62893-20-3

Basic information

• Product Name: Cefoperazone sodium
• Synonyms: sodiumcefoperazone;-tetrazol-5-yl)thio)methyl)-8-oxo-,monosodiumsalt,(6r-(6-alpha,7-beta(r*)));CEFAZONE;CEFOBID;CEFOBID SODIUM SALT;CEFOPERAZONE SODIUM;CEFOPERAZONE SODIUM SALT;CP-52640-2
• CAS NO: 62893-20-3
• Molecular Formula: C₂₅H₂₆N₉O₈S₂*Na
• Molecular Weight: 667.65
• EINECS: 263-751-5
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Interferes with Cell Wall SynthesisAntibiotics;Penicillins and Cephalosporins (beta-Lactams);A - KAntibiotics;Antibacterial;Antibiotics A to;Antibiotics A-FAntibiotics;Chemical Structure Class;Mechanism of Action;Spectrum of Activity;Chiral Reagents;Heterocycles;Sulfur & Selenium Compounds;Pharmaceutical intermediate;VIIBRYD;BPC
• Mol File: 62893-20-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 200-202°C
• Appearance: Faint beige powder
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL, clear, faintly yellow
• Water Solubility: Soluble in water. Slightly soluble in alcohol.
• Stability: Hygroscopic
• Merck: 13,1943
• BRN: 4902135
• CAS DataBase Reference: Cefoperazone sodium(CAS DataBase Reference)
• NIST Chemistry Reference: Cefoperazone sodium(62893-20-3)
• EPA Substance Registry System: Cefoperazone sodium(62893-20-3)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-36/37
• WGK Germany: 2
• RTECS: XI0374000
• Hazardous Substances Data: 62893-20-3(Hazardous Substances Data)

Usage

Chemical Properties

Faint beige powder

Uses

Different sources of media describe the Uses of 62893-20-3 differently. You can refer to the following data:
1. Broad spectrum third generation cephalosporin antibiotic. An antibacterial.
2. antidepressant, serotonin reuptake inhibitor, 5HT1A agonist
3. For studying the expression, binding, and inhibition of penicillin-binding proteins.Cefoperazone sodium salt is used in the study of drug-protein binding, expression and inhibition of penicillin-binding proteins during cell wall synthesis. It is as an antibacterial and antimicrobial agent useful for prevention of postoperative infection. It is used as an inhibitor of inactivation of alfa-antitrypsin.

Therapeutic Function

Antibiotic

Biological Activity

cefoperazone is a new semisynthetic cephalosporin with a broad spectrum of antibacterial activity. cefoperazone shows high activity against gram-positive bacteria and gram-negative bacilli, such as escherichia coli, klebsiella pneumoniae, and proteus species [1].

Clinical Use

Cefoperazone sodium is a third-generation, antipseudomonalcephalosporin that resembles piperacillinchemically and microbiologically. It is active against manystrains of P. aeruginosa, indole-positive Proteus spp.,Enterobacter spp., and S. marcescens that are resistant tocefamandole. It is less active than cephalothin againstGram-positive bacteria and less active than cefamandoleagainst most of the Enterobacteriaceae. Like piperacillin,cefoperazone is hydrolyzed by many of the β-lactamasesthat hydrolyze penicillins. Unlike piperacillin, however, itis resistant to some (but not all) of the β-lactamases thathydrolyze cephalosporins.Cefoperazone is excreted primarily in the bile. Hepaticdysfunction can affect its clearance from the body.

Veterinary Drugs and Treatments

Cefoperazone is used to treat serious infections, particularly susceptible Enterobacteriaceae not susceptible to other less expensive agents or when aminoglycosides are not indicated (due to their potential toxicity).

in vitro

there was only a small spread between the minimum inhibitory concentrations and the minimum bactericidal concentrations of cefoperazone and a significant decrease in activity with an increase in inoculum size. cefoperazone is relatively stable to hydrolysis to β-lactamases produced by gram-negative bacteria. relative rates of hydrolysis of cefoperazone by cephalosporinases were 7.0 to 0.01[1]. in 50 strains of n. gonorrhoeae, the mic50 of cefoperazone was ≤ 0.004-0.06 μg/ml [2].

in vivo

in four patients with cholelithiasis and one patient with carcinoma of the head of the pancreas, all of whom had normal renal functions, cefoperazone was intravenously administrated. in common duct bile, the maximum concentrations of cefoperazone ranged from 373.4 to 3,100 μg/ml while the concentrations ranged from 6.8 to 680 μg/ml in gall bladder bile. cefoperazone concentrations of the gall bladder wall ranged from 16.8 to 48.0 μg/g [3].

references

[1] matsubara n, minami s, muraoka t, et al. in vitro antibacterial activity of cefoperazone (t-1551), a new semisynthetic cephalosporin[j]. antimicrobial agents and chemotherapy, 1979, 16(6): 731-735.[2] baker c n, thornsberry c, jones r n. in vitro antimicrobial activity of cefoperazone, cefotaxime, moxalactam (ly127935), azlocillin, mezlocillin, and other beta-lactam antibiotics against neisseria gonorrhoeae and haemophilus influenzae, including beta-lactamase-producing strains[j]. antimicrobial agents and chemotherapy, 1980, 17(4): 757-761.[3] nakamura t, hashimoto i, sawada y, et al. cefoperazone concentrations in bile and gall bladder wall after intravenous administration[j]. antimicrobial agents and chemotherapy, 1980, 18(6): 980-982.

InChI:InChI=1/C25H27N9O8S2.Na/c1-3-32-8-9-33(21(39)20(32)38)24(42)27-15(12-4-6-14(35)7-5-12)18(36)26-16-19(37)34-17(23(40)41)13(10-43-22(16)34)11-44-25-28-29-30-31(25)2;/h4-7,15-16,22,35H,3,8-11H2,1-2H3,(H,26,36)(H,27,42)(H,40,41);/q;+1/p-1/t15-,16-,22-;/m1./s1

Synthetic route

cefoperazone (62893-19-0, 68779-10-2) → Cefobis (62893-20-3)

Conditions	Yield
With sodium hydrogencarbonate In water; acetone at 15 - 25℃; for 0.666667h; pH=6.5 - 6.6;	98.1%
With sodium isooctanoate; pyrographite In acetone at 25℃; pH=6.6; Reagent/catalyst; pH-value;	71.8%
With sodium carbonate In water; ethyl acetate at 25℃; pH=6.2; Temperature; Solvent; pH-value;	102.61 g
With sodium hydrogencarbonate In ethanol; water at 30℃; pH=6; Reagent/catalyst; Solvent; Temperature; pH-value;	453g

7-Aminocephalosporanic acid (957-68-6) → Cefobis (62893-20-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; titanium tetrachloride; tetrabutoxytitanium / acetonitrile / 3 h / 5 - 30 °C 2: chloro-trimethyl-silane / N,N-dimethyl-formamide / 4 h / -25 - -20 °C 3: sodium isooctanoate; pyrographite / acetone / 25 °C / pH 6.6 View Scheme

iron(II) chloride tetrahydrate + Cefobis (62893-20-3) → C25H26N9O8S2(1-)*Fe(2+)*Cl(1-) (1448807-93-9)

Conditions	Yield
In methanol at 20℃; for 5h; Inert atmosphere;

iron(III) chloride hexahydrate + Cefobis (62893-20-3) → C25H26N9O8S2(1-)*Fe(3+)*2Cl(1-)*3H2O

Conditions	Yield
In methanol at 20℃; for 5h; Inert atmosphere;

cobalt(II) chloride hexahydrate + Cefobis (62893-20-3) → C25H26N9O8S2(1-)*Co(2+)*Cl(1-)*H2O

Conditions	Yield
In methanol at 20℃; for 5h; Inert atmosphere;

nickel(II) chloride hexahydrate + Cefobis (62893-20-3) → C25H26N9O8S2(1-)*Ni(1+)*Cl(1-)

Conditions	Yield
In methanol at 20℃; for 5h; Inert atmosphere;

copper(II) choride dihydrate + Cefobis (62893-20-3) → C25H26N9O8S2(1-)*Cu(2+)*Cl(1-)*H2O

Conditions	Yield
In methanol at 20℃; for 5h; Inert atmosphere;

Cefobis (62893-20-3) + cadmium(II) chloride (10108-64-2) → C25H26N9O8S2(1-)*Cd(2+)*Cl(1-) (1448808-06-7)

Conditions	Yield
In methanol at 20℃; for 5h; Inert atmosphere;

Cefobis (62893-20-3) → cefoperazone sodium hemihydrate

Conditions	Yield
With water; pyrographite at 30℃; for 0.5h; Temperature;	48.5 g

Upstream product

• 957-68-6 7-Aminocephalosporanic acid 
• 62893-19-0 cefoperazone 

Downstream Products

• 1448808-06-7 C₂₅H₂₆N₉O₈S₂^(1-)*Cd⁽²⁺⁾*Cl^(1-) 
• 1448807-93-9 C₂₅H₂₆N₉O₈S₂^(1-)*Fe⁽²⁺⁾*Cl^(1-) 

Relevant articles and documents

New adaptation diseases of cefoperazone medicinal preparation for treating endometritis and other gynecological genital tract infections

The invention discloses new adaptation diseases of cefoperazone medicinal preparation for treating gynecological genital tract infections of gynecology department. The cefoperazone sodium provided bya specific raw material production process is extremely low in impurity content and remarkable in medicine effect, so that the quality of a preparation product is improved, the safety and effectiveness of the preparation product are guaranteed, and the invention provides the application of preparing the medicine for treating endometritis and other gynecological genital tract infections.

Cefoperazone sodium compound and sulbactam sodium compound prepared with strong-field coupling crystallization technology as well as prepared composition

The invention discloses a cefoperazone sodium compound and a sulbactam sodium compound. The cefoperazone sodium compound and the sulbactam sodium compound are both prepared with a strong-field coupling crystallization technology, specifically, ultrasonic out-field strengthened crystals are added in the compound crystallization process, and the high-purity compounds are prepared. 'Research & Development of the Industrialization Project of High-end Medicine Product Refining Crystallization Technologies' wins the 2015 national scientific and technological progress second prize, and the high-field coupling crystallization technology belongs to one of high-end medicine product refining crystallization technologies. The two compounds have the characteristics of high purity and good stability. Besides, the invention further discloses cefoperazone sodium and sulbactam sodium medicinal composition. The cefoperazone sodium and sulbactam sodium medicinal composition is prepared from components in parts by weight as follows: 0.25-2 parts of cefoperazone sodium (on the basis of C25H27N9O8S2) and 0.25-2 parts of sulbactam sodium (on the basis of C8H11NO5S).

Process for the preparation of highly crystalline sodium cefoperazone

Highly crystalline, highly filterable sodium Cefoperazone in the form of needle crystal aggregates, obtainable by a process comprising the controlled addition of acetone to a solution of water/acetone/alcohols/sodium Cefoperazone at 20?40° C.