Pivmecillinam
Identification
- Name
- Pivmecillinam
- Accession Number
- DB01605
- Description
Pivmecillinam is a mecillinam prodrug, a 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. [PubChem]
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pivmecillinam (DB01605)
- Weight
- Average: 439.569
Monoisotopic: 439.214091871 - Chemical Formula
- C21H33N3O5S
- Synonyms
- Amdinocillin pivoxil
- amdinocillin, pivaloyloxymethyl ester
- Pivmecilinamo
- Pivmecillinam
- Pivmecillinamum
- External IDs
- RO 10-9071
Pharmacology
- Indication
Used to treat infections due to mecillinam-sensitive organisms such as urinary tract infections, salmonellosis and typhoid fever.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Pivmecillinam is a 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.
- Mechanism of action
Pivmecillinam interferes with the biosynthesis of the bacterial cell wall however its activity is slightly different from that of other penicillins and cephalosporins
Target Actions Organism APenicillin-binding protein 1A inhibitorClostridium perfringens (strain 13 / Type A) - Absorption
Well absorbed following oral administration.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAcemetacin Acemetacin may decrease the excretion rate of Pivmecillinam which could result in a higher serum level. Acenocoumarol Pivmecillinam may increase the anticoagulant activities of Acenocoumarol. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Pivmecillinam. Atracurium The therapeutic efficacy of Atracurium can be increased when used in combination with Pivmecillinam. Atracurium besylate The therapeutic efficacy of Atracurium besylate can be increased when used in combination with Pivmecillinam. Capreomycin The serum concentration of Capreomycin can be decreased when it is combined with Pivmecillinam. Cinoxacin The serum concentration of Cinoxacin can be increased when it is combined with Pivmecillinam. Ciprofloxacin The serum concentration of Ciprofloxacin can be increased when it is combined with Pivmecillinam. Cisatracurium The therapeutic efficacy of Cisatracurium can be increased when used in combination with Pivmecillinam. Colistin The serum concentration of Colistin can be decreased when it is combined with Pivmecillinam. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Pivmecillinam hydrochloride 48FX7N21H2 32887-03-9 UHPXMYLONAGUPC-WKLLBTDKSA-N - International/Other Brands
- Coactabs
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataSelexid Tablet Oral Knight Therapeutics Inc. Not applicable Not applicable Canada 
Selexid Tablet Oral Knight Therapeutics Inc. Not applicable Not applicable Canada Selexid Tab 185mg Tablet Oral Leo Pharma 1985-12-31 2012-08-02 Canada Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Anti-Infective Agents, Urinary
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Beta-Lactam Antibacterials
- beta-Lactams
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Penicillins
- Penicillins With Extended Spectrum
- Renal Agents
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acid esters
- Alternative Parents
- Penams / Acylals / Azepanes / Dicarboxylic acids and derivatives / Thiazolidines / Tertiary carboxylic acid amides / Azetidines / Formamidines / Dialkylthioethers / Carboximidamides show 9 more
- Substituents
- Acetal / Acylal / Aliphatic heteropolycyclic compound / Alpha-amino acid ester / Amidine / Azacycle / Azepane / Azetidine / Beta-lactam / Carbonyl group show 23 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- penicillanic acid ester, penicillin (CHEBI:51210)
Chemical Identifiers
- UNII
- 1WAM1OQ30B
- CAS number
- 32886-97-8
- InChI Key
- NPGNOVNWUSPMDP-HLLBOEOZSA-N
- InChI
- InChI=1S/C21H33N3O5S/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/t14-,15+,17-/m1/s1
- IUPAC Name
- [(2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
- SMILES
- [H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)OCOC(=O)C(C)(C)C)C(C)(C)S[C@]12[H])N1CCCCCC1
References
- General References
- Sjovall J, Huitfeldt B, Magni L, Nord CE: Effect of beta-lactam prodrugs on human intestinal microflora. Scand J Infect Dis Suppl. 1986;49:73-84. [PubMed:3547627]
- Graninger W: Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. [PubMed:14527775]
- Authors unspecified: Pivmecillinam (selexid). Drug Ther Bull. 1978 Dec 22;16(26):103-4. [PubMed:214285]
- External Links
- Human Metabolome Database
- HMDB0015543
- KEGG Drug
- D02889
- PubChem Compound
- 115163
- PubChem Substance
- 46506880
- ChemSpider
- 16735658
- 627
- ChEBI
- 51210
- ChEMBL
- CHEMBL1616433
- Therapeutic Targets Database
- DAP001174
- PharmGKB
- PA164750167
- Wikipedia
- Pivmecillinam
- AHFS Codes
- 08:12.16 — Penicillins
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Pyelonephritis / Urinary Tract Infection 1 4 Recruiting Prevention Complications / Infection / Prostate Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Granule 100 MG Tablet Oral 200 MG Tablet Oral 50 MG Tablet, film coated Oral 200 mg Tablet, film coated Oral 400 mg Tablet Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 119 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0526 mg/mL ALOGPS logP 3.23 ALOGPS logP 2.91 ChemAxon logS -3.9 ALOGPS pKa (Strongest Acidic) 13.66 ChemAxon pKa (Strongest Basic) 7.91 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 88.51 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 113.03 m3·mol-1 ChemAxon Polarizability 47.7 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.962 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.5577 P-glycoprotein substrate Substrate 0.7368 P-glycoprotein inhibitor I Inhibitor 0.603 P-glycoprotein inhibitor II Non-inhibitor 0.5211 Renal organic cation transporter Non-inhibitor 0.7087 CYP450 2C9 substrate Non-substrate 0.8243 CYP450 2D6 substrate Non-substrate 0.8069 CYP450 3A4 substrate Substrate 0.5997 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9396 Ames test Non AMES toxic 0.6178 Carcinogenicity Non-carcinogens 0.8141 Biodegradation Not ready biodegradable 0.5067 Rat acute toxicity 2.1874 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9925 hERG inhibition (predictor II) Non-inhibitor 0.6363
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Clostridium perfringens (strain 13 / Type A)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring glycosyl groups
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- pbpA
- Uniprot ID
- Q8XJ01
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 75176.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Graninger W: Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. [PubMed:14527775]
Drug created on August 29, 2007 12:48 / Updated on January 18, 2021 16:18