(6R,7R)-7-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 4138
• Molecular Formular: C20H20N6O9S
• Molecular Mass: 520.4726
• Monoisotopic Mass: 520.10124725
• SMILES: S(CC1=C(N2[C@H](OC1)[C@](OC)(NC(=O)C(c1ccc(O)cc1)C(=O)O)C2=O)C(=O)O)c1n(nnn1)C
• Canonical SMILES: CO[C@@]1(NC(=O)C(c2ccc(cc2)O)C(=O)O)C(=O)N2[C@@H]1OCC(=C2C(=O)O)CSc1nnnn1C
• InChI: InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1
• InChIKey: JWCSIUVGFCSJCK-CAVRMKNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: latamoxef
• Synonyms: Listeria MOX Supplement; Moxalactam Supplement; moxalactam; Latamoxef; 李斯特菌 MOX 添加剂; 拉氧头孢添加剂

Database IDs

• CAS Number: 64952-97-2
• EC Number: 265-287-9
• MDL Number: MFCD00865991
• PubChem SID: 46505546; 160967570
• PubChem CID: 47499

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.920229
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -4.256628
• LogD (pH = 7.4): -6.684071
• Log P: 0.17177607
• Molar Refractivity: 133.7041 cm^3
• Polarizability: 46.10878 Å^3
• Polar Surface Area: 206.3 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.22
• LOG S: -2.84
• Solubility (Water): 7.51e-01 g/l

PROPERTIES

Safety Information

• RTECS: RN6824500
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Grade: for microbiology
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C20H20N6O9S

DETAILS

DrugBank - DB04570

• Drug Groups: approved
• Description: Broad- spectrum beta-lactam antibiotic similar in structure to the cephalosporins except for the substitution of an oxaazabicyclo moiety for the thiaazabicyclo moiety of certain cephalosporins. It has been proposed especially for the meningitides because it passes the blood-brain barrier and for anaerobic infections. [PubChem]
• Indication: Latamoxef is an oxacephem antibiotic usually grouped with the cephalosporins. It is used to treat bacterial infections. Latamoxef is primarily indicated in conditions like Bone and joint infection, GI infections, Gynecological infections, Meningitis, Respiratory tract infections, Septicaemia, Skin infections, Soft tissue infections, UTI.
• Pharmacology: Latamoxef works by inhibiting bacterial cell wall biosynthesis.
• Toxicity: Latamoxef produces potentially life-threatening effects which include Bleeding, Hypothrombinemia, Platelet dysfunctioning. which are responsible for the discontinuation of Latamoxef therapy.; The symptomatic adverse reactions produced by Latamoxef are more or less tolerable and if they become severe, they can be treated symptomatically, these include Diarrhea, Skin rashes, Hematuria, Hyperuricemia, Pyuria, Raised serum creatinine.
• Absorption: Rapidly absorbed after oral administration.
• Half Life: 1.6 hours
• Protein Binding: 40%
• Elimination: Renal Excretion accounts for 75 %
• Distribution: 8.51 L
• References: Weitekamp MR, Aber RC: Prolonged bleeding times and bleeding diathesis associated with moxalactam administration. JAMA. 1983 Jan 7;249(1):69-71. [Pubmed] ; Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M: Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients. Arch Intern Med. 1986 Nov;146(11):2159-64. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 43963

Components
(per vial, sufficient for 1000 ml medium) Moxalactam 20.0 mg
General description
An antibiotic supplement recommended for selective isolation and cultivation of Listeria monocytogenes.

REFERENCES

• Weitekamp MR, Aber RC: Prolonged bleeding times and bleeding diathesis associated with moxalactam administration. JAMA. 1983 Jan 7;249(1):69-71. Pubmed
• Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M: Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients. Arch Intern Med. 1986 Nov;146(11):2159-64. Pubmed