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

• ChemBase ID: 640
• Molecular Formular: C17H25N3O5S
• Molecular Mass: 383.4625
• Monoisotopic Mass: 383.15149192
• SMILES: S(C1=C(N2[C@@H]([C@H](C2=O)[C@H](O)C)[C@H]1C)C(=O)O)[C@@H]1N[C@@H](CC1)C(=O)N(C)C
• Canonical SMILES: C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)O)S[C@H]1CC[C@H](N1)C(=O)N(C)C)O
• InChI: InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-10-6-5-9(18-10)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
• InChIKey: FSTGLKRHSQANLP-PQTSNVLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5S,6S)-3-{[(2S,5S)-5-(dimethylcarbamoyl)pyrrolidin-2-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• IUPAC Traditional name: merrem I.V.; meropenem
• Brand Name: Merrem I.V.; Merrem; Meronem
• Synonyms: Meropenemum [INN-Latin]; Meropenem anhydrous; Antibiotic SM 7338; meropenem; Meropenem

Database IDs

• CAS Number: 119478-56-7; 96036-03-2
• MDL Number: MFCD00864966
• PubChem SID: 160964103
• PubChem CID: 64778

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4608822
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -3.8944511
• LogD (pH = 7.4): -4.1434183
• Log P: -3.898237
• Molar Refractivity: 97.7742 cm^3
• Polarizability: 37.882397 Å^3
• Polar Surface Area: 110.18 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.8
• LOG S: -1.83
• Solubility (Water): 5.64e+00 g/l

PROPERTIES

Physical Property

• Solubility: Sparingly
• Hydrophobicity(logP): -0.6

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB00760

• Drug Groups: approved; investigational
• Description: Meropenem 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.
• Indication: For use as single agent therapy for the treatment of the following infections when caused by susceptible isolates of the designated microorganisms: complicated skin and skin structure infections due to Staphylococcus aureus (b-lactamase and non-b-lactamase producing, methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (excluding vancomycin-resistant isolates), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis and Peptostreptococcus species; complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. Also for use in the treatment of bacterial meningitis caused by Streptococcus pneumoniae, Haemophilus influenzae (b-lactamase and non-b-lactamase-producing isolates), and Neisseria meningitidis.
• Pharmacology: Meropenem 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.
• Toxicity: In mice and rats, large intravenous doses of meropenem (2200-4000 mg/kg) have been associated with ataxia, dyspnea, convulsions, and mortalities.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Primarily excreted unchanged. There is one metabolite which is microbiologically inactive.
• Half Life: Approximately 1 hour in adults and children 2 years of age and older with normal renal function. Approximately 1.5 hours in children 3 months to 2 years of age.
• Protein Binding: Approximately 2%.
• Elimination: Approximately 70% of the intravenously administered dose is recovered as unchanged meropenem in the urine over 12 hours, after which little further urinary excretion is detectable.
• External Links: Wikipedia; RxList; Drugs.com