Pivampicillin

Identification

Name
Pivampicillin
Accession Number
DB01604
Description

Pivalate ester analog of ampicillin.

Type
Small Molecule
Groups
Approved
Structure
Thumb
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.

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

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.

TargetActionsOrganism
APenicillin-binding protein 1A
inhibitor
Clostridium 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
Learn about our commercial Adverse Effects data.
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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.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Pivampicillin which could result in a higher serum level.
AcenocoumarolPivampicillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Pivampicillin.
AtracuriumThe therapeutic efficacy of Atracurium can be increased when used in combination with Pivampicillin.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be increased when used in combination with Pivampicillin.
CapreomycinThe serum concentration of Capreomycin can be decreased when it is combined with Pivampicillin.
CinoxacinThe serum concentration of Cinoxacin can be increased when it is combined with Pivampicillin.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Pivampicillin.
CisatracuriumThe therapeutic efficacy of Cisatracurium can be increased when used in combination with Pivampicillin.
Cyproterone acetateThe therapeutic efficacy of Cyproterone acetate can be decreased when used in combination with Pivampicillin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

International/Other Brands
Pondocillin
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Pondocillin Pws 175mg/5mlPowder, for solutionOralLeo Pharma1989-12-312006-10-13Canada
Pondocillin Tab 500mgTabletOralLeo Pharma1984-12-312008-03-28Canada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CA02 — Pivampicillin
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)

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][[email protected]]12SC(C)(C)[[email protected]@H](N1C(=O)[[email protected]]2NC(=O)[[email protected]](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C

References

General References
  1. 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. [PubMed:20398122]
  2. 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. [PubMed:15793098]
Human Metabolome Database
HMDB0015542
KEGG Compound
C11750
PubChem Compound
33478
PubChem Substance
46505340
ChemSpider
30899
RxNav
8372
ChEBI
8255
ChEMBL
CHEMBL3182343
ZINC
ZINC000034967244
Therapeutic Targets Database
DAP001171
PharmGKB
PA164776912
Wikipedia
Pivampicillin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule350 mg
Powder, for solutionOral
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0354 mg/mLALOGPS
logP1.43ALOGPS
logP2.07ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area128.03 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity116.25 m3·mol-1ChemAxon
Polarizability47.54 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9213
Blood Brain Barrier-0.9918
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5543
P-glycoprotein inhibitor INon-inhibitor0.9052
P-glycoprotein inhibitor IINon-inhibitor0.9543
Renal organic cation transporterNon-inhibitor0.9423
CYP450 2C9 substrateNon-substrate0.8983
CYP450 2D6 substrateNon-substrate0.8513
CYP450 3A4 substrateNon-substrate0.5094
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9283
Ames testNon AMES toxic0.8164
CarcinogenicityNon-carcinogens0.6461
BiodegradationNot ready biodegradable0.9769
Rat acute toxicity1.9193 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9996
hERG inhibition (predictor II)Non-inhibitor0.815
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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
  1. 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]
  2. 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]
  3. 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. [PubMed:12461003]

Drug created on August 29, 2007 12:48 / Updated on June 12, 2020 10:51

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