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Identification
Name Ampicillin
Accession Number DB00415 (APRD00320)
Type small molecule
Groups approved
Description

Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Aminobenzylpenicillin
Ampicilina [INN-Spanish]
Ampicillin [Usan:Ban:Inn:Jan]
Ampicillin Acid
Ampicillin Anhydrate
Ampicillin Anhydrous
Ampicillin Base
Ampicillin Sodium
Ampicillin Trihydrate
Ampicillina [Dcit]
Ampicilline
Ampicilline [INN-French]
Ampicillinum [INN-Latin]
Anhydrous Ampicillin
Bayer 5427
D-Ampicillin
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Salts Not Available
Brand names
Name Company
AB-PC
Ab-Pc Sol
Acillin
Adobacillin
Alpen
Amblosin
Amcill
Amfipen
Amfipen V
Amipenix S
Ampen
Ampi-Bol
Ampi-Co
Ampi-Tab
Ampichel
Ampicil
Ampicillin A
Ampicin
Ampifarm
Ampikel
Ampimed
Ampipenin
Ampipenin, Nt3
Ampiscel
Ampisyn
Ampivax
Ampivet
Amplacilina
Amplin
Amplipenyl
Amplisom
Amplital
Ampy-Penyl
Austrapen
Binotal
Bonapicillin
Britacil
Campicillin
Cimex
Copharcilin
D-Cillin
Delcillin
Deripen
Divercillin
Doktacillin
Duphacillin
Grampenil
Guicitrina
Guicitrine
Lifeampil
Morepen
Norobrittin
Novo-Ampicillin
Nuvapen
Olin Kid
Omnipen
Omnipen-N
Orbicilina
Pen A
Pen a Oral
Pen Ampil
Penbristol
Penbritin
Penbritin Paediatric
Penbritin Syrup
Penbritin-S
Penbrock
Penicline
Penimic
Pensyn
Pentrex
Pentrexl
Pentrexyl
Pfizerpen A
Polycillin
Ponecil
Princillin
Principen
Qidamp
Racenacillin
Ro-Ampen
Rosampline
Roscillin
Semicillin
Servicillin
Sumipanto
Supen
Synpenin
Texcillin
Tokiocillin
Tolomol
Totacillin
Totalciclina
Totapen
Trifacilina
Ultrabion
Ultrabron
Vampen
Viccillin
Viccillin S
Wypicil
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Brand mixtures
Brand Name Ingredients
Pro Biosan Kit Ampicillin + Probenecid
Synergistin Injectable Suspension Ampicillin + Sulbactam (Sulbactam Benzathine)
Categories
  • Anti-Bacterial Agents
  • Penicillins
CAS number 69-53-4
Weight Average: 349.405
Monoisotopic: 349.109626801
Chemical Formula C16H19N3O4S
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Penicillins
  • Phenethylamines
Substructures
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Beta Lactams
  • Penicillins
  • Thiazoles
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Lactams
  • Azetidines
  • Thiazolidines
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
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.
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
Pathways Not Available
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
Dosage forms
Form Route Strength
Capsule Oral
Liquid Oral
Powder, for solution Intramuscular
Powder, for solution Intravenous
Powder, for solution Oral
Suspension Oral
Tablet Oral
Prices
Unit description Cost Unit
Ampicillin 10 gm vial 107.77 USD vial
Ampicillin 2 gm vial 16.75 USD vial
Principen 250 mg/5ml Suspension 200ml Bottle 16.27 USD bottle
Ampicillin 1 gm vial 8.64 USD vial
Principen 250 mg/5ml Suspension 100ml Bottle 7.99 USD bottle
Ampicillin Sodium 2 g/vial 7.56 USD vial
Ampicillin Sodium 1 g/vial 3.78 USD vial
Ampicillin tr 250 mg capsule 3.53 USD capsule
Ampicillin Sodium 500 mg/vial 2.26 USD vial
Ampicillin Sodium 250 mg/vial 2.15 USD vial
Ampicillin tr 500 mg capsule 0.61 USD capsule
Ampicillin 500 mg capsule 0.5 USD capsule
Ampicillin 250 mg capsule 0.44 USD capsule
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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 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 6.05e-01 g/l 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 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 87.52 ChemAxon
polarizability 34.54 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00204 Link_out
KEGG Compound C06574 Link_out
PubChem Compound 6249 Link_out
PubChem Substance 46505346 Link_out
ChemSpider 6013 Link_out
ChEBI 28971 Link_out
ChEMBL 28971 Link_out
Therapeutic Targets Database DAP000432 Link_out
PharmGKB PA448419 Link_out
HET AIC Link_out
Drug Product Database 2227029 Link_out
RxList http://www.rxlist.com/cgi/generic/ampicillin.htm Link_out
Drugs.com http://www.drugs.com/cdi/ampicillin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Ampicillin Link_out
ATC Codes
  • J01CA01
  • J01CA02
  • J01CA06
  • J01CA14
  • J01CA15
  • S01AA19
AHFS Codes
  • 08:12.16.08
PDB Entries Not Available
FDA label Not Available
MSDS show (71.8 KB)
Interactions
Drug Interactions
Drug Interaction
Atenolol Ampicillin decreases bioavailability of atenolol
Demeclocycline Possible antagonism of action
Doxycycline Possible antagonism of action
Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
Mestranol This anti-infectious agent could decrease the effect of the oral contraceptive
Methacycline Possible antagonism of action
Methotrexate The penicillin increases the effect and toxicity of methotrexate
Minocycline Possible antagonism of action
Oxytetracycline Possible antagonism of action
Rolitetracycline Possible antagonism of action
Tetracycline Possible antagonism of action
Food Interactions
  • Take on an empty stomach.
Targets

1. Penicillin-binding protein 2a

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q8DNB6 Link_out
Gene: pbp2a
SNPs: SNPJam Report Link_out

References:
  1. 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

2. Penicillin-binding protein 1b

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q7CRA4 Link_out
Gene: pbp1b Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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
  6. 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
  7. 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

3. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out
Gene: pbp3
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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

4. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation

Organism class: bacterial
UniProt ID: Q8DR59 Link_out
Gene: pbpA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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

5. Penicillin-binding protein 2B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: P0A3M6 Link_out
Gene: penA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
Transporters

1. Organic cation/carnitine transporter 2

Actions: inhibitor

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 cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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

2. Oligopeptide transporter, small intestine isoform

Actions: inhibitor

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

UniProt ID: P46059 Link_out
Gene: SLC15A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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
  3. 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
  4. 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
  5. 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

3. Oligopeptide transporter, kidney isoform

Actions: inhibitor

Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides

UniProt ID: Q16348 Link_out
Gene: SLC15A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
  2. 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

4. Monocarboxylate transporter 1

Proton-linked monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate

UniProt ID: P53985 Link_out
Gene: SLC16A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. 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
Carriers

1. Serum albumin

Actions: other/unknown

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 colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on March 08, 2013 12:19