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Identification
NameAmpicillin
Accession NumberDB00415  (APRD00320)
Typesmall molecule
Groupsapproved
Description

Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
ABPCNot AvailableNot Available
AminobenzylpenicillinNot AvailableNot Available
AMPNot AvailableNot Available
AmpicilinaSpanishINN
AmpicillinNot AvailableINN, BAN, USAN, JAN
Ampicillin AcidNot AvailableNot Available
Ampicillin AnhydrousNot AvailableNot Available
AmpicillineFrenchINN
AmpicillinumLatinINN
D-(−)-6-(α-aminophenylacetamido)penicillanic acidNot AvailableNot Available
D-(−)-ampicillinNot AvailableNot Available
Salts
Name/CAS Structure Properties
Ampicillin sodium
69-52-3
Thumb
  • InChI Key: KLOHDWPABZXLGI-YWUHCJSESA-M
  • Monoisotopic Mass: 371.091571444
  • Average Mass: 371.387
DBSALT000533
Brand names
NameCompany
AustrapenLennon Healthcare
BinotalBayer
PenbritinGlaxoSmithKline
PrincipenNot Available
ViccillinMeiji
Brand mixtures
Brand NameIngredients
Pro Biosan KitAmpicillin + Probenecid
Synergistin Injectable SuspensionAmpicillin + Sulbactam (Sulbactam Benzathine)
Categories
CAS number69-53-4
WeightAverage: 349.405
Monoisotopic: 349.109626801
Chemical FormulaC16H19N3O4S
InChI KeyAVKUERGKIZMTKX-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassLactams
SubclassBeta Lactams
Direct parentPenicillins
Alternative parentsN-acyl-alpha Amino Acids and Derivatives; Alpha Amino Acid Amides; Benzene and Substituted Derivatives; Thiazolidines; Tertiary Carboxylic Acid Amides; Secondary Carboxylic Acid Amides; Azetidines; Tertiary Amines; Hemiaminals; Thioethers; Carboxylic Acids; Enolates; Polyamines; Aminals; Monoalkylamines
Substituentsn-acyl-alpha amino acid or derivative; alpha-amino acid amide; alpha-amino acid or derivative; benzene; thiazolidine; tertiary carboxylic acid amide; hemiaminal; tertiary amine; carboxamide group; secondary carboxylic acid amide; azetidine; thioether; carboxylic acid derivative; polyamine; enolate; aminal; carboxylic acid; amine; primary amine; primary aliphatic amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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].
Pharmacology
IndicationFor 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
PharmacodynamicsAmpicillin 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 actionBy 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationAmpicillin is excreted largely unchanged in the urine.
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9402
CYP450 2D6 substrate Non-inhibitor 0.9401
CYP450 2C19 substrate Non-inhibitor 0.9399
CYP450 3A4 substrate 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
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
FormRouteStrength
CapsuleOral
LiquidOral
Powder, for solutionIntramuscular
Powder, for solutionIntravenous
Powder, for solutionOral
SuspensionOral
TabletOral
Prices
Unit descriptionCostUnit
Ampicillin 10 gm vial107.77USDvial
Ampicillin 2 gm vial16.75USDvial
Principen 250 mg/5ml Suspension 200ml Bottle16.27USDbottle
Ampicillin 1 gm vial8.64USDvial
Principen 250 mg/5ml Suspension 100ml Bottle7.99USDbottle
Ampicillin Sodium 2 g/vial7.56USDvial
Ampicillin Sodium 1 g/vial3.78USDvial
Ampicillin tr 250 mg capsule3.53USDcapsule
Ampicillin Sodium 500 mg/vial2.26USDvial
Ampicillin Sodium 250 mg/vial2.15USDvial
Ampicillin tr 500 mg capsule0.61USDcapsule
Ampicillin 500 mg capsule0.5USDcapsule
Ampicillin 250 mg capsule0.44USDcapsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point208 dec °CPhysProp
water solubility1.01E+004 mg/L (at 21 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.35SANGSTER (1994)
Predicted Properties
PropertyValueSource
water solubility6.05e-01 g/lALOGPS
logP0.88ALOGPS
logP-2ChemAxon
logS-2.8ALOGPS
pKa (strongest acidic)3.24ChemAxon
pKa (strongest basic)7.44ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area112.73ChemAxon
rotatable bond count4ChemAxon
refractivity87.52ChemAxon
polarizability34.54ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
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 ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00204
KEGG CompoundC06574
PubChem Compound6249
PubChem Substance46505346
ChemSpider6013
ChEBI28971
ChEMBLCHEMBL174
Therapeutic Targets DatabaseDAP000432
PharmGKBPA448419
HETAIC
Drug Product Database2227029
RxListhttp://www.rxlist.com/cgi/generic/ampicillin.htm
Drugs.comhttp://www.drugs.com/cdi/ampicillin.html
WikipediaAmpicillin
ATC CodesJ01CA01J01CA02J01CA06J01CA14J01CA15S01AA19
AHFS Codes
  • 08:12.16.08
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(71.8 KB)
Interactions
Drug Interactions
Drug
AtenololAmpicillin decreases bioavailability of atenolol
DemeclocyclinePossible antagonism of action
DoxycyclinePossible antagonism of action
Ethinyl EstradiolThis anti-infectious agent could decrease the effect of the oral contraceptive
MestranolThis anti-infectious agent could decrease the effect of the oral contraceptive
MethacyclinePossible antagonism of action
MethotrexateThe penicillin increases the effect and toxicity of methotrexate
MinocyclinePossible antagonism of action
OxytetracyclinePossible antagonism of action
RolitetracyclinePossible antagonism of action
TetracyclinePossible antagonism of action
Food Interactions
  • Take on an empty stomach.

Targets

1. Penicillin-binding protein 2a

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2a Q8DNB6 Details

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

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1b Q7CRA4 Details

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

Kind: protein

Organism: Streptococcus pneumoniae

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 3 Q75Y35 Details

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

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 1A Q8DR59 Details

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

Kind: protein

Organism: Streptococcus pneumoniae (strain ATCC BAA-255 / R6)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Penicillin-binding protein 2B P0A3M6 Details

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

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. Pubmed

Transporters

1. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

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. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 1 P46059 Details

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. Solute carrier family 15 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 15 member 2 Q16348 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Monocarboxylate transporter 1 P53985 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:10