Basic information
- CAS
85287-61-2- Standard SMILES
O=C([O-])C1=C(C[n+]2ccc(CCS(=O)(=O)[O-])cc2)CS[C@@H]2[C@H](NC(=O)[C@@H](NC(=O)c3nc[nH]c3C(=O)O)c3ccccc3)C(=O)N12.[Na+]- InChIKey
JLUNZNNMKVKUOH-TZVBBFNXSA-M- Molecular formula
- C28H25N6NaO10S2
- Average molar mass
- 692.7 g/mol
- Monoisotopic mass
- 692.09712764
Overview
Cefpimizole Sodium is the sodium salt form of cefpimizole, a semisynthetic, broad-spectrum, third-generation cephalosporin with antibacterial activity. Cefpimizole binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
Names & identifiers
- Preferred name
- Cefpimizole Sodium
- IUPAC
- sodium (6R,7R)-7-[[(2S)-2-[(5-carboxy-1H-imidazole-4-carbonyl)amino]-2-phenylacetyl]amino]-8-oxo-3-[[4-(2-sulfonatoethyl)pyridin-1-ium-1-yl]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
- English name
- Cefpimizole sodium
- Molecular formula
- C28H25N6NaO10S2
- Molecular weight
- 693.66
Names & synonyms
cefpimizole sodiumRenilanAjicef85287-61-2U 63196ECefpimizole monosodium saltX4628IMC52Pyridinium, 1-((2-carboxy-7-(((((5-carboxy-1H-imidazol-4-yl)carbonyl)amino)phenylacetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-4-(2-sulfoethyl)-, hydroxide, inner salt, monosodium salt, (6R-(6alpha,7beta(R*)))-U-63,196ERefChem:124245U-63196Esodium;(6R,7R)-7-[[(2S)-2-[(5-carboxy-1H-imidazole-4-carbonyl)amino]-2-phenylacetyl]amino]-8-oxo-3-[[4-(2-sulfonatoethyl)pyridin-1-ium-1-yl]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Show more names
CPIZAC 1370Cefpimizole sodium USP/EP/BP1-[[(6R)-2-Carboxylato-7α-[[(R)-[[(5-carboxy-1H-imidazol-4-yl)carbonyl]amino]phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-4-(2-sodiooxysulfonylethyl)pyridinium1-[[(6R)-2-Carboxylato-7α-[[(R)-[[(5-carboxy-1H-imidazol-4-yl)carbonyl]amino]phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-4-[2-(sodiooxysulfonyl)ethyl]pyridinium
AC 1370 sodiumCefpimizole sodium [USAN:JAN]1-(((6R,7R)-2-Carboxy-7-((R)-2-(5-carboxyimidazole-4-carboxamido)-2-phenylacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-4-(2-sulfoethyl)pyridinium hydroxide, inner salt, monosodium saltUNII-X4628IMC52Sodium (6R,7R)-7-((R)-2-(4-carboxy-1H-imidazole-5-carboxamido)-2-phenylacetamido)-8-oxo-3-((4-(2-sulfonatoethyl)pyridin-1-ium-1-yl)methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Database identifiers
- CAS
85287-61-2- PubChem CID
- 55324
- ChEMBL
CHEMBL2106385
Properties
Computed structural properties
- Topological polar surface area
- 279 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 10
- Heavy atoms
- 47
- Formal charge
- 0
- Complexity
- 1,340
Physicochemical properties
- alpha
- 20 · D20 -28.2° (c = 0.5 in water)
- FDA UNII
- 4628 IMC52 · X4628IMC52
- Toxicity
- 50 in · LD50 in male, female mice, male, female rats (g/kg): 2.7, 2.9, 4.2, 3.5 i.v.; 8.2, 6.8, 12.2, 11.5 s.c.; all >15.0 orally (Hashimoto)
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
- Toxicity
- LD50 in male, female mice, male, female rats (g/kg): 2.7, 2.9, 4.2, 3.5 i.v.; 8.2, 6.8, 12.2, 11.5 s.c.; all >15.0 orally (Hashimoto)
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Applications
UsesAntibacterial.
Suppliers6 total
北京华美互利生物化工010-56205725 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
重庆卡兰医药有限公司[email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
Related reactions
0 records
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Compound notes
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