(2S,5R,6R)-6-[(2R)-2-[(3-methanesulfonyl-2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 824
• Molecular Formular: C21H25N5O8S2
• Molecular Mass: 539.5819
• Monoisotopic Mass: 539.11445479
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)[C@H](NC(=O)N1CCN(S(=O)(=O)C)C1=O)c1ccccc1
• Canonical SMILES: O=C([C@@H](c1ccccc1)NC(=O)N1CCN(C1=O)S(=O)(=O)C)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C21H25N5O8S2/c1-21(2)14(18(29)30)26-16(28)13(17(26)35-21)22-15(27)12(11-7-5-4-6-8-11)23-19(31)24-9-10-25(20(24)32)36(3,33)34/h4-8,12-14,17H,9-10H2,1-3H3,(H,22,27)(H,23,31)(H,29,30)/t12-,13-,14+,17-/m1/s1
• InChIKey: YPBATNHYBCGSSN-VWPFQQQWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[(2R)-2-[(3-methanesulfonyl-2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: (2S,5R,6R)-6-[(2R)-2-(3-methanesulfonyl-2-oxoimidazolidine-1-carbonylamino)-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Brand Name: Mezlin
• Synonyms: Mezlocillin

Database IDs

• CAS Number: 51481-65-3
• PubChem SID: 160964287; 46506692
• PubChem CID: 656511

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4850655
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.8475525
• LogD (pH = 7.4): -4.221354
• Log P: -0.8415242
• Molar Refractivity: 124.8779 cm^3
• Polarizability: 49.81825 Å^3
• Polar Surface Area: 173.5 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.21
• LOG S: -3.06
• Solubility (Water): 4.71e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0

DETAILS

DrugBank - DB00948

• Drug Groups: approved
• Description: Semisynthetic ampicillin-derived acylureido penicillin. It has been proposed for infections with certain anaerobes and may be useful in inner ear, bile, and CNS infections. [PubChem]
• Indication: Used to treat serious gram–negative infections of the lungs, urinary tract, and skin.
• Pharmacology: Mezlocillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Mezlocillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of mezlocillin results from the inhibition of cell wall synthesis and is mediated through mezlocillin binding to penicillin binding proteins (PBPs). Mezlocillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Mezlocillin can be used to treat susceptible strains of H. influenzae, Klebsiella species, Pseudomonas species, Proteus mirabilis, E. coli, Enterobacter species, Streptococcus faecelis, Peptococcus species, Peptostreptococcus species, Bacteriodes species (including B. fragilis), Morganella morganii, Serratia species, N. gonorrhoeae, P. vulgaris, and Providencia rettgeri. This drug is discontinued in the U.S.
• Toxicity: Symptoms of overdose include rash, fever, chills, and peeling skin.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Unlike many other penicillins, mezlocillin is either extensively metabolized or is subject to biliary excretion, as only about 50% of the dose was accounted for in normal urine.
• Half Life: 1.3 to 4.4 hours
• Protein Binding: 16-59%
• References: Kristof RA, Clusmann H, Koehler W, Fink KB, Schramm J: Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange. J Neurol Neurosurg Psychiatry. 1998 Mar;64(3):379-81. [Pubmed] ; McCormick PA, Greenslade L, Kibbler CC, Chin JK, Burroughs AK, McIntyre N: A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients. Hepatology. 1997 Apr;25(4):833-6. [Pubmed] ; Rohde B, Werner U, Hickstein H, Ehmcke H, Drewelow B: Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure. Eur J Clin Pharmacol. 1997;53(2):111-5. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Kristof RA, Clusmann H, Koehler W, Fink KB, Schramm J: Treatment of accidental high dose intraventricular mezlocillin application by cerebrospinal fluid exchange. J Neurol Neurosurg Psychiatry. 1998 Mar;64(3):379-81. Pubmed
• McCormick PA, Greenslade L, Kibbler CC, Chin JK, Burroughs AK, McIntyre N: A prospective randomized trial of ceftazidime versus netilmicin plus mezlocillin in the empirical therapy of presumed sepsis in cirrhotic patients. Hepatology. 1997 Apr;25(4):833-6. Pubmed
• Rohde B, Werner U, Hickstein H, Ehmcke H, Drewelow B: Pharmacokinetics of mezlocillin and sulbactam under continuous veno-venous hemodialysis (CVVHD) in intensive care patients with acute renal failure. Eur J Clin Pharmacol. 1997;53(2):111-5. Pubmed