MEM

(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Created: 2012-04-30
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count51
Chiral Atom Count6
Bond Count53
Aromatic Bond Count0
2D diagram of MEM

Chemical Component Summary

Name(4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
SynonymsMeropenem (closed form)
Systematic Name (OpenEye OEToolkits)(4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-4-methyl-6-[(1R)-1-oxidanylethyl]-7-oxidanylidene-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
FormulaC17 H25 N3 O5 S
Molecular Weight383.463
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(N(C)C)C3NCC(SC2=C(C(=O)O)N1C(=O)C(C(O)C)C1C2C)C3
SMILESCACTVS3.370C[CH](O)[CH]1[CH]2[CH](C)C(=C(N2C1=O)C(O)=O)S[CH]3CN[CH](C3)C(=O)N(C)C
SMILESOpenEye OEToolkits1.7.6CC1C2C(C(=O)N2C(=C1SC3CC(NC3)C(=O)N(C)C)C(=O)O)C(C)O
Canonical SMILESCACTVS3.370 C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(=C(N2C1=O)C(O)=O)S[C@@H]3CN[C@@H](C3)C(=O)N(C)C
Canonical SMILESOpenEye OEToolkits1.7.6 C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O
InChIInChI1.03 InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
InChIKeyInChI1.03 DMJNNHOOLUXYBV-PQTSNVLCSA-N

Drug Info: DrugBank

DrugBank IDDB00760 
NameMeropenem
Groups
  • approved
  • investigational
DescriptionMeropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death. In August 2017, a combination antibacterial therapy under the market name vabomere was approved for treatment of adult patients with complicated urinary tract infections (cUTI). Vabomere consists of meropenem and [DB12107] and is intravenously admininstered. The treatment aims to resolve infection-related symptoms and achieve negative urine culture, where the infections are proven or strongly suspected to be caused by susceptible bacteria.
Synonyms
  • Meropenem trihydrate
  • Meropenem anhydrous
  • Meropenem sodium
  • Meropenem
  • (4R,5S,6S)-3-{[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]thio}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Brand Names
  • Merrem IV
  • Vabomere
  • Vaborem
  • Meropenem for Injection, USP
  • Taro-meropenem
IndicationFor use as single agent therapy for the treatment of the following infections when caused by susceptible isolates of the designated microorganisms: <b>complicated skin and skin structure infections</b> due to <i>Staphylococcus aureus</i> (b-lactamase and non-b-lactamase producing, methicillin-susceptible isolates only), <i>Streptococcus pyogenes</i>, <i>Streptococcus agalactiae</i>, viridans group streptococci, <i>Enterococcus faecalis</i> (excluding vancomycin-resistant isolates), <i>Pseudomonas aeruginosa</i>, <i>Escherichia coli</i>, <i>Proteus mirabilis</i>, <i>Bacteroides fragilis</i> and <i>Peptostreptococcus</i> species; <b>complicated appendicitis and peritonitis</b> caused by viridans group streptococci, <i>Escherichia coli</i>, <i>Klebsiella pneumoniae</i>, <i>Pseudomonas aeruginosa</i>, <i>Bacteroides fragilis</i>, <i>B. thetaiotaomicron</i>, and <i>Peptostreptococcus</i> species. Also for use in the treatment of bacterial meningitis caused by <i>Streptococcus pneumoniae</i>, <i>Haemophilus influenzae</i> (b-lactamase and non-b-lactamase-producing isolates), and <i>Neisseria meningitidis</i>.
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-Code
  • J01DH02
  • J01DH52
CAS number96036-03-2

Drug Targets

NameTarget SequencePharmacological ActionActions
D-alanyl-D-alanine carboxypeptidase DacBMRFSRFIIGLTSCIAFSVQAANVDEYITQLPAGANLALMVQKVGASAPAI...unknowninhibitor
Beta-lactamase OXA-10MKTFAAYVIIACLSSTALAGSITENTSWNKEFSAEAVNGVFVLCKSSSKS...unknownsubstrate
Dipeptidase 1MWSGWWLWPLVAVCTADFFRDEAERIMRDSPVIDGHNDLPWQLLDMFNNR...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 441130, 40466974
ChEMBL CHEMBL127
ChEBI CHEBI:43968