cyclacillin
Trade name: cyclapen-w
Approved
Sep 13, 1979
Cyclacillin is a cyclohexylamido analog of penicillanic acid. It is used for the treatment of bacterial infections caused by susceptible organisms. Cyclacillin is more resistant to beta-lactamase hydrolysis than ampicillin, is much better absorbed when given by mouth and, as a result, the levels reached in the blood and in the urine are considerably higher than those obtained with the same dose of ampicillin. The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin has been replaced by newer penicillin treatments. — NCATS
Clinical trial activity
0 trials · 0 clinical orgs · 3 marketing orgs
Timeline
1970s
- Sep 13, 1979
Earliest FDA Approval
- Sep 13, 1979
American Home Products — NDA Secondary Org
- Sep 14, 1979
Wyeth — First NDA Organization
- Sep 14, 1979
Wyeth — NDA Organization
1980s
- May 4, 1988
Teva — Marketing Organization
Indications
Approved for
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
- approvedSep 13, 1979
Chemistry & pharmacology
SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(O)=O- Mol. weight
- 341.426 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Discontinued
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaCiclacillin ↗
- NCATS72ZJ154X86 ↗
- ChEMBLCHEMBL1200356 ↗
Also known as
- (1-aminocyclohexyl)penicillin
- (1-aminocyclohexyl)penicillin
- (2s,5r,6r)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- (2s,5r,6r)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- 6-(1-aminocyclohexanecarboxamido)penicillanic acid
- 6-(1-aminocyclohexanecarboxamido)penicillanic acid
- 6-(1-aminocyclohexylcarboxamido)penicillanic acid
- 6-(1-aminocyclohexylcarboxamido)penicillanic acid
- aminocyclohexylpenicillin
- aminocyclohexylpenicillin
- aminocyclohexylpenicillin
- bastcillin
- bastcillin
- calthor
- calthor
- calthor
- ciclacilina
- ciclacilina
- ciclacillin
- ciclacillin
- ciclacillin
- ciclacillin
- ciclacillin
- ciclacillin
- ciclacilline
- ciclacilline
- ciclacillinum
- ciclacillinum
- ciclacillum
- ciclacillum
- ciclacillum
- citosarin
- citosarin
- cyclacillin
- cyclacillin
- cyclacillin
- cyclacillin
- cyclacillin
- cyclacillin
- cyclacillin
- cyclacillin
- cyclacillin
- cyclapen
- cyclapen
- cyclapen
- cyclapen
- cyclapen-w
- cyclapen-w
- cyclapen-w
- syngacillin
- syngacillin
- ultracillin
- ultracillin
- vastcillin
- vastcillin
- vasticillin
- vipicil
- vipicil
- wy-4508
- wy-4508
- wyvital
- wyvital
Organizations
Marketing (3)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| American Home Products | For profit | NDA2 | Sep 13, 1979 |
| Teva | For profit | MKTG | May 4, 1988 |
| Wyeth | For profit | NDA | Sep 14, 1979 |