Pivmecillinam hydrochloride is a prodrug of mecillinam, a beta-lactam antibiotic. It is synthesized by reacting mecillinam with pivaloyl chloride, forming a pivaloyloxymethyl ester. Pivmecillinam hydrochloride is well absorbed orally and hydrolyzed in the body to release mecillinam, which exhibits antibacterial activity against gram-negative bacteria, particularly Escherichia coli, Proteus mirabilis, and Klebsiella pneumoniae. It is primarily used to treat urinary tract infections. Pivmecillinam hydrochloride is studied due to its enhanced oral bioavailability and improved stability compared to mecillinam. Its importance lies in providing an effective and convenient treatment option for urinary tract infections, particularly in patients with compromised renal function.'
| ID Source | ID |
|---|---|
| PubMed CID | 115162 |
| CHEMBL ID | 1355196 |
| CHEMBL ID | 4303519 |
| SCHEMBL ID | 232687 |
| MeSH ID | M0475062 |
| Synonym |
|---|
| smr001233435 |
| MLS002154128 , |
| amdinocillin pivoxil hydrochloride |
| cas-32887-03-9 |
| NCGC00016813-01 |
| 32887-03-9 |
| D01499 |
| pivmecillinam hydrochloride (jp17) |
| melysin (tn) |
| pivmecilinamo clorhidrato [spanish] |
| melysin |
| fl-1039 |
| 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, monohydrochloride, (2s,5r,6r)- |
| pivmecillinam hydrochloride |
| 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, monohydrochloride, (2s-(2alpha,5alpha,6beta))- |
| einecs 251-278-7 |
| HMS1571C08 |
| tox21_110625 |
| dtxcid9025453 |
| dtxsid1045453 , |
| 48fx7n21h2 , |
| unii-48fx7n21h2 |
| pivmecillinam hydrochloride [jan] |
| 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 |
| amdinocillin pivoxil hydrochloride [mi] |
| pivmecillinam hydrochloride [mart.] |
| pivmecillinam hydrochloride [ep monograph] |
| pivmecillinam hydrochloride [who-dd] |
| 1h-azepin-1-yl)methylene)amino)-3,3-dimethyl-7-oxo-, hydroxymethyl ester pivalate (ester), monohydrochloride, (+)- |
| S5473 |
| SCHEMBL232687 |
| CCG-221053 |
| CHEMBL1355196 |
| 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;hydrochloride |
| pivmecillinam hcl |
| HY-B0810A |
| pivmecillinam (hydrochloride) , |
| 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, monohydrochloride, [2s-(2alpha,5alpha,6beta)]- |
| AKOS030526136 |
| SR-01000838842-3 |
| sr-01000838842 |
| J-018915 |
| BCP07839 |
| BS-17014 |
| Q27104782 |
| CHEMBL4303519 |
| C74675 |
| (pivaloyloxy)methyl (2s,5r,6r)-6-((azepan-1-ylmethylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride |
| A913043 |
| (pivaloyloxy)methyl (2s,5r,6r)-6-(((e)-azepan-1-ylmethylene)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride |
| pivmecillinamhydrochloride |
| Excerpt | Reference | Relevance |
|---|---|---|
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
| Class | Description |
|---|---|
| hydrochloride | A salt formally resulting from the reaction of hydrochloric acid with an organic base. |
| [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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, Beta-lactamase | Escherichia coli K-12 | Potency | 5.0119 | 0.0447 | 17.8581 | 100.0000 | AID485294 |
| Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 79.4328 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
| apical membrane antigen 1, AMA1 | Plasmodium falciparum 3D7 | Potency | 7.9433 | 0.7079 | 12.1943 | 39.8107 | AID720542 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 6.4418 | 0.0002 | 29.3054 | 16,493.5996 | AID743075 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID540299 | A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis | 2010 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21 | Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. |
| AID588519 | A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities | 2011 | Antiviral research, Sep, Volume: 91, Issue:3 | High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 1 (11.11) | 29.6817 |
| 2010's | 6 (66.67) | 24.3611 |
| 2020's | 2 (22.22) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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 strong demand-to-supply ratio for research on this compound.
| This Compound (46.22) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 9 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||