Identification
- Summary
Pivmecillinam is a prodrug of the beta lactam antibiotic mecillinam, indicated for the treatment of uncomplicated urinary tract infections (UTIs).
- Generic Name
- Pivmecillinam
- DrugBank Accession Number
- DB01605
- Background
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.
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
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Not Available
- 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 Integrate drug-drug
interactions in your softwareAcemetacin 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. Articaine The risk or severity of methemoglobinemia can be increased when Pivmecillinam is combined with Articaine. 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. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Pivmecillinam. Benzocaine The risk or severity of methemoglobinemia can be increased when Pivmecillinam is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Pivmecillinam is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Pivmecillinam is combined with Bupivacaine. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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 Selexid Tablet 400 mg Oral Knight Therapeutics Inc. Not applicable Not applicable Canada 
Selexid Tablet 200 mg Oral Knight Therapeutics Inc. Not applicable Not applicable Canada Selexid Tab 185mg Tablet 185 mg Oral Leo Pharma 1985-12-31 2012-08-02 Canada
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
- 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)
- Affected organisms
- Enteric bacteria and other eubacteria
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-yl)methylidene]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. [Article]
- Graninger W: Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. [Article]
- Authors unspecified: Pivmecillinam (selexid). Drug Ther Bull. 1978 Dec 22;16(26):103-4. [Article]
- 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
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Complications / Infection / Prostate Cancer 1 4 Completed Treatment Pyelonephritis / Urinary Tract Infection 1 4 Recruiting Treatment Urinary Tract Infection 1 3 Not Yet Recruiting Treatment Antibiotic Resistant Infection / Bacteremia / Urinary Tract Infection 1 3 Recruiting Treatment Uncomplicated Urinary Tract Infections 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Granule Tablet Oral Tablet Oral 200 mg Tablet Oral 400 mg Tablet, film coated Oral 200 mg Tablet Oral 185 mg Tablet, film coated 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 47.68 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
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- 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. [Article]
- 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. [Article]
- Graninger W: Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. [Article]
Drug created at August 29, 2007 18:48 / Updated at March 24, 2023 20:19