Cefoperazone
A semisynthetic, broad-spectrum third-generation cephalosporin antibiotic used for the treatment of susceptible bacterial infections, including respiratory tract, urinary tract, intra-abdominal, skin and soft tissue infections, and septicemia. Cefoperazone exhibits bactericidal activity by binding to penicillin-binding proteins (PBPs) and inhibiting bacterial peptidoglycan synthesis, thereby disrupting cell wall formation. It is commonly administered as the sodium salt and is also used in combination with sulbactam
CAS Number: 62893-19-0
Molecular Mass: 645.7 g/mol
Formula: C25H27N9O8S2
Smiles: CCN1CCN(C(=O)N[C@@H](C(=O)N[C@@H]2C(=O)N3C(C(=O)O)=C(CSc4nnnn4C)CS[C@H]23)c2ccc(O)cc2)C(=O)C1=O
Synonymes:
Cefoperazone, cefoperazone, 62893-19-0, Cefoperazono, Cefoperazonum, Peracef, Cefoperazon, Cefoperazona, CHEBI:3493, 7U75I1278D, DTXSID2022759, (6R,7R)-7-((R)-2-(4-Ethyl-2,3-dioxo-1-piperazinylcarboxamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1H-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure, (6R,7R)-7-[[(2R)-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, (6R,7R)-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, 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)(4-hydroxyphenyl)acetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-(6-alpha,7-beta(R*)))-, (6R,7R)-7-(((2R)-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, (6R,7R)-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, RefChem:918190, DTXCID702759, J01DA32, 263-749-4, 2-methyl-1H-benzimidazole-5-carbohydrazide, Cefobid, Cefoperazone acid, MFCD00865067, Cefoperazone (Cefobid), Cefoperazine, 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2R)-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-,(6R,7R)-, Cefoperazone (sodium salt), Cefoperazone (INN), (6R,7R)-7-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetamido)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, C25H27N9O8S2, Cefob, Cefobid (TN), CEFOPERAZONE [INN], Cefoperazonum [INN-Latin], Cefoperazono [INN-Spanish], Cefozon, Medocef, Cefoperazone [INN:BAN], Bioperazone, Myticef, Pathozone, UNII-7U75I1278D, EINECS 263-749-4, Cefoperazone free acid, BRN 0603333, CP 52640, Cefoperazone (Standard), Prestwick0_000327, Prestwick1_000327, Prestwick2_000327, Prestwick3_000327, CEFOPERAZONE [MI], Cefoperazone dihydrate CRS, Epitope ID:174845, C4X-114937Cefoperazone, CEFOPERAZONE [VANDF], Peracef [veterinary] (TN), SCHEMBL37056, BSPBio_000333, BIDD:GT0677, CEFOPERAZONE [WHO-DD], SPBio_002254, BPBio1_000367, CHEMBL507674, orb1300769, orb1691954, GTPL12025, HY-B0210R, GLXC-23143, HMS2090M09, HY-B0210, BDBM50390999, EBC-13165, MSK000937, s1611, AKOS015895629, AC64974, CCG-270325, DB01329, NCGC00179599-01, (6R,7R)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, AS-13298, SY116078, C2768, Cefoperazone 1000 microg/mL in Acetonitrile, NS00098776, SW198793-3, C06883, D07645, T38513, EN300-6733818, F802041, Q2325775, BRD-K02292852-001-02-1, BRD-K02292852-335-03-1, Z2242164637, (6R,7R)-7-((R)-2-(4-ETHYL-2,3-DIOXO-1-PIPERAZINECARBOXAMIDO)-2-(P-HYDROXYPHENYL)ACETAMIDO-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, (6R,7R)-7-((R)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1H-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-[[(2R)-2-[(4-ethyl-2,3-dioxo-piperazine-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, (6r,7r)-7-[[(2r)-2-[[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl] amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1h-tetrazol-5-yl) sulfanyl]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-{[(2R)-2-(4-Ethyl-2,3-dioxopiperazine-1-carboxamido)-2-(4-hydroxyphenyl)acetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-7-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)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, 5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((((4-ETHYL-2,3-DIOXO-1-PIPERAZINYL)CARBONYL)AMINO)(4-HYDROXYPHENYL)ACETYL)AMINO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO, (6R-(6.ALPHA.,7.BETA.(R*)))-, 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 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-, (6R,7R)-, 7beta-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-3-[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl-3,4-didehydrocepham-4-carboxylic acid
Bioactivity: Third-generation cephalosporin antibiotic; bacterial penicillin-binding protein (PBP) inhibitor
Solubility in Different Solvents
| Solvent | Temperature [K] | Crystal form | Solubility [mg/mL] | Reference |
|---|---|---|---|---|
| Acetone | 278.15 | - | 57.09 | [55] |
| Acetone | 283.15 | - | 52.7 | [55] |
| Acetone | 288.15 | - | 50.03 | [55] |
| Acetone | 293.15 | - | 47.98 | [55] |
| Acetone | 298.15 | - | 46.16 | [55] |
| Acetone | 303.15 | - | 44.7 | [55] |
| Acetone | 308.15 | - | 43.7 | [55] |
| Acetone | 313.15 | - | 42.28 | [55] |
| Ethanol | 278.15 | - | 0.1873 | [55] |
| Ethanol | 283.15 | - | 0.2267 | [55] |
| Ethanol | 288.15 | - | 0.2831 | [55] |
| Ethanol | 293.15 | - | 0.3444 | [55] |
| Ethanol | 298.15 | - | 0.4096 | [55] |
| Ethanol | 303.15 | - | 0.5 | [55] |
| Ethanol | 308.15 | - | 0.624 | [55] |
| Ethanol | 313.15 | - | 0.8108 | [55] |
| Isopropanol | 278.15 | - | 0.2768 | [55] |
| Isopropanol | 283.15 | - | 0.3624 | [55] |
| Isopropanol | 288.15 | - | 0.4743 | [55] |
| Isopropanol | 293.15 | - | 0.597 | [55] |
| Isopropanol | 298.15 | - | 0.7189 | [55] |
| Isopropanol | 303.15 | - | 0.9084 | [55] |
| Isopropanol | 308.15 | - | 1.265 | [55] |
| Isopropanol | 313.15 | - | 1.7 | [55] |
| Water | 278.15 | - | 0.267 | [55] |
| Water | 283.15 | - | 0.2985 | [55] |
| Water | 288.15 | - | 0.3911 | [55] |
| Water | 293.15 | - | 0.4522 | [55] |
| Water | 298.15 | - | 0.5396 | [55] |
| Water | 303.15 | - | 0.6584 | [55] |
| Water | 308.15 | - | 0.792 | [55] |
| Water | 313.15 | - | 0.8923 | [55] |
Molecule 3D descriptors
| Descriptor | Value |
|---|---|
| PMI1 | 3573.4912 |
| PMI2 | 21454.5033 |
| PMI3 | 22172.3650 |
| NPR1 | 0.1612 |
| NPR2 | 0.9676 |
| RadiusOfGyration | 6.0457 |
| InertialShapeFactor | 0.0003 |
| Eccentricity | 0.9869 |
| Asphericity | 0.5980 |
| SpherocityIndex | 0.1806 |
| PBF | 1.3512 |