Azlocillin Sodium

Synopsis, Chemistry

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Also known as: Schembl718621, Akos015896474

Molecular Formula

C₂₀H₂₂N₅NaO₆S

Molecular Weight

483.5 g/mol

InChI Key

UVOCNBWUHNCKJM-QXKADHPISA-M

Azlocillin Sodium is the sodium salt form of azlocillin, a semisynthetic, extended spectrum acylampicillin with antibacterial activity. Azlocillin binds to penicillin-binding proteins (PBPs) located inside the bacterial cell wall, thereby inhibiting the cross-linkage of peptidoglycans, which are critical components of the bacterial cell wall. This prevents proper bacterial cell wall synthesis, thereby results in the weakening of the bacterial cell wall and eventually leading to cell lysis.

1 2D Structure

Azlocillin Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(2R,5S,6S)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C20H23N5O6S.Na/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30;/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29);/q;+1/p-1/t11-,12+,13-,16+;/m1./s1

2.1.3 InChI Key

UVOCNBWUHNCKJM-QXKADHPISA-M

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)[O-])C.[Na+]

2.1.5 Isomeric SMILES

CC1([C@H](N2[C@@H](S1)[C@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)[O-])C.[Na+]

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. Schembl718621

2. Akos015896474

2.3 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₂N₅NaO₆S
Molecular Weight	483.5 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	483.11884889 g/mol
Monoisotopic Mass	483.11884889 g/mol
Topological Polar Surface Area	176 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	851
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2