(6R,7S)-7-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
Basic information
- CAS
62893-20-3- Standard SMILES
CCN1CCN(C(=O)NC(C(=O)NC2C(=O)N3C(C(=O)O)=C(CSc4nnnn4C)CSC23)c2ccc(O)cc2)C(=O)C1=O- InChIKey
GCFBRXLSHGKWDP-UHFFFAOYSA-N- Molecular formula
- C25H27N9O8S2
- Average molar mass
- 645.7 g/mol
- Monoisotopic mass
- 645.1424012
Names & identifiers
- Preferred name
- (6R,7S)-7-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid
- IUPAC
- 7-[[2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefoperazone sodium
- Molecular formula
- C25H28N9NaO8S2
- Molecular weight
- 668.66
Names & synonyms
(6R,7S)-7-[[(2R)-2-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic AcidC25H27N9O8S2SR-05000001802CefoperazonedihydrateSpectrum_001439Spectrum2_001764Spectrum3_000746Spectrum4_000322Spectrum5_001140ChemDiv1_024737Cefoperazone Impurity N12BSPBio_002332
Show more names
CEFOBIDCefoperazone Sodium, USP, Antibacterial.T-1551DardumCefobisCefonegFarecefKefazonPeracefPerocef
KBioGR_000663KBioSS_001919MLS006011828DivK1c_000128SPBio_001627CHEMBL1331919SCHEMBL18061225KBio1_000128
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 271 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 13
- Rotatable bonds
- 9
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 1,250
Physicochemical properties
- Melting point
- 200 · 200-202°C
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL, clear, faintly yellow
- form
- powder
- color
- White to Off-White
- Water Solubility
- Soluble in water. Slightly soluble in alcohol.
- Merck
- 13 · 13,1943
- BRN
- 4902135 · 4902135
- Stability
- Hygroscopic
- InChIKey
- NCFTXMQPRQZFMZ-WERGMSTESA-M
- SMILES
- C(C1=C(CS[C@]2([H])[C@H](NC(=O)[C@@H](C3C=CC(O)=CC=3)NC(N3CCN(CC)C(=O)C3=O)=O)C(=O)N12)CSC1=NN=NN1C)(=O)O.[NaH] |&1:5,7,11,r|
- CAS DataBase Reference
- 62893 · 62893-20-3(CAS DataBase Reference)
- FDA UNII
- 5 FQG9774WD · 5FQG9774WD
- UNSPSC Code
- 51102829 · 51102829
- NACRES
- 85 · NA.85
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 2
- rtecs
- XI0374000
- hs_code
- 29419000
- risk_code
- 42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 22-36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317-H334
- Hazard Classifications
- Resp. Sens. 1Skin Sens. 1
- Precautionary statements
- P261-P280-P342+P311
Chemistry & industry
Applications
DescriptionCefoperazone was synthesized by Toyama Chemicals Co. in 1978. Except for the hydroxyl group, the side chain attached to the cephem nucleus is the same as that of piperacillin. Cefoperazone shows excellent activity against gram-positive (except Staphylococcus) and gram- negative bacteria, including Pseudomonas aeruginosa. Its pharmacological characteristics are unique. Cefoperazone is excreted mainly in bile, and a concentration five to tenfold higher in bile than in serum is obtained. The transfer into cerebrospinal fluid is 10 – 30 % of the serum concentration; the half-life in serum is 2.0 – 2.6h, and the degree of binding with serum protein is as high as 86.6 %.
UsesBroad spectrum third generation cephalosporin antibiotic. An antibacterial.
Usesantidepressant, serotonin reuptake inhibitor, 5HT1A agonist
UsesFor 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.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Cefoperazone sodium is an organic molecular entity.
Related reactions
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Compound notes
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