Identification
- Summary
Pivampicillin is an ampicillin prodrug used to treat a variety of infections.
- Generic Name
- Pivampicillin
- DrugBank Accession Number
- DB01604
- Background
Pivalate ester analog of ampicillin.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pivampicillin (DB01604)
- Weight
- Average: 463.547
Monoisotopic: 463.177706365 - Chemical Formula
- C22H29N3O6S
- Synonyms
- Ampicillin pivaloyloxymethyl ester
- Pivaloylampicillin
- Pivaloyloxymethyl ampicillinate
- Pivampicilina
- Pivampicillin
- Pivampicilline
- Pivampicillinum
- External IDs
- MK-191
Pharmacology
- Indication
or the treatment of respiratory tract infections (including acute bronchitis, acute exacerbations of chronic bronchitis and pneumonia); ear, nose and throat infections; gynecological infections; urinary tract infections (including acute uncomplicated gonococcal urethritis) when caused by non penicillinase-producing susceptible strains of the following organisms: gram-positive organisms, e.g., streptococci, pneumococci and staphylococci; gram-negative organisms, e.g., H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis.
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- Contraindications & Blackbox Warnings
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Pivampicillin is the pivaloyloxymethyl ester of (the semi-synthetic penicillin) ampicillin. It is an inactive pro-drug, which is converted during its absorption from the gastrointestinal tract to the microbiologically active ampicillin, together with formaldehyde and pivalic acid, by non-specific esterases present in most body tissues. Amounts in excess of 99% of the pivampicillin absorbed are converted to ampicillin within 15 minutes of absorption.
- Mechanism of action
Ampicillin (the active metabolite of pivampicillin) has a bactericidal action resulting from inhibition of cell wall mucopeptide biosynthesis.
Target Actions Organism APenicillin-binding protein 1A inhibitorClostridium perfringens (strain 13 / Type A) - Absorption
Absorbed following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Approximately 1 hour.
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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 Pivampicillin which could result in a higher serum level. Acenocoumarol Pivampicillin may increase the anticoagulant activities of Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Pivampicillin is combined with Ambroxol. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Pivampicillin. Articaine The risk or severity of methemoglobinemia can be increased when Pivampicillin is combined with Articaine. Atracurium The therapeutic efficacy of Atracurium can be increased when used in combination with Pivampicillin. Atracurium besylate The therapeutic efficacy of Atracurium besylate can be increased when used in combination with Pivampicillin. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Pivampicillin. Benzocaine The risk or severity of methemoglobinemia can be increased when Pivampicillin is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Pivampicillin is combined with Benzyl alcohol. 
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- 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.- International/Other Brands
- Pondocillin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Pondocillin Pws 175mg/5ml Powder, for solution 175 mg / 5 mL Oral Leo Pharma 1989-12-31 2006-10-13 Canada 
Pondocillin Tab 500mg Tablet 500 mg Oral Leo Pharma 1984-12-31 2008-03-28 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 n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-acyl-alpha amino acids and derivatives
- Alternative Parents
- Alpha amino acid esters / Penams / Acylals / Aralkylamines / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Thiazolidines / Azetidines / Thiohemiaminal derivatives show 10 more
- Substituents
- Acetal / Acylal / Alpha-amino acid ester / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / Beta-lactam show 27 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillanic acid ester (CHEBI:8255)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 0HLM346LL7
- CAS number
- 33817-20-8
- InChI Key
- ZEMIJUDPLILVNQ-ZXFNITATSA-N
- InChI
- InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1
- IUPAC Name
- [(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
- SMILES
- [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C
References
- General References
- Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. doi: 10.1111/j.1532-5415.2010.02741.x. [Article]
- Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. [Article]
- External Links
- Human Metabolome Database
- HMDB0015542
- KEGG Compound
- C11750
- PubChem Compound
- 33478
- PubChem Substance
- 46505340
- ChemSpider
- 30899
- 8372
- ChEBI
- 8255
- ChEMBL
- CHEMBL3182343
- ZINC
- ZINC000034967244
- Therapeutic Targets Database
- DAP001171
- PharmGKB
- PA164776912
- Wikipedia
- Pivampicillin
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Powder, for solution Oral 175 mg / 5 mL Tablet Oral 500 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0354 mg/mL ALOGPS logP 1.43 ALOGPS logP 2.07 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 11.71 Chemaxon pKa (Strongest Basic) 7.23 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 128.03 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 116.25 m3·mol-1 Chemaxon Polarizability 47.54 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 - 0.9213 Blood Brain Barrier - 0.9918 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.5543 P-glycoprotein inhibitor I Non-inhibitor 0.9052 P-glycoprotein inhibitor II Non-inhibitor 0.9543 Renal organic cation transporter Non-inhibitor 0.9423 CYP450 2C9 substrate Non-substrate 0.8983 CYP450 2D6 substrate Non-substrate 0.8513 CYP450 3A4 substrate Non-substrate 0.5094 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9283 Ames test Non AMES toxic 0.8164 Carcinogenicity Non-carcinogens 0.6461 Biodegradation Not ready biodegradable 0.9769 Rat acute toxicity 1.9193 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9996 hERG inhibition (predictor II) Non-inhibitor 0.815
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]
- Okamoto T, Yoshiyama H, Nakazawa T, Park ID, Chang MW, Yanai H, Okita K, Shirai M: A change in PBP1 is involved in amoxicillin resistance of clinical isolates of Helicobacter pylori. J Antimicrob Chemother. 2002 Dec;50(6):849-56. [Article]
Drug created at August 29, 2007 18:48 / Updated at February 21, 2021 18:51