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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H18N6O5S2
Molecular Weight 462.503
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEFATRIZINE

SMILES

[H][C@]12SCC(CSC3=CN=NN3)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C4=CC=C(O)C=C4)C(O)=O

InChI

InChIKey=UOCJDOLVGGIYIQ-PBFPGSCMSA-N
InChI=1S/C18H18N6O5S2/c19-12(8-1-3-10(25)4-2-8)15(26)21-13-16(27)24-14(18(28)29)9(7-31-17(13)24)6-30-11-5-20-23-22-11/h1-5,12-13,17,25H,6-7,19H2,(H,21,26)(H,28,29)(H,20,22,23)/t12-,13-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H18N6O5S2
Molecular Weight 462.503
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cefatrizine is a broad-spectrum, semisynthetic, first-generation cephalosporin with antibacterial activity. Cefatrizine binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis. Cefatrizine is used to treat a large variety of bacterial infections, such as respiratory tract, ear, skin and urinary tract infections. Cefatrizine is less effective against gram positive bacteria than first generation drugs. Antibiotics require constant drug level in body for therapeutic effect.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown
Curative
Unknown
Curative
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
It is given by mouth as the base or, more commonly, as a compound with propylene glycol, in usual doses equivalent to 500 mg twice daily of cefatrizine.
Route of Administration: Oral
In Vitro Use Guide
A total of 90% of isolates were inhibited by 1.6 ug of cefatrizine per ml
Substance Class Chemical
Record UNII
8P4W949T8K
Record Status Validated (UNII)
Record Version