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Cemandil sodium salt

Cemandil sodium salt Structure
CAS No.
42540-40-9
Chemical Name:
Cemandil sodium salt
Synonyms
CEFAMANDOLE NAFATE;Fado;CefaM;Cedol;CeMado;Nafate;mandol;Cefiran;Kefadol;Pavecef
CBNumber:
CB5430833
Molecular Formula:
C19H17N6NaO6S2
Molecular Weight:
512.49
MOL File:
42540-40-9.mol
Modify Date:
2024/7/2 8:55:11

Cemandil sodium salt Properties

Melting point 190-193°C
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility Freely soluble in water, sparingly soluble in methanol.
form Solid
pka 2.6-3.0(at 25℃)
color White to Off-White
Water Solubility Freely soluble in water. Sparingly soluble in methanol
CAS DataBase Reference 42540-40-9(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Danger
Hazard statements  H315-H317-H319-H334-H335
Precautionary statements  P261-P280-P284-P304+P340-P305+P351+P338-P342+P311
Hazard Codes  Xn
Risk Statements  36/37/38-42/43
Safety Statements  26-36
WGK Germany  3
RTECS  XI0380000
HS Code  2941906000
NFPA 704
0
2 0

Cemandil sodium salt Chemical Properties,Uses,Production

Chemical Properties

White Solid

Uses

Cephalosporin antibacterial.

Definition

ChEBI: A cephalosporin prodrug having (R)-O-formylmandelamido and N-methylthiotetrazole side-groups.

Mechanism of action

Cefamandole nafate has a formylated D-mandelic amide moiety at C-7. The formate ester is cleaved rapidly in the host to release the more active cefamandole. The esterification also apparently overcomes the instability of cefamandole when it is stored in dry form. This agent has increased activity against Haemophil us influenzae and some Gram-negative bacilli as compared with the first-generation cephalosporins. Loss of the 5-thio-l-methyl-l-H-tetrazole moiety (referred to sometimes by the acronym MT T) from C-3 is associated with prothrombin deficiency and bleeding problems as well as with an Antabuse-like acute alcohol intolerance. On the other hand, this grouping enhances potency and prevents metabolism by deacetylation. Like the other second-generation cephalosporins, cefamandole is more active against Gram-negative bacteria. The principle clinical use is for lower respiratory tract, skin and skin structures, and bone and joint infections as well as septicemia and urinary tract infections when the organisms are sensitive.

Clinical Use

The D-mandeloyl moiety of Cemandil sodium salt appears toconfer resistance to a few β-lactamases, since some β-lactamase–producing, Gram-negative bacteria (particularlyEnterobacteriaceae) that show resistance to cefazolin andother first-generation cephalosporins are sensitive tocefamandole. Additionally, it is active against some ampicillin-resistant strains of Neisseria and Haemophilus spp.Although resistance to β-lactamases may be a factor in determiningthe sensitivity of individual bacterial strains tocefamandole, an early study indicated that other factors,such as permeability and intrinsic activity, are frequentlymore important. The L-mandeloyl isomer is significantlyless active than the D-isomer.

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,(6r-(6-alpha,7-beta(r)))- Cemandil sodium salt Sodium [6R-[6alpha,7beta(R*)]]-7-[[(formyloxy)phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Cefamandole nafate,Cefamandole formate sodium salt Cefamandole Nafate (250 mg) Cefamandole Nafate (200 mg) (6R,7R)-7-[[(2R)-2-(ForMyloxy)-2-phenylacetyl]aMino]-3-[[(1-Methyl-1H-tetrazol-5-yl)thio]Methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid SodiuM Salt Bergacef Cedol CefaM CefaMandole ForMate SodiuM Cefiran CeMado CeMandil Fado Kefadol Kefandol LaMpoMandol Mandokef Mandolsan Neocefal NSC 299588 Pavecef Nafate 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid,7-[[(2R)-2-(forMyloxy)-2-phenylacetyl]aMino]-3-[[(1-Methyl-1H-tetrazol-5-yl)thio]Methyl]-8-oxo-,sodiuM salt (1:1), (6R,7R)- 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-(((formyloxy)phenylace cefamandolnafato cephamandolenafate mandol o-formylcefamandolesodium CEFAMANDOLE FORMATE SODIUM SALT Cefamandole Nafate -Delta-3- Isomer Cefamandole nafate Sodium sodium:(6R,7R)-7-[(2-formyloxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Sodium (6R,7R)-7-(R)-mandelamido-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate formate (ester) Cefamandole Nafate sterila 7-[(2-formyloxy-1-oxo-2-phenylethyl)amino]-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium [6R-[6α,7β(R*)]]-7-[[(formyloxy)phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Cefamandole nafate CRS Cemandil sodium salt USP/EP/BP Cemandil Sodium sodium [6R-[6α,7β(R*)]]-7-[[(formyloxy)phenylacetyl]amino]... sodium (6R,7R)-7-[(2R)-2-(formyloxy)-2-phenylacetamido]- 3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]met hyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-ca rboxylate Cefamandole Nafate API Cefamandole Nafate (1097400) CEFAMANDOLE NAFATE Cefamandole Nafate (250 mg) (DISCONTINUED) 42540-40-9 2540-40-9 C19H18N6NaO6S2 C19H17N6O6S2Na C19H17N6NaO6S2 Antibiotics A-F Antibiotics A to Z Antibiotics BioChemical MANDOL Intermediates & Fine Chemicals