MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 317534 | Name: Cinoxacin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cinoxacin was an older synthetic antimicrobial related to the quinolone class of antibiotics with activity similar to oxolinic acid and nalidixic acid. It was commonly used thirty years ago to treat urinary tract infections in adults. There are reports that cinoxacin had also been used to treat initial and recurrent urinary tract infections and bacterial prostatitis in dogs however this veterinary use was never approved by the FDA. In complicated UTI, the older gyrase-inhibitors such as cinoxacin are no longer indicated.

Chemical Structure

Cinoxacin
Cinoxacin
CAS#28657-80-9

Theoretical Analysis

MedKoo Cat#: 317534

Name: Cinoxacin

CAS#: 28657-80-9

Chemical Formula: C12H10N2O5

Exact Mass: 262.0590

Molecular Weight: 262.22

Elemental Analysis: C, 54.97; H, 3.84; N, 10.68; O, 30.51

Price and Availability

Size Price Availability Quantity
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Cinoxacin; Cinobac; Compound 64716; Cinoxacine; Cinoxacino; Cinoxacinum;Acid, Azolinic; Azolinic Acid;
IUPAC/Chemical Name
1-Ethyl-1,4-dihydro-4-oxo[1,3]dioxolo[4,5-g]cinnoline-3-carboxylic acid
InChi Key
VDUWPHTZYNWKRN-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H10N2O5/c1-2-14-7-4-9-8(18-5-19-9)3-6(7)11(15)10(13-14)12(16)17/h3-4H,2,5H2,1H3,(H,16,17)
SMILES Code
CCN1C2=CC3=C(C=C2C(=O)C(=N1)C(=O)O)OCO3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 262.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Quercia O, Rafanelli S, Emiliani F, Stefanini GF. Anaphylactic reaction to cinoxacin: report of one case associated with inferior acute myocardial infarction. Eur Ann Allergy Clin Immunol. 2003 Feb;35(2):61-3. PubMed PMID: 12674041. 2: López-Gresa MP, Ortiz R, Perelló L, Latorre J, Liu-González M, García-Granda S, Pérez-Priede M, Cantón E. Interactions of metal ions with two quinolone antimicrobial agents (cinoxacin and ciprofloxacin). Spectroscopic and X-ray structural characterization. Antibacterial studies. J Inorg Biochem. 2002 Sep 30;92(1):65-74. PubMed PMID: 12230989. 3: Parshikov IA, Moody JD, Heinze TM, Freeman JP, Williams AJ, Sutherland JB. Transformation of cinoxacin by Beauveria bassiana. FEMS Microbiol Lett. 2002 Aug 27;214(1):133-6. PubMed PMID: 12204384. 4: Sesia G, Cauda F, Alladio F. [Comparison of efficacy and tolerability among 3 quinolones in the treatment of lower urinary tract infections (cinoxacin versus ciprofloxacin and pefloxacin]. Minerva Urol Nefrol. 1992 Jul-Sep;44(3):217-8. Italian. PubMed PMID: 1492275. 5: Cristiano P, Morelli G, Simioli F, Iovene MR, Della Vittoria Scarpati M, Manguso L. [Comparative evaluation of norfloxacin and cinoxacin in the therapy of complicated infections of the urinary tract]. Minerva Med. 1989 Apr;80(4):393-5. Italian. PubMed PMID: 2657499. 6: Izumi T, Nagayama T, Kitagawa T. Protein binding of quinolonecarboxylic acids. II. Spectral changes on the interaction of cinoxacin, nalidixic acid and pipemidic acid with human and rat albumins. Chem Pharm Bull (Tokyo). 1989 Mar;37(3):746-52. PubMed PMID: 2752488. 7: Pino A, Maura A, Grillo P. Absence of cinoxacin-induced DNA fragmentation and mutations in the rat granuloma pouch. Environ Mol Mutagen. 1989;13(2):112-5. PubMed PMID: 2917551. 8: Bardi M, Manzoni A. [Treatment of postoperative urinary infections in obstetrics and gynecology with cinoxacin]. Clin Ter. 1988 Nov 15;127(3):185-8. Italian. PubMed PMID: 2976355. 9: Pfau A, Sacks TG, Shapiro M. Prevention of recurrent urinary tract infections in premenopausal women by post-coital administration of cinoxacin. J Urol. 1988 Jun;139(6):1250-2. PubMed PMID: 3286892. 10: Seppänen J. Cinoxacin vs trimethoprim--safety and efficacy in the prophylaxis of uncomplicated urinary tract infections. Drugs Exp Clin Res. 1988;14(10):669-71. PubMed PMID: 3246212. 11: Hayashi Y, Terao E, Yamasaki I. [Study of clinical efficacy and safety of long-term cinoxacin therapy of chronic urogenital organ infection]. Hinyokika Kiyo. 1987 May;33(5):799-805. Japanese. PubMed PMID: 3661347. 12: Goldstein EJ, Kahn RM, Alpert ML, Ginsberg BP, Greenway FL, Citron DM. Ciprofloxacin versus cinoxacin in therapy of urinary tract infections. A randomized, double-blind trial. Am J Med. 1987 Apr 27;82(4A):284-7. PubMed PMID: 3555049. 13: Aimè G, Governa M, Polledro P. [Comparative evaluation of cinoxacin, cotrimoxazole and pipemidic acid in recurrent infections of the lower urinary tract in long-term therapy]. Minerva Urol Nefrol. 1987 Apr-Jun;39(2):129-34. Italian. PubMed PMID: 3498226. 14: Pennisi M, Viscusi G, Salanitri G, Cammarata E, Gazzo G. [Comparative clinical study of the antibacterial activity of cinoxacin and norfloxacin in urinary tract infections]. Minerva Urol Nefrol. 1987 Jan-Mar;39(1):51-6. Italian. PubMed PMID: 3616862. 15: Digranes A, Dibb WL, Benonisen E. In vitro activities of ciprofloxacin, ofloxacin, norfloxacin and rosoxacin compared with cinoxacin and trimethoprim. Chemotherapy. 1985;31(6):466-71. PubMed PMID: 2934234. 16: Martorana G, Giberti C, Damonte P. [Preventive treatment of recurrent cystitis in women. Double-blind randomized study using cinoxacin and placebo]. Minerva Urol Nefrol. 1984 Jan-Mar;36(1):43-9. Italian. PubMed PMID: 6398519. 17: Burt RA. Review of adverse reactions associated with cinoxacin and other drugs used to treat urinary tract infections. Urology. 1984 Jan;23(1):101-7. PubMed PMID: 6362163. 18: Heessen FW, Muytjens HL. In vitro activities of ciprofloxacin, norfloxacin, pipemidic acid, cinoxacin, and nalidixic acid against Chlamydia trachomatis. Antimicrob Agents Chemother. 1984 Jan;25(1):123-4. PubMed PMID: 6230988; PubMed Central PMCID: PMC185448. 19: Brogard JM, Comte F, Lavillaureix J. Comparative pharmacokinetic profiles of cinoxacin and pipemidic acid in humans. Eur J Drug Metab Pharmacokinet. 1983 Jul-Sep;8(3):251-9. PubMed PMID: 6653617. 20: Vuye A. In vitro comparison of norfloxacin with nalidixic acid, cinoxacin and oxolinic acid. Arzneimittelforschung. 1983;33(12):1623-7. PubMed PMID: 6230083.