Page last updated: 2024-12-07

amdinocillin pivoxil

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Amdinocillin Pivoxil: Pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

pivmecillinam : A penicillanic acid ester that is the [(2,2-dimethylpropanoyl)oxy]methyl ester and prodrug of mecillinam. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID115163
CHEMBL ID1650818
CHEMBL ID1616433
CHEMBL ID1525183
CHEBI ID51210
SCHEMBL ID33907
SCHEMBL ID33908
MeSH IDM0000877

Synonyms (63)

Synonym
pivmecillinamum
[(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(azepan-1-ylmethylidene)amino]-2,2-dimethylpenam-3alpha-carboxylate
[(2,2-dimethylpropanoyl)oxy]methyl (2s,5r,6r)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
CHEBI:51210 ,
pivmecilinamo
BRD-K67100011-003-03-0
BSPBIO_001006
D02889
coactabs (tn)
amdinocillin pivoxil (usan)
32886-97-8
pivmecillinam (inn)
BPBIO1_001108
PRESTWICK2_001053
NCGC00179344-01
PRESTWICK3_001053
AB00514713
amdinocillin, pivaloyloxymethyl ester
pivmecillinam
amdinocillin pivoxil
DB01605
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)
einecs 251-276-6
ro 10-9071
pivmecilinamo [inn-spanish]
amdinocillin pivoxil [usan]
pivmecillinamum [inn-latin]
coactabs
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2s-(2alpha,5alpha,6beta))-
PRESTWICK1_001053
SPBIO_002933
PRESTWICK0_001053
2,2-dimethylpropanoyloxymethyl (2s,5r,6r)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
CHEMBL1650818
ro-10-9071
1wam1oq30b ,
unii-1wam1oq30b
pivmecillinam [inn]
pivmecillinam [mart.]
4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2s-(2.alpha.,5.alpha.,6.beta.))-
amdinocillin pivoxil [mi]
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)
pivmecillinam [jan]
pivmecillinam [who-dd]
SCHEMBL33907
SCHEMBL33908
DTXSID7048538
CHEMBL1616433
CHEMBL1525183
HY-B0810
SR-01000838842-2
pivmecillinam, >=98% (hplc)
(2s,6r)-pivaloyloxymethyl 6-((e)-azepan-1-ylmethyleneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
BCP07843
Q418086
NCGC00179344-07
gtpl10922
NCGC00179344-04
ro-109071
A918810
[(2s,5r,6r)-6-{[(azepan-1-yl)methylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
EN300-19766372
AKOS040750399

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" In late pregnancy (39-40 weeks of gestation) the plasma mean peak concentration (Cmax = (29 +/- 14 micrograms ml-1) after parenteral administration of 200 mg mecillinam was slightly lower and the volume of distribution (V = 65 +/- 29."( The pharmacokinetics of mecillinam and pivmecillinam in pregnant and non-pregnant women.
Erkkola, R; Heikkilä, A; Iisalo, E; Pyykkö, K, 1992
)
0.28
"The pharmacokinetic parameters of amdinocillin and pivamdinocillin were studied in 12 normal volunteers."( Pharmacokinetics of amdinocillin and pivamdinocillin in normal volunteers.
Christenson, JG; Francke, EL; Neu, HC; Ortiz-Neu, C; Srinivasan, S, 1983
)
0.27
" Both methods were applied to a pharmacokinetic study of pivmecillinam and mecillinam after oral administration of 400 mg pivmecillinam hydrochloride tablets in healthy Chinese subjects."( LC-MS/MS methods for determination of unstable pivmecillinam and mecillinam in acidified human plasma: Application to a pharmacokinetic study.
Ding, L; Gao, HY; Qian, XP; Sun, LN; Sun, SY; Wang, Y; Wang, YQ; Yang, YL; Zhao, Y, 2022
)
0.72

Compound-Compound Interactions

ExcerptReferenceRelevance
"The results of three separate studies aimed at evaluating the efficacy of long-term, low-dose treatment with pivmecillinam alone, and in combination with pivampicillin, in patients prone to recurrent bacteriuria, are presented."( Long-term, low-dose treatment with pivmecillinam alone and in combination with pivampicillin in patients prone to recurrent bacteriuria.
Barclay, RP; Mejlhede, A; Nilsson, LB, 1982
)
0.26
"3 patients with salmonella infections who continued to excrete salmonella in fecal samples for more than 6 months were treated with pivmecillinam alone or in combination with pivampicillin."( Treatment of Salmonella carriers with pivmecillinam alone or in combination with pivampicillin: experience with three patients.
Bruun, JN; Bøe, J; Digranes, A; Maeland, A, 1983
)
0.27

Bioavailability

ExcerptReferenceRelevance
"The bioavailability of amdinocillin was not altered when amdinocillin pivoxil was ingested 1 h before a standard breakfast, and it increased by 20% when amdinocillin pivoxil was ingested with or 1 h after a standard breakfast."( Influence of food on bioavailability of amdinocillin pivoxil.
Bornemann, LD; Castellano, S; Enthoven, D; Lin, AH; Patel, IH, 1988
)
0.79
" There was a tendency for the new PA tablets to produce a higher peak serum level as well as greater bioavailability of mecillinam."( Gastroscopic and pharmacokinetic evaluation of a new pivmecillinam tablet.
Andersen, JT; Frederiksen, HJ; Hey, H, 1982
)
0.26
" Bioavailability was 45 percent after the 250 mg dose and 38 percent after the 500 mg dose."( Pharmacokinetics of amdinocillin and pivamdinocillin in normal volunteers.
Christenson, JG; Francke, EL; Neu, HC; Ortiz-Neu, C; Srinivasan, S, 1983
)
0.27
" Pharmacokinetics were studied in 8 volunteers (CAE versus ampicillin), relative bioavailability and tolerance were studied in 100 volunteers (CAE versus pivmecillinam and CAE versus pivampicillin), and tolerance alone was studied in 50 volunteers (CAE versus ampicillin)."( Pharmacokinetics and tolerance of cefuroxime axetil in volunteers during repeated dosing.
Harding, SM; Sommers, DK; Van Wyk, M; Williams, PE, 1984
)
0.27

Dosage Studied

ExcerptRelevanceReference
" Pivmecillinam was given in dosage of 400 mg (potency) per day which was one-fifth the dose of amoxicillin 2,000 mg (potency) per day."( Clinical evaluation of pivmecillinam in intractable urinary-tract infections with complications. A comparative study with amoxicillin by a randomized double-blind technique.
Akita, Y; Hara, S; Hikosaka, K; Hirooka, K; Ishigami, J; Kaneda, K; Kataoka, N; Kobayashi, M; Kuroda, K; Kuroda, M; Mita, T; Miyazaki, S; Nakatsuka, E; Okano, H; Ono, S; Suemitsu, H; Sugimoto, M; Takahashi, Y; Tanaka, K; Tanikaze, S; Terasoma, K; Tomioka, S; Ueharaguchi, H; Yasumuro, T, 1977
)
0.26
" The dosage of pivamdinocillin in adults was 400 to 800 mg, every 6 hours, for 10 to 16 days; dosage in children was half this amount for 11 to 15 days."( Management of enteric fever with amdinocillin.
Ball, AP; Geddes, AM, 1983
)
0.27
"In a multi-centre study in general practice, 292 female patients with acute urinary tract infection received a 5-day course of pivmecillinam at a dosage of either 200 mg or 400 mg twice-daily."( A general practice evaluation of pivmecillinam given twice daily as a treatment for acute urinary tract infection.
Sheldon, MG; Skinner, JL; Venables, TL, 1984
)
0.27
" Bacteriological cure rates observed in these trials were consistently >85%, and studies of different dosing regimens suggested that a 3 day course was appropriate."( Pivmecillinam in the treatment of urinary tract infections.
Nicolle, LE, 2000
)
0.31
" coli from 155 women with community-acquired lower urinary tract infections (UTIs) randomized to one of three dosing regiments of pivmecillinam and aimed to identify associations between the presence of 29 virulence factor genes (VFGs), phylogenetic groups and biofilm formation and the course of infection during follow-up visits at 8-10 and 35-49 days post-inclusion, respectively."( Characteristics of Escherichia coli causing persistence or relapse of urinary tract infections: phylogenetic groups, virulence factors and biofilm formation.
Ejrnæs, K; Ferry, S; Frimodt-Møller, N; Holm, SE; Lundgren, B; Monsen, T; Reisner, A; Stegger, M,
)
0.13
" low dosage comparisons (mean difference 0, 95% confidence interval -0."( Optimal dosage and duration of pivmecillinam treatment for uncomplicated lower urinary tract infections: a systematic review and meta-analysis.
Jensen, K; Kranz, J; Kunath, F; Naber, K; Pinart, M; Proctor, T; Schmidt, S; Wagenlehner, F, 2017
)
0.46
" There was no evidence of a dose-response relationship."( Prenatal exposure to nitrofurantoin and risk of childhood leukaemia: a registry-based cohort study in four Nordic countries.
Broe, A; Hargreave, M; Hemmingsen, CH; Hjorth, S; Leinonen, MK; Nörby, U; Nordeng, H; Pottegård, A, 2022
)
0.72
" The lack of a dose-response relationship and a clear biological mechanism to explain the findings suggests against a causal association."( Prenatal exposure to nitrofurantoin and risk of childhood leukaemia: a registry-based cohort study in four Nordic countries.
Broe, A; Hargreave, M; Hemmingsen, CH; Hjorth, S; Leinonen, MK; Nörby, U; Nordeng, H; Pottegård, A, 2022
)
0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
antiinfective agentA substance used in the prophylaxis or therapy of infectious diseases.
antibacterial drugA drug used to treat or prevent bacterial infections.
prodrugA compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
penicillanic acid ester
penicillinAny member of the group of substituted penams containing two methyl substituents at position 2, a carboxylate substituent at position 3 and a carboxamido group at position 6.
pivaloyloxymethyl esterA acetal obtained from a carboxylic acid by replacement of the hydrogen attached to the carboxy group by a pivaloyloxymethyl group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
peripheral myelin protein 22Rattus norvegicus (Norway rat)Potency0.61590.005612.367736.1254AID624032
lamin isoform A-delta10Homo sapiens (human)Potency0.39810.891312.067628.1838AID1487
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency15.84890.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (25)

Assay IDTitleYearJournalArticle
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID567465Antimicrobial activity against xtended-spectrum-beta-lactamase-producing Escherichia coli obtained from urinary tract infection patient assessed as percent susceptible isolates by Etest2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
Oral treatment options for ambulatory patients with urinary tract infections caused by extended-spectrum-beta-lactamase-producing Escherichia coli.
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID567466Antimicrobial activity against xtended-spectrum-beta-lactamase-producing Escherichia coli obtained from urinary tract infection patient by Etest2010Antimicrobial agents and chemotherapy, Sep, Volume: 54, Issue:9
Oral treatment options for ambulatory patients with urinary tract infections caused by extended-spectrum-beta-lactamase-producing Escherichia coli.
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (233)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990119 (51.07)18.7374
1990's36 (15.45)18.2507
2000's29 (12.45)29.6817
2010's36 (15.45)24.3611
2020's13 (5.58)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.00

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.00 (24.57)
Research Supply Index5.80 (2.92)
Research Growth Index4.50 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.00)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials89 (37.08%)5.53%
Reviews10 (4.17%)6.00%
Case Studies11 (4.58%)4.05%
Observational2 (0.83%)0.25%
Other128 (53.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (6)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Mecillinam for Treatment of Genital Chlamydia Infection in Asymptomatic Men [NCT02083276]Phase 220 participants (Actual)Interventional2014-03-31Terminated(stopped due to Treatment failure on study medication observed)
Pivmecillinam Hydrochloride Tablets Versus Fosfomycin Tromethamine Granules for Uncomplicated Urinary Tract Infection in Women -A Randomized, Double-blind, Double Simulation, Positive Drug Parallel-controlled, Multi Center Phase III Clinical Trial in Chin [NCT05545137]Phase 3320 participants (Anticipated)Interventional2022-09-29Recruiting
Pivmecillinam With Amoxicillin/Clavulanic Acid for Step Down Oral Therapy in Febrile UTIs Caused by ESBL-producing Enterobacterales (PACUTI) [NCT05224401]Phase 3330 participants (Anticipated)Interventional2023-05-29Recruiting
Clinical Effectiveness and Bacteriological Eradication of Three Different Short-course Antibiotic Regimens and Single-dose Fosfomycin for Uncomplicated Lower Urinary Tract Infections in Adult Women. [NCT04959331]Phase 41,000 participants (Anticipated)Interventional2021-11-02Recruiting
The Efficacy and Safety of Pivmecillinam in Treating Bacteriemic Urosepsis Caused by E.Coli [NCT03282006]Phase 453 participants (Actual)Interventional2017-09-29Completed
The Effect of Rectal Swab Culture-guided Antimicrobial Prophylaxis in Men Undergoing Prostate Biopsy on Infectious Complications and Cost of Care: A Randomized Controlled Trial in the Netherlands. [NCT03228108]Phase 41,538 participants (Actual)Interventional2018-04-03Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]