Ciprofloxacin

A broad-spectrum fluoroquinolone antibacterial agent used to treat susceptible bacterial infections, including urinary tract infections, gastrointestinal infections, certain respiratory infections, and complicated skin, bone, and joint infections. Ciprofloxacin inhibits bacterial DNA gyrase and topoisomerase IV, preventing DNA replication, transcription, and chromosome segregation, resulting in bactericidal activity. It is particularly active against many Gram-negative bacteria, including Pseudomonas aeruginosa. Available in oral, intravenous, ophthalmic, and otic formulations, ciprofloxacin carries important warnings for tendinitis and tendon rupture, peripheral neuropathy, central nervous system effects, and exacerbation of myasthenia gravis

CAS Number: 85721-33-1

Molecular Mass: 331.34 g/mol

Formula: C₁₇H₁₈FN₃O₃

Smiles: O=C(O)c1cn(C2CC2)c2cc(N3CCNCC3)c(F)cc2c1=O

Synonymes:

Ciprofloxacin, ciprofloxacin, 85721-33-1, Ciprofloxacine, Ciprobay, Cipro, Ciprofloxacina, 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid, Ciprofloxacino, Ciprofloxacinum, 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid, Ciprocinol, Bacquinor, Cifloxin, Ciprodar, Otiprio, BAY q 3939, CPFX, BAYQ3939, 1-Cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-3-quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid, 1-CYCLOPROPYL-6-FLUORO-4-OXO-7-PIPERAZIN-1-YL-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID, Velmonit, NSC-758467, 5E8K9I0O4U, CIPRO IN DEXTROSE 5% IN PLASTIC CONTAINER, BAY O 9867 FREE BASE, BAY-O-9867 FREE BASE, BAY-Q-3939, CIPRO IN SODIUM CHLORIDE 0.9% IN PLASTIC CONTAINER, 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, Bay 09867, DTXSID8022824, CHEBI:100241, 3-Quinolinecarboxylic acid, 1,4-dihydro-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-, 1-Cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic acid, 1-cyclopropyl-6-fluoro-7-hexahydro-1-pyrazinyl-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid, 1-Cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, Ciprofloxacin In Dextrose 5%, RefChem:6412, Ciprofloxacin in Dextrose, ciprofloxacin by-compound a, Ciprofloxacin In Dextrose 5% In Plastic Container, Bay09867, ciprofloxacin desfluoro-compound, DTXCID002824, J01MA02, S01AE03, S02AA15, S03AA07, Ciprofloxacin fluoroquinolonic acid, Ciprofloxacin Otic Solution, 0.2%, Anhydrous, Ciprofloxacin Hydrochloride, Hydrochloride Anhydrous, Ciprofloxacin, 617-751-0, 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-4-ium-1-ylquinoline-3-carboxylate, Ciproxan, Cipro IV, Ciproxina, Cipro XR, MFCD00185755, Ciproxin, Bay-09867, CHEMBL8, Cipromycin, Ciproquinol, Bernoflox, Septicide, 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-quinoline-3-carboxylic acid, Ciprofloxacin monohydrochloride, Ciprecu, Ciprinol, Ciprogis, Ciprolin, Ciprolon, Ciprowin, Ciproxine, Citopcin, Corsacin, Fimoflox, Ipiflox, Italnik, Probiox, Proflaxin, Quinolid, Quintor, Roxytal, Spitacin, Superocin, Zumaflox, Baflox, Ciplus, Ciriax, Rancif, Cilab, Cixan, Cycin, Loxan, Unex, Sophixin Ofteno, Ciprobay Uro, Alcon Cilox, Bi-Cipro, Cipro (TN), Ciprofloxacin Base, CPF, Proksi 250, Proksi 500, Cyprobay, AuriPro, Eni, 1-cyclopropyl-6-fluoro-4-oxo-7-piperazinylhydroquinoline-3-carboxylic acid, 1-Cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline-carboxylic acid, BAY-o 9867, Ciprofloxacine [INN-French], Ciprofloxacinum [INN-Latin], 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, hydrochloride, SMR000471901, Ciprofloxacino [INN-Spanish], CCRIS 5241, HSDB 6987, SR-05000001863, NCGC00016959-01, CAS-93107-08-5, BRN 3568352, rubrum, UNII-5E8K9I0O4U, Ciprooxacin, Ciprine, Linhaliq, Ciprofloxacin RS, Ciprofloxacin CRS, Otiprio (TN), Ciprofloxacin [USAN:USP:INN:BAN], Ciprofloxacin (Cipro), Spectrum_000162, Ciprofloxacin (Cipro)?, Ciprofloxacin protomer I, Ciprofloxacin (Standard), Ciprofloxacin protomer II, Prestwick0_000113, Prestwick1_000113, Prestwick2_000113, Prestwick3_000113, Spectrum2_001567, Spectrum3_001872, Spectrum4_000874, Spectrum5_001089, Cipro (*Hydrochloride*), CBMicro_048498, CIPROFLOXACIN [MI], Ciloxan (*Hydrochloride*), CIPROFLOXACIN [INN], CIPROFLOXACIN [JAN], SCHEMBL2900, CIPROFLOXACIN [HSDB], CIPROFLOXACIN [USAN], Oprea1_008239, Oprea1_313572, BSPBio_000126, BSPBio_003344, CIPROFLOXACIN [VANDF], KBioGR_001567, KBioSS_000642, ANHYDROUS CIPROFLOXACIN, MLS001336035, MLS006011837, BIDD:GT0205, CIPROFLOXACIN [MART.], DivK1c_000095, SPECTRUM1503614, SPBio_001474, SPBio_002065, CIPROFLOXACIN [USP-RS], CIPROFLOXACIN [WHO-DD], CIPROFLOXACIN [WHO-IP], BPBio1_000140, orb1307927, orb3025773, BAY-O9867, BDBM21690, GTPL10902, HMS500E17, HY-B0356R, KBio1_000095, KBio2_000642, KBio2_003210, KBio2_005778, KBio3_002846, Linhaliq [Liposomal Formulation], Ciprofloxacin (JP18/USP/INN), MSK5703, NINDS_000095, Perfluorohexaldehyde hydrate(diol), Bay o 9867 (*Hydrochloride*), HMS1922E18, HMS2090O07, HMS2093I03, HMS6019C09, Pharmakon1600-01503614, CIPROFLOXACIN [ORANGE BOOK], ALBB-015909, FVB05035, HY-B0356, RKL10073, CIPROFLOXACIN [EP MONOGRAPH], BBL005612, CCG-39345, CIPROFLOXACIN [USP MONOGRAPH], CIPROFLOXACIN EXTENDED RELEASE, Ciprofloxacin, >=98.0% (HPLC), EBC-12960, MSK5703-100M, NSC758467, NSC759028, s2027, SBB012554, STK021082, 719 - Quinolone antibiotics in fish, AKOS000269653, CIPRODEX COMPONENT CIPROFLOXACIN, CIPROFLOXACINUM [WHO-IP LATIN], MSK5703-1000M, AC-7613, AC58172, DB00537, KS-5006, NSC 758467, NSC-759028, IDI1_000095, SMP1_000125, Ciprofloxacin 100 microg/mL in Methanol, NCGC00016959-02, NCGC00016959-03, NCGC00016959-04, NCGC00016959-05, NCGC00016959-07, NCGC00095058-01, NCGC00095058-02, NCGC00178128-01, Ciprofloxacin, Enrofloxacin EP Impurity B, ST024751, SBI-0048462.P003, C2510, NS00008031, Ciprofloxacin Solution in Methanol, 100ug/mL, EN300-08481, C05349, Ciprofloxacin Solution in Methanol, 1000ug/mL, D00186, Ciprofloxacin, VETRANAL(TM), analytical standard, F358017, Q256602, SR-05000001863-1, SR-05000001863-3, BRD-K04804440-001-08-7, BRD-K04804440-001-09-5, BRD-K04804440-001-13-7, BRD-K04804440-311-02-3, Z56933707, Ciprofloxacin, European Pharmacopoeia (EP) Reference Standard, ENROFLOXACIN FOR VETERINARY USE IMPURITY B [EP IMPURITY], Ciprofloxacin, United States Pharmacopeia (USP) Reference Standard, 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)-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-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline carboxylic acid, 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylicacid, 1-cyclopropyl-6-fluoro-7-(piperazin-1-yl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, Ciprofloxacin, Pharmaceutical Secondary Standard, Certified Reference Material, 1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

Bioactivity: Second-generation fluoroquinolone antibiotic; bacterial DNA gyrase (topoisomerase II) and topoisomerase IV inhibitor

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Octanol	293.15	-	5.0 × 10⁻⁴	[170]
1-Octanol	298.15	-	9.0 × 10⁻⁴	[170]
1-Octanol	303.15	-	0.0013	[170]
1-Octanol	308.15	-	0.002	[170]
1-Octanol	313.15	-	0.0029	[170]
1-Octanol	318.15	-	0.004	[170]
1-Octanol	323.15	-	0.0055	[170]
1-Octanol	328.15	-	0.00737	[170]
1-Octanol	333.15	-	0.0096	[170]
1-Propanol	293.15	-	0.0091	[168]
1-Propanol	298.15	-	0.015	[168]
1-Propanol	303.15	-	0.0232	[168]
1-Propanol	308.15	-	0.0337	[168]
1-Propanol	313.15	-	0.0473	[168]
1-Propanol	318.15	-	0.0634	[168]
1-Propanol	323.15	-	0.08282	[168]
1-Propanol	328.15	-	0.1052	[168]
1-Propanol	333.15	-	0.1269	[168]
Acetone	293.15	-	0.0419	[168]
Acetone	298.15	-	0.05664	[168]
Acetone	303.15	-	0.0739	[168]
Acetone	308.15	-	0.0951	[168]
Acetone	313.15	-	0.1178	[168]
Acetone	318.15	-	0.1455	[168]
Acetone	323.15	-	0.1789	[168]
Acetone	328.15	-	0.2132	[168]
Acetone	333.15	-	0.2544	[168]
Chloroform	293.15	-	0.3246	[168]
Chloroform	298.15	-	0.3867	[168]
Chloroform	303.15	-	0.4519	[168]
Chloroform	308.15	-	0.5198	[168]
Chloroform	313.15	-	0.5941	[168]
Chloroform	318.15	-	0.6668	[168]
Chloroform	323.15	-	0.748	[168]
Chloroform	328.15	-	0.8358	[168]
Chloroform	333.15	-	0.9191	[168]
Ethanol	293.15	-	0.0457	[168]
Ethanol	298.15	-	0.0577	[168]
Ethanol	303.15	-	0.0707	[168]
Ethanol	308.15	-	0.0858	[168]
Ethanol	313.15	-	0.103	[168]
Ethanol	318.15	-	0.1238	[168]
Ethanol	323.15	-	0.1489	[168]
Ethanol	328.15	-	0.1769	[168]
Ethanol	333.15	-	0.2109	[168]
Methanol	293.15	-	0.0666	[168]
Methanol	298.15	-	0.0916	[168]
Methanol	303.15	-	0.1203	[168]
Methanol	308.15	-	0.1563	[168]
Methanol	313.15	-	0.1971	[168]
Methanol	318.15	-	0.2519	[168]
Methanol	323.15	-	0.3082	[168]
Methanol	328.15	-	0.3718	[168]
Methanol	333.15	-	0.4454	[168]
Water	293.15	-	0.0658	[169]
Water	298.15	-	0.08546	[169]
Water	303.15	-	0.1063	[169]
Water	308.15	-	0.1361	[169]
Water	313.15	-	0.1689	[169]
Water	318.15	-	0.2138	[169]
Water	323.15	-	0.2595	[169]

Molecule 3D descriptors

Descriptor	Value
PMI1	1106.1141
PMI2	3908.9334
PMI3	4873.0350
NPR1	0.2270
NPR2	0.8022
RadiusOfGyration	3.8628
InertialShapeFactor	0.0007
Eccentricity	0.9739
Asphericity	0.4700
SpherocityIndex	0.0910
PBF	0.5431