(5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

• ChemBase ID: 1375
• Molecular Formular: C12H17N3O4S
• Molecular Mass: 299.34608
• Monoisotopic Mass: 299.09397704
• SMILES: S(C1=C(N2[C@@H]([C@H](C2=O)[C@H](O)C)C1)C(=O)O)CC/N=C/N
• Canonical SMILES: C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCC/N=C/N)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
• InChIKey: ZSKVGTPCRGIANV-ZXFLCMHBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,6S)-3-({2-[(E)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• IUPAC Traditional name: IPM
• Brand Name: Tienamycin
• Synonyms: IMP; N-formimidoylthienamycin; Imipenem, n-formimidoyl thienamycin; Imipemide; Imipenem

Database IDs

• CAS Number: 74431-23-5
• PubChem SID: 160964835; 46505744
• PubChem CID: 104838

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.633336
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -3.8558762
• LogD (pH = 7.4): -3.8512151
• Log P: -3.8512225
• Molar Refractivity: 75.8434 cm^3
• Polarizability: 28.54953 Å^3
• Polar Surface Area: 116.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.19
• LOG S: -2.59
• Solubility (Water): 7.76e-01 g/l

PROPERTIES

Physical Property

• Solubility: 10 mg/mL [MERCK INDEX (1996)]

DETAILS

DrugBank - DB01598

• Drug Groups: approved
• Description: Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with cilastatin, a renal dipeptidase inhibitor. [PubChem]
• Indication: For the treatment of bacterial infections caused by susceptible bacteria.
• Pharmacology: Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. Imipenem has a broad spectrum of activity against aerobic and anaerobic Gram positive as well as Gram negative bacteria. It is particularly important for its activity against Pseudomonas aeruginosa and the Enterococcus species. Imipenem is rapidly degraded by the renal enzyme dehydropeptidase when administered alone, and is always co-administered with cilastatin to prevent this inactivation.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Renal.
• Absorption: Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally.
• Half Life: 1 hour
• Protein Binding: 20% binds to plasma proteins
• References: Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. [Pubmed] ; Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. [Pubmed] ; Clissold SP, Todd PA, Campoli-Richards DM: Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1987 Mar;33(3):183-241. [Pubmed] ; Buckley MM, Brogden RN, Barradell LB, Goa KL: Imipenem/cilastatin. A reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1992 Sep;44(3):408-44. [Pubmed] ; Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. [Pubmed] ; Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. [Pubmed] ; Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. [Pubmed] ; Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Kattan JN, Villegas MV, Quinn JP: New developments in carbapenems. Clin Microbiol Infect. 2008 Dec;14(12):1102-11. Pubmed
• Pastel DA: Imipenem-cilastatin sodium, a broad-spectrum carbapenem antibiotic combination. Clin Pharm. 1986 Sep;5(9):719-36. Pubmed
• Clissold SP, Todd PA, Campoli-Richards DM: Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1987 Mar;33(3):183-241. Pubmed
• Buckley MM, Brogden RN, Barradell LB, Goa KL: Imipenem/cilastatin. A reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1992 Sep;44(3):408-44. Pubmed
• Richerson MA, Ambrose PG, Quintiliani R, Nightingale CH: Formulary review of the carbapenems: comparison of imipenem/cilastatin and meropenem. Conn Med. 1998 Mar;62(3):165-9. Pubmed
• Birnbaum J, Kahan FM, Kropp H, MacDonald JS: Carbapenems, a new class of beta-lactam antibiotics. Discovery and development of imipenem/cilastatin. Am J Med. 1985 Jun 7;78(6A):3-21. Pubmed
• Kahan FM, Kropp H, Sundelof JG, Birnbaum J: Thienamycin: development of imipenen-cilastatin. J Antimicrob Chemother. 1983 Dec;12 Suppl D:1-35. Pubmed
• Hellinger WC, Brewer NS: Imipenem. Mayo Clin Proc. 1991 Oct;66(10):1074-81. Pubmed