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Cemandil sodium salt

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
MDL Number:
MFCD00864877
MOL File:
42540-40-9.mol
Last updated:2024-07-02 08:55:11

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)
FDA UNII 8HDO7941DO

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
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 price More Price(23)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C0682300 Cefamandole nafate European Pharmacopoeia (EP) Reference Standard 42540-40-9 c0682300 $220 2024-03-01 Buy
Sigma-Aldrich 1097400 Cefamandole nafate United States Pharmacopeia (USP) Reference Standard 42540-40-9 250mg $412 2024-03-01 Buy
Alfa Aesar J66735 Cefamandole nafate 42540-40-9 5g $168.65 2024-03-01 Buy
Alfa Aesar J66735 Cefamandole nafate 42540-40-9 10g $336 2024-03-01 Buy
Cayman Chemical 23988 Cefamandole Nafate ≥95% 42540-40-9 1g $88 2024-03-01 Buy
Product number Packaging Price Buy
C0682300 c0682300 $220 Buy
1097400 250mg $412 Buy
J66735 5g $168.65 Buy
J66735 10g $336 Buy
23988 1g $88 Buy

Cemandil sodium salt Chemical Properties,Uses,Production

Chemical Properties

White Solid

Originator

Mandokef,Lilly,W. Germany,1977

Uses

A second generation cephalosporin antibiotic.

Uses

Cephalosporin antibacterial.

Definition

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

Manufacturing Process

To 21.6 kg (17.8 l) of 98% formic acid was added 1.14 kg (7.5 mols) of D-(-)- mandelic acid and the reaction mixture was heated for 4 hours at 70°C with stirring. The excess formic acid was evaporated off in vacuo and the residual syrup was dissolved in 6 l of benzene. The solution was washed twice with 6 l portions of water and was dried over magnesium sulfate. The drying agent was filtered and washed with 1.5 l of benzene, the washes being added to the filtrate. The dried filtrate was evaporated in vacuo to obtain the D-(-)- mandelic acid formate ether as a syrup. The product can be crystallized from cyclohexane to yield material melting at about 55°C to 58°C.
The mandelic acid formate ester obtained as a syrup as described above is stirred for 2 hours with 2.9 kg (~1.75 l) of thionyl chloride at a temperature of about 70°C. The excess thionyl chloride is removed by evaporation and the residual green solution is vacuum distilled. The product, O-formyl mandeloyl chloride, distills over at 127°C to 130°C (15 mm) or at 108°C to 112°C (7 mm).
To 13 l of ethyl acetate were added 85.1 g (2.59 mols) of 7-amino-3-(1- methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid and 1,361 g (10.37 mols) of monotrimethylsilyl acetamide, and the mixture was stirred at 50°C until a clear solution was obtained. The solution was cooled to 20°C and 514 g (2.59 mold of O-formyl mandeloyl chloride was added at a rate such that the temperature of the reaction solution was maintained between about 20°C to 25% with ice-cooling.
The reaction mixture was stirred for 1.5 hours at about room temperature after the addition of the mandeloyl chloride was completed. Five liters of water were then added to the reaction mixture and the diluted mixture was stirred for about 10 minutes. The organic layer was separated and was washed twice with water. The combined washes are extracted with 1.5 l of ethyl acetate and the extract is combined with the washed organic layer. The whole was dried over magnesium sulfate, filtered and evaporated in vacuo on a 25°C water bath to yield 1,460 g of product, 7-(D-2-formyloxy-2- phenylacetamido)-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4- carboxylic acid, as a yellow foam.
The product was dissolved in 5 l of acetone and the solution was mixed with a solution of 430 g (2.59 mols) of sodium 2-ethylhexanoate in 5.4 l of acetone. The combined solutions were seeded and stirred in an ice bath for 1.5 hours. The crystalline precipitate of sodium 7-(D-2-formyloxy-2-phenylacetamido)-3- (1-methyl-1H-tetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate was filtered and washed with 5 l of acetone. The crystalline salt was dried overnight in a vacuum oven at 40°C to yield 1,060 g (80%)of product, melting at 182°C to 184°C.

brand name

Mandol (Lilly).

Therapeutic Function

Antibiotic

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.

80543-51-7
24209-38-9
42540-40-9
Synthesis of Cemandil sodium salt from O-FORMYLMANDELOYL CHLORIDE and 7-TMCA
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View Lastest Price from Cemandil sodium salt manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Cemandil sodium salt pictures 2024-08-20 Cemandil sodium salt
42540-40-9
US $10.00-7.00 / kg 1kg 99.9% 20ton Hebei Ganmiao New material Technology Co., LTD
Cefamandole Nafate pictures 2024-04-29 Cefamandole Nafate
42540-40-9
US $0.00 / kg 1kg 99% 20tons Shaanxi TNJONE Pharmaceutical Co., Ltd
Cemandil sodium salt pictures 2019-08-08 Cemandil sodium salt
42540-40-9
US $3.00 / KG 1KG 99% 100kg Career Henan Chemical Co
  • Cemandil sodium salt pictures
  • Cemandil sodium salt
    42540-40-9
  • US $10.00-7.00 / kg
  • 99.9%
  • Hebei Ganmiao New material Technology Co., LTD
,(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