Identification

Name
Bacampicillin
Accession Number
DB01602
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
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-alpha-aminophenylacetamido)penicillanate
  • Bacampicilina
  • Bacampicilline
  • Bacampicillinum
Product Ingredients
IngredientUNIICASInChI Key
Bacampicillin hydrochloridePM034U953T37661-08-8IWVTXAGTHUECPN-ANBBSHPLSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Penglobe Tab 400 mgTablet400 mgOralAstra Zeneca1984-12-312003-07-24Canada
Penglobe Tab 800 mgTablet800 mgOralAstra Zeneca1984-12-312000-07-20Canada
International/Other Brands
Ambaxin (Upjohn) / BacaciI (Pfizer) / Bamaxin (Upjohn) / Penglobe (AstraZeneca) / Spectrobid (Pfizer)
Categories
UNII
8GM2J22278
CAS number
50972-17-3
Weight
Average: 465.52
Monoisotopic: 465.156970923
Chemical Formula
C21H27N3O7S
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

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.

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 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
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinBacampicillin may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinBacampicillin may increase the anticoagulant activities of (S)-Warfarin.
4-hydroxycoumarinBacampicillin may increase the anticoagulant activities of 4-hydroxycoumarin.
AcemetacinAcemetacin may decrease the excretion rate of Bacampicillin which could result in a higher serum level.
AcenocoumarolBacampicillin may increase the anticoagulant activities of Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Bacampicillin.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Bacampicillin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Bacampicillin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Bacampicillin.
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Bacampicillin.
Food Interactions
Not Available

References

Synthesis Reference

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

US4619785
General References
Not Available
External Links
Human Metabolome Database
HMDB0015540
KEGG Compound
C08122
PubChem Compound
441397
PubChem Substance
46507859
ChemSpider
390135
ChEBI
2968
ChEMBL
CHEMBL1583
Therapeutic Targets Database
DAP001162
PharmGKB
PA164745461
Drugs.com
Drugs.com Drug Page
Wikipedia
Bacampicillin
ATC Codes
J01CR50 — Combinations of penicillinsJ01CA06 — Bacampicillin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
Dosage forms
FormRouteStrength
TabletOral400 mg
TabletOral800 mg
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

Taxonomy

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
Penicillin / Alpha-amino acid ester / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / Aralkylamine / Monocyclic benzene moiety / Carbonic acid diester / Benzenoid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillanic acid ester (CHEBI:2968)

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]

Drug created on August 29, 2007 12:46 / Updated on November 02, 2018 08:42