylic acid,1-ethyl-1,4-dihydro-4-oxo-;1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid;Compound 64716;Cinoxacin;Cinobac;1-Ethyl-3-carboxy-6,7-methylenedioxy-4-cinnolone;Uronorm;Noxigram;NSC 304467;Cinobactin;1-Ethyl-4-oxo-1H,4H,7H-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid;1-Ethyl-4-oxo-1,4-dihydro-[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid

  • Categories:

    Active Pharmaceutical Ingredients  >  Synthetic Anti-infective Drugs

Description

Cinoxacin was an older synthetic antimicrobial related to the quinolone class of antibiotics, with activity similar to oxolinic acid and nalidixic acid.


Solid


Cinoxacin is a member of the class of cinnolines that is 6,7-methylenedioxycinnolin-4(1H)-one bearing an ethyl group at position 1 and a carboxylic acid group at position 3. An analogue of oxolinic acid, it has similar antibacterial actions. It was formerly used for the treatment of urinary tract infections. It has a role as an antibacterial drug and an antiinfective agent. It is a member of cinnolines, an oxo carboxylic acid and an oxacycle.|Synthetic antimicrobial related to oxolinic acid and nalidixic acid and used in urinary tract infections.|Synthetic antimicrobial related to OXOLINIC ACID and NALIDIXIC ACID and used in URINARY TRACT INFECTIONS.

Cinoxacin Basic Attributes

262.22

262.22

249-133-8

LMK22VUH23

756695|304467

DTXSID8022822

J - Antiinfectives for systemic use

2934999090

Characteristics

88.4

1.5

Solid

1.6±0.1 g/cm3

261 °C (decomp)

517.2±60.0 °C at 760 mmHg

266.6±32.9 °C

1.709

1 M NaOH: soluble 50mg/mL

LD50 in rats (mg/kg): 4160 orally; 900 i.v. (Narama)

148.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|152.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|165.2 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]

Safety Information

NONH for all modes of transport

2

JI4640000

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Toxicity

Oral, subcutaneous, and intravenous LD50 in the rat is 3610 mg/kg, 1380 mg/kg, and 860 mg/kg, respectively. Oral, subcutaneous, and intravenous LD50 in the mouse is 2330 mg/kg, 900 mg/kg, and 850 mg/kg, respectively. Symptoms following an overdose of cinoxacin may include gastrointestinal effects such as anorexia, nausea, vomiting, epigastric distress, and diarrhea; the severity of the epigastric distress and diarrhea are dose-related. Headache, dizziness, insomnia, photophobia, tinnitus, and a tingling sensation have also been reported in some patients.

60 to 80%

Drug Information

For the treatment of initial and recurrent urinary tract infections in adults caused by the following susceptible microorganisms: Escherichia coli, Proteus mirabilis, Proteus vulgaris, Klebsiella species (including K. pneumoniae), and Enterobacter species.|FDA Label

Cinoxacin is a synthetic antibacterial agent with in vitro activity against many gram-negative aerobic bacteria, particularly strains of the Enterobacteriaceae family. Cinoxacin inhibits bacterial deoxyribonucleic acid (DNA) synthesis, is bactericidal, and is active over the entire urinary pH range. Cross resistance with nalidixic acid has been demonstrated.

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)|Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

Rapidly absorbed after oral administration. While concurrent food intake may delay the drug absorption, the total drug absorption is not affected.

Hepatic, with approximately 30-40% metabolized to inactive metabolites.

While the mean serum half-life is 1.5 hours, the half-life may exceed 10 hours in case of renal impairment.

Evidence exists that cinoxacin binds strongly, but reversibly, to DNA, interfering with synthesis of RNA and, consequently, with protein synthesis. It appears to also inhibit DNA gyrase. This enzyme is necessary for proper replicated DNA separation. By inhibiting this enzyme, DNA replication and cell division is inhibited.

Acid, Azolinic

Cinoxacin Use and Manufacturing

Uses

antibacterial

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:262.22
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:262.05897142
Monoisotopic Mass:262.05897142
Topological Polar Surface Area:88.4
Heavy Atom Count:19
Complexity:449
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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