ampicillin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, 6-aminopenicillanic acid derivatives 198 69-53-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ampicillin hydrate
  • ampicillin
  • ampicillin sodium
  • ampicillin trihydrate
Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.
  • Molecular weight: 349.41
  • Formula: C16H19N3O4S
  • CLOGP: -1.20
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 112.73
  • ALOGS: -2.76
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
2 g O
6 g P
2 g R
6 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 7.80 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 88 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 166.85 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 62 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.22 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.80 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.85 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 17, 1965 FDA WYETH AYERST

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 1017.78 59.37 274 774 46369 2310668
Therapeutic product cross-reactivity 358.37 59.37 53 995 325 2356712
Type IV hypersensitivity reaction 350.73 59.37 55 993 522 2356515
Rash maculo-papular 284.93 59.37 63 985 4189 2352848
Rash 186.26 59.37 84 964 59474 2297563
Oedema 175.33 59.37 51 997 10152 2346885
Toxic epidermal necrolysis 137.44 59.37 33 1015 3111 2353926
Drug reaction with eosinophilia and systemic symptoms 123.65 59.37 34 1014 5484 2351553
Exposure during pregnancy 123.01 59.37 49 999 25170 2331867
Foetal exposure during pregnancy 120.63 59.37 33 1015 5219 2351818
Enterocolitis haemorrhagic 115.75 59.37 20 1028 352 2356685
Erythema 89.22 59.37 39 1009 25120 2331917
Anaphylactic reaction 84.71 59.37 29 1019 9676 2347361
Laryngeal stenosis 81.56 59.37 12 1036 69 2356968
Maternal exposure during pregnancy 79.70 59.37 31 1017 14832 2342205
Pseudomembranous colitis 76.51 59.37 15 1033 539 2356498
Urticaria 74.41 59.37 34 1014 24227 2332810
Premature baby 72.86 59.37 20 1028 3184 2353853
Hepatic function abnormal 72.40 59.37 23 1025 6069 2350968
Jarisch-Herxheimer reaction 71.38 59.37 11 1037 90 2356947
Pyrexia 68.97 59.37 42 1006 53666 2303371
Acute respiratory distress syndrome 67.73 59.37 19 1029 3273 2353764
Septic shock 65.11 59.37 22 1026 7032 2350005
Low birth weight baby 64.81 59.37 14 1034 815 2356222
Systemic candida 64.54 59.37 12 1036 323 2356714
Premature delivery 63.70 59.37 18 1030 3182 2353855
Pruritus 63.69 59.37 37 1011 43303 2313734
Stevens-Johnson syndrome 62.90 59.37 19 1029 4240 2352797
Klebsiella infection 59.40 59.37 13 1035 804 2356233

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 210.62 44.93 68 751 15067 1730895
Rash 142.18 44.93 66 753 38627 1707335
Drug ineffective 124.45 44.93 71 748 63730 1682232
Foetal exposure during pregnancy 110.42 44.93 34 785 6325 1739637
Pyrexia 107.56 44.93 58 761 46342 1699620
Systemic candida 78.78 44.93 15 804 354 1745608
Premature baby 74.03 44.93 21 798 2921 1743041
Candida infection 67.93 44.93 18 801 1940 1744022
Toxic epidermal necrolysis 59.96 44.93 17 802 2354 1743608
Acute generalised exanthematous pustulosis 57.05 44.93 14 805 1108 1744854
Drug resistance 54.77 44.93 17 802 3213 1742749
Kidney duplex 52.62 44.93 8 811 44 1745918
Hypotension 51.85 44.93 31 788 29623 1716339
Cardiac septal defect 51.21 44.93 8 811 54 1745908
Enterocolitis haemorrhagic 50.99 44.93 10 809 276 1745686
Erythema 50.93 44.93 24 795 14164 1731798
Aspartate aminotransferase increased 47.41 44.93 21 798 10735 1735227
Pathogen resistance 47.40 44.93 12 807 1077 1744885

Pharmacologic Action:

SourceCodeDescription
ATC J01CA01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Penicillins with extended spectrum
ATC J01CA51 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Penicillins with extended spectrum
ATC J01CR01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Combinations of penicillins, incl. beta-lactamase inhibitors
ATC S01AA19 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Antibiotics
FDA EPC N0000175497 Penicillin-class Antibacterial
FDA Chemical/Ingredient N0000011281 Penicillins
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute otitis media indication 3110003
Septicemia due to Escherichia coli indication 9323009
Bacterial septicemia indication 10001005 DOID:0040085
Gonorrhea indication 15628003 DOID:7551
Infection of skin AND/OR subcutaneous tissue indication 19824006
Acute gonococcal cervicitis indication 20943002 DOID:10615
Acute bacterial epiglottitis indication 21060003
Staphylococcal pneumonia indication 22754005
Streptococcal septicemia indication 29577008
Acute epiglottitis indication 29608009 DOID:9398
Acute gonococcal urethritis indication 29864006
Pneumonia due to Streptococcus indication 34020007
Shigellosis indication 36188001
Sinusitis indication 36971009
Streptococcal tonsillitis indication 41582007
Gonorrhea of rectum indication 42746002
Salmonella septicemia indication 49786009
Pneumococcal meningitis indication 51169003
Bacterial pneumonia indication 53084003 DOID:874
Acute gonococcal endometritis indication 65295003 DOID:7527
Urinary tract infectious disease indication 68566005
Haemophilus influenzae pneumonia indication 70036007
Infection due to Escherichia coli indication 71057007
Rhinoscleroma indication 72409005 DOID:11336
Staphylococcal endocarditis indication 73028002
Acute bacterial sinusitis indication 75498004
Pneumococcal pharyngitis indication 76651006
Cholangitis indication 82403002 DOID:9446
Paratyphoid fever indication 85904008 DOID:3055
Bacterial meningitis indication 95883001 DOID:9470
Dysentery indication 111939009
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Infection due to Enterobacteriaceae indication 128945009
Meningococcal meningitis indication 192644005
Escherichia coli meningitis indication 192655005
Bacterial peritonitis indication 197171003
Pneumococcal pneumonia indication 233607000
Proteus septicemia indication 300986008
Proteus urinary tract infection indication 301012009
Bacterial endocarditis indication 301183007
Septicemia due to enterococcus indication 310669007
Bacterial urinary infection indication 312124009
Infective otitis media indication 312218008
Pharyngitis indication 405737000 DOID:2275
Infection due to Staphylococcus aureus indication 406602003
Acute exacerbation of chronic bronchitis indication 425748003
Sepsis due to Staphylococcus aureus indication 448417001
Bacteroides Gynecological Infections indication
Haemophilus Influenzae Acute Otitis Media indication
Skin and Skin Structure Acinetobacter Infection indication
Haemophilus Influenzae Pharyngitis indication
Skin and Skin Structure Proteus Infection indication
Cesarean Section Infection Prevention indication
Streptococcus Pneumoniae Chronic Bronchitis indication
Haemophilus Influenzae Chronic Bronchitis indication
Skin and Skin Structure Bacteroides Fragilis Infection indication
Vaginal Hysterectomy Infection Prevention indication
Pneumococcal Acute Otitis Media indication
Staphylococcus Epidermidis Skin and Skin Structure Infection indication
Streptococcal Endocarditis indication
Bacteroides Peritonitis indication
E. Coli Peritonitis indication
Staphylococcus Acute Otitis Media indication
Gastroenteritis due to Salmonella indication
Enterococcus Urinary Tract Infection indication
Neonatal Group B Streptococcal Septicemia indication
Klebsiella Pneumoniae Peritonitis indication
Genitourinary Tract Infections indication
Inflammatory Disease of Female Pelvic Organs indication
Intra-Abdominal E. Coli Abscess indication
E. Coli Gynecological Infections indication
Infection Prevention for GI Surgery indication
Necrotizing enterocolitis in fetus OR newborn off-label use 2707005
Listeriosis off-label use 4241002 DOID:11573
Streptococcal meningitis off-label use 4510004 DOID:11574
Typhoid fever off-label use 4834000 DOID:13258
Pyrexia of unknown origin off-label use 7520000
Inhalational anthrax off-label use 11389007
Listeria meningitis off-label use 31568009 DOID:11572
Pseudotuberculosis off-label use 36753006
Enterocolitis off-label use 43752006
Infection of bone off-label use 111253001
Gastrointestinal anthrax off-label use 111798006 DOID:13386
Infection by Campylobacter fetus off-label use 111835002
Listerial endocarditis off-label use 186318004
Sepsis of the newborn off-label use 206376005
Neonatal pneumonia off-label use 233619008
Human bite - wound off-label use 262555007
Diverticulitis of gastrointestinal tract off-label use 271366000
Neonatal meningitis off-label use 276674008
Dog bite - wound off-label use 283734005
Cat bite - wound off-label use 283782004
Cutaneous listeriosis off-label use 402128003
Anthrax off-label use 409498004 DOID:7427
Prevention of Bacterial Endocarditis off-label use
Haemophilus Parainfluenzae Chronic Bronchitis off-label use
Listeria Osteomyelitis off-label use
Haemophilus Parainfluenzae Acute Otitis Media off-label use
Diabetic Foot Infection off-label use
Haemophilus Parainfluenzae Pneumonia off-label use
H. Influenzae Meningitis off-label use
Listeria Septic Arthritis off-label use
Pharyngitis due to Haemophilus Parainfluenzae off-label use
Listeria Monocytogenes Septicemia off-label use
Prevention of Neonatal Group B Streptococcal Infection off-label use
Granulomatosis Infantiseptica off-label use
Peptic ulcer contraindication 13200003 DOID:750
Acute nephropathy contraindication 58574008
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Impaired renal function disorder contraindication 197663003
Infectious mononucleosis contraindication 271558008 DOID:8568
Uric acid renal calculus contraindication 274401005
Pseudomembranous enterocolitis contraindication 397683000
Uric Acid Nephropathy Gout contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 2.79 acidic
pKa2 7.67 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Transient receptor potential cation channel subfamily M member 4 Ion channel IC50 4.72 CHEMBL
Angiopoietin-1 receptor Kinase Kd 4.09 CHEMBL
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
D000667 MESH_DESCRIPTOR_UI
4017545 VUID
N0000145927 NUI
C0002680 UMLSCUI
D01251 KEGG_DRUG
7C782967RD UNII
1339 INN_ID
31087008 SNOMEDCT_US
4017545 VANDF
3783 MMSL
733 RXNORM
387170002 SNOMEDCT_US
d00003 MMSL
002692 NDDF
CHEMBL174 ChEMBL_ID
DB00415 DRUGBANK_ID
CHEMBL453388 ChEMBL_ID
CHEMBL1200758 ChEMBL_ID
7177-48-2 SECONDARY_CAS_RN
AIC PDB_CHEM_ID
CHEBI:28971 CHEBI
6249 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0013 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 15 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0014 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR NDA 15 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0022 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 15 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0023 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR NDA 15 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0024 INJECTION, POWDER, FOR SOLUTION 100 mg INTRAMUSCULAR NDA 13 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0031 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 15 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0032 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 15 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-2689 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 15 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-2987 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 15 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3718 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 13 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3719 INJECTION, POWDER, FOR SOLUTION 250 mg INTRAVENOUS ANDA 13 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3720 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 13 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3725 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 13 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3726 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 13 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0463-1118 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 12 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6116 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 14 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6117 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 14 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6118 INJECTION, POWDER, FOR SOLUTION 100 mg INTRAVENOUS ANDA 14 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6119 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 15 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6120 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 15 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6121 INJECTION, POWDER, FOR SOLUTION 100 mg INTRAVENOUS ANDA 15 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6122 INJECTION, POWDER, FOR SOLUTION 250 mg INTRAVENOUS ANDA 15 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6123 INJECTION, POWDER, FOR SOLUTION 250 mg INTRAVENOUS ANDA 15 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-2144 CAPSULE 250 mg ORAL ANDA 13 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-2145 CAPSULE 500 mg ORAL ANDA 13 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3032 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 15 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3033 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 15 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0781-3034 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 15 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3400 INJECTION, POWDER, FOR SOLUTION 125 mg INTRAVENOUS ANDA 13 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3402 INJECTION, POWDER, FOR SOLUTION 250 mg INTRAVENOUS ANDA 13 sections