PIVMECILLINAM HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H33N3O5S.ClH
Molecular Weight	476.03
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of PIVMECILLINAM HYDROCHLORIDE

Structure Search

SMILES

Cl.CC(C)(C)C(=O)OCOC(=O)[C@@H]1N2[C@H](SC1(C)C)[C@H](N=CN3CCCCCC3)C2=O

InChI

InChIKey=UHPXMYLONAGUPC-YKBWBZKYSA-N

InChI=1S/C21H33N3O5S.ClH/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23;/h12,14-15,17H,6-11,13H2,1-5H3;1H/b22-12+;/t14-,15+,17-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H33N3O5S
Molecular Weight	439.569
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Penicillin-binding protein 1A 45 Target ID: Q8DR59 Gene ID: 934791.0 Gene Symbol: pbpA Target Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25845878	Inhibitor 8504	0.224 µM [IC50]
UniProtKB - Q7CRA4, pbp1b, Streptococcus pneumoniae 3 Target ID: UniProtKB - Q7CRA4, pbp1b, Streptococcus pneumoniae Sources: https://www.ncbi.nlm.nih.gov/pubmed/25845878	Inhibitor 8504	0.147 µM [IC50]
UniProtKB - Q8DNB6, pbp2a, Streptococcus pneumoniae 3 Target ID: UniProtKB - Q8DNB6, pbp2a, Streptococcus pneumoniae Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8504	30.0 nM [IC50]
UniProtKB - A0A0E9DY48, PBP1, Chlamydia trachomatis 3 Target ID: UniProtKB - A0A0E9DY48, PBP1, Chlamydia trachomatis Sources: https://www.ncbi.nlm.nih.gov/pubmed/11120983	Inhibitor 8504	0.6 nM [IC50]
UniProtKB - L0BBN1, pbp3, Haemophilus influenzae 3 Target ID: UniProtKB - L0BBN1, pbp3, Haemophilus influenzae Sources: https://www.ncbi.nlm.nih.gov/pubmed/6972731	Inhibitor 8504	3.7 nM [IC50]
Penicillin-binding protein 2 24 Target ID: P0AD65 Gene ID: 945240.0 Gene Symbol: mrdA Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25733506	Inhibitor 8504	0.06 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.mims.com/india/drug/info/mecillinam?type=full&mtype=generic	Curative		Approved 8583	Mecillinam Approved Use Urinary tract infections Launch Date 1984

C_max

Value	Dose	Analyte	Population
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
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
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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
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
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
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
0.96 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

Doses

Dose	Population	Adverse events
500 mg single, intravenous Highest studied dose Dose: 500 mg Route: intravenous Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6311007	healthy, 25 - 43 Health Status: healthy Age Group: 25 - 43 Sources: https://pubmed.ncbi.nlm.nih.gov/6311007	Sources: https://pubmed.ncbi.nlm.nih.gov/6311007
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: https://pubmed.ncbi.nlm.nih.gov/6310997	unhealthy, 25-94 Health Status: unhealthy Age Group: 25-94 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6310997	Other AEs: Diarrhea, Aspartate aminotransferase abnormal... Other AEs: Diarrhea (2.6%) Aspartate aminotransferase abnormal (10.52%) Alkaline phosphatase increased (7.9%) Sources: https://pubmed.ncbi.nlm.nih.gov/6310997

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: https://pubmed.ncbi.nlm.nih.gov/6310997	unhealthy, 25-94 Health Status: unhealthy Age Group: 25-94 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6310997
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: https://pubmed.ncbi.nlm.nih.gov/6310997	unhealthy, 25-94 Health Status: unhealthy Age Group: 25-94 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6310997
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: https://pubmed.ncbi.nlm.nih.gov/6310997	unhealthy, 25-94 Health Status: unhealthy Age Group: 25-94 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6310997

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-3276	http://www.3bsc.com/index/pro_info.php?id=76217
Aaron Chemicals	AR00JL85	http://www.aaronchem.com/prod/32887-01-7
abcr GmbH	AB479645	http://www.abcr.com/shop/en/AB479645
AHH Chemical co.,ltd	MT-53466	http://www.ahhchemical.com/product/MT-53466.html
Ambeed	A678129	https://www.ambeed.com/products/32887-01-7.html
Aurora Fine Chemicals LLC	A17.900.971	http://online.aurorafinechemicals.com/info?ID=A17.900.971
BLD Pharm	BD137305	http://www.bldpharm.com/products/32887-01-7.html
Chem Scene	CS-0017618	http://www.chemscene.com/32887-01-7.html
Chemspace	CSSB00016995348	https://chem-space.com/CSSB00016995348
CSNpharm	CSN11365	https://www.csnpharm.com/products/mecillinam.html
eNovation Chemicals	D673770	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673770
Glentham Life Sciences	GA6807	http://www.glentham.com/products/product/GA6807/
Lab Network	LN01267525	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01267525
MedChem Express	HY-A0269	https://www.medchemexpress.com/mecillinam.html
Selleck Chemicals	S6584	http://www.selleckchem.com/products/amdinocillin.html
Sigma-Aldrich	33447_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/33447?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral

PubMed

Title	Date	PubMed
Do different susceptibility breakpoints affect the selection of antimicrobials for treatment of uncomplicated cystitis?	2010-10	21123159
Molecular and evolutionary bases of within-patient genotypic and phenotypic diversity in Escherichia coli extraintestinal infections.	2010-09-30	20941353
Extended-spectrum β-lactamases in Gram Negative Bacteria.	2010-09	20927289
Septal and lateral wall localization of PBP5, the major D,D-carboxypeptidase of Escherichia coli, requires substrate recognition and membrane attachment.	2010-07	20545860
Low frequency of antibiotic resistance among urine isolates of Escherichia coli in the community, despite a major hospital outbreak with Klebsiella pneumoniae producing CTX-M-15 in Uppsala County.	2010-04	20085420
Molecular characterisation of trimethoprim resistance in Escherichia coli and Klebsiella pneumoniae during a two year intervention on trimethoprim use.	2010-02-16	20169085
[Clinical aspects and epidemiology of uncomplicated cystitis in women. German results of the ARESC Study].	2010-02	19943031
Activity of mecillinam against Escherichia coli resistant to third-generation cephalosporins.	2010-01	19915068
Acute uncomplicated cystitis: from surveillance data to a rationale for empirical treatment.	2010-01	19906513
Secondary syphilis with exclusive peno-scrotal localization.	2009-12	19907410
Influence of RpoS, cAMP-receptor protein, and ppGpp on expression of the opgGH operon and osmoregulated periplasmic glucan content of Salmonella enterica serovar Typhimurium.	2009-11	19940937
The ARESC study: an international survey on the antimicrobial resistance of pathogens involved in uncomplicated urinary tract infections.	2009-11	19505803
Empiric antibiotic therapy in acute uncomplicated urinary tract infections and fluoroquinolone resistance: a prospective observational study.	2009-10-24	19852849
Actinomyces species: A danish survey on human infections and microbiological characteristics.	2009-07-23	19657460
Bend into shape.	2009-05-06	19421162
Mecillinam: a low-risk antimicrobial agent for induction of Clostridium difficile infection in an in vitro human gut model.	2009-04	19211576
Multi-resistant Escherichia coli and mycotic aneurysm: two case reports.	2009-03-10	19830106
RodZ, a new player in bacterial cell morphogenesis.	2009-02-04	19194484
Evolutionary diversification of plant shikimate kinase gene duplicates.	2008-12	19057671
Transfer of antimicrobial resistance plasmids from Klebsiella pneumoniae to Escherichia coli in the mouse intestine.	2008-11	18703526
Surveillance study in Europe and Brazil on clinical aspects and Antimicrobial Resistance Epidemiology in Females with Cystitis (ARESC): implications for empiric therapy.	2008-11	18511178
Endemic and epidemic lineages of Escherichia coli that cause urinary tract infections.	2008-10	18826822
In vitro interaction between mecillinam and piperacillin-tazobactam in the presence of azithromycin against members of the Enterobacteriaceae family and Pseudomonas aeruginosa.	2008-01	18437840
Dissemination of multidrug-resistant bacteria into the Arctic.	2008-01	18258081
Spontaneous zygogenesis (Z-mating) in mecillinam-rounded bacteria.	2007-12	17687545
Characterization of HMW-PBPs from the rod-shaped actinomycete Corynebacterium glutamicum: peptidoglycan synthesis in cells lacking actin-like cytoskeletal structures.	2007-11	17877698
The essential peptidoglycan glycosyltransferase MurG forms a complex with proteins involved in lateral envelope growth as well as with proteins involved in cell division in Escherichia coli.	2007-08	17640276
DNA and origin region segregation are not affected by the transition from rod to sphere after inhibition of Escherichia coli MreB by A22.	2007-07	17581120
Increasing spectrum in antimicrobial resistance of Shigella isolates in Bangladesh: resistance to azithromycin and ceftriaxone and decreased susceptibility to ciprofloxacin.	2007-06	17985817
A novel serovar of Shigella dysenteriae from patients with diarrhoea in Bangladesh.	2007-05	17446289
Antimicrobial resistance among enterobacteriaceae causing uncomplicated urinary tract infections in Mauritius: consequences of past misuse of antibiotics.	2007-04	17434833
Function of penicillin-binding protein 2 in viability and morphology of Pseudomonas aeruginosa.	2007-03	17289762
The diversity of multi-drug resistance profiles in tetracycline-resistant Vibrio species isolated from coastal sediments and seawater.	2007-02	17342058
The emerging strains of Shigella dysenteriae type 2 in Bangladesh are clonal.	2006-12	16684401
Activity of mecillinam against AmpC beta-lactamase-producing Escherichia coli.	2006-07	16698846
[Increasing antibiotic resistance in urinary tract infections].	2006-04-06	16619066
Partition of old murein in small patches over the entire wall of E. coli cells forced to grow as a coccoid.	2006-04	16550459
High-level resistance to mecillinam produced by inactivation of soluble lytic transglycosylase in Salmonella enterica serovar Typhimurium.	2006-03	16499622
Activity of mecillinam against ESBL producers in vitro.	2006-02	16354745
Prevalence of Shigella species and their antimicrobial resistance patterns in Eastern Nepal.	2005-12	16599104
Uncomplicated urinary tract infections. Bacterial findings and efficacy of empirical antibacterial treatment.	2005-06	16036551
Iron limitation induces SpoT-dependent accumulation of ppGpp in Escherichia coli.	2005-05	15853883
Isolation and characterization of provisional serovar Shigella boydii E16553 from diarrhoeal patients in Bangladesh.	2005-05	15824427
Susceptibility testing of urinary isolates of Escherichia coli to mecillinam using NCCLS methodology.	2005-03	15737512
Intracellular persistence of Escherichia coli in urinary bladders from mecillinam-treated mice.	2005-03	15681580
Antimicrobial resistance in urinary bacterial isolates from pregnant women in rural Tanzania: implications for public health.	2005	15871165
Shigella serotypes among hospitalized patients in urban Bangladesh and their antimicrobial resistance.	2004-08	15310182
Susceptibility of community Gram-negative urinary tract isolates to mecillinam and other oral agents.	2001-09	18159352
Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death.	1983-08-29	6311012
Efficacy of amdinocillin and lack of nephrotoxicity when combined with a second beta-lactam antibiotic for therapy of serious gram-negative bacillary infections.	1983-08-29	6310997

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:37 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:37 GMT 2025`
Record UNII	48FX7N21H2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMDINOCILLIN PIVOXIL HYDROCHLORIDE

Preferred Name

English

PIVMECILLINAM HYDROCHLORIDE

Common Name

English

Pivmecillinam hydrochloride [WHO-DD]

Common Name

English

PIVMECILLINAM HYDROCHLORIDE [MART.]

Common Name

English

PIVMECILLINAM HYDROCHLORIDE [JAN]

Common Name

English

PIVMECILLINAM HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

AMDINOCILLIN PIVOXIL HYDROCHLORIDE [MI]

Common Name

English

HYDROXYMETHYL (2S,5R,6R)-6-(((HEXAHYDRO-1H-AZEPIN-1-YL)METHYLENE)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE PIVALATE (ESTER) HYDROCHLORIDE

Common Name

English

1H-AZEPIN-1-YL)METHYLENE)AMINO)-3,3-DIMETHYL-7-OXO-, HYDROXYMETHYL ESTER PIVALATE (ESTER), MONOHYDROCHLORIDE, (+)-

Common Name

English

PIVYA

Brand Name

English

Code System Code Type Description

EVMPD

SUB03884MIG