Ampicillin
Explore a selection of our essential drug information below, or:
Overview
- Description
- An antibiotic related to penicillin that is used to treat a wide variety of infections in the body caused by bacteria.
- Description
- An antibiotic related to penicillin that is used to treat a wide variety of infections in the body caused by bacteria.
- DrugBank ID
- DB00415
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 1
- Phase 1
- 2
- Phase 2
- 12
- Phase 3
- 18
- Phase 4
- 28
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
- 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
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Bacterial infection Combination Product in combination with: Sulbactam (DB09324) •••••••••••• Treatment of Bacterial meningitis •••••••••••• •••••••••• ••••••• ••• •••••••• Treatment of Endocarditis •••••••••••• •••••••••• ••••••• ••• •••••••• Treatment of Gastrointestinal infections •••••••••••• Treatment of Genitourinary tract infection •••••••••••• - 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
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. 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 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. - 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 Italia S.R.L. Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution 1 g / vial Intramuscular; Intravenous Fresenius Kabi Italia S.R.L. 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 2 g / vial Intravenous Fresenius Kabi Italia S.R.L. 1998-07-27 Not applicable Canada - Generic Prescription Products
- 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. 2011-06-08 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. 2011-01-20 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. 2009-07-03 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. 2009-07-03 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. 2008-05-14 Not applicable Turkey - 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
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 dataNot Available Completed Not Available Antibiotic Resistant Infection / Bacterial Infections / Surgical Site Infections 1 somestatus stop reason just information to hide Not Available Completed Not Available Drug Metabolism During Pregnancy 1 somestatus stop reason just information to hide Not Available Completed Not Available Infection 1 somestatus stop reason just information to hide Not Available Completed Not Available Listeria Monocytogenes 1 somestatus stop reason just information to hide Not Available Completed Not Available Lung Abscess / Peritonitis / Pneumonia 1 somestatus stop reason just information to hide
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 Tablet, film coated Oral Injection, powder, for solution Intramuscular; Intravenous 1.5 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 250000 g Capsule, coated Oral 500 mg Capsule, coated Oral 50000000 mg Injection, powder, for suspension Parenteral 500 mg Capsule, coated Oral 250 mg Tablet Oral 250 mg Tablet Oral 1 g Powder, for suspension Oral 5 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/1mL Injection, powder, for solution Intravenous 2 g/1 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 Syrup Tablet Oral 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 Injection, powder, for solution Parenteral Capsule Oral 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 Suspension Oral Powder, for solution Intravenous 2 g / vial Ointment Ophthalmic Solution / drops Oral Injection Intramuscular; Intravenous 1 gr Injection Intramuscular; Intravenous 250 mg Injection Intramuscular; Intravenous 500 mg Tablet Oral 1000 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/5ML Powder, for suspension Oral 250 MG 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 Liquid Oral 125 mg / 5 mL Tablet Oral Injection Intramuscular Tablet Oral 1.00 g Tablet Oral 500.000 mg Powder, for suspension Oral 5000 mg Injection, solution Intramuscular Syrup 125 MG/5ML 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 Capsule Oral Injection, powder, for solution Injection, powder, for solution Intramuscular; Intravenous 250 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 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 Syrup 250 MG/5ML Injection, powder, for solution Parenteral 1 g Injection, powder, for solution Parenteral 2 g Injection, powder, for solution Parenteral 500 mg Injection, powder, for solution Intramuscular; Intravenous 500 mg Injection, solution Intramuscular; Intravenous Injection Intramuscular; Intravenous 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.2334665 predictedDarkChem Lite v0.1.0 [M-H]- 186.2928665 predictedDarkChem Lite v0.1.0 [M-H]- 186.1541665 predictedDarkChem Lite v0.1.0 [M-H]- 187.8294665 predictedDarkChem Lite v0.1.0 [M-H]- 181.85304 predictedDeepCCS 1.0 (2019) [M+H]+ 186.2035665 predictedDarkChem Lite v0.1.0 [M+H]+ 184.6127665 predictedDarkChem Lite v0.1.0 [M+H]+ 184.6295665 predictedDarkChem Lite v0.1.0 [M+H]+ 187.0363665 predictedDarkChem Lite v0.1.0 [M+H]+ 184.24861 predictedDeepCCS 1.0 (2019) [M+Na]+ 185.7261665 predictedDarkChem Lite v0.1.0 [M+Na]+ 185.2847665 predictedDarkChem Lite v0.1.0 [M+Na]+ 190.3734641 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.2603665 predictedDarkChem Lite v0.1.0 [M+Na]+ 190.16115 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan (PG) from the lipid intermediates (By similarity). Binds dansylated lipid II and catalyzes the polymerization of glycan chains (PubMed:12867450, PubMed:22487093). Hydrolyzes S2d (N-benzoyl-D-alanylmercaptoacetic acid) molecule, a synthetic thiolester analog of cell wall stem peptide (PubMed:10217767, PubMed:22487093). Active against bocillin, a fluorescent penicillin. No transpeptidase activity with non-fluorescent lysine-containing lipid II as substrate (PubMed:22487093).
- Specific Function
- acyltransferase activity
- 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
- Not Available
- Specific Function
- acyltransferase activity
- 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
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- serine-type D-Ala-D-Ala carboxypeptidase activity
- 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
- Cell wall formation.
- Specific Function
- penicillin binding
- 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
- A transpeptidase that forms peptide cross-links between adjacent glycan strands in cell wall peptidoglycan (PG). Part of the elongasome machinery that synthesizes peripheral PG.
- 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
- Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
- Specific Function
- dipeptide transmembrane transporter activity
- 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
- Proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides (PubMed:16434549, PubMed:18367661, PubMed:7756356). Transports neutral and anionic dipeptides with a proton to peptide stoichiometry of 2:1 or 3:1 (By similarity). In kidney, involved in the absorption of circulating di- and tripeptides from the glomerular filtrate (PubMed:7756356). Can also transport beta-lactam antibiotics, such as the aminocephalosporin cefadroxil, and other antiviral and anticancer drugs (PubMed:16434549). Transports the dipeptide-like aminopeptidase inhibitor bestatin (By similarity). Also able to transport carnosine (PubMed:31073693). Involved in innate immunity by promoting the detection of microbial pathogens by NOD-like receptors (NLRs) (By similarity). Mediates transport of bacterial peptidoglycans across the plasma membrane or, in macrophages, the phagosome membrane: catalyzes the transport of certain bacterial peptidoglycans, such as muramyl dipeptide (MDP), the NOD2 ligand (PubMed:20406817)
- Specific Function
- dipeptide transmembrane transporter activity
- 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
- Tyrosine-protein kinase that acts as a cell-surface receptor for ANGPT1, ANGPT2 and ANGPT4 and regulates angiogenesis, endothelial cell survival, proliferation, migration, adhesion and cell spreading, reorganization of the actin cytoskeleton, but also maintenance of vascular quiescence. Has anti-inflammatory effects by preventing the leakage of pro-inflammatory plasma proteins and leukocytes from blood vessels. Required for normal angiogenesis and heart development during embryogenesis. Required for post-natal hematopoiesis. After birth, activates or inhibits angiogenesis, depending on the context. Inhibits angiogenesis and promotes vascular stability in quiescent vessels, where endothelial cells have tight contacts. In quiescent vessels, ANGPT1 oligomers recruit TEK to cell-cell contacts, forming complexes with TEK molecules from adjoining cells, and this leads to preferential activation of phosphatidylinositol 3-kinase and the AKT1 signaling cascades. In migrating endothelial cells that lack cell-cell adhesions, ANGT1 recruits TEK to contacts with the extracellular matrix, leading to the formation of focal adhesion complexes, activation of PTK2/FAK and of the downstream kinases MAPK1/ERK2 and MAPK3/ERK1, and ultimately to the stimulation of sprouting angiogenesis. ANGPT1 signaling triggers receptor dimerization and autophosphorylation at specific tyrosine residues that then serve as binding sites for scaffold proteins and effectors. Signaling is modulated by ANGPT2 that has lower affinity for TEK, can promote TEK autophosphorylation in the absence of ANGPT1, but inhibits ANGPT1-mediated signaling by competing for the same binding site. Signaling is also modulated by formation of heterodimers with TIE1, and by proteolytic processing that gives rise to a soluble TEK extracellular domain. The soluble extracellular domain modulates signaling by functioning as decoy receptor for angiopoietins. TEK phosphorylates DOK2, GRB7, GRB14, PIK3R1; SHC1 and TIE1
- Specific Function
- ATP binding
- 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
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- 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
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- (R)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Organic cation/carnitine transporter 2
- 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
- Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
- Specific Function
- dipeptide transmembrane transporter activity
- 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
- Proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides (PubMed:16434549, PubMed:18367661, PubMed:7756356). Transports neutral and anionic dipeptides with a proton to peptide stoichiometry of 2:1 or 3:1 (By similarity). In kidney, involved in the absorption of circulating di- and tripeptides from the glomerular filtrate (PubMed:7756356). Can also transport beta-lactam antibiotics, such as the aminocephalosporin cefadroxil, and other antiviral and anticancer drugs (PubMed:16434549). Transports the dipeptide-like aminopeptidase inhibitor bestatin (By similarity). Also able to transport carnosine (PubMed:31073693). Involved in innate immunity by promoting the detection of microbial pathogens by NOD-like receptors (NLRs) (By similarity). Mediates transport of bacterial peptidoglycans across the plasma membrane or, in macrophages, the phagosome membrane: catalyzes the transport of certain bacterial peptidoglycans, such as muramyl dipeptide (MDP), the NOD2 ligand (PubMed:20406817)
- Specific Function
- dipeptide transmembrane transporter activity
- 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
- Bidirectional proton-coupled monocarboxylate transporter (PubMed:12946269, PubMed:32946811, PubMed:33333023). Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, acetate and the ketone bodies acetoacetate and beta-hydroxybutyrate, and thus contributes to the maintenance of intracellular pH (PubMed:12946269, PubMed:33333023). The transport direction is determined by the proton motive force and the concentration gradient of the substrate monocarboxylate. MCT1 is a major lactate exporter (By similarity). Plays a role in cellular responses to a high-fat diet by modulating the cellular levels of lactate and pyruvate that contribute to the regulation of central metabolic pathways and insulin secretion, with concomitant effects on plasma insulin levels and blood glucose homeostasis (By similarity). Facilitates the protonated monocarboxylate form of succinate export, that its transient protonation upon muscle cell acidification in exercising muscle and ischemic heart (PubMed:32946811). Functions via alternate outward- and inward-open conformation states. Protonation and deprotonation of 309-Asp is essential for the conformational transition (PubMed:33333023)
- Specific Function
- carboxylic acid transmembrane transporter activity
- 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 November 06, 2024 19:54