Amdinocillin
Basic information
- CAS
32887-01-7- Standard SMILES
CC1(C)S[C@@H]2[C@H](N=CN3CCCCCC3)C(=O)N2[C@H]1C(=O)O- InChIKey
BWWVAEOLVKTZFQ-NTZNESFSSA-N- Molecular formula
- C15H23N3O3S
- Average molar mass
- 325.4 g/mol
- Monoisotopic mass
- 325.14601278
Overview
Mecillinam is a penicillin in which the 6beta substituent is [(azepan-1-yl)methylidene]amino; an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria. It has a role as an antiinfective agent and an antibacterial drug.
Names & identifiers
- Preferred name
- Amdinocillin
- IUPAC
- (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- English name
- Mecillinam
- Molecular formula
- C15H23N3O3S
- Molecular weight
- 325.43
Names & synonyms
AMDINOCILLINPenicillin HXCoactinSelexidinFL 1060Ro 10-9070FL-1060DTXSID3022584Ro-10-9070SELECIDINV10579P3QZ4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1H-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
Show more names
Mecillinam (technical product)HexapenFL10606ro10-9070Mecill·Nam
FL1060RefChem:56292DTXCID901511053251-277-1SelexidMecillinam32887-01-7Mecilinamo
Database identifiers
- CAS
32887-01-7- PubChem CID
- 36273
- DTXSID
DTXSID3022584- ChEMBL
CHEMBL258646、CHEMBL530- ChEBI
CHEBI:51208- UNII
- V10579P3QZ
- EC Number
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 98.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 500
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
LogP1.3
Solubility9.79e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point156 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 156 °C · 156°C
- Boiling point
- 551 ℃ · 551℃
- alpha
- 20 · D20 +285° (c = 1 in 0.1N HCl)
- Density
- 1.44 · 1.44±0.1 g/cm3(Predicted)
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- XI0185000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Pharmacodynamics
Amdinocillin is a novel, semisynthetic penicillin effective against many gram-negative bacteria. The antibacterial activity of amdinocillin is derived from its ability to bind specifically and avidly to Penicillin Binding Protein-2 (PBP 2). Amdinocillin is active alone against many gram-negative organisms. Pseudomonas and non-fermenting gram-negative bacteria, however, are usually resistant. Amdinocillin, in combination with many beta-lactams, exhibits marked synergy against many enterobacteriaceae. No such synergy can be demonstrated for gram-positive organisms or pseudomonas species. Amdinocillin is not beta-lactamase stable. Organisms which produce high levels of plasma-mediated beta-lactamase are resistant to the drug. Co-administration of probenecid results in markedly elevated plasma levels of amdinocillin and delays its excretion.
Mechanism of Action
Amdinocillin is a stong and specific antagonist of Penicillin Binding Protein-2 (PBP 2). It is active against gram negative bacteria, preventing cell wall synthesis by inhibiting the activity of PBP2. PBP2 is a peptidoglycan elongation initiating enzyme. Peptidoglycan is a polymer of sugars and amino acids that is the main component of bacterial cell walls.
Biological Half-LifeApproximately 1 hour in patients with normal renal function. Increases to 3 to 6 hours in anephric patients.
MeSH Pharmacological Classification
Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.
Substances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionPoorly absorbed if given orally.
Cellular LocationsMembrane
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Compound notes
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