Bacampicillin

Identification

Summary

Bacampicillin is an ampicillin prodrug used to treat various susceptible bacterial infections in the body, such as respiratory infections and skin and subcutaneous tissue infections.

Generic Name
Bacampicillin
DrugBank Accession Number
DB01602
Background

Bacampicillin is a prodrug of ampicillin and is microbiologically inactive. It is absorbed following oral administration. During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 465.52
Monoisotopic: 465.156970923
Chemical Formula
C21H27N3O7S
Synonyms
  • 1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • 1'-ethoxycarbonyloxyethyl-(6-D-α-aminophenylacetamido)penicillanate
  • Bacampicilina
  • Bacampicillin
  • Bacampicilline
  • Bacampicillinum

Pharmacology

Indication

For infections at the following sites: upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis, when due to sensitive strains of the following organisms: Gram-positive: streptococci (including S. faecalis and S. pneumoniae) and nonpenicillinase-producing staphylococci; Gram-negative: H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis, Salmonellae and Shigellae.

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Bacampicillin is a prodrug of ampicillin and is microbiologically inactive.

Mechanism of action

During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides.

TargetActionsOrganism
APenicillin-binding protein
inhibitor
Gram positive and gram negative bacteria
Absorption

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
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Bacampicillin which could result in a higher serum level.
AcenocoumarolBacampicillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Bacampicillin.
AtracuriumThe therapeutic efficacy of Atracurium can be increased when used in combination with Bacampicillin.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be increased when used in combination with Bacampicillin.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Bacampicillin.
CapreomycinThe serum concentration of Capreomycin can be decreased when it is combined with Bacampicillin.
CinoxacinThe serum concentration of Cinoxacin can be increased when it is combined with Bacampicillin.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Bacampicillin.
CisatracuriumThe therapeutic efficacy of Cisatracurium can be increased when used in combination with Bacampicillin.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
  • Take separate from antacids. Elevated gastric pH may reduce the bioavailability of bacampicillin.
  • Take with or without food. Food may reduce the bioavailability of bacampicillin.

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Bacampicillin hydrochloridePM034U953T37661-08-8IWVTXAGTHUECPN-ANBBSHPLSA-N
International/Other Brands
Ambaxin (Upjohn) / BacaciI (Pfizer) / Bamaxin (Upjohn) / Penglobe (AstraZeneca) / Spectrobid (Pfizer)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Penglobe Tab 400 mgTablet400 mgOralAstra Zeneca1984-12-312003-07-24Canada flag
Penglobe Tab 800 mgTablet800 mg / tabOralAstra Zeneca1984-12-312000-07-20Canada flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CA06 — Bacampicillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Penicillins
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid esters / Alpha amino acid amides / Phenylacetamides / Aralkylamines / Carbonic acid diesters / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Carboxylic acid esters
show 11 more
Substituents
Acetal / Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azetidine
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillanic acid ester (CHEBI:2968)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
8GM2J22278
CAS number
50972-17-3
InChI Key
PFOLLRNADZZWEX-FFGRCDKISA-N
InChI
InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
IUPAC Name
1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OC(C)OC(=O)OCC

References

Synthesis Reference

Luigi Ratti, "Novel synthesis route for bacampicillin." U.S. Patent US4619785, issued July, 1976.

US4619785
General References
  1. Cho H, Uehara T, Bernhardt TG: Beta-lactam antibiotics induce a lethal malfunctioning of the bacterial cell wall synthesis machinery. Cell. 2014 Dec 4;159(6):1300-11. doi: 10.1016/j.cell.2014.11.017. [Article]
Human Metabolome Database
HMDB0015540
KEGG Compound
C08122
PubChem Compound
441397
PubChem Substance
46507859
ChemSpider
390135
RxNav
18687
ChEBI
2968
ChEMBL
CHEMBL1583
Therapeutic Targets Database
DAP001162
PharmGKB
PA164745461
Drugs.com
Drugs.com Drug Page
Wikipedia
Bacampicillin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0TerminatedTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
Dosage Forms
FormRouteStrength
TabletOral100 ML
TabletOral800 MG
Tablet, film coatedOral1.2 G
Tablet, film coatedOral400 MG
Tablet, film coatedOral800 MG
Tablet, film coatedOral1200 MG
Tablet, film coatedOral
Tablet, coated
TabletOral400 mg
TabletOral
TabletOral800 mg / tab
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)171-176Ekstrom, B.A. and Sjoberg, B.O.H.; U S . Patents 3,873,521; March 25, 1975; and 3,939,270; February 17, 1976; both assigned to Astra Lakemedal A.B.
Predicted Properties
PropertyValueSource
Water Solubility0.123 mg/mLALOGPS
logP1.17ALOGPS
logP1.47ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)11.72ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area137.26 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity113.76 m3·mol-1ChemAxon
Polarizability46.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6112
Blood Brain Barrier-0.9916
Caco-2 permeable+0.5859
P-glycoprotein substrateSubstrate0.6099
P-glycoprotein inhibitor INon-inhibitor0.8604
P-glycoprotein inhibitor IINon-inhibitor0.9967
Renal organic cation transporterNon-inhibitor0.9576
CYP450 2C9 substrateNon-substrate0.8941
CYP450 2D6 substrateNon-substrate0.8509
CYP450 3A4 substrateNon-substrate0.5721
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.954
Ames testNon AMES toxic0.8334
CarcinogenicityNon-carcinogens0.6384
BiodegradationNot ready biodegradable0.9843
Rat acute toxicity2.0733 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9993
hERG inhibition (predictor II)Non-inhibitor0.8531
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

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein group
Organism
Gram positive and gram negative bacteria
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Note: The above was chosen as a representative target protein in a representative bacterium, and does not encompass all proteins/bacteria affected by this agent.
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.

Components:
References
  1. Cho H, Uehara T, Bernhardt TG: Beta-lactam antibiotics induce a lethal malfunctioning of the bacterial cell wall synthesis machinery. Cell. 2014 Dec 4;159(6):1300-11. doi: 10.1016/j.cell.2014.11.017. [Article]

Drug created on August 29, 2007 18:46 / Updated on August 07, 2021 00:41