1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid,3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-,hydrate (1:3), (4R,5S,6S)-

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1. Introduction of Meropenem

 

Meropenem is an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections. It is a beta-lactam and belongs to the subgroup of carbapenem, similar to imipenem and ertapenem. Meropenem was originally developed by MJ Pharmaceuticals. It is marketed in India by Nirlife and Positive Medicare with the brand name Meronir and Carnem respectively & outside India by AstraZeneca with the brand names Monan and Meronem. It gained US FDA approval in July 1996. It penetrates well into many tissues and body fluids including the cerebrospinal fluid, bile, heart valves, lung, and peritoneal fluid

 

2. Properties of Meropenem

 

(1) ACD/LogP: -0.482   (2) ACD/LogD (pH 5.5): -2.90   (3) ACD/LogD (pH 7.4): -3.17
(4) ACD/BCF (pH 5.5): 1.00   (5) ACD/BCF (pH 7.4): 1.00
(6) ACD/KOC (pH 5.5): 1.00   (7) ACD/KOC (pH 7.4): 1.00
(8) #H bond acceptors: 8   (9) #H bond donors: 3
(10) #Freely Rotating Bonds: 6   (11) Polar Surface Area: 135.48 ?2
(12) Index of Refraction: 1.639   (13) Molar Refractivity: 96.8 cm3
(14) Molar Volume: 268.88 cm3   (15) Polarizability: 38.375 10-24cm3
(16) Surface Tension: 68.4059982299805 dyne/cm   (17) Density: 1.426 g/cm3
(18) Flash Point: 333.217 °C   (19) Enthalpy of Vaporization: 106.42 kJ/mol
(20) Boiling Point: 627.363 °C at 760 mmHg
 

 

3. Structure descriptors of Meropenem

 

SMILES:O=C3N2\C(=C(\S[C@@H]1N[C@H](C(=O)N(C)C)CC1)[C@H](C)[C@@H]2[C@H]3[C@H](O)C)C(=O)O

Std. 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

Std. InChIKey:FSTGLKRHSQANLP-PQTSNVLCSA-N

 

4. Mechanism of action

 

Meropenem is bactericidal except against Listeria monocytogenes where it is bacteriostatic. It inhibits bacterial wall synthesis like other beta-lactam antibiotics. In contrast to other beta-lactams, it is highly resistant to degradation by beta-lactamases or cephalosporinases. Resistance generally arises due to mutations in penicillin binding proteins, production of metallo-beta-lactamases, or resistance to diffusion across the bacterial outer membrane. Unlike imipenem, it is stable to dehydropeptidase-1 and can therefore be given without cilastatin.