0RN

SULBACTAM

Created:2012-06-11
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count26
Chiral Atom Count2
Bond Count27
Aromatic Bond Count0
2D diagram of 0RN
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Chemical Component Summary

NameSULBACTAM
Synonyms(2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
Systematic Name (OpenEye OEToolkits)(2S,5R)-3,3-dimethyl-4,4,7-tris(oxidanylidene)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
FormulaC8 H11 N O5 S
Molecular Weight233.242
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs12.01O=S2(=O)C(C(N1C(=O)CC12)C(=O)O)(C)C
SMILESCACTVS3.370CC1(C)[CH](N2[CH](CC2=O)[S]1(=O)=O)C(O)=O
SMILESOpenEye OEToolkits1.7.6CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)C
Canonical SMILESCACTVS3.370 CC1(C)[C@@H](N2[C@@H](CC2=O)[S]1(=O)=O)C(O)=O
Canonical SMILESOpenEye OEToolkits1.7.6 CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)C
InChIInChI1.03 InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
InChIKeyInChI1.03 FKENQMMABCRJMK-RITPCOANSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB09324 
NameSulbactam
Groups approved
DescriptionSulbactam is a beta (β)-lactamase inhibitor and a derivative of the basic penicillin nucleus.[L50131] When given in combination with β-lactam antibiotics, sulbactam produces a synergistic effect as it blocks the enzyme responsible for drug resistance by hydrolyzing β-lactams.[A263296]
Synonyms
  • Penicillanic acid 1,1-dioxide
  • (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid 4,4-dioxide
  • (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
  • Sulbactam benzathine
  • Penicillanic acid sulfone
Brand Names
  • Ampicillin Sodium and Sulbactam Sodium
  • AMPICILLIN and SULBACTAM
  • Xacduro
  • Unasyn
  • Ampicillin and Sulbactam
IndicationSulbactam is used in combination with other antibacterial agents. With [ampicillin], it is used to treat skin and skin structure infections, intra-abdominal infections, and gynecological infections caused by susceptible bacteria.[L50131] In combination with [durlobactam], sulbactam is indicated in adults for the treatment of hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia (HABP/VABP), caused by susceptible isolates of _Acinetobacter baumannii-calcoaceticus_ complex.[L47336]
Categories
  • Amides
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
  • Beta-Lactam Antibacterials
ATC-CodeJ01CG01
CAS number68373-14-8

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Beta-lactamaseMKKLIFLIVIALVLSACNSNSSHAKELNDLEKKYNAHIGVYALDTKSGKE...unknowninhibitor
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 130313
ChEMBL CHEMBL403
ChEBI CHEBI:9321
CCDC/CSD BAFVOT