Chemical Component Summary

NameDoripenem
Synonyms(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-({(3S,5S)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl}sulfanyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Identifiers(4~{R},5~{S},6~{S})-4-methyl-6-[(1~{R})-1-oxidanylethyl]-7-oxidanylidene-3-[(3~{S},5~{S})-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
FormulaC15 H24 N4 O6 S2
Molecular Weight420.504
TypeNON-POLYMER
Isomeric SMILESC[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)CNS(=O)(=O)N)C(=O)O)[C@@H](C)O
InChIInChI=1S/C15H24N4O6S2/c1-6-11-10(7(2)20)14(21)19(11)12(15(22)23)13(6)26-9-3-8(17-5-9)4-18-27(16,24)25/h6-11,17-18,20H,3-5H2,1-2H3,(H,22,23)(H2,16,24,25)/t6-,7-,8+,9+,10-,11-/m1/s1
InChIKeyAVAACINZEOAHHE-VFZPANTDSA-N

Chemical Details

Formal Charge0
Atom Count51
Chiral Atom Count6
Bond Count53
Aromatic Bond Count0

Drug Info: DrugBank

DrugBank IDDB06211 
NameDoripenem
Groups
  • investigational
  • approved
DescriptionDoripenem is a broad-spectrum, carbapenem antibiotic marketed under the brand name Doribax by Janssen. Doripenem injection was approved by the FDA in 2007 to treat complicated urinary tract and intra-abdominal infections. In a clinical trial of doripenem treatment in ventilator associated pneumonia (vs. imipenem and cilastatin), it was found that doripenem carried an increased risk of death and lower clinical cure rates, resulting in a premature termination of the trial. The FDA revised the doripenem label in 2014 to include a warning against use in ventilator-associated pneumonia and to reiterate its safety and efficacy for its approved indications.
Synonyms
  • Doripenem hydrate
  • Doripenem
Brand Names
  • Doripenem
  • Doribax
IndicationDoripenem is indicated in the treatment of complicated intra-abdominal infections and complicated urinary tract infections, including pyelonephritis, caused by designated susceptible bacteria.
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-CodeJ01DH04
CAS number148016-81-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 1AMKFVKYFLILAVCCILLGAGSIYGLYRYIEPQLPDVATLKDVRLQIPMQI...unknownantagonist,inhibitor
Penicillin-binding protein 1BMAGNDREPIGRKGKPTRPVKQKVSRRRYEDDDDYDDYDDYEDEEPMPRKG...unknownantagonist,inhibitor
Penicillin-binding protein 2MKLQNSFRDYTAESALFVRRALVAFLGILLLTGVLIANLYNLQIVRFTDY...unknownantagonist,inhibitor
Penicillin-binding protein 3MKLNYFQGALYPWRFCVIVGLLLAMVGAIVWRIVDLHVIDHDFLKGQGDA...unknownantagonist,inhibitor
Penicillin-binding protein 4MKNLISIIIILCLTLSIMTPYAQATNSDVTPVQAANQYGYAGLSAAYEPT...unknownantagonist,inhibitor
View More
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
Pharos CHEMBL491571
PubChem 73303, 6918242
ChEMBL CHEMBL491571
ChEBI CHEBI:135928
CCDC/CSD IHUHAW, IHUGUP