sulbactam 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 -2.053 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 3.664 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 0.265 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 2.871 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 70.670 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 55.160 % High 1
herg hERG pIC50 4.767 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.186 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 4.467 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 51.210 % High 1
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AURKA,AXL,BRAF,BTK,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PIK3CB,PIK3CD,PIK3CG,PIM2,PLK1,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 52
kinase-selectivity-class ACVR2B,AXL,CDK9,EIF2AK3,GRK2,MAP2K6,TEK,TGFBR1 8
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.653 High 1
mh-clint Mouse hepatocyte intrinsic clearance 3.327 High 1
mppb Mouse plasma protein binding (% unbound) 74.910 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.379 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 63.470 % High 1
rh-clint Rat hepatocyte intrinsic clearance 2.280 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 93.230 % High 1
rppb Rat plasma protein binding (% unbound) 43.480 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 807.235 uM High 1

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 70.58 26.94 14 1739 1718 90624976
Hepatic function abnormal 59.30 26.94 25 1728 46263 90580431
Culture stool positive 41.94 26.94 7 1746 327 90626367
Stevens-Johnson syndrome 34.73 26.94 15 1738 29361 90597333
Klebsiella infection 33.36 26.94 11 1742 10286 90616408
Toxic epidermal necrolysis 33.26 26.94 15 1738 32513 90594181
Epidermolysis 30.51 26.94 6 1747 703 90625991

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
Kidney duplex 64.67 21.63 12 2088 399 42618836
Cardiac septal defect 54.52 21.63 12 2088 948 42618287
Enterocolitis haemorrhagic 42.34 21.63 10 2090 1081 42618154
Hepatic function abnormal 39.50 21.63 27 2073 51540 42567695
Interstitial lung disease 25.64 21.63 25 2075 78437 42540798
Pyrexia 24.15 21.63 57 2043 393985 42225250
Aspartate aminotransferase increased 22.29 21.63 23 2077 77140 42542095
Respiratory failure 21.65 21.63 29 2071 128103 42491132

FDA Adverse Event Reporting System (Geriatric)

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 108.34 23.24 23 3234 2581 110583461
Hepatic function abnormal 77.24 23.24 42 3215 89253 110496789
Culture stool positive 46.03 23.24 9 3248 669 110585373
Aspartate aminotransferase increased 38.05 23.24 34 3223 159902 110426140
Stevens-Johnson syndrome 34.89 23.24 20 3237 46881 110539161
Toxic epidermal necrolysis 31.37 23.24 20 3237 56707 110529335
Alanine aminotransferase increased 28.62 23.24 31 3226 183742 110402300
Respiratory failure 26.24 23.24 32 3225 215300 110370742
Interstitial lung disease 26.18 23.24 26 3231 139308 110446734
Pneumonia 25.94 23.24 70 3187 876644 109709398
Epidermolysis 24.96 23.24 6 3251 1172 110584870
Klebsiella infection 24.77 23.24 12 3245 19997 110566045
Rash 24.73 23.24 66 3191 820898 109765144
Sepsis 23.89 23.24 38 3219 327308 110258734

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01CG01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase inhibitors
ATC J01CG30 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
BETA-LACTAM ANTIBACTERIALS, PENICILLINS
Beta-lactamase inhibitors
FDA MoA N0000000202 beta Lactamase Inhibitors
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D065093 beta-Lactamase Inhibitors
FDA EPC N0000175930 beta Lactamase Inhibitor
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:35441 antiinfective agent

Related Drugs by ATC class:

J01CG Beta-lactamase inhibitors 2 drugs
durlobactamtazobactam

Drug Use | Suggest Off label Use Form| |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
Ventilator-associated bacterial pneumonia caused by acinetobacter baumannii-calcoaceticus complex indication 429271009
Infection caused by carbapenem-resistant acinetobacter baumannii-calcoaceticus complex indication 445780006
Hospital-acquired bacterial pneumonia caused by acinetobacter baumannii-calcoaceticus complex indication 1010634002
Intra-Abdominal E. Coli Abscess indication
E. Coli Peritonitis indication
Skin and Skin Structure Acinetobacter Infection indication
E. Coli Gynecological Infections indication
Klebsiella Pneumoniae Peritonitis indication
Skin and Skin Structure Bacteroides Fragilis Infection indication
Bacteroides Gynecological Infections indication
Inflammatory Disease of Female Pelvic Organs indication
Bacteroides Peritonitis indication
Skin and Skin Structure Proteus Infection 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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 500MG BASE/VIAL; EQ 500MG BASE/VIAL;EQ 1GM BASE/VIAL XACDURO (COPACKAGED) ENTASIS THERAP N216974 May 23, 2023 RX POWDER INTRAVENOUS 9623014 April 2, 2033 TREATMENT OF HOSPITAL-ACQUIRED BACTERIAL PNEUMONIA AND VENTILATOR-ASSOCIATED BACTERIAL PNEUMONIA (HABP/VABP)
EQ 500MG BASE/VIAL; EQ 500MG BASE/VIAL;EQ 1GM BASE/VIAL XACDURO (COPACKAGED) ENTASIS THERAP N216974 May 23, 2023 RX POWDER INTRAVENOUS 10376499 Nov. 17, 2035 TREATMENT OF HOSPITAL-ACQUIRED BACTERIAL PNEUMONIA AND VENTILATOR-ASSOCIATED BACTERIAL PNEUMONIA (HABP/VABP)
EQ 500MG BASE/VIAL; EQ 500MG BASE/VIAL;EQ 1GM BASE/VIAL XACDURO (COPACKAGED) ENTASIS THERAP N216974 May 23, 2023 RX POWDER INTRAVENOUS 9968593 Nov. 17, 2035 TREATMENT OF HOSPITAL-ACQUIRED BACTERIAL PNEUMONIA AND VENTILATOR-ASSOCIATED BACTERIAL PNEUMONIA (HABP/VABP)

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 500MG BASE/VIAL; EQ 500MG BASE/VIAL;EQ 1GM BASE/VIAL XACDURO (COPACKAGED) ENTASIS THERAP N216974 May 23, 2023 RX POWDER INTRAVENOUS May 23, 2028 NEW CHEMICAL ENTITY
EQ 500MG BASE/VIAL; EQ 500MG BASE/VIAL;EQ 1GM BASE/VIAL XACDURO (COPACKAGED) ENTASIS THERAP N216974 May 23, 2023 RX POWDER INTRAVENOUS May 23, 2033 GENERATING ANTIBIOTIC INCENTIVES NOW

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 5.19 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 Enzyme 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 5.52 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
10769 IUPHAR_LIGAND_ID
4845 INN_ID
S4TF6I2330 UNII
10167 RXNORM
5520 MMSL
d04403 MMSL
002811 NDDF
002812 NDDF
398916003 SNOMEDCT_US
412516007 SNOMEDCT_US
96008003 SNOMEDCT_US
S4TF6I2330 INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0013 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAMUSCULAR NDA 25 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-0014 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 25 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 0049-0710 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAMUSCULAR NDA 25 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-1515 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAMUSCULAR NDA 25 sections
UNASYN HUMAN PRESCRIPTION DRUG LABEL 2 0049-3003 INJECTION, POWDER, FOR SOLUTION 1 g INTRAMUSCULAR NDA 25 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 25021-142 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAVENOUS ANDA 26 sections
ampicillin and sulbactam HUMAN PRESCRIPTION DRUG LABEL 2 25021-143 INJECTION, POWDER, FOR SOLUTION 1 g INTRAVENOUS ANDA 26 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 55150-116 INJECTION, POWDER, FOR SOLUTION 0.50 g INTRAMUSCULAR ANDA 23 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 55150-117 INJECTION, POWDER, FOR SOLUTION 1 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 55150-118 INJECTION, POWDER, FOR SOLUTION 50 mg INTRAVENOUS 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 23 sections