ChemicalBook > CAS DataBase List > Cemandil sodium salt

Cemandil sodium salt

Product Name
Cemandil sodium salt
CAS No.
42540-40-9
Chemical Name
Cemandil sodium salt
Synonyms
CEFAMANDOLE NAFATE;Fado;Cedol;CefaM;CeMado;Nafate;mandol;Cefiran;Kefadol;Pavecef
CBNumber
CB5430833
Molecular Formula
C19H17N6NaO6S2
Formula Weight
512.49
MOL File
42540-40-9.mol
More
Less

Cemandil sodium salt Property

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)
More
Less

Safety

Hazard Codes 
Xn
Risk Statements 
36/37/38-42/43
Safety Statements 
26-36
WGK Germany 
3
RTECS 
XI0380000
HS Code 
2941906000
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

More
Less

N-Bromosuccinimide Price

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

Cemandil sodium salt Chemical Properties,Usage,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.

Cemandil sodium salt Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Cemandil sodium salt Suppliers

Belgium 1 Canada 2 China 197 Europe 1 France 2 Germany 4 India 7 South Korea 1 Spain 1 Switzerland 2 United Kingdom 7 United States 38 Global 263
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
Advantage
58
Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
Country
United States
ProdList
4660
Advantage
60
BOC Sciences
Tel
16314854226; +16314854226
Email
inquiry@bocsci.com
Country
United States
ProdList
19741
Advantage
58
Cato Research Chemicals Inc.
Tel
020-81215950 4000-868-328
Email
customer@uwalab.com
Country
United States
ProdList
10404
Advantage
58
Protheragen-ING
Tel
+16313385890
Email
info@protheragen-ing.com
Country
United States
ProdList
3868
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
BOC Sciences
Tel
16314854226
Email
info@bocsci.com
Country
United States
ProdList
9923
Advantage
65
Molcan Corporation
Tel
--
Fax
--
Email
info@molcan.com
Country
United States
ProdList
686
Advantage
60
MP Biomedicals, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6561
Advantage
81
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
MilliporeSigma (Sigma-Aldrich Corp.)
Tel
--
Fax
--
Email
@sial.com
Country
United States
ProdList
5414
Advantage
58
MP Biomedicals, LLC. (Division of Valiant FC Co., Ltd.)
Tel
--
Fax
--
Email
serv@mpbio.com
Country
United States
ProdList
1854
Advantage
58
Selleck Chemicals LLC
Tel
--
Fax
--
Email
sales@selleckchem.com
Country
United States
ProdList
1848
Advantage
58
OChem Incorporation
Tel
--
Fax
--
Email
sales@ocheminc.com
Country
United States
ProdList
6501
Advantage
60
United States Biological
Tel
--
Fax
--
Email
chemicals@usbio.net
Country
United States
ProdList
6214
Advantage
80
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
Matrix Scientific
Tel
--
Fax
--
Email
sales@matrixscientific.com
Country
United States
ProdList
6632
Advantage
80
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6962
Advantage
56
TOKU-E Company
Tel
--
Fax
--
Email
info@toku-e.com
Country
United States
ProdList
320
Advantage
50
W & J PharmaChem, Inc.
Tel
--
Fax
--
Email
info@wjpharmachem.com
Country
United States
ProdList
595
Advantage
50
AlliChem, LLC
Tel
--
Fax
--
Email
sales@allichemllc.com
Country
United States
ProdList
6516
Advantage
60
Oakwood Products, Inc.
Tel
--
Fax
--
Email
sales@oakwoodchemical.com
Country
United States
ProdList
6193
Advantage
74
AstaTech, Inc
Tel
--
Fax
--
Email
sales@astatechinc.com
Country
United States
ProdList
6371
Advantage
58
Spectrum Chemicals & Laboratory Products
Tel
--
Fax
--
Email
sales@spectrumchemical.com
Country
United States
ProdList
6699
Advantage
77
Advance Scientific & Chemical
Tel
--
Fax
--
Email
sales@advance-scientific.com
Country
United States
ProdList
6419
Advantage
71
Chem-Impex International, Inc.
Tel
--
Fax
--
Country
United States
ProdList
6730
Advantage
64
Waterstone Technology, LLC
Tel
--
Fax
--
Email
sales@waterstonetech.com
Country
United States
ProdList
6786
Advantage
30
HONEST JOY HOLDINGS LIMITED
Tel
--
Fax
--
Email
sales@honestjoy.cn
Country
United States
ProdList
6675
Advantage
54
2A PharmaChem USA
Tel
--
Fax
--
Email
sales@2apharmachem.com
Country
United States
ProdList
6137
Advantage
39
3B Scientific Corporation
Tel
--
Fax
--
Email
sales@3bsc.com
Country
United States
ProdList
6718
Advantage
47
AK Scientific, Inc.
Tel
--
Fax
--
Email
sales@aksci.com
Country
United States
ProdList
6347
Advantage
65
APAC Pharmaceutical, LLC
Tel
--
Fax
--
Email
sales@apacpharma.com
Country
United States
ProdList
6322
Advantage
38
CGeneTech, Inc.
Tel
--
Fax
--
Email
qyu@cgenetech.com
Country
United States
ProdList
959
Advantage
30
American Custom Chemicals Corporation
Tel
--
Fax
--
Email
sales@acccorporation.com
Country
United States
ProdList
6820
Advantage
51
BOSCHE SCIENTIFIC, LLC
Tel
--
Fax
--
Email
Sales@BoscheSci.com
Country
United States
ProdList
6477
Advantage
55
ChemPacific Corporation
Tel
--
Fax
--
Email
sales@chempacific.com
Country
United States
ProdList
6891
Advantage
51
More
Less

View Lastest Price from Cemandil sodium salt manufacturers

Hebei Ganmiao New material Technology Co., LTD
Product
Cemandil sodium salt 42540-40-9
Price
US $10.00-7.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
20ton
Release date
2024-06-07
Shaanxi TNJONE Pharmaceutical Co., Ltd
Product
Cefamandole Nafate 42540-40-9
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20tons
Release date
2024-04-29
Career Henan Chemical Co
Product
Cemandil sodium salt 42540-40-9
Price
US $3.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100kg
Release date
2019-08-07

42540-40-9, Cemandil sodium saltRelated Search:

5-Methyl-1H-benzotriazole Cefamandole Dimethyl sulfone Sodium chloride Sodium benzoate Sodium citrate 1-CHLOROMETHYL-1H-1,2,4-TRIAZOLE Sodium bicarbonate Sodium hydroxide N,N-Dimethylacetamide Trisodium phosphate Sodium acetate Hexamethylphosphoramide Diclofenac sodium 8-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT Cefamandole nafate impurity G Cefamandole nafate double bond displacement impurity Cefamandole nafate impurity H

  • ,(6r-(6-alpha,7-beta(r)))-
  • Cefamandole Nafate -Delta-3- Isomer
  • 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 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
  • 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)
  • 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)-
  • 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
  • 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 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 (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