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

Stem definitionDrug idCAS RN
beta-lactamase inhibitors 2492 68373-14-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • sulbactam
  • penicillanic acid dioxide
  • sulbactam sodium
A beta-lactamase inhibitor with very weak antibacterial action. The compound prevents antibiotic destruction of beta-lactam antibiotics by inhibiting beta-lactamases, thus extending their spectrum activity. Combinations of sulbactam with beta-lactam antibiotics have been used successfully for the therapy of infections caused by organisms resistant to the antibiotic alone.
  • Molecular weight: 233.24
  • Formula: C8H11NO5S
  • CLOGP: 0.31
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 1
  • TPSA: 91.75
  • ALOGS: -0.68
  • ROTB: 1

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1 g P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 285.97 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 0.32 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 5.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.62 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 31, 1986 FDA PFIZER

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
Enterocolitis haemorrhagic 89.50 20.58 23 5915 1544 53341584
Hepatic function abnormal 81.77 20.58 51 5887 36848 53306280
Pyrexia 73.18 20.58 147 5791 403046 52940082
Drug eruption 69.38 20.58 40 5898 25054 53318074
Klebsiella infection 59.54 20.58 25 5913 7901 53335227
Renal impairment 47.08 20.58 52 5886 83266 53259862
Enterococcal infection 44.14 20.58 20 5918 7578 53335550
Lemierre syndrome 41.29 20.58 8 5930 144 53342984
Disseminated intravascular coagulation 40.52 20.58 26 5912 19693 53323435
Infective aneurysm 37.80 20.58 9 5929 440 53342688
Fatigue 36.51 20.58 18 5920 730488 52612640
Linear IgA disease 35.46 20.58 11 5927 1459 53341669
Toxic epidermal necrolysis 34.04 20.58 25 5913 23525 53319603
Pneumonia aspiration 33.67 20.58 29 5909 34272 53308856
Arthralgia 32.71 20.58 5 5933 439778 52903350
Interstitial lung disease 32.08 20.58 36 5902 58586 53284542
Multiple organ dysfunction syndrome 31.86 20.58 35 5903 55642 53287486
Culture stool positive 30.07 20.58 7 5931 310 53342818
Pneumonia 29.70 20.58 106 5832 407063 52936065
Pathogen resistance 28.10 20.58 14 5924 6546 53336582
Eosinophilic pneumonia acute 27.95 20.58 7 5931 423 53342705
Premature delivery 27.52 20.58 23 5915 26081 53317047
Crystal nephropathy 27.50 20.58 8 5930 853 53342275
Acute disseminated encephalomyelitis 26.96 20.58 6 5932 217 53342911
Pseudomembranous colitis 26.80 20.58 11 5927 3280 53339848
Sepsis 24.74 20.58 52 5886 146377 53196751
Red blood cells urine positive 24.59 20.58 10 5928 2914 53340214
Candida infection 24.06 20.58 21 5917 25252 53317876
Platelet count decreased 23.88 20.58 43 5895 108056 53235072
Chorioretinopathy 22.89 20.58 7 5931 886 53342242
Proteus infection 22.75 20.58 7 5931 904 53342224
Acute generalised exanthematous pustulosis 22.22 20.58 14 5924 10267 53332861
Klebsiella test positive 21.88 20.58 7 5931 1026 53342102
Implant site hypersensitivity 21.66 20.58 4 5934 55 53343073
Neuromuscular block prolonged 21.54 20.58 6 5932 547 53342581
Shock haemorrhagic 21.09 20.58 13 5925 9170 53333958
Septic shock 20.95 20.58 30 5908 62199 53280929
Systemic candida 20.82 20.58 9 5929 3048 53340080

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
Hepatic function abnormal 120.38 18.58 94 7761 44746 32460925
Pneumonia 73.12 18.58 219 7636 355033 32150638
Enterocolitis haemorrhagic 72.81 18.58 21 7834 990 32504681
Pneumonia aspiration 54.38 18.58 58 7797 41098 32464573
Interstitial lung disease 53.55 18.58 72 7783 64929 32440742
Cardiac septal defect 51.29 18.58 12 7843 244 32505427
Hangover 49.86 18.58 16 7839 1083 32504588
Pathogen resistance 46.87 18.58 29 7826 9481 32496190
Kidney duplex 45.79 18.58 12 7843 394 32505277
Pyrexia 43.44 18.58 172 7683 319796 32185875
Drug eruption 42.53 18.58 36 7819 19130 32486541
Rash 41.82 18.58 128 7727 209205 32296466
Klebsiella infection 38.39 18.58 24 7831 7988 32497683
Incision site pain 36.76 18.58 15 7840 2022 32503649
Toxic epidermal necrolysis 36.37 18.58 34 7821 20559 32485112
Wound dehiscence 31.92 18.58 16 7839 3480 32502191
C-reactive protein increased 31.79 18.58 48 7807 48054 32457617
Clostridium test positive 31.64 18.58 14 7841 2303 32503368
Drug-induced liver injury 30.16 18.58 33 7822 24030 32481641
Stevens-Johnson syndrome 29.46 18.58 29 7826 18680 32486991
Liver disorder 29.04 18.58 37 7818 31617 32474054
Multiple-drug resistance 27.93 18.58 15 7840 3760 32501911
Pseudomembranous colitis 27.88 18.58 14 7841 3058 32502613
Death 27.80 18.58 31 7824 382486 32123185
Septic shock 27.43 18.58 55 7800 68934 32436737
Pneumonia bacterial 25.57 18.58 21 7834 10695 32494976
Megacolon 24.99 18.58 11 7844 1787 32503884
Acute generalised exanthematous pustulosis 24.81 18.58 17 7838 6596 32499075
Lymphocyte count decreased 24.81 18.58 28 7827 21091 32484580
Enterococcus test positive 24.79 18.58 9 7846 885 32504786
Fungaemia 24.31 18.58 12 7843 2527 32503144
Stenotrophomonas test positive 24.26 18.58 7 7848 330 32505341
Platelet count decreased 23.67 18.58 71 7784 114520 32391151
Respiratory failure 23.66 18.58 68 7787 107114 32398557
Rebound effect 23.58 18.58 11 7844 2045 32503626
Alanine aminotransferase increased 22.62 18.58 55 7800 78424 32427247
Multiple organ dysfunction syndrome 22.35 18.58 51 7804 69803 32435868
Renal impairment 21.91 18.58 60 7795 91912 32413759
Red blood cells urine positive 21.87 18.58 10 7845 1776 32503895
Pulmonary alveolar haemorrhage 21.40 18.58 16 7839 7113 32498558
Coagulopathy 21.38 18.58 25 7830 19552 32486119
Off label use 21.01 18.58 136 7719 306184 32199487
Kounis syndrome 20.94 18.58 10 7845 1958 32503713
Aspartate aminotransferase increased 20.70 18.58 48 7807 66381 32439290
Arteriospasm coronary 20.14 18.58 11 7844 2849 32502822
Paradoxical drug reaction 20.01 18.58 11 7844 2885 32502786
Toxicity to various agents 20.01 18.58 9 7846 178032 32327639
Disseminated intravascular coagulation 19.55 18.58 26 7829 23150 32482521
Fall 19.00 18.58 12 7843 196189 32309482
Blood creatine phosphokinase increased 18.96 18.58 37 7818 45439 32460232
White blood cell count increased 18.88 18.58 35 7820 41367 32464304
Protein urine present 18.88 18.58 13 7842 5084 32500587
Condition aggravated 18.88 18.58 81 7774 155580 32350091

Pharmacologic Action:

SourceCodeDescription
ATC J01CG01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase inhibitors
FDA MoA N0000000202 beta Lactamase Inhibitors
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D065093 beta-Lactamase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
FDA EPC N0000175930 beta Lactamase Inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Infection of skin AND/OR subcutaneous tissue indication 19824006
Infection due to Escherichia coli indication 71057007
Rhinoscleroma indication 72409005 DOID:11336
Cholangitis indication 82403002 DOID:9446
Female genital tract infection indication 125585007
Infectious disease of abdomen indication 128070006
Infection due to Enterobacteriaceae indication 128945009
Bacterial peritonitis indication 197171003
Infection due to Staphylococcus aureus indication 406602003
E. Coli Gynecological Infections indication
Klebsiella Pneumoniae Peritonitis indication
E. Coli Peritonitis indication
Skin and Skin Structure Bacteroides Fragilis Infection indication
Bacteroides Gynecological Infections indication
Inflammatory Disease of Female Pelvic Organs indication
Skin and Skin Structure Acinetobacter Infection indication
Bacteroides Peritonitis indication
Skin and Skin Structure Proteus Infection indication
Intra-Abdominal E. Coli Abscess indication
Streptococcal meningitis off-label use 4510004 DOID:11574
Pyrexia of unknown origin off-label use 7520000
Bacterial pneumonia off-label use 53084003 DOID:874
Infection of bone off-label use 111253001
Meningococcal meningitis off-label use 192644005
Sepsis of the newborn off-label use 206376005
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
Infective otitis media off-label use 312218008
Diabetic Foot Infection off-label use
Kidney disease contraindication 90708001 DOID:557
Infectious mononucleosis contraindication 271558008 DOID:8568
Pseudomembranous enterocolitis contraindication 397683000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.1 acidic

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
Serine beta-lactamase-like protein LACTB, mitochondrial Enzyme IC50 5.01 WOMBAT-PK
Beta-lactamase TEM Enzyme INHIBITOR Ki 6.10 CHEMBL CHEMBL
Beta-lactamase Enzyme IC50 4.18 CHEMBL
Beta-lactamase SHV-1 Enzyme IC50 5.41 CHEMBL
Beta-lactamase Enzyme IC50 6 CHEMBL
Beta-lactamase OXA-1 Enzyme IC50 4.66 CHEMBL
Beta-lactamase Enzyme IC50 4.57 CHEMBL
Beta-lactamase Enzyme IC50 5.21 CHEMBL
Beta-lactamase Enzyme IC50 7.12 CHEMBL
Carbapenem-hydrolizing beta-lactamase SFC-1 Enzyme IC50 4.64 CHEMBL
Beta-lactamase GES-13 Enzyme IC50 6.43 CHEMBL
Class D beta-lactamase Unclassified IC50 4.92 CHEMBL
Beta-lactamase Enzyme IC50 5.62 CHEMBL
Beta-lactamase Enzyme IC50 5.95 CHEMBL
Beta-lactamase Enzyme IC50 5.11 CHEMBL
Beta-lactamase Enzyme IC50 5.40 CHEMBL
Beta-lactamase TEM Enzyme Ki 6.10 WOMBAT-PK
ADC-18 protein Enzyme IC50 4.93 CHEMBL
Beta-lactamase 1 Enzyme IC50 4.60 CHEMBL
Beta-lactamase Enzyme IC50 5.52 CHEMBL
Beta-lactamase Enzyme IC50 5.19 CHEMBL
Beta-lactamase Enzyme IC50 5.52 CHEMBL

External reference:

IDSource
4019937 VUID
N0000148022 NUI
D02223 KEGG_DRUG
69388-84-7 SECONDARY_CAS_RN
4019381 VANDF
4019937 VANDF
C0038665 UMLSCUI
CHEBI:9321 CHEBI
0RN PDB_CHEM_ID
CHEMBL403 ChEMBL_ID
DB09324 DRUGBANK_ID
CHEMBL1200944 ChEMBL_ID
D013407 MESH_DESCRIPTOR_UI
130313 PUBCHEM_CID
4845 INN_ID
10769 IUPHAR_LIGAND_ID
S4TF6I2330 UNII
10167 RXNORM
5520 MMSL
d04403 MMSL
002811 NDDF
002812 NDDF
398916003 SNOMEDCT_US
412516007 SNOMEDCT_US
96008003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0013 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAMUSCULAR NDA 26 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0014 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 26 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0024 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAMUSCULAR NDA 25 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0031 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAMUSCULAR ANDA 26 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0032 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 26 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-2689 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0409-2987 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6116 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 24 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6117 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 24 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6118 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAVENOUS ANDA 24 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6119 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6120 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6121 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAVENOUS ANDA 24 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6122 INJECTION, POWDER, FOR SOLUTION 125 mg INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 0641-6123 INJECTION, POWDER, FOR SOLUTION 125 mg INTRAVENOUS ANDA 25 sections
ampicillin and sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 25021-142 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 25 sections
ampicillin and sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 25021-143 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 25 sections
ampicillin and sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 25021-144 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAVENOUS ANDA 25 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 36000-094 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 26 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 36000-095 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 26 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 44567-150 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 23 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 44567-210 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 23 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 44567-211 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 23 sections
Ampicillin and Sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 44567-212 INJECTION, POWDER, FOR SOLUTION 5 g INTRAVENOUS ANDA 21 sections
Ampicillin and Sulbactam Human Prescription Drug Label 2 55150-116 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAMUSCULAR ANDA 23 sections
Ampicillin and Sulbactam Human Prescription Drug Label 2 55150-117 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR ANDA 23 sections
Ampicillin and Sulbactam Human Prescription Drug Label 2 55150-118 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAVENOUS ANDA 23 sections
Ampicillin and Sulbactam Human Prescription Drug Label 2 55150-178 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 22 sections
Ampicillin and Sulbactam Human Prescription Drug Label 2 55150-179 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 22 sections
ampicillin and sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 66794-206 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 13 sections