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
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
| Molecular Formula | C15H23N3O3S |
| Molecular Weight | 325.426 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB01163Curator's Comment: Description was created based on several sources, including
http://www.mims.com/india/drug/info/mecillinam?type=full&mtype=generic and https://www.ncbi.nlm.nih.gov/pubmed/3885172
Sources: http://www.drugbank.ca/drugs/DB01163
Curator's Comment: Description was created based on several sources, including
http://www.mims.com/india/drug/info/mecillinam?type=full&mtype=generic and https://www.ncbi.nlm.nih.gov/pubmed/3885172
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q8DR59 Gene ID: 934791.0 Gene Symbol: pbpA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) |
0.224 µM [IC50] | ||
Target ID: UniProtKB - Q7CRA4, pbp1b, Streptococcus pneumoniae |
0.147 µM [IC50] | ||
Target ID: UniProtKB - Q8DNB6, pbp2a, Streptococcus pneumoniae |
30.0 nM [IC50] | ||
Target ID: UniProtKB - A0A0E9DY48, PBP1, Chlamydia trachomatis |
0.6 nM [IC50] | ||
Target ID: UniProtKB - L0BBN1, pbp3, Haemophilus influenzae |
3.7 nM [IC50] | ||
Target ID: P0AD65 Gene ID: 945240.0 Gene Symbol: mrdA Target Organism: Escherichia coli (strain K12) |
0.06 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Mecillinam Approved UseUrinary tract infections Launch Date1984 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
87.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
3.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
4.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
49.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6282208/ |
10 mg/kg bw 6 times / day steady-state, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
26.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
10 mg/kg bw single, intramuscular dose: 10 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
AMDINOCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
29.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
15 mg/kg bw single, intramuscular dose: 15 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
AMDINOCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
49.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
112.97 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
10 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
7.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
8.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
9.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
47.94 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
10 mg/kg bw single, intramuscular dose: 10 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
AMDINOCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
72.15 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
15 mg/kg bw single, intramuscular dose: 15 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
AMDINOCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
58.81 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.886 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
15 mg/kg bw single, intravenous dose: 15 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3377469/ |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
52.39 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6282208/ |
10 mg/kg bw 6 times / day steady-state, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
54.38 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6282208/ |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.96 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
10 mg/kg bw single, intramuscular dose: 10 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
AMDINOCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.859 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
15 mg/kg bw single, intramuscular dose: 15 mg/kg bw route of administration: Intramuscular experiment type: SINGLE co-administered: |
AMDINOCILLIN serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
|
0.888 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6311087/ |
10 mg/kg bw single, intravenous dose: 10 mg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered: |
AMDINOCILLIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
500 mg single, intravenous Highest studied dose Dose: 500 mg Route: intravenous Route: single Dose: 500 mg Sources: Page: p.83 |
healthy, 25 - 43 n = 12 Health Status: healthy Age Group: 25 - 43 Population Size: 12 Sources: Page: p.83 |
|
10 mg/kg 4 times / day multiple, intravenous Studied dose Dose: 10 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 10 mg/kg, 4 times / day Sources: Page: p.110 |
unhealthy, 25-94 n = 38 Health Status: unhealthy Condition: gram-negative baciliary infections Age Group: 25-94 Sex: M+F Population Size: 38 Sources: Page: p.110 |
Other AEs: Diarrhea, Aspartate aminotransferase abnormal... Other AEs: Diarrhea (2.6%) Sources: Page: p.110Aspartate aminotransferase abnormal (10.52%) Alkaline phosphatase increased (7.9%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Aspartate aminotransferase abnormal | 10.52% | 10 mg/kg 4 times / day multiple, intravenous Studied dose Dose: 10 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 10 mg/kg, 4 times / day Sources: Page: p.110 |
unhealthy, 25-94 n = 38 Health Status: unhealthy Condition: gram-negative baciliary infections Age Group: 25-94 Sex: M+F Population Size: 38 Sources: Page: p.110 |
| Diarrhea | 2.6% | 10 mg/kg 4 times / day multiple, intravenous Studied dose Dose: 10 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 10 mg/kg, 4 times / day Sources: Page: p.110 |
unhealthy, 25-94 n = 38 Health Status: unhealthy Condition: gram-negative baciliary infections Age Group: 25-94 Sex: M+F Population Size: 38 Sources: Page: p.110 |
| Alkaline phosphatase increased | 7.9% | 10 mg/kg 4 times / day multiple, intravenous Studied dose Dose: 10 mg/kg, 4 times / day Route: intravenous Route: multiple Dose: 10 mg/kg, 4 times / day Sources: Page: p.110 |
unhealthy, 25-94 n = 38 Health Status: unhealthy Condition: gram-negative baciliary infections Age Group: 25-94 Sex: M+F Population Size: 38 Sources: Page: p.110 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death. | 1983 Aug 29 |
|
| Efficacy of amdinocillin and lack of nephrotoxicity when combined with a second beta-lactam antibiotic for therapy of serious gram-negative bacillary infections. | 1983 Aug 29 |
|
| Role of the ftsA1p promoter in the resistance of mucoid mutants of Salmonella enterica to mecillinam: characterization of a new type of mucoid mutant. | 2001 Jun 25 |
|
| [New drugs]. | 2001 Sep |
|
| Novel S-benzylisothiourea compound that induces spherical cells in Escherichia coli probably by acting on a rod-shape-determining protein(s) other than penicillin-binding protein 2. | 2002 Dec |
|
| Mecillinam susceptibility as an indicator of beta-lactamase production in Staphylococcus aureus. | 2002 Feb |
|
| Mecillinam susceptibility of Auckland urinary isolates. | 2002 Feb 8 |
|
| [Urinary tract pathogens in uncomplicated lower urinary tract infections in women in Norway]. | 2003 Aug 14 |
|
| A new method for normalized interpretation of antimicrobial resistance from disk test results for comparative purposes. | 2003 Feb |
|
| Identification of the CysB-regulated gene, hslJ, related to the Escherichia coli novobiocin resistance phenotype. | 2003 Jul 29 |
|
| Null mutations in the essential gene yrfF (mucM) are not lethal in rcsB, yojN or rcsC strains of Salmonella enterica serovar Typhimurium. | 2003 May 16 |
|
| Localizing cell division in spherical Escherichia coli by nucleoid occlusion. | 2003 Sep 26 |
|
| Shigella serotypes among hospitalized patients in urban Bangladesh and their antimicrobial resistance. | 2004 Aug |
|
| Prevalence of Shigella species and their antimicrobial resistance patterns in Eastern Nepal. | 2005 Dec |
|
| Uncomplicated urinary tract infections. Bacterial findings and efficacy of empirical antibacterial treatment. | 2005 Jun |
|
| Susceptibility testing of urinary isolates of Escherichia coli to mecillinam using NCCLS methodology. | 2005 Mar |
|
| Iron limitation induces SpoT-dependent accumulation of ppGpp in Escherichia coli. | 2005 May |
|
| Isolation and characterization of provisional serovar Shigella boydii E16553 from diarrhoeal patients in Bangladesh. | 2005 May |
|
| [Increasing antibiotic resistance in urinary tract infections]. | 2006 Apr 6 |
|
| Activity of mecillinam against ESBL producers in vitro. | 2006 Feb |
|
| Activity of mecillinam against AmpC beta-lactamase-producing Escherichia coli. | 2006 Jul |
|
| High-level resistance to mecillinam produced by inactivation of soluble lytic transglycosylase in Salmonella enterica serovar Typhimurium. | 2006 Mar |
|
| Spontaneous zygogenesis (Z-mating) in mecillinam-rounded bacteria. | 2007 Dec |
|
| DNA and origin region segregation are not affected by the transition from rod to sphere after inhibition of Escherichia coli MreB by A22. | 2007 Jul |
|
| In vitro interaction between mecillinam and piperacillin-tazobactam in the presence of azithromycin against members of the Enterobacteriaceae family and Pseudomonas aeruginosa. | 2008 Jan |
|
| Dissemination of multidrug-resistant bacteria into the Arctic. | 2008 Jan |
|
| Surveillance study in Europe and Brazil on clinical aspects and Antimicrobial Resistance Epidemiology in Females with Cystitis (ARESC): implications for empiric therapy. | 2008 Nov |
|
| Endemic and epidemic lineages of Escherichia coli that cause urinary tract infections. | 2008 Oct |
|
| RodZ, a new player in bacterial cell morphogenesis. | 2009 Feb 4 |
|
| Actinomyces species: A danish survey on human infections and microbiological characteristics. | 2009 Jul 23 |
|
| Bend into shape. | 2009 May 6 |
|
| Influence of RpoS, cAMP-receptor protein, and ppGpp on expression of the opgGH operon and osmoregulated periplasmic glucan content of Salmonella enterica serovar Typhimurium. | 2009 Nov |
|
| The ARESC study: an international survey on the antimicrobial resistance of pathogens involved in uncomplicated urinary tract infections. | 2009 Nov |
|
| Acute uncomplicated cystitis: from surveillance data to a rationale for empirical treatment. | 2010 Jan |
|
| Do different susceptibility breakpoints affect the selection of antimicrobials for treatment of uncomplicated cystitis? | 2010 Oct |
|
| Molecular and evolutionary bases of within-patient genotypic and phenotypic diversity in Escherichia coli extraintestinal infections. | 2010 Sep 30 |
Patents
Sample Use Guides
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
| Substance Class |
Chemical
Created
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| Record UNII |
V10579P3QZ
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Validated (UNII)
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NCI_THESAURUS |
C1500
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WHO-ATC |
J01CA11
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WHO-VATC |
QJ01CA11
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32887-01-7
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MECILLINAM
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C65229
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3494
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51213
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m1653
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SUB08675MIG
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1648
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DB01163
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D000560
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METABOLITE INACTIVE -> PARENT |
Unit: percent of total dose; in 6hr pooled urine after single oral administration of Pivmecillinam (500mg as Amdinocillin); two adult male
IN-VIVO
URINE
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METABOLITE INACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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URINE
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METABOLITE INACTIVE -> PARENT |
Unit: percent of total dose; in 6hr pooled urine after single oral administration of Pivmecillinam (500mg as Amdinocillin); two adult male
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ACTIVE MOIETY |
