Compound ID | 86

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Imipenem + cilastatin/relebactam

Synonym(s): MK-7655

Class: Drug combination: beta-lactam (carbapenem) + beta-lactamase inhibitor (non-beta-lactam beta-lactamase inhibitor, diazabicyclooctane [DBO])

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Complicated urinary tract infections (cUTI), acute pyelonephritis, Complicated urinary tract infections (cUTI), acute pyelonephritis, complicated intra-abdominal infections (cIAI), hospital-acquired bacterial pneumonia/ventilator-associated bacterial pneumonia (approved by FDA in 2020)
Combined with other compounds: Yes
Institute where first reported: Merck & Co
Year first mentioned: 2011
Highest developmental phase: Approved by FDA in 2019
Development status: Approved
Chemical structure(s):
Imipenem
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Molecular weight: 299.35
Iso. SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
InChI Key: ZSKVGTPCRGIANV-ZXFLCMHBSA-N
Can. SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(C(=O)O)N2C1=O)SCCN=CN)O
InChI: InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
Relebactam
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Molecular weight: 348.38
Iso. SMILES: C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)NC3CCNCC3
InChI Key: SMOBCLHAZXOKDQ-ZJUUUORDSA-N
Can. SMILES: C1C[C@@H](C(=O)NC2CCNCC2)N3C[C@@H]1N(C3=O)OS(=O)(=O)O
InChI: InChI=1S/C12H20N4O6S/c17-11(14-8-3-5-13-6-4-8)10-2-1-9-7-15(10)12(18)16(9)22-23(19,20)21/h8-10,13H,1-7H2,(H,14,17)(H,19,20,21)/t9-,10+/m1/s1
Cilastatin
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Molecular weight: 358.45
Iso. SMILES: CC1(C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)O)C
InChI Key: DHSUYTOATWAVLW-WFVMDLQDSA-N
Can. SMILES: CC1(C)C[C@@H]1C(=O)N/C(=C\CCCCSC[C@@H](C(=O)O)N)/C(=O)O
InChI: InChI=1S/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/104838
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/44129647
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6435415
Guide to Pharmacology: cilastatin
Citations:
  • https://clinicaltrials.gov/ct2/show/NCT02452047

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