Basic information
- CAS
121412-77-9- Standard SMILES
C/C=C\C1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1- InChIKey
WDLWHQDACQUCJR-AGGBKSKLSA-N- Molecular formula
- C18H19N3O5S
- Average molar mass
- 389.4 g/mol
- Monoisotopic mass
- 389.10454189
Overview
Cefprozil Anhydrous, (Z)- is the anhydrous form of the Z-isomer of a semi-synthetic cephalosporin and a beta-lactam antibiotic with bactericidal activity. Cefprozil's effect is dependent on its binding to penicillin-binding proteins (PBPs) located in the bacterial cytoplasmic membrane. Binding results in the inhibition of the transpeptidase enzymes, thereby preventing cross-linking of the pentaglycine bridge with the fourth residue of the pentapeptide and interrupting consequent synthesis of peptidoglycan chains. As a result, cefprozil inhibits bacterial septum and cell wall synthesis formation.
Names & identifiers
- Preferred name
- Cefprozil Anhydrous, (Z)-
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- CEFPROZIL (Z)-ISOMER (200 MG)H0E054927UG/MG(AI)
- Molecular formula
- C18H19N3O5S
- Molecular weight
- 389.43
Names & synonyms
121412-77-9W5T767OA4GCefprozil anhydrous, (Z)-Cefprozil Anhydrous, Z-RefChem:1081321Z-CefprozilCefprozil anhydrous, Z-isomerCefprozil Impurity 7(Z)-CefprozilUNII-W5T767OA4GBrisoral(6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Show more names
Cefprozil (Z)-IsoMerCefprozil (Z)-Isomer (200 mg)Cefprozil (Z)-Isomer (1098050)Cefprozil Impurity 1 (Z-Cefprozil)CEFPROZIL (Z)-ISOMER (200 MG)H0E054927UG/MG(AI)5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(1Z)-1-propen-1-yl-, (6R,7R)-Cefprozil (Z)-Isomer/(Z)-(6R,7R)-7-[[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(1-propen-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-((R)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((Z)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-[(1Z)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCEFPROZIL Z-FORM [MI]SCHEMBL13581439DTXSID50873544Cefprozil Impurity N1(Z-Cefprozil)NCGC00160532-01Q27292357
Properties
Computed structural properties
- XLogP
- -1.4
- Topological polar surface area
- 158 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 699
Physicochemical properties
- Melting point
- 218 · 218-220° (dec)
- Boiling point
- 803.1 · 803.1±65.0 °C(Predicted)
- Density
- 1.53 · 1.53±0.1 g/cm3(Predicted)
- pka
- 2.92 · 2.92±0.50(Predicted)
- InChIKey
- WDLWHQDACQUCJR-AGGBKSKLSA-N
- SMILES
- N12[C@@]([H])([C@H](NC([C@H](N)C3=CC=C(O)C=C3)=O)C1=O)SCC(/C=C\C)=C2C(O)=O
- FDA UNII
- 5 T767OA4G · W5T767OA4G
- HS Code
- 2941906000 · 2941906000
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
- hs_code
- 2941906000
Chemistry & industry
Applications
UsesCefprozil (Z)-Isomer is a stereoisomer of Cefprozil (C243910), a semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture. Antibacterial.
Suppliers21 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
欧利希（湖北）医药科技有限公司17316404525 17316404525 · [email protected]
上海尺水药物研究有限公司[email protected] 13564957716 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
常州翔龙医药科技有限公司18915873328 18915873328 · [email protected]
TLC梯尔希（南京）药物研发有限公司18012923235 · [email protected]
坛墨质检科技股份有限公司19850211281 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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