(2S,3S)-3-[(2E)-2-(2-azaniumyl-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-methyl-4-oxoazetidine-1-sulfonate

• ChemBase ID: 72714
• Molecular Formular: C13H17N5O8S2
• Molecular Mass: 435.43278
• Monoisotopic Mass: 435.05185453
• SMILES: [C@H]1(C(=O)N([C@H]1C)S(=O)(=O)O)NC(=O)/C(=N\OC(C(=O)O)(C)C)/c1nc(sc1)N
• Canonical SMILES: C[C@H]1[C@H](NC(=O)/C(=N\OC(C(=O)O)(C)C)/c2csc(n2)N)C(=O)N1S(=O)(=O)O
• InChI: InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1
• InChIKey: WZPBZJONDBGPKJ-VEHQQRBSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-3-[(2E)-2-(2-azaniumyl-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-methyl-4-oxoazetidine-1-sulfonate; 2-{[(Z)-[(2-amino-1,3-thiazol-4-yl)({[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene]amino]oxy}-2-methylpropanoic acid
• IUPAC Traditional name: aztreonam; @aztreonam
• Brand Name: Azactam; Dynabiotic; Primbactam; Corus 1020; Monobactam
• Synonyms: [2S-[2α,3β(Z)]]-2-[[(Z)-[1-(2-Amino-4-thiazolyl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic Acid; Aztreon; Nebactam; Azthreonam; Azactam; [2S-[2α,3β(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic acid; AZT; Aztreonam; Monobactam; SQ 26776; Squibb 26776; Aztreonam(Azactam)

Database IDs

• CAS Number: 78110-38-0
• EC Number: 278-839-9
• PubChem SID: 162037635
• PubChem CID: 5742832

CALCULATED PROPERTIES

JChem

• Acid pKa: -1.8779534
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -4.6863904
• LogD (pH = 7.4): -6.120788
• Log P: -1.9186332
• Molar Refractivity: 92.9853 cm^3
• Polarizability: 36.662426 Å^3
• Polar Surface Area: 201.58 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.04
• LOG S: -4.06
• Solubility (Water): 4.29e-02 g/l

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Dimethylformamide; DMSO; Insoluble; Water
• Apperance: White Solid
• Melting Point: >205°C (dec); 227°C (dec.)

Safety Information

• Storage Condition: -20°C; -20°C Freezer; 2-8°C
• RTECS: UA2451400

Product Information

• Salt Data: Free Base

DETAILS

MP Biomedicals - 02150415

The first totally synthetic monocyclic β-lactam antibiotic that displays a high degree of resistance to β-lactamase degradation. High specificity for gram-negative aerobic rods.

DrugBank - DB00355

• Drug Groups: approved
• Description: A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms. [PubChem]
• Indication: For the treatment of the following infections caused by susceptible gram-negative microorganisms: urinary tract infections, lower respiratory tract infections, septicemia, skin and skin-structure infections, intra-abdominal infections, and gynecologic infections.
• Pharmacology: Aztreonam is a monocyclic beta-lactam antibiotic (a monobactam) originally isolated from Chromobacterium violaceum. Aztreonam exhibits potent and specific activity in vitro against a wide spectrum of gram-negative aerobic pathogens including Pseudomonas aeruginosa. It has no useful activity against gram-positive bacteria or anaerobes, but has very broad spectrum against gram-negative aerobes, including Pseudomonas aeruginosa. This has given it the nickname "the magic bullet for aerobic gram-negative bacteria". Aztreonam, unlike the majority of beta-lactam antibiotics, does not induce beta-lactamase activity and its molecular structure confers a high degree of resistance to hydrolysis by beta-lactamases (such as penicillinases and cephalosporinases) produced by most gram-negative and gram-positive pathogens; it is, therefore, usually active against gram-negative aerobic microorganisms that are resistant to antibiotics hydrolyzed by beta-lactamases. It is active against many strains that are multiply-resistant to other antibiotics, such as certain cephalosporins, penicillin, and aminoglycosides. Aztreonam maintains its antimicrobial activity over a pH range of 6 to 8 in vitro, as well as in the presence of human serum and under anaerobic conditions.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Approximately 6 to 16% metabolized to inactive metabolites by hydrolysis of the beta-lactam bond, resulting in an open-ring compound.
• Absorption: Less than 1% absorbed from the gastrointestinal tract following oral administration. Completely absorbed following intramuscular administration.
• Half Life: The serum half-life of aztreonam averaged 1.7 hours (1.5 to 2.0) in subjects with normal renal function, independent of the dose. In elderly patients and in patients with impaired renal function, the mean serum half-life of aztreonam increased (4.7 to 6 hours and 2.1 hours, respectively).
• Protein Binding: Serum protein binding averaged 56% and is independent of dose. Impaired renal function, 36 to 43%.
• Elimination: In healthy subjects, aztreonam is excreted in the urine about equally by active tubular secretion and glomerular filtration. Urinary excretion of a single parenteral dose was essentially complete by 12 hours after injection.
• Distribution: * 12.6 L
• Clearance: * 91 mL/min [healthy]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1505

Research Area: Infection
Biological Activity:
Aztreonam(Azactam, Cayston) is a synthetic monocyclic beta-lactam antibiotic (a monobactam), with the nucleus based on a simpler monobactam isolated from Chromobacterium violaceum. It inhibits mucopeptide synthesis in the bacterial cell wall, thereby blocking peptidoglycan crosslinking. It has a very high affinity for penicillin-binding protein 3 (PBP-3) and mild affinity for PBP-1a. Aztreonam binds to the penicillin-binding proteins of gram-positive and anaerobic bacteria very poorly and is largely ineffective against them. [1]

Toronto Research Chemicals - A965200

The first totally synthetic monocyclic β-lactam antibiotic.

REFERENCES

• R.B. Sykes, et al., Antimicrob. Ag. Chemother, 21: 85, (1982).
• http://en.wikipedia.org/wiki/Aztreonam
• Sykes, R.B., et al.: Antimicrob. Agents Chemother., 21, 85 (1982)
• Florey, K., et al.: Anal. Profiles Drug Subs., 17, 1 (1982)