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92665-29-7 molecular structure
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(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-[(1E)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ChemBase ID: 1021
Molecular Formular: C18H19N3O5S
Molecular Mass: 389.42556
Monoisotopic Mass: 389.10454172
SMILES and InChIs

SMILES:
S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](N)c2ccc(O)cc2)C(=C(C1)/C=C/C)C(=O)O
Canonical SMILES:
C/C=C/C1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)[C@@H](c1ccc(cc1)O)N
InChI:
InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/b3-2+/t12-,13-,17-/m1/s1
InChIKey:
WDLWHQDACQUCJR-ZAMMOSSLSA-N

Cite this record

CBID:1021 http://www.chembase.cn/molecule-1021.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-[(1E)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC Traditional name
cefprozil
Brand Name
Arzimol
Brisoral
Cronocef
Procef
Serozil
Synonyms
Cefprozilo [INN-Spanish]
Cefprozil anhydrous
Cefprozilum [INN-Latin]
Cefprozil
(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
BMY 28100
Cefprozile
Cefzil
Cephprozyl
Procef
Prozef
CAS Number
92665-29-7
PubChem SID
160964484
PubChem CID
5281006

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
C243910 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.5293207  H Acceptors
H Donor LogD (pH = 5.5) -1.9168022 
LogD (pH = 7.4) -2.175604  Log P -1.9216894 
Molar Refractivity 101.2731 cm3 Polarizability 38.68424 Å3
Polar Surface Area 132.96 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.94  LOG S -3.42 
Solubility (Water) 1.49e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
55 mg/L expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
Pale Yellow Solid expand Show data source
Melting Point
215-217°C (dec.) expand Show data source
Hydrophobicity(logP)
0.6 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB01150 external link
Item Information
Drug Groups approved
Description Cefprozil is a cephalosporin antibiotic. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.
Indication For the treatment of the following infections (respiratory, skin, soft tissue, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staph
Pharmacology Cefprozil, a semisynthetic, second-generation cephalosporin, is used to treat otitis media, soft-tissue infections, and respiratory tract infections.
Toxicity Single 5000 mg/kg oral doses of cefprozil caused no mortality or signs of toxicity in adult, weaning or neonatal rats, or adult mice. A single oral dose of 3000 mg/kg caused diarrhea and loss of appetite in cynomolgus monkeys, but no mortality.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Cefprozil is eliminated primarily by the kidneys
Absorption Oral bioavailability is approximately 95%.
Half Life 1.3 hours
Protein Binding 36%
Distribution * 0.23 L/kg
Clearance * 3 mL/min/kg [fasting subjects]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Toronto Research Chemicals - C243910 external link
Semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture. Antibacterial.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Jones, R.N., et al.: Diagn. Microb. Infect. Dis., 9, 11 (1988)
  • • Barbhaiya, R.H., et al.: Antimicrob. Agents Chemother., 34, 1204 (1990)
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PATENTS

PATENTS

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INTERNET

INTERNET

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