ceforanide
Trade name: precef
Approved
May 24, 1984
Ceforanide is a new cephalosporin with a longer elimination half-life than any currently available cephalosporin. Its activity is very similar to that of cefamandole, a second-generation cephalosporin, except that ceforanide is less active against most gram-positive organisms. The bactericidal activity of ceforanide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Ceforanide is primarily indicated in conditions like bone and joint infection, endocarditis, respiratory tract infections, skin infections, surgical infections, urinary tract infection. Rash and pruritus, and nausea, vomiting and other mild gastrointestinal side effects were noted in a few of the subjects but were mild and transient. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 2 marketing orgs
Timeline
1980s
- May 24, 1984
Bristol-Myers — Earliest FDA Approval
- May 24, 1984
Bristol-Myers — NDA Organization
Indications
Mechanism of action
- Bacterial penicillin-binding proteinINHIBITOR
Bacterial penicillin-binding protein inhibitor
- D-alanyl-D-alanine carboxypeptidase DacB (dacB) ↗
- Peptidoglycan D,D-transpeptidase FtsI (ftsI) ↗
- Penicillin-binding protein 1A (mrcA) ↗
- Penicillin-binding protein 1B (mrcB) ↗
- D-alanyl-D-alanine carboxypeptidase DacA (dacA) ↗
- Peptidoglycan D,D-transpeptidase MrdA (mrdA) ↗
- D-alanyl-D-alanine carboxypeptidase DacC (dacC) ↗
Approval history
- approvedMay 24, 1984
Chemistry & pharmacology
SMILES
NCC1=CC=CC=C1CC(=O)N[C@H]2[C@H]3SCC(CSC4=NN=NN4CC(O)=O)=C(N3C2=O)C(O)=O- Mol. weight
- 519.554 g/mol
- Lipinski Ro5
- 2 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Parenteral
- Availability
- Discontinued
Oral
No
Parenteral
Yes
Topical
No
Sources
- WikipediaCeforanide ↗
- NCATS8M1YF8951V ↗
- ChEMBLCHEMBL1201046 ↗
Also known as
- (6r,7r)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r,7r)-7-[[2-[2-(aminomethyl)phenyl]acetyl]amino]-3-[[1-(carboxymethyl)tetrazol-5-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- (6r-trans)-7-(((2-(aminomethyl)phenyl)acetyl)amino)-3-(((1-(carboxymethyl)-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
- 7-(alpha-(2-aminomethylphenyl)acetamido)-3-((1-carboxymethyltetrazol-5-ylthio)methyl)-3-cephem-4-carboxylic acid
- 7beta-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1h-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic acid
- 7beta-[2-(aminomethyl)phenyl]acetamido-3-{[1-(carboxymethyl)-1h-tetrazol-5-yl]sulfanyl}methyl-3,4-didehydrocepham-4-carboxylic acid
- 7-[o-(aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1h-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylic acid
- 7-[o-(aminomethyl)phenylacetamido]-3-[[[1-(carboxymethyl)-1h-tetrazol-5-yl]thio]methyl]-3-cephem-4-carboxylic acid
- bl-s786
- bl-s786
- bl-s 786
- bl-s786r
- cefaronide
- ceforanide
- ceforanide
- ceforanide
- ceforanide
- ceforanide
- ceforanide
- ceforanide
- ceforanide
- ceforanide
- ceforanide
- ceforanide, monosodium salt
- ceforanido
- ceforanido
- ceforanidum
- ceforanidum
- precef
- precef
- precef
Organizations
Marketing (2)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Apothecon | For profit | MKTG | — |
| Bristol-Myers | For profit | NDA | May 24, 1984 |