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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Ampicillin
- Accession Number
- DB00415 (APRD00320)
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Description
Ampicillin is a semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
- Structure
Structure for Ampicillin (DB00415)
- 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
- 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
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAmpicillin for Injection Powder, for solution Intramuscular; Intravenous Fresenius Kabi Not applicable Not applicable Canada 
Ampicillin for Injection, USP Powder, for solution Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution Intramuscular; Intravenous Fresenius Kabi 1998-08-14 Not applicable Canada Ampicillin for Injection, USP Powder, for solution Intramuscular; Intravenous Fresenius Kabi 1998-08-14 Not applicable Canada Ampicillin for Injection, USP Powder, for solution Intramuscular; Intravenous Fresenius Kabi 1998-08-14 Not applicable Canada Ampicillin for Injection, USP Powder, for solution Intravenous Fresenius Kabi 1998-07-27 Not applicable Canada Ampicillin for Injection, USP Powder, for solution Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Ampicillin for Injection, USP Powder, for solution Intramuscular; Intravenous Sterimax Inc Not applicable Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAmpicillin Injection, powder, for solution 2 g/1 Intramuscular; Intravenous Hospira, Inc 1971-03-03 Not applicable US 
Ampicillin Injection, powder, for solution 125 mg/1 Intramuscular; Intravenous Sandoz GmbH 1971-03-03 Not applicable US Ampicillin Injection, powder, for solution 500 mg/1 Intramuscular; Intravenous Fresenius Kabi USA, LLC 2016-09-30 Not applicable US Ampicillin Injection, powder, for solution 500 mg/1 Intramuscular; Intravenous Aurobindo Pharma 2010-08-17 2010-08-19 US Ampicillin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous AuroMedics Pharma LLC 2012-02-01 Not applicable US Ampicillin Injection, powder, for solution 10 g/100mL Intravenous AuroMedics Pharma LLC 2012-02-01 Not applicable US Ampicillin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Fresenius Kabi USA, LLC 2001-01-03 2019-03-31 US Ampicillin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Mylan Institutional LLC 2016-09-12 Not applicable US Ampicillin Injection, powder, for solution 125 mg/1 Intramuscular; Intravenous Sandoz Inc 1971-03-03 Not applicable US Ampicillin Injection, powder, for solution 1 g/1 Intramuscular; Intravenous Pfizer Laboratories, Division of Pfizer Inc 2010-08-17 2013-10-31 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Ampicillin and Sulbactam Ampicillin sodium (100 mg/1mL) + Sulbactam sodium (50 mg/1mL) Injection, powder, for solution Intramuscular; Intravenous Baxter Laboratories 2010-04-15 2013-02-27 US Ampicillin and Sulbactam Ampicillin sodium (2 g/1) + Sulbactam sodium (1 g/1) Injection, powder, for solution Intramuscular; Intravenous Fresenius Kabi USA, LLC 2005-11-29 2016-05-05 US Ampicillin and Sulbactam Ampicillin sodium (250 mg/1mL) + Sulbactam sodium (125 mg/1mL) Injection, powder, for suspension Intramuscular; Intravenous Mylan Institutional 2012-11-27 2014-03-31 US Ampicillin and Sulbactam Ampicillin sodium (250 mg/1mL) + Sulbactam sodium (125 mg/1mL) Injection, powder, for solution Intravenous Hikma Pharmaceuticals USA Inc. 2009-12-22 Not applicable US Ampicillin and Sulbactam Ampicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1) Injection, powder, for solution Intramuscular; Intravenous Meitheal Pharmaceuticals Inc. 2018-12-17 Not applicable US Ampicillin and Sulbactam Ampicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1) Injection, powder, for suspension Intramuscular; Intravenous Cardinal Health 2007-06-29 2013-10-31 US Ampicillin and Sulbactam Ampicillin sodium (250 mg/1mL) + Sulbactam sodium (125 mg/1mL) Injection, powder, for solution Intramuscular; Intravenous Baxter Laboratories 2010-02-24 2013-07-30 US Ampicillin and Sulbactam Ampicillin sodium (2 g/1) + Sulbactam sodium (1 g/1) Injection, powder, for solution Intramuscular; Intravenous AuroMedics Pharma LLC 2012-02-10 Not applicable US Ampicillin and Sulbactam Ampicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1) Injection, powder, for solution Intramuscular; Intravenous AuroMedics Pharma LLC 2012-02-10 Not applicable US Ampicillin and Sulbactam Ampicillin sodium (1 g/1) + Sulbactam sodium (0.5 g/1) Injection, powder, for solution Intramuscular; Intravenous Fresenius Kabi USA, LLC 2005-11-29 2016-05-05 US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End 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 - International/Other Brands
- Austrapen (Lennon Healthcare) / Binotal (Bayer) / Penbritin (GlaxoSmithKline) / Principen / Redicilin / Semicillin / Tokiocillin / Ultrabion / Viccillin (Meiji)
- 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
- UNII
- 7C782967RD
- CAS number
- 69-53-4
- Weight
- Average: 349.405
Monoisotopic: 349.109626801 - Chemical Formula
- C16H19N3O4S
- 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
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
- Associated Conditions
- Bacterial Infections
- Bloodstream Infections
- Endocarditis
- Gastrointestinal Infections
- Genitourinary tract infection
- Infection
- Infection caused by eikenella corrodens
- Listeria infection
- Meningitis, Bacterial
- Pertussis
- Respiratory Tract Infections (RTI)
- Salmonella
- Salmonella Typhi Infection
- Shigella
- Skin bacterial infection
- Subcutaneous bacterial infection
- Urinary Tract Infection
- Perinatal group B streptococcus
- 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
- Toxicity
- Not Available
- Affected organisms
- Enteric bacteria and other eubacteria
- Gram-negative Bacteria
- Gram-positive Bacteria
- Streptococcus pyogenes
- Streptococcus pneumoniae
- Neisseria meningitidis
- Listeria monocytogenes
- Haemophilus influenzae
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
Additional Data Available
Adverse Effects
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn more Additional Data Available
Contraindications
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn more Additional Data Available
Blackbox Warnings
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- 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 Unlock Additional Data(R)-warfarin Ampicillin may increase the anticoagulant activities of (R)-warfarin. (S)-Warfarin Ampicillin may increase the anticoagulant activities of (S)-Warfarin. 4-hydroxycoumarin Ampicillin may increase the anticoagulant activities of 4-hydroxycoumarin. Abacavir Ampicillin may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Ampicillin 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. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take on an empty stomach.
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
- RxNav
- 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
- 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
- AHFS Codes
- 08:12.16.08 — Aminopenicillins
- PDB Entries
- 1h8s / 1nx9 / 2rdd / 3ita / 3kp3 / 3ndv / 4gcp / 4kr4
- MSDS
- Download (71.8 KB)
Clinical Trials
- Clinical Trials
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 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 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 Liquid Oral Tablet Oral Powder, for solution Oral Capsule Oral Suspension Oral Liquid Intramuscular; Intravenous Powder, for solution Intravenous Capsule; tablet Oral - 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) 7.44 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
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Penicillins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Aralkylamines / Thiazolidines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines / Thiohemiaminal derivatives show 9 more
- Substituents
- Penicillin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Thiazolidine / Tertiary carboxylic acid amide show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin, beta-lactam antibiotic (CHEBI:28971) / penams (C06574)
Targets
- 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. [PubMed:7447421]
- 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. [PubMed:7447421]
- 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. [PubMed:16627568]
- 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. [PubMed:7447421]
- 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. [PubMed:10564841]
- 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. [PubMed:7447421]
- 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. [PubMed:7447421]
- 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. [PubMed:15567297]
- 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. [PubMed:21741846]
- 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. [PubMed:22406116]
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. [PubMed:1031216]
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. [PubMed:10636865]
- 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. [PubMed:8956326]
- 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. [PubMed:10087037]
- 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. [PubMed:15567297]
- 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. [PubMed:9374833]
- 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. [PubMed:16627568]
- 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. [PubMed:9374833]
- 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. [PubMed:15567297]
- 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. [PubMed:10564841]
Drug created on June 13, 2005 07:24 / Updated on July 09, 2020 11:59
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