Identification
- Summary
Ampicillin is a penicillin derivative used for the treatment of a variety of infections caused by gram-positive and gram-negative bacteria as well as some anaerobes.
- Brand Names
- Unasyn
- Generic Name
- Ampicillin
- DrugBank Accession Number
- DB00415
- Background
Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Ampicillin (DB00415)
- Weight
- Average: 349.405
Monoisotopic: 349.109626801 - Chemical Formula
- C16H19N3O4S
- Synonyms
- ABPC
- Aminobenzylpenicillin
- Ampicilina
- Ampicillin
- Ampicillin (anhydrous)
- Ampicillin acid
- Ampicillin anhydrous
- Ampicillin, anhydrous
- Ampicilline
- Ampicillinum
- Anhydrous ampicillin
- AP
- D-(−)-6-(α-aminophenylacetamido)penicillanic acid
- D-(−)-ampicillin
- External IDs
- AY-6108
- Bayer 5427
- BRL-1341
- NSC-528986
- P-50
- WY 5103
Pharmacology
- Indication
For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
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
- Bacterial Infections
- Endocarditis
- Gastrointestinal Tract Infections
- Genitourinary tract infection
- Infection
- Infection caused by eikenella corrodens
- Listeria infection
- Meningitis, Bacterial
- Pertussis
- Respiratory Tract Infections (RTI)
- Salmonella
- Septicemia
- Shigella
- Subcutaneous bacterial infection
- Urinary Tract Infection
- Bacterial skin infections
- Disease caused by Salmonella typhi
- Perinatal group B streptococcus
- Susceptible Bacterial Infections
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Ampicillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Ampicillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ampicillin results from the inhibition of cell wall synthesis and is mediated through Ampicillin binding to penicillin binding proteins (PBPs). Ampicillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
- Mechanism of action
By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Ampicillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Ampicillin interferes with an autolysin inhibitor.
Target Actions Organism APenicillin-binding protein 2a inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 1b inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 3 inhibitorStreptococcus pneumoniae APenicillin-binding protein 1A inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 2B inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) USolute carrier family 15 member 1 Not Available Humans USolute carrier family 15 member 2 Not Available Humans UAngiopoietin-1 receptor Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Ampicillin is excreted largely unchanged in the urine.
- 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.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 softwareAbacavir Ampicillin may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Ampicillin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Ampicillin which could result in a higher serum level. Acenocoumarol Ampicillin may increase the anticoagulant activities of Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Ampicillin which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Ampicillin which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Ampicillin which could result in a higher serum level. Aclidinium Ampicillin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Ampicillin may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Ampicillin which could result in a higher serum level. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Take on an empty stomach.
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 Ampicillin sodium JFN36L5S8K 69-52-3 KLOHDWPABZXLGI-UHFFFAOYSA-M Ampicillin trihydrate HXQ6A1N7R6 7177-48-2 RXDALBZNGVATNY-CWLIKTDRSA-N - Product Images
- International/Other Brands
- Austrapen (Lennon Healthcare) / Binotal (Bayer) / Penbritin (GlaxoSmithKline) / Principen / Redicilin / Semicillin / Tokiocillin / Ultrabion / Viccillin (Meiji)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ampicillin for Injection Powder, for solution 125 mg / vial Intramuscular; Intravenous Fresenius Kabi Not applicable Not applicable Canada 
Ampicillin for Injection, USP Powder, for solution 500 mg / vial Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution 1 g / vial Intramuscular; Intravenous Fresenius Kabi 1998-08-14 Not applicable Canada Ampicillin for Injection, USP Powder, for solution 2 g / vial Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution 250 mg / vial Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution 250 mg / vial Intramuscular; Intravenous Fresenius Kabi 1998-08-14 Not applicable Canada Ampicillin for Injection, USP Powder, for solution 2 g / vial Intravenous Fresenius Kabi 1998-07-27 Not applicable Canada Ampicillin for Injection, USP Powder, for solution 1 g / vial Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution 500 mg / vial Intramuscular; Intravenous Fresenius Kabi 1998-08-14 Not applicable Canada Ampicillin for Injection, USP Powder, for solution 10 g / vial Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ampicillin Injection, powder, for solution 2 g/1 Intramuscular; Intravenous Fresenius Kabi USA, LLC 2001-03-29 2019-03-31 US 
Ampicillin Injection, powder, for solution 2 g/1 Intravenous Sandoz GmbH 1971-03-03 Not applicable US Ampicillin Injection, powder, for solution 2 g/1 Intravenous Athenex Pharmaceutical Division, Llc. 2018-08-01 Not applicable US Ampicillin Capsule 500 mg/1 Oral bryant ranch prepack 1988-02-25 Not applicable US Ampicillin Injection, powder, for solution 2 g/1 Intravenous Medical Purchasing Solutions, Llc 2012-02-01 Not applicable US Ampicillin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Sandoz Inc 1971-03-03 Not applicable US Ampicillin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Physicians Total Care, Inc. 1995-01-25 2011-06-30 US Ampicillin Injection, powder, for solution 250 mg/1 Intramuscular; Intravenous WG Critical Care, LLC 2012-05-10 2016-03-31 US Ampicillin Injection, powder, for solution 500 mg/1 Intramuscular; Intravenous Hospira, Inc 2017-08-01 Not applicable US Ampicillin Injection, powder, for solution 2 g/1 Intravenous Pfizer Laboratories, Division of Pfizer Inc 2010-08-17 2013-10-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ALFASID 1 G IM/IV ENJEKSIYON ICIN TOZ ICEREN FLAKON, 1 ADET Ampicillin (1000 mg) + Sulbactam (500 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
ALFASID 1 GR IM ENJ. ICIN TOZ ICEREN FLAKON, 1 ADET Ampicillin (1000 mg) + Sulbactam (500 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey ALFASID 250 MG IM ENJ.ICIN TOZ ICEREN FLAKON, 1 ADET Ampicillin sodium (250 mg) + Sulbactam (125 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey ALFASID 250 MG IM/IV ENJ.ICIN TOZ ICEREN FLAKON, 1 ADET Ampicillin sodium (250 mg) + Sulbactam (125 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey ALFASID 500 MG IM ENJ.ICIN TOZ ICEREN FLAKON Ampicillin (1000 mg) + Sulbactam (500 mg) Injection, powder, for solution Intramuscular YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey ALFASID 500 MG IM/IV ENJ.ICIN TOZ ICEREN FLAKON Ampicillin (1000 mg) + Sulbactam (500 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey AMPICILINA + SULBACTAM 1.5 G POLVO PARASOLUCIÓN INYECTABLE Ampicillin sodium (1 g) + Sulbactam sodium (0.5 g) Injection, powder, for solution Intramuscular; Intravenous PHARMAYECT S.A. 2008-06-25 Not applicable Colombia 
AMPICILINA 1 G TABLETAS. Ampicillin (200 mg) + Ampicillin (800 mg) Tablet Oral SYNTOFARMA 2019-06-28 Not applicable Colombia AMPICILINA 1 G TABLETAS. Ampicillin (200 mg) + Ampicillin (800 mg) Tablet Oral SYNTOFARMA 2019-06-28 Not applicable Colombia AMPICILINA Y SULBACTAM 1.5 G. Ampicillin sodium (1 g) + Sulbactam (0.5 g) Injection, powder, for solution Intramuscular; Intravenous FARMALOGICA S.A. 2006-11-10 2020-04-07 Colombia - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ampicillin and Sulbactam Ampicillin sodium (2 g/1) + Sulbactam sodium (1 g/1) Injection, powder, for suspension Intramuscular; Intravenous Cardinal Health 2011-05-20 2014-02-28 US
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
- J01CA — Penicillins with extended spectrum
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01CA — Penicillins with extended spectrum
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Aminopenicillins
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Beta-Lactam Antibacterials
- beta-Lactams
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Ophthalmologicals
- Penicillin G
- Penicillins
- Penicillins With Extended Spectrum
- Sensory Organs
- Sulfur Compounds
- 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 amides / Phenylacetamides / Aralkylamines / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives show 9 more
- Substituents
- Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin, beta-lactam antibiotic (CHEBI:28971) / penams (C06574)
- Affected organisms
- Enteric bacteria and other eubacteria
- Gram-negative Bacteria
- Gram-positive Bacteria
- Streptococcus pyogenes
- Streptococcus pneumoniae
- Neisseria meningitidis
- Listeria monocytogenes
- Haemophilus influenzae
Chemical Identifiers
- UNII
- 7C782967RD
- CAS number
- 69-53-4
- InChI Key
- AVKUERGKIZMTKX-NJBDSQKTSA-N
- InChI
- InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/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-carboxylic acid
- SMILES
- [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O
References
- Synthesis Reference
Jean Bouchaudon, Pierre Le Roy, Mayer Naoum Messer, "Process for the preparation of ampicillin." U.S. Patent US3978078, issued December, 1974.
US3978078- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014559
- KEGG Drug
- D00204
- KEGG Compound
- C06574
- PubChem Compound
- 6249
- PubChem Substance
- 46505346
- ChemSpider
- 6013
- BindingDB
- 50350465
- 221058
- ChEBI
- 28971
- ChEMBL
- CHEMBL174
- ZINC
- ZINC000003830218
- Therapeutic Targets Database
- DAP000432
- PharmGKB
- PA448419
- PDBe Ligand
- AIC
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Ampicillin
- PDB Entries
- 1h8s / 1nx9 / 2rdd / 3ita / 3kp3 / 3ndv / 4gcp / 4kr4
- MSDS
- Download (71.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Breast Cancer 1 4 Completed Prevention Kidney Stones / Urinary Tract Infection 1 4 Completed Prevention Surgical Site Infections 1 4 Completed Treatment Bacterial skin infections 1 4 Completed Treatment Complicated Appendicitis 1 4 Completed Treatment Intraabdominal Infections 2 4 Completed Treatment Pneumonia 1 4 Enrolling by Invitation Prevention Kidney Stones 1 4 Enrolling by Invitation Treatment Endocarditis 1 4 Not Yet Recruiting Treatment Acinetobacter Bacteremia / Acinetobacter Pneumonia / Carbapenem Resistant Bacterial Infection 1
Pharmacoeconomics
- Manufacturers
- Acic fine chemicals inc
- Apothecon inc div bristol myers squibb
- Baxter healthcare corp anesthesia and critical care
- Consolidated pharmaceutical group inc
- Gc hanford manufacturing co
- Istituto biochimico italiano spa
- Instituto biochemico italiano spa
- International medication systems ltd
- Eli lilly and co
- Marsam pharmaceuticals llc
- Sandoz inc
- Wyeth ayerst laboratories
- Bristol laboratories inc div bristol myers co
- Glaxosmithkline
- Parke davis div warner lambert co
- American antibiotics llc
- Dava pharmaceuticals inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Lederle laboratories div american cyanamid co
- Mylan pharmaceuticals inc
- Purepac pharmaceutical co
- Teva pharmaceuticals usa inc
- Vitarine pharmaceuticals inc
- Pfizer laboratories div pfizer inc
- Bristol myers squibb co
- Apothecon sub bristol myers squibb co
- Packagers
- American Antibiotics LLC
- Apotheca Inc.
- APP Pharmaceuticals
- A-S Medication Solutions LLC
- Bryant Ranch Prepack
- C.O. Truxton Inc.
- Cardinal Health
- Carlisle Laboratories Inc.
- Central Texas Community Health Centers
- Claris Lifesciences Inc.
- Clonmel Healthcare Ltd.
- Comprehensive Consultant Services Inc.
- Comptoir Francaise De Productores
- Cura Pharmaceutical Co. Inc.
- Darby Dental Supply Co. Inc.
- DAVA Pharmaceuticals
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- E.R. Squibb and Sons LLC
- GC Hanford Manufacturing Co.
- H and H Laboratories
- H.J. Harkins Co. Inc.
- Ibi Istituto Biochimico Italiano Giovanni Lorenzini SPA
- Major Pharmaceuticals
- Marnel Pharmaceuticals Inc.
- Mead Johnson and Co.
- Medpharm Inc.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Par Pharmaceuticals
- PCA LLC
- PD-Rx Pharmaceuticals Inc.
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prescript Pharmaceuticals
- Putney Inc.
- Sagent Pharmaceuticals
- Sandhills Packaging Inc.
- Sandoz
- SC Antibiotice SA
- Signal Health Ltd.
- Southwood Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- WG Critical Care LLC
- Dosage Forms
Form Route Strength Injection, solution Intravenous 1 g/3mL Tablet, film coated Oral 500 mg Solution Intramuscular 500.000 mg Capsule, coated Oral 500 mg Tablet, film coated Oral Injection, powder, for solution Intramuscular; Intravenous 1.5 g Injection, powder, for solution Parenteral 1 g Injection, powder, for solution Intramuscular; Intravenous 1 g Suspension Oral 2.5 g Injection, powder, for solution Parenteral 1000 mg Powder, for suspension Oral 5 g Injection, powder, for solution Intramuscular; Intravenous 500 mg Injection, powder, for suspension Parenteral 500 mg Injection, powder, for solution Parenteral 500 mg Capsule, coated Oral 250 mg Tablet Oral 250 mg Tablet Oral 1 g Powder, for suspension Oral 2.5 g Capsule Oral 250 mg/1 Capsule Oral 500 mg/1 Injection, powder, for solution Intramuscular; Intravenous 1 g/1 Injection, powder, for solution Intramuscular; Intravenous 1 g/1mL Injection, powder, for solution Intramuscular; Intravenous 125 mg/1 Injection, powder, for solution Intramuscular; Intravenous 2 g/1 Injection, powder, for solution Intramuscular; Intravenous 250 mg/1mL Injection, powder, for solution Intramuscular; Intravenous 250 mg/1 Injection, powder, for solution Intramuscular; Intravenous 500 mg/1mL Injection, powder, for solution Intramuscular; Intravenous 500 mg/1 Injection, powder, for solution Intravenous 1 g/1 Injection, powder, for solution Intravenous 10 g/1 Injection, powder, for solution Intravenous 10 g/100mL Injection, powder, for solution Intravenous 2 g/1 Injection, powder, for solution Intravenous 2 g/1mL Injection, powder, for solution Intravenous 250 mg/1 Injection, powder, for solution Intravenous 500 mg/1 Powder, for solution Intramuscular; Intravenous 1 g/1g Powder, for solution Intramuscular; Intravenous 2 g/2g Powder, for solution Intramuscular; Intravenous 250 mg/250mg Powder, for solution Intramuscular; Intravenous 500 mg/500mg Suspension Oral 125 mg/5mL Suspension Oral 25 mg/1mL Suspension Oral 250 mg/5mL Suspension Oral 50 mg/1mL Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for solution Intravenous Injection, powder, for suspension Intramuscular; Intravenous Powder, for solution Intramuscular; Intravenous 10 g / vial Powder, for solution Intramuscular; Intravenous 2 g / vial Powder, for solution Intramuscular; Intravenous 1000 mg / vial Powder, for solution Intramuscular; Intravenous 2000 mg / vial Powder, for solution Intramuscular; Intravenous 500 mg / vial Suspension Oral Tablet Oral Injection, powder, for solution Parenteral Injection, powder, for solution 1 G Injection, powder, for solution Intramuscular; Intravenous 500 MG/2.5ML Powder Intramuscular; Intravenous 1000 MG Powder Intramuscular; Intravenous 250 MG Injection, powder, for solution Intramuscular Powder, for solution Intravenous 2 g / vial Ointment Ophthalmic Solution / drops Oral Injection Intramuscular; Intravenous 250 mg Injection, powder, for solution Intramuscular; Intravenous 2 g Injection, powder, for solution Parenteral 1 G/4mL Injection, powder, for solution Parenteral 500 MG/2.5mL Powder, for suspension Oral 250 MG Powder, for suspension Oral 250 MG/5ML Solution Intramuscular 1 G Solution Intramuscular 250 MG Solution Intramuscular 500 MG Solution / drops Oral 2 g/20ml Suspension Oral 3 g Granule Tablet, soluble Oral 250 mg Solution Parenteral 250.000 mg Injection, solution Intramuscular; Intravenous Liquid Oral 125 mg / 5 mL Injection Intramuscular; Intravenous Tablet Oral Injection Intramuscular Injection, powder, for solution Suspension Oral 9.000 g Tablet Oral 1.00 g Tablet Oral 500.000 mg Powder, for suspension Oral 5000 mg Tablet Oral 1000 mg Injection, solution Intramuscular Injection Intramuscular; Intravenous Tablet Oral 1 gr Tablet Oral 500 mg Capsule Oral 500.00 mg Suspension Oral 4.500 g Suspension Oral 1.500 g Powder, for solution Oral 500 mg / 5 mL Powder, for solution Oral 125 mg / 5 mL Powder, for solution Oral 250 mg / 5 mL Suspension Oral 125 mg / 5 mL Suspension Oral 250 mg / 5 mL Injection Intramuscular; Intravenous 1 g Injection Intramuscular; Intravenous 500 mg Capsule Oral Injection, powder, for solution Injection, powder, for solution Intramuscular; Intravenous 250 mg Capsule Oral 250.00 mg Suspension Oral 10.0000 g Powder, for solution Intramuscular; Intravenous 1 g / vial Liquid Intramuscular; Intravenous 2 g / vial Powder, for solution Intravenous 1 g / vial Powder, for solution Intramuscular; Intravenous 125 mg / vial Powder, for solution Intramuscular; Intravenous 250 mg / vial Syrup Suspension Oral 80 ml Solution / drops Oral 30 ml Suspension Oral 8 ml Capsule Oral 500.000 mg Tablet Oral 500.00 mg Powder, for suspension Oral Capsule; tablet Oral Injection, powder, for solution Parenteral Capsule Oral Capsule Oral 250 mg / cap Capsule Oral 500 mg / cap Powder Injection, powder, for solution Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular; Intravenous 2 g Injection, powder, for solution Intramuscular; Intravenous 500 mg Injection, powder, lyophilized, for solution Intramuscular; Intravenous Injection, powder, for solution 1 g/vial Injection, powder, for solution 250 mg Injection, powder, for solution 500 mg Capsule Oral 250 mg Capsule Oral 500 mg Powder, for suspension Oral 125 mg/5ml Tablet Oral 125 mg Tablet, film coated Oral 125 mg - Prices
Unit description Cost Unit Ampicillin 10 gm vial 107.77USD vial Ampicillin 2 gm vial 16.75USD vial Principen 250 mg/5ml Suspension 200ml Bottle 16.27USD bottle Ampicillin 1 gm vial 8.64USD vial Principen 250 mg/5ml Suspension 100ml Bottle 7.99USD bottle Ampicillin Sodium 2 g/vial 7.56USD vial Ampicillin Sodium 1 g/vial 3.78USD vial Ampicillin tr 250 mg capsule 3.53USD capsule Ampicillin Sodium 500 mg/vial 2.26USD vial Ampicillin Sodium 250 mg/vial 2.15USD vial Ampicillin tr 500 mg capsule 0.61USD capsule Ampicillin 500 mg capsule 0.5USD capsule Ampicillin 250 mg capsule 0.44USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 208 dec °C PhysProp water solubility 1.01E+004 mg/L (at 21 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.35 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.605 mg/mL ALOGPS logP 0.88 ALOGPS logP -2 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 3.24 Chemaxon pKa (Strongest Basic) 7.23 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 112.73 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 87.52 m3·mol-1 Chemaxon Polarizability 34.54 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.927 Blood Brain Barrier - 0.9961 Caco-2 permeable - 0.8956 P-glycoprotein substrate Substrate 0.5603 P-glycoprotein inhibitor I Non-inhibitor 0.9626 P-glycoprotein inhibitor II Non-inhibitor 0.9971 Renal organic cation transporter Non-inhibitor 0.9689 CYP450 2C9 substrate Non-substrate 0.8297 CYP450 2D6 substrate Non-substrate 0.8447 CYP450 3A4 substrate Non-substrate 0.5825 CYP450 1A2 substrate Non-inhibitor 0.9253 CYP450 2C9 inhibitor Non-inhibitor 0.9402 CYP450 2D6 inhibitor Non-inhibitor 0.9401 CYP450 2C19 inhibitor Non-inhibitor 0.9399 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9884 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.5363 Biodegradation Not ready biodegradable 0.9844 Rat acute toxicity 1.5620 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9998 hERG inhibition (predictor II) Non-inhibitor 0.9031
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring acyl groups
- Specific Function
- Not Available
- Gene Name
- pbp2a
- Uniprot ID
- Q8DNB6
- Uniprot Name
- Penicillin-binding protein 2a
- Molecular Weight
- 80797.94 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Transferase activity, transferring acyl groups
- Specific Function
- Not Available
- Gene Name
- pbp1b
- Uniprot ID
- Q7CRA4
- Uniprot Name
- Penicillin-binding protein 1b
- Molecular Weight
- 89479.92 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Not Available
- Gene Name
- pbp3
- Uniprot ID
- Q75Y35
- Uniprot Name
- Penicillin-binding protein 3
- Molecular Weight
- 45209.84 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Li YH, Tanno M, Itoh T, Yamada H: Role of the monocarboxylic acid transport system in the intestinal absorption of an orally active beta-lactam prodrug: carindacillin as a model. Int J Pharm. 1999 Nov 30;191(2):151-9. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Penicillin binding
- Specific Function
- Cell wall formation.
- Gene Name
- pbpA
- Uniprot ID
- Q8DR59
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79700.9 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- Penicillin binding
- Gene Name
- penA
- Uniprot ID
- P0A3M6
- Uniprot Name
- Penicillin-binding protein 2B
- Molecular Weight
- 73872.305 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Pedretti A, De Luca L, Marconi C, Regazzoni L, Aldini G, Vistoli G: Fragmental modeling of hPepT2 and analysis of its binding features by docking studies and pharmacophore mapping. Bioorg Med Chem. 2011 Aug 1;19(15):4544-51. doi: 10.1016/j.bmc.2011.06.027. Epub 2011 Jun 16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane receptor protein tyrosine kinase activity
- Specific Function
- Tyrosine-protein kinase that acts as cell-surface receptor for ANGPT1, ANGPT2 and ANGPT4 and regulates angiogenesis, endothelial cell survival, proliferation, migration, adhesion and cell spreading...
- Gene Name
- TEK
- Uniprot ID
- Q02763
- Uniprot Name
- Angiopoietin-1 receptor
- Molecular Weight
- 125829.005 Da
References
- Gong XW, Mai JH, Xu YH: Discovery of loperamide as an antagonist of angiopoietin1 and angiopoietin2 by virtual screening. Bioorg Med Chem Lett. 2012 Apr 1;22(7):2388-92. doi: 10.1016/j.bmcl.2012.02.036. Epub 2012 Feb 22. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Other/unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Symporter activity
- Specific Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Solute carrier family 22 member 5
- Molecular Weight
- 62751.08 Da
References
- Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Covitz KM, Amidon GL, Sadee W: Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. Pharm Res. 1996 Nov;13(11):1631-4. [Article]
- Guo A, Hu P, Balimane PV, Leibach FH, Sinko PJ: Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther. 1999 Apr;289(1):448-54. [Article]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
- Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Symporter activity
- Specific Function
- Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucin...
- Gene Name
- SLC16A1
- Uniprot ID
- P53985
- Uniprot Name
- Monocarboxylate transporter 1
- Molecular Weight
- 53943.685 Da
References
- Li YH, Tanno M, Itoh T, Yamada H: Role of the monocarboxylic acid transport system in the intestinal absorption of an orally active beta-lactam prodrug: carindacillin as a model. Int J Pharm. 1999 Nov 30;191(2):151-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 28, 2023 01:14