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Showing drug card for Ampicillin (DB00415)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:59
Primary Accession Number DB00415
Secondary Accession Number
  • APRD00320
Name Ampicillin
Drug Type
  • Approved
  • Small Molecule
Description Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. [PubChem]
Synonyms
  1. Aminobenzylpenicillin
  2. Ampicilina [INN-Spanish]
  3. Ampicillin Acid
  4. Ampicillin Anhydrate
  5. Ampicillin Anhydrous
  6. Ampicillin Base
  7. Ampicillin Sodium
  8. Ampicillin Trihydrate
  9. Ampicillin [Usan:Ban:Inn:Jan]
  10. Ampicillina [Dcit]
  11. Ampicilline
  12. Ampicilline [INN-French]
  13. Ampicillinum [INN-Latin]
  14. Anhydrous Ampicillin
  15. Bayer 5427
  16. D-Ampicillin
Brand Names
  1. AB-PC
  2. Ab-Pc Sol
  3. Acillin
  4. Adobacillin
  5. Alpen
  6. Amblosin
  7. Amcill
  8. Amfipen
  9. Amfipen V
  10. Amipenix S
  11. Ampen
  12. Ampi
  13. Ampi-Bol
  14. Ampi-Co
  15. Ampi-Tab
  16. Ampichel
  17. Ampicil
  18. Ampicillin A
  19. Ampicin
  20. Ampifarm
  21. Ampikel
  22. Ampimed
  23. Ampipenin
  24. Ampipenin, Nt3
  25. Ampiscel
  26. Ampisyn
  27. Ampivax
  28. Ampivet
  29. Amplacilina
  30. Amplin
  31. Amplipenyl
  32. Amplisom
  33. Amplital
  34. Ampy-Penyl
  35. Austrapen
  36. BRL
  37. Binotal
  38. Bonapicillin
  39. Britacil
  40. Campicillin
  41. Cimex
  42. Copharcilin
  43. D-Cillin
  44. Delcillin
  45. Deripen
  46. Divercillin
  47. Doktacillin
  48. Duphacillin
  49. Geocillin
  50. Grampenil
  51. Guicitrina
  52. Guicitrine
  53. Lifeampil
  54. Morepen
  55. Norobrittin
  56. Novo-Ampicillin
  57. Nuvapen
  58. Olin Kid
  59. Omnipen
  60. Omnipen-N
  61. Orbicilina
  62. Pen A
  63. Pen Ampil
  64. Pen a Oral
  65. Penbristol
  66. Penbritin
  67. Penbritin Paediatric
  68. Penbritin Syrup
  69. Penbritin-S
  70. Penbrock
  71. Penicline
  72. Penimic
  73. Pensyn
  74. Pentrex
  75. Pentrexl
  76. Pentrexyl
  77. Pfizerpen A
  78. Pfizerpen-A
  79. Polycillin
  80. Polycillin-N
  81. Ponecil
  82. Princillin
  83. Principen
  84. Principen '125'
  85. Principen '250'
  86. Principen '500'
  87. Qidamp
  88. Racenacillin
  89. Ro-Ampen
  90. Rosampline
  91. Roscillin
  92. Semicillin
  93. Semicillin R
  94. Servicillin
  95. Sk-Ampicillin
  96. Spectrobid
  97. Sumipanto
  98. Supen
  99. Synpenin
  100. Texcillin
  101. Tokiocillin
  102. Tolomol
  103. Totacillin
  104. Totacillin-N
  105. Totalciclina
  106. Totapen
  107. Trifacilina
  108. Ultrabion
  109. Ultrabron
  110. Vampen
  111. Viccillin
  112. Viccillin S
  113. Wypicil
Brand Mixtures
  1. Pro Biosan Kit (Ampicillin + Probenecid)
  2. Synergistin Injectable Suspension (Ampicillin + Sulbactam (Sulbactam Benzathine))
Chemical IUPAC Name (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Chemical Formula C16H19N3O4S
Chemical Structure Structure
CAS Registry Number 69-53-4
InChI Identifier InChI=1/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/f/h18,22H
InChI Key AVKUERGKIZMTKX-KXDAXDHGDU
KEGG Drug D00204 Link Image
KEGG Compound C06574 Link Image
PubChem Compound 6249 Link Image
PubChem Substance 149171 Link Image
ChEBI ID Not Available
PharmGKB ID PA448419 Link Image
HET ID AIC Link Image
GenBank ID Not Available
Drug ID Number [DIN] 02227029 Link Image
RxList Link http://www.rxlist.com/cgi/generic/ampicillin.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Ampicillin Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 349.4050
Monoisotopic Molecular Weight 349.1096
State Solid
Melting Point 208 oC
Experimental Water Solubility 1.01E+004 mg/L Source: PhysProp
Predicted Water Solubility 6.05e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.4 Source: PhysProp
Predicted LogP 0.88 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.76 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C(=O)N2[C@H]1C(O)=O
Canonical SMILES CC1(C)SC2C(NC(=O)C(N)C3=CC=CC=C3)C(=O)N2C1C(O)=O
Drug Category
  • Anti-Bacterial Agents
  • Penicillins
ATC Codes
AHFS Codes
  • 08:12.16.08
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
Pharmacology 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
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Capsule Oral
Liquid Oral
Powder, for solution Intramuscular
Powder, for solution Intravenous
Powder, for solution Oral
Suspension Oral
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The IV penicillin increases the anticoagulant effect
Anisindione The IV penicillin increases the anticoagulant effect
Atenolol Ampicillin decreases bioavailability of atenolol
Demeclocycline Possible antagonism of action
Dicumarol The IV penicillin increases the anticoagulant effect
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
Warfarin The IV penicillin increases the anticoagulant effect
Food Interactions
  • Take on an empty stomach.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. Penicillin-binding proteins 1A/1B
Drug Target 1 [top]
Target 1 ID 633
Target 1 Name Penicillin-binding proteins 1A/1B
Target 1 Synonyms Not Available
Target 1 Gene Name pbpA
Target 1 Protein Sequence >Penicillin-binding proteins 1A/1B 
MTERKREHKDRKQNKNSPKNQSKVTKFLKWFFIGILLLGITAVTVVGIYVLSIIRSSPEL
DVQAIQSLNQPSILYDDQGNFMDNVITREQRYVVKSEEIPDNLKKAFVAIEDERFYEHKG
IDIKRIFGVIASNIKGKLSGSNTVQGASTITQQLIKNAVLTNEVSYERKIKEMYLALELE
KHLSKDEILTTYLNTIPMGGYQYGVSAAAQRFFSKNVSDLNLVECAYLGGLTQAPTSYDG
LSEANKENPSRYLNRTKSVLFKMHELGYISSEQYNDAINEIDTNGIKFTPNNKLSKTNFE
WFTRPAITQVKQDLMDKYKYTQEEVDKLIANGGLKIYTSMDRNLQNNVQKVLDDPNNYKA
ITNNPNEKNEDGVYKLQASATIIDYKTGHVKALVGGRGEQPAMSHNRAYYDLKSIGSATK
PLTVYGPAIDLGLGGAGSVVNDSPLSNKELSSTGYKDQPKNEYNSYRGPLTFREAIKISS
NLAAIKVANEVGVSNSIAYGEKLGLVYGPHSRGISTTALGQFQNDPNNPDGGNTYTLASA
FGVFGNNGVKTNAKLYTKVLDSHGNVILDTSTPEETKIFSPQASYIVYDMLKDQVESGSA
KSAKFGNIPVAGKTGTTTGDKDYLFAGLTPYYSAAIWIGYDKPREMRTSSGTVTSPIFGK
IMGLAHKDLQYKEVDNLVE
Target 1 Number of Residues 690
Target 1 Molecular Weight 75178
Target 1 Theoretical pI 9.09
Target 1 GO Classification
Function
binding
drug binding
penicillin binding
transferase activity
transferase activity, transferring glycosyl groups
transferase activity, transferring pentosyl groups
hydrolase activity
peptidase activity
catalytic activity
Process
cellular physiological process
cell organization and biogenesis
external encapsulating structure organization and biogenesis
cell wall organization and biogenesis
cell wall organization and biogenesis (sensu Bacteria)
cell wall biosynthesis (sensu Bacteria)
response to stimulus
response to abiotic stimulus
response to chemical stimulus
response to drug
response to antibiotic
physiological process
metabolism
macromolecule metabolism
carbohydrate metabolism
cellular carbohydrate metabolism
peptidoglycan metabolism
peptidoglycan biosynthesis
Component
cell
external encapsulating structure
cell wall
cell wall (sensu Bacteria)
Target 1 General Function Cell wall/membrane/envelope biogenesis
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 30-52
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 18145626 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q8XJ01 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name Q8XJ01_CLOPE Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >2040 bp 
ATGACTGAAAGAAAAAGAGAGCATAAAGATAGAAAGCAGAATAAAAATTCACCTAAAAAT
CAATCGAAAGTAACAAAATTTTTGAAATGGTTCTTTATAGGGATTCTGCTTCTAGGGATA
ACTGCCGTAACAGTAGTTGGAATTTACGTTCTTTCTATTATACGTTCATCTCCAGAGTTA
GATGTTCAGGCAATTCAATCTCTAAATCAGCCATCCATTCTTTACGATGATCAGGGAAAC
TTTATGGATAATGTTATAACTCGTGAACAACGTTATGTAGTTAAATCTGAAGAGATACCT
GATAACTTAAAAAAGGCTTTTGTAGCTATTGAAGACGAAAGATTTTATGAGCATAAAGGA
ATAGACATTAAAAGAATTTTTGGGGTAATAGCTTCTAATATTAAAGGTAAACTTTCAGGA
AGTAATACAGTTCAAGGGGCTTCAACCATAACTCAGCAACTTATAAAAAATGCCGTACTT
ACTAATGAAGTTAGTTATGAAAGAAAAATTAAAGAAATGTACTTAGCTTTGGAATTAGAA
AAGCACCTTTCAAAAGATGAAATCCTTACTACGTATTTAAATACAATTCCTATGGGTGGA
TACCAATATGGGGTTAGCGCAGCTGCTCAAAGATTTTTTAGTAAGAATGTTTCAGATTTG
AATTTAGTTGAGTGCGCTTATTTAGGAGGACTTACTCAAGCACCAACTTCTTATGATGGT
CTTTCAGAAGCAAATAAAGAAAATCCAAGTAGATATTTAAATAGAACTAAATCTGTACTA
TTTAAAATGCATGAACTTGGATATATTTCAAGTGAACAATATAATGACGCAATAAATGAA
ATTGACACAAATGGTATAAAATTCACACCAAATAATAAATTAAGTAAAACTAACTTTGAG
TGGTTCACAAGACCAGCTATAACTCAAGTTAAACAAGACTTAATGGATAAATATAAATAT
ACACAAGAGGAAGTTGACAAACTTATAGCTAATGGTGGATTAAAAATCTATACTTCAATG
GATAGAAATCTTCAAAATAATGTTCAAAAAGTTTTAGATGATCCAAATAACTATAAAGCT
ATAACTAATAATCCTAATGAAAAAAATGAAGATGGTGTTTATAAATTACAAGCATCTGCC
ACAATAATAGACTATAAAACAGGCCATGTTAAGGCTTTAGTTGGAGGAAGAGGGGAACAA
CCTGCTATGTCTCACAATAGAGCTTATTATGATTTAAAATCTATAGGTTCTGCAACAAAA
CCATTAACAGTTTATGGTCCTGCTATTGATTTAGGACTTGGTGGCGCTGGCTCTGTAGTA
AATGATTCTCCATTAAGTAATAAAGAGTTATCTTCTACAGGATATAAAGATCAACCTAAG
AATGAATACAATAGTTATAGAGGCCCTTTAACTTTTAGAGAAGCAATTAAAATCTCTAGT
AACTTAGCAGCCATAAAAGTTGCTAATGAAGTAGGTGTTTCAAACTCTATAGCTTATGGA
GAAAAATTAGGTCTTGTTTATGGACCTCATTCTAGAGGTATTTCCACAACAGCCTTAGGT
CAATTCCAAAATGACCCTAATAATCCTGATGGAGGAAATACTTATACTCTAGCTTCAGCC
TTCGGTGTTTTTGGTAATAACGGTGTTAAAACAAATGCTAAATTATATACAAAGGTATTA
GATTCTCATGGAAATGTAATTCTTGATACAAGTACTCCAGAAGAAACTAAAATATTTAGT
CCTCAAGCGTCTTATATAGTTTATGATATGCTTAAGGATCAAGTAGAAAGTGGCTCTGCA
AAATCTGCTAAATTTGGTAATATTCCTGTGGCGGGTAAAACAGGAACTACTACTGGAGAT
AAAGACTATTTATTTGCAGGATTAACTCCATATTATTCTGCGGCTATTTGGATTGGATAT
GATAAGCCTAGAGAAATGAGAACTAGTAGTGGTACTGTTACCTCTCCTATTTTCGGAAAA
ATAATGGGCTTAGCTCATAAAGACTTACAGTACAAAGAGGTTGACAACCTAGTGGAATAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Shimizu T, Ohtani K, Hirakawa H, Ohshima K, Yamashita A, Shiba T, Ogasawara N, Hattori M, Kuhara S, Hayashi H: Complete genome sequence of Clostridium perfringens, an anaerobic flesh-eater. Proc Natl Acad Sci U S A. 2002 Jan 22;99(2):996-1001. Epub 2002 Jan 15. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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