Explore a selection of our essential drug information below, or:
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
Structure for Bacampicillin (DB01602)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Genital infection •••••••••••• •••••• Treatment of Infections, intestinal •••••••••••• •••••• Treatment of Lower respiratory tract infection (lrti) •••••••••••• •••••• Treatment of Oral infection •••••••••••• •••••• Treatment of Pneumonia •••••••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism APenicillin-binding protein inhibitorGram 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
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 Bacampicillin which could result in a higher serum level. Acenocoumarol Bacampicillin may increase the anticoagulant activities of Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Bacampicillin is combined with Ambroxol. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Bacampicillin. Articaine The risk or severity of methemoglobinemia can be increased when Bacampicillin is combined with Articaine. - 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
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 Bacampicillin hydrochloride PM034U953T 37661-08-8 IWVTXAGTHUECPN-ANBBSHPLSA-N - International/Other Brands
- Ambaxin (Upjohn) / BacaciI (Pfizer) / Bamaxin (Upjohn) / Penglobe (AstraZeneca) / Spectrobid (Pfizer)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Penglobe Tab 400 mg Tablet 400 mg Oral Astrazeneca Ab 1984-12-31 2003-07-24 Canada 
Penglobe Tab 800 mg Tablet 800 mg / tab Oral Astrazeneca Ab 1984-12-31 2000-07-20 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 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
- 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]
- External Links
- Human Metabolome Database
- HMDB0015540
- KEGG Compound
- C08122
- PubChem Compound
- 441397
- PubChem Substance
- 46507859
- ChemSpider
- 390135
- 18687
- ChEBI
- 2968
- ChEMBL
- CHEMBL1583
- Therapeutic Targets Database
- DAP001162
- PharmGKB
- PA164745461
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Bacampicillin
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data0 Terminated Treatment Osteomyelitis 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Pfizer Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Dosage Forms
Form Route Strength Tablet Oral 100 ML Tablet Oral 800 MG Tablet, film coated Oral 1.2 G Tablet, film coated Oral 1200 MG Tablet, film coated Oral Tablet, coated Tablet, film coated Oral 400 mg Tablet, film coated Oral 800 mg Tablet Oral Tablet Oral 400 mg Tablet Oral 800 mg / tab - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 171-176 Ekstrom, 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
Property Value Source Water Solubility 0.123 mg/mL ALOGPS logP 1.17 ALOGPS logP 1.47 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 11.72 Chemaxon pKa (Strongest Basic) 7.23 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 137.26 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 113.76 m3·mol-1 Chemaxon Polarizability 46.8 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 + 0.6112 Blood Brain Barrier - 0.9916 Caco-2 permeable + 0.5859 P-glycoprotein substrate Substrate 0.6099 P-glycoprotein inhibitor I Non-inhibitor 0.8604 P-glycoprotein inhibitor II Non-inhibitor 0.9967 Renal organic cation transporter Non-inhibitor 0.9576 CYP450 2C9 substrate Non-substrate 0.8941 CYP450 2D6 substrate Non-substrate 0.8509 CYP450 3A4 substrate Non-substrate 0.5721 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.954 Ames test Non AMES toxic 0.8334 Carcinogenicity Non-carcinogens 0.6384 Biodegradation Not ready biodegradable 0.9843 Rat acute toxicity 2.0733 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9993 hERG inhibition (predictor II) Non-inhibitor 0.8531
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4i-1900000000-210a80ea99d7d8b19c7c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-05r0-0136900000-b2e481885b4fe511abf6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00g0-7209000000-7a862627b43b8ed4c8fe Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0005-9103100000-9d72f04ab82014fb459e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a6r-2219200000-8e3315c939064a9184f5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0q2c-5779300000-850a2dd4f88543d75fff Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6y-9421000000-996673e155baff746750 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 216.4357323 predictedDarkChem Lite v0.1.0 [M-H]- 209.8563 predictedDeepCCS 1.0 (2019) [M+H]+ 216.1164323 predictedDarkChem Lite v0.1.0 [M+H]+ 211.90266 predictedDeepCCS 1.0 (2019) [M+Na]+ 216.1705323 predictedDarkChem Lite v0.1.0 [M+Na]+ 217.81543 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- beta-lactamase activity
Components:
References
- 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 at August 29, 2007 18:46 / Updated at October 14, 2024 09:58