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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H23N3O3S
Molecular Weight 325.426
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AMDINOCILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N=CN3CCCCCC3)C(O)=O

InChI

InChIKey=BWWVAEOLVKTZFQ-ISVUSNJMSA-N
InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/b16-9+/t10-,11+,13-/m1/s1

HIDE SMILES / InChI

Description

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. Used in the treatment of urinary tract infections caused by some strains of E. coli and klebsiella and enterobacter species. Used mainly against Gram negative organisms. Amdinocillin is not available in the United States.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.224 µM [IC50]
0.147 µM [IC50]
30.0 nM [IC50]
0.6 nM [IC50]
3.7 nM [IC50]
0.06 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Mecillinam

Cmax

ValueDoseCo-administeredAnalytePopulation
87.3 μg/mL
15 mg/kg bw single, intravenous
AMDINOCILLIN plasma
Homo sapiens
4.3 μg/mL
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
3.2 μg/mL
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
3.6 μg/mL
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
4.1 μg/mL
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
49.5 μg/mL
10 mg/kg bw 6 times / day steady-state, intravenous
AMDINOCILLIN plasma
Homo sapiens
26.2 μg/mL
10 mg/kg bw single, intramuscular
AMDINOCILLIN serum
Homo sapiens
29.6 μg/mL
15 mg/kg bw single, intramuscular
AMDINOCILLIN serum
Homo sapiens
49.4 μg/mL
10 mg/kg bw single, intravenous
AMDINOCILLIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
112.97 μg × h/mL
15 mg/kg bw single, intravenous
AMDINOCILLIN plasma
Homo sapiens
10 μg × h/mL
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
7.7 μg × h/mL
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
8.1 μg × h/mL
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
9.7 μg × h/mL
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
47.94 μg × h/mL
10 mg/kg bw single, intramuscular
AMDINOCILLIN serum
Homo sapiens
72.15 μg × h/mL
15 mg/kg bw single, intramuscular
AMDINOCILLIN serum
Homo sapiens
58.81 μg × h/mL
10 mg/kg bw single, intravenous
AMDINOCILLIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.886 h
15 mg/kg bw single, intravenous
AMDINOCILLIN plasma
Homo sapiens
0.9 h
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
1 h
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
1 h
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
0.9 h
400 mg single, oral
AMDINOCILLIN plasma
Homo sapiens
52.39 min
10 mg/kg bw 6 times / day steady-state, intravenous
AMDINOCILLIN plasma
Homo sapiens
54.38 min
10 mg/kg bw single, intravenous
AMDINOCILLIN plasma
Homo sapiens
0.96 h
10 mg/kg bw single, intramuscular
AMDINOCILLIN serum
Homo sapiens
0.859 h
15 mg/kg bw single, intramuscular
AMDINOCILLIN serum
Homo sapiens
0.888 h
10 mg/kg bw single, intravenous
AMDINOCILLIN plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Parenteral Urinary tract infections Adult: 800 mg every 6-8 hr by IM, slow IV inj or IV infusion. Severe infections: Up to 60 mg/kg/day.
Route of Administration: Parenteral
In Vitro Use Guide
Amdinocillin (Mecillinam) selectively inhibited PBP1, with a 50% inhibitory concentration for PBP1 binding (0.2 ug/ml) similar to the MIC (0.1 ug/ml) and minimum bactericidal concentration (0.25 ug/ml).