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 316.26 14.81 359 13007 264883 53070817
Type IV hypersensitivity reaction 255.82 14.81 70 13296 2622 53333078
Cross sensitivity reaction 220.48 14.81 59 13307 2028 53333672
Foetal exposure during pregnancy 148.35 14.81 98 13268 34617 53301083
Exposure during pregnancy 134.69 14.81 161 13205 124699 53211001
Premature baby 115.13 14.81 68 13298 19733 53315967
Rash maculo-papular 108.11 14.81 76 13290 29673 53306027
Premature delivery 107.41 14.81 72 13294 26032 53309668
Enterocolitis haemorrhagic 100.51 14.81 30 13336 1537 53334163
Pathogen resistance 79.91 14.81 37 13329 6523 53329177
Toxic epidermal necrolysis 78.28 14.81 57 13309 23493 53312207
Maternal exposure during pregnancy 77.05 14.81 139 13227 155500 53180200
Low birth weight baby 71.81 14.81 34 13332 6303 53329397
Drug reaction with eosinophilia and systemic symptoms 71.62 14.81 62 13304 32738 53302962
Enterococcal infection 65.95 14.81 34 13332 7564 53328136
Candida infection 59.73 14.81 50 13316 25223 53310477
Systemic candida 59.46 14.81 24 13342 3033 53332667
Amniotic cavity infection 59.03 14.81 19 13347 1251 53334449
Klebsiella infection 58.97 14.81 32 13334 7894 53327806
Jarisch-Herxheimer reaction 53.52 14.81 13 13353 300 53335400
Premature rupture of membranes 51.40 14.81 25 13341 4915 53330785
Respiratory acidosis 50.92 14.81 27 13339 6361 53329339
Drug eruption 49.91 14.81 45 13321 25049 53310651
Oedema 49.62 14.81 76 13290 74270 53261430
Caesarean section 44.55 14.81 36 13330 17284 53318416
Neonatal disorder 43.83 14.81 13 13353 651 53335049
Multiple organ dysfunction syndrome 43.04 14.81 61 13305 55616 53280084
Acute respiratory distress syndrome 42.82 14.81 40 13326 23292 53312408
Anaphylactic reaction 42.30 14.81 62 13304 58264 53277436
Thymus disorder 41.76 14.81 10 13356 217 53335483
Pseudomembranous colitis 41.45 14.81 19 13347 3272 53332428
Death neonatal 40.48 14.81 10 13356 248 53335452
Intraventricular haemorrhage 39.79 14.81 16 13350 2002 53333698
Appetite disorder 39.41 14.81 23 13343 6520 53329180
Premature labour 38.99 14.81 29 13337 12333 53323367
Sepsis neonatal 38.64 14.81 11 13355 476 53335224
Umbilical erythema 38.24 14.81 8 13358 91 53335609
Intraventricular haemorrhage neonatal 38.23 14.81 9 13357 181 53335519
Fatigue 38.06 14.81 79 13287 730427 52605273
Long QT syndrome congenital 38.03 14.81 7 13359 38 53335662
Rheumatoid arthritis 37.44 14.81 16 13350 314515 53021185
Pyrexia 37.31 14.81 199 13167 402994 52932706
Laryngeal stenosis 37.22 14.81 12 13354 794 53334906
Hepatic function abnormal 37.11 14.81 46 13320 36853 53298847
Septic shock 35.18 14.81 59 13307 62170 53273530
Lemierre syndrome 34.82 14.81 8 13358 144 53335556
Patent ductus arteriosus 34.51 14.81 18 13348 4100 53331600
Neonatal respiratory distress syndrome 34.07 14.81 16 13350 2911 53332789
Neuromuscular block prolonged 32.93 14.81 10 13356 543 53335157
Infective aneurysm 30.55 14.81 9 13357 440 53335260
Hypotonia 30.52 14.81 22 13344 8919 53326781
Linear IgA disease 30.18 14.81 12 13354 1458 53334242
Enterobacter infection 29.74 14.81 13 13353 2003 53333697
Perinatal stroke 29.53 14.81 5 13361 15 53335685
Alopecia 29.42 14.81 11 13355 234572 53101128
Malaise 29.17 14.81 28 13338 357589 52978111
Disseminated intravascular coagulation 29.08 14.81 30 13336 19689 53316011
Arthralgia 28.83 14.81 41 13325 439742 52895958
Liver abscess 28.27 14.81 14 13352 2861 53332839
Acute generalised exanthematous pustulosis 27.78 14.81 22 13344 10259 53325441
Hydrops foetalis 27.76 14.81 8 13358 362 53335338
Pseudomonas infection 27.50 14.81 22 13344 10406 53325294
Neonatal respiratory failure 27.03 14.81 7 13359 211 53335489
Sepsis 26.66 14.81 89 13277 146340 53189360
Renal impairment 26.43 14.81 62 13304 83256 53252444
Stillbirth 26.16 14.81 18 13348 6779 53328921
Pulmonary haemorrhage 25.84 14.81 18 13348 6915 53328785
Stevens-Johnson syndrome 25.28 14.81 31 13335 24551 53311149
Arthropathy 25.07 14.81 3 13363 141450 53194250
Maternal drugs affecting foetus 24.50 14.81 16 13350 5530 53330170
Culture stool positive 24.43 14.81 7 13359 310 53335390
Preterm premature rupture of membranes 24.26 14.81 10 13356 1333 53334367
Tubulointerstitial nephritis 24.14 14.81 25 13341 16479 53319221
Foetal heart rate decreased 24.02 14.81 6 13360 156 53335544
Erythema 23.94 14.81 90 13276 156879 53178821
Fall 23.89 14.81 33 13333 358407 52977293
Listeriosis 23.67 14.81 10 13356 1417 53334283
Pain in extremity 23.60 14.81 22 13344 285028 53050672
Drug resistance 23.55 14.81 27 13339 19935 53315765
Joint swelling 23.37 14.81 15 13351 234623 53101077
Escherichia infection 22.76 14.81 21 13345 12029 53323671
Haemorrhagic diathesis 22.46 14.81 14 13352 4464 53331236
Polyhydramnios 22.37 14.81 11 13355 2214 53333486
Eosinophilic pneumonia acute 22.33 14.81 7 13359 423 53335277
Ventricular dysfunction 22.14 14.81 12 13354 2951 53332749
Acute disseminated encephalomyelitis 22.12 14.81 6 13360 217 53335483
Atelectasis neonatal 21.84 14.81 4 13362 21 53335679
Thrombocytopenia neonatal 21.69 14.81 4 13362 22 53335678
Interstitial lung disease 21.24 14.81 46 13320 58576 53277124
Crystal nephropathy 21.12 14.81 8 13358 853 53334847
Bradypnoea 20.94 14.81 12 13354 3285 53332415
Bradycardia neonatal 20.75 14.81 8 13358 896 53334804
Proteus infection 20.69 14.81 8 13358 903 53334797
Selective eating disorder 20.64 14.81 10 13356 1948 53333752
Generalised anxiety disorder 20.44 14.81 10 13356 1990 53333710
Endocarditis candida 20.39 14.81 4 13362 32 53335668
Dysphoria 20.19 14.81 14 13352 5335 53330365
Pain 19.95 14.81 78 13288 588320 52747380
Klebsiella test positive 19.71 14.81 8 13358 1025 53334675
Nasopharyngitis 19.55 14.81 12 13354 192283 53143417
Apnoea 19.51 14.81 16 13350 7837 53327863
Product dose omission issue 19.42 14.81 12 13354 191608 53144092
Circulatory collapse 19.21 14.81 26 13340 22688 53313012
Systemic lupus erythematosus 19.20 14.81 4 13362 125410 53210290
Death 19.05 14.81 38 13328 357194 52978506
Headache 18.94 14.81 70 13296 536751 52798949
Arthritis infective 18.84 14.81 14 13352 5941 53329759
Implant site hypersensitivity 18.42 14.81 4 13362 55 53335645
Rash morbilliform 18.42 14.81 11 13355 3252 53332448
Nausea 18.27 14.81 113 13253 755978 52579722
Hydrocephalus 18.13 14.81 13 13353 5223 53330477
Premature separation of placenta 18.08 14.81 9 13357 1858 53333842
Ventricular septal defect 17.88 14.81 12 13354 4338 53331362
Clostridial infection 17.75 14.81 12 13354 4390 53331310
Contraindicated product administered 17.61 14.81 6 13360 135623 53200077
Umbilical cord around neck 17.35 14.81 5 13361 226 53335474
Clostridium difficile colitis 17.29 14.81 23 13343 19742 53315958
Neonatal infection 17.27 14.81 5 13361 230 53335470
Neonatal cardiac failure 17.26 14.81 3 13363 11 53335689
Oliguria 17.26 14.81 16 13350 9222 53326478
Meningoencephalitis bacterial 17.16 14.81 4 13362 77 53335623
Congenital lymphoedema 17.05 14.81 3 13363 12 53335688
Lip erosion 17.00 14.81 7 13359 930 53334770
Guillain-Barre syndrome 16.94 14.81 11 13355 3764 53331936
Pneumonia klebsiella 16.81 14.81 9 13357 2160 53333540
Meconium in amniotic fluid 16.69 14.81 5 13361 259 53335441
Aeromonas infection 16.56 14.81 4 13362 90 53335610
Sinusitis 16.47 14.81 11 13355 168553 53167147
Morganella infection 16.43 14.81 6 13360 578 53335122
Pneumonia aspiration 16.12 14.81 30 13336 34271 53301429
Streptococcal infection 16.11 14.81 12 13354 5110 53330590
Hypotonia neonatal 16.09 14.81 7 13359 1066 53334634
Hyporesponsive to stimuli 16.02 14.81 7 13359 1077 53334623
Listeria sepsis 15.94 14.81 6 13360 629 53335071
Retained placenta or membranes 15.89 14.81 5 13361 306 53335394
Cervical incompetence 15.87 14.81 6 13360 637 53335063
Glossodynia 15.77 14.81 3 13363 100288 53235412
Stenotrophomonas infection 15.73 14.81 8 13358 1728 53333972
Hepatic infarction 15.69 14.81 6 13360 657 53335043
Renal failure 15.69 14.81 65 13301 118387 53217313
Hepatomegaly 15.66 14.81 17 13349 11814 53323886
Sweat test abnormal 15.40 14.81 3 13363 23 53335677
Neuromuscular blockade 15.39 14.81 5 13361 339 53335361
Blood pressure increased 15.37 14.81 8 13358 140471 53195229
Pseudohyperphosphataemia 15.29 14.81 3 13363 24 53335676
Perineal necrosis 15.13 14.81 4 13362 131 53335569
Moraxella infection 15.07 14.81 5 13361 362 53335338
Abdominal discomfort 15.06 14.81 20 13346 221042 53114658
Bacteraemia 15.01 14.81 19 13347 15530 53320170
Atrial septal defect 14.94 14.81 13 13353 6901 53328799
Completed suicide 14.93 14.81 8 13358 138193 53197507
Insomnia 14.82 14.81 15 13351 187057 53148643

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
Foetal exposure during pregnancy 141.97 15.05 119 11797 41182 32460428
Premature baby 117.02 15.05 77 11839 18441 32483169
Sepsis neonatal 81.36 15.05 19 11897 246 32501364
Neonatal disorder 69.33 15.05 22 11894 939 32500671
Enterocolitis haemorrhagic 64.17 15.05 21 11895 990 32500620
Type IV hypersensitivity reaction 54.82 15.05 20 11896 1308 32500302
Cardiac septal defect 51.21 15.05 13 11903 243 32501367
Death 50.45 15.05 40 11876 382477 32119133
Drug hypersensitivity 48.21 15.05 92 11824 73308 32428302
Hepatic function abnormal 46.55 15.05 69 11847 44771 32456839
Pleocytosis 46.35 15.05 14 11902 506 32501104
Pyrexia 44.81 15.05 233 11683 319735 32181875
Pathogen resistance 44.70 15.05 33 11883 9477 32492133
Low birth weight baby 43.95 15.05 29 11887 6965 32494645
Hangover 43.32 15.05 16 11900 1083 32500527
Kidney duplex 40.84 15.05 12 11904 394 32501216
Acute generalised exanthematous pustulosis 40.53 15.05 27 11889 6586 32495024
Drug eruption 40.18 15.05 42 11874 19124 32482486
Pneumonia aspiration 39.41 15.05 61 11855 41095 32460515
Drug resistance 38.91 15.05 45 11871 22920 32478690
Hydrops foetalis 36.26 15.05 10 11906 260 32501350
Systemic candida 36.13 15.05 19 11897 3002 32498608
Intraventricular haemorrhage 35.27 15.05 19 11897 3151 32498459
Rash 34.62 15.05 160 11756 209173 32292437
Brain abscess 33.81 15.05 18 11898 2916 32498694
Neonatal respiratory distress syndrome 33.08 15.05 20 11896 4127 32497483
Intraventricular haemorrhage neonatal 33.01 15.05 9 11907 224 32501386
Congenital cystic lung 32.86 15.05 9 11907 228 32501382
Fatigue 32.55 15.05 49 11867 350652 32150958
Nocardiosis 32.38 15.05 19 11897 3712 32497898
Cross sensitivity reaction 32.24 15.05 14 11902 1446 32500164
Respiratory failure 31.94 15.05 99 11817 107083 32394527
Pulmonary haemorrhage 30.94 15.05 27 11889 9830 32491780
Listeriosis 30.80 15.05 12 11904 941 32500669
Interstitial lung disease 30.45 15.05 71 11845 64930 32436680
Leukocytosis 30.12 15.05 40 11876 23427 32478183
Mucormycosis 29.72 15.05 21 11895 5633 32495977
Neonatal respiratory failure 29.19 15.05 9 11907 349 32501261
Type I hypersensitivity 28.46 15.05 12 11904 1153 32500457
Toxic epidermal necrolysis 27.83 15.05 36 11880 20557 32481053
Disseminated intravascular coagulation 27.46 15.05 38 11878 23138 32478472
Janeway lesion 27.39 15.05 5 11911 16 32501594
Congenital skin dimples 26.12 15.05 7 11909 163 32501447
Stenotrophomonas test positive 25.49 15.05 8 11908 329 32501281
Drug withdrawal syndrome neonatal 25.40 15.05 16 11900 3548 32498062
Fall 25.17 15.05 21 11895 196180 32305430
Dizziness 25.02 15.05 24 11892 209594 32292016
Nail bed bleeding 24.70 15.05 5 11911 31 32501579
Death neonatal 24.69 15.05 8 11908 365 32501245
Septic shock 24.64 15.05 68 11848 68921 32432689
Meningitis aseptic 24.60 15.05 14 11902 2583 32499027
Tubulointerstitial nephritis 24.56 15.05 33 11883 19544 32482066
Patent ductus arteriosus 24.05 15.05 15 11901 3270 32498340
Candida infection 23.68 15.05 30 11886 16773 32484837
Bradycardia neonatal 23.42 15.05 10 11906 991 32500619
Polyhydramnios 23.23 15.05 7 11909 251 32501359
Necrotising colitis 22.86 15.05 10 11906 1051 32500559
Stevens-Johnson syndrome 22.65 15.05 31 11885 18678 32482932
Nutritional condition abnormal 22.15 15.05 8 11908 508 32501102
Pneumonia bacterial 21.60 15.05 23 11893 10693 32490917
Pseudo-Bartter syndrome 21.42 15.05 4 11912 15 32501595
Bronchopulmonary dysplasia 21.33 15.05 8 11908 565 32501045
Sepsis 20.96 15.05 114 11802 158720 32342890
Klebsiella test positive 20.86 15.05 8 11908 601 32501009
Multiple organ dysfunction syndrome 20.30 15.05 64 11852 69790 32431820
Apnoea 20.22 15.05 18 11898 6725 32494885
Condition aggravated 20.06 15.05 111 11805 155550 32346060
Respiratory acidosis 19.99 15.05 15 11901 4413 32497197
Conjunctivitis 19.87 15.05 20 11896 8706 32492904
Pulmonary physical examination abnormal 19.73 15.05 4 11912 25 32501585
Strongyloidiasis 19.52 15.05 12 11904 2549 32499061
Klebsiella infection 19.43 15.05 19 11897 7993 32493617
Drug ineffective 19.40 15.05 220 11696 383257 32118353
Clostridium bacteraemia 19.33 15.05 5 11911 101 32501509
Rebound effect 19.25 15.05 11 11905 2045 32499565
Enterococcal infection 19.09 15.05 20 11896 9127 32492483
Shock symptom 18.92 15.05 5 11911 110 32501500
Grey syndrome neonatal 18.66 15.05 3 11913 3 32501607
Pneumonia 18.04 15.05 204 11712 355048 32146562
Drug reaction with eosinophilia and systemic symptoms 18.04 15.05 38 11878 32447 32469163
Pulmonary alveolar haemorrhage 17.46 15.05 17 11899 7112 32494498
Apgar score low 17.40 15.05 8 11908 945 32500665
Immobilisation syndrome 17.38 15.05 5 11911 152 32501458
Exposure during pregnancy 17.18 15.05 19 11897 9210 32492400
Porencephaly 17.13 15.05 3 11913 7 32501603
Neonatal hypoxia 17.07 15.05 6 11910 352 32501258
Kounis syndrome 17.02 15.05 10 11906 1958 32499652
Fungal skin infection 16.88 15.05 11 11905 2586 32499024
Complication of device removal 16.77 15.05 4 11912 57 32501553
Aspartate aminotransferase increased 16.74 15.05 58 11858 66371 32435239
Nausea 16.69 15.05 61 11855 320788 32180822
Wound dehiscence 16.13 15.05 12 11904 3484 32498126
Dry gangrene 16.11 15.05 6 11910 416 32501194
Eosinophilia 16.01 15.05 31 11885 24927 32476683
Arteriospasm coronary 15.91 15.05 11 11905 2849 32498761
Neonatal candida infection 15.91 15.05 3 11913 12 32501598
Myalgia 15.88 15.05 5 11911 81225 32420385
Atrial septal defect 15.81 15.05 16 11900 7009 32494601
Rash maculo-papular 15.81 15.05 33 11883 27989 32473621
Paradoxical drug reaction 15.79 15.05 11 11905 2885 32498725
Acute respiratory distress syndrome 15.75 15.05 31 11885 25222 32476388
Asthenia 15.73 15.05 40 11876 235904 32265706
Cerebrovascular accident 15.69 15.05 6 11910 86314 32415296
Liver abscess 15.67 15.05 12 11904 3639 32497971
Generalised oedema 15.59 15.05 21 11895 12462 32489148
Trichosporon infection 15.55 15.05 7 11909 788 32500822
Congenital syphilis 15.54 15.05 3 11913 14 32501596
Myocardial infarction 15.43 15.05 14 11902 125662 32375948
Blood creatine phosphokinase increased 15.41 15.05 44 11872 45432 32456178

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 CS M0016152 Penicillins
FDA EPC N0000175497 Penicillin-class Antibacterial
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
CHEBI has role CHEBI:36047 antibacterial drugs

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
Angiopoietin-1 receptor Kinase Kd 4.09 CHEMBL
Transient receptor potential cation channel subfamily M member 4 Ion channel IC50 4.72 CHEMBL
Bacterial penicillin-binding protein Enzyme INHIBITOR CHEMBL CHEMBL
Penicillin-binding protein 1A Enzyme WOMBAT-PK

External reference:

IDSource
4017545 VUID
N0000145927 NUI
D01251 KEGG_DRUG
69-52-3 SECONDARY_CAS_RN
203115 RXNORM
C0002680 UMLSCUI
CHEBI:28971 CHEBI
AIC PDB_CHEM_ID
CHEMBL174 ChEMBL_ID
CHEMBL1200758 ChEMBL_ID
CHEMBL453388 ChEMBL_ID
DB00415 DRUGBANK_ID
D000667 MESH_DESCRIPTOR_UI
6249 PUBCHEM_CID
10896 IUPHAR_LIGAND_ID
1339 INN_ID
7C782967RD UNII
17720 MMSL
3783 MMSL
4195 MMSL
71827 MMSL
d00003 MMSL
002692 NDDF
002694 NDDF
002695 NDDF
31087008 SNOMEDCT_US
387170002 SNOMEDCT_US
96070009 SNOMEDCT_US
96071008 SNOMEDCT_US
4017543 VANDF
4017544 VANDF
4017545 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0013 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 26 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0014 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR NDA 26 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0024 INJECTION, POWDER, FOR SOLUTION 100 mg INTRAMUSCULAR NDA 25 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0031 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 26 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0032 INJECTION, POWDER, FOR SOLUTION 2 g INTRAMUSCULAR ANDA 26 sections
AMPICILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0404-9816 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 13 sections
AMPICILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0404-9817 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAMUSCULAR ANDA 13 sections
AMPICILLIN HUMAN PRESCRIPTION DRUG LABEL 1 0404-9818 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 13 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-2689 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-2987 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 25 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3718 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 23 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3719 INJECTION, POWDER, FOR SOLUTION 250 mg INTRAVENOUS ANDA 23 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3720 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 23 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3725 INJECTION, POWDER, FOR SOLUTION 10 g INTRAVENOUS ANDA 22 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0409-3726 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 23 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0463-1118 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 21 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6116 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6117 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 24 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6118 INJECTION, POWDER, FOR SOLUTION 100 mg INTRAVENOUS ANDA 24 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6119 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6120 INJECTION, POWDER, FOR SOLUTION 2 g INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6121 INJECTION, POWDER, FOR SOLUTION 100 mg INTRAVENOUS ANDA 24 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6122 INJECTION, POWDER, FOR SOLUTION 250 mg INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6123 INJECTION, POWDER, FOR SOLUTION 250 mg INTRAVENOUS ANDA 25 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-2144 CAPSULE 250 mg ORAL ANDA 25 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-2145 CAPSULE 500 mg ORAL ANDA 25 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3400 INJECTION, POWDER, FOR SOLUTION 125 mg INTRAVENOUS ANDA 22 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3402 INJECTION, POWDER, FOR SOLUTION 250 mg INTRAVENOUS ANDA 22 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3404 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 22 sections
Ampicillin HUMAN PRESCRIPTION DRUG LABEL 1 0781-3407 INJECTION, POWDER, FOR SOLUTION 500 mg INTRAVENOUS ANDA 22 sections