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Cemandil sodium salt

Product Name
Cemandil sodium salt
CAS No.
42540-40-9
Chemical Name
Cemandil sodium salt
Synonyms
Fado;Cedol;CefaM;CeMado;Nafate;mandol;Cefiran;Kefadol;Pavecef;Bergacef
CBNumber
CB5430833
Molecular Formula
C19H17N6NaO6S2
Formula Weight
512.49
MOL File
42540-40-9.mol
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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.
pka
2.6-3.0(at 25℃)
form 
neat
Water Solubility 
Freely soluble in water. Sparingly soluble in methanol
CAS DataBase Reference
42540-40-9(CAS DataBase Reference)
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Safety

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

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C0682300
Product name
Cefamandole nafate
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
c0682300
Price
$190
Updated
2020/08/18
Sigma-Aldrich
Product number
C0682300
Product name
Cefamandole nafate
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/03/22
Sigma-Aldrich
Product number
1097400
Product name
Cefamandole nafate
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
250mg
Price
$350
Updated
2021/03/22
Alfa Aesar
Product number
J66735
Product name
Cefamandole nafate
Packaging
5g
Price
$164
Updated
2020/06/24
Alfa Aesar
Product number
J66735
Product name
Cefamandole nafate
Packaging
10g
Price
$288
Updated
2020/06/24
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Cemandil sodium salt Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Mandokef,Lilly,W. Germany,1977

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

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Cemandil sodium salt Suppliers

Hubei widely chemical technology Co., Ltd.
Tel
027-59402396-
Fax
027-83989310
Email
13419635609@163.com
Country
China
ProdList
4441
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Wuhan Chemwish Technology Co., Ltd
Tel
86-027-67849912
Fax
86-027-87531808
Email
sales@chemwish.com
Country
China
ProdList
35909
Advantage
56
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32358
Advantage
50
XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-2580635- ;0712-2580635
Email
1791901229@qq.com;1791901229@qq.com;
Country
China
ProdList
8941
Advantage
52
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9844
Advantage
79
Wuhan Fortuna Chemical Co., Ltd
Tel
027-59207852-
Fax
QQ3130921841
Email
buy@fortunachem.com
Country
China
ProdList
2959
Advantage
58
Dalian Meilun Biotech Co., Ltd.
Tel
0411-66864596- ;0411-66864952-
Email
sales@meilune.com;sales@meilune.com
Country
China
ProdList
3572
Advantage
58
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725;010-86181995
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12341
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
86-21-58998985
Fax
(86) 21-58955996
Email
apisales@chemexpress.com.cn
Country
China
ProdList
7557
Advantage
61
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View Lastest Price from Cemandil sodium salt manufacturers

Dideu Industries Group Limited
Product
Cemandil sodium salt USP/EP/BP 42540-40-9
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-06-28
Shaanxi Dideu Medichem Co. Ltd
Product
Cemandil sodium salt 42540-40-9
Price
US $0.00-0.00/Kg
Min. Order
1KG
Purity
99.0%+
Supply Ability
300 MT
Release date
2020-05-23
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

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