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Cefamandole

Product Name
Cefamandole
CAS No.
34444-01-4
Chemical Name
Cefamandole
Synonyms
Florfenicol-d3 AMine;(r*)))-;cefadole;cephadole;cefamandol;CEFAMANDOLE;cephamandole;l-cefamandole;R hidalgoense;Compound-83405
CBNumber
CB2398185
Molecular Formula
C18H18N6O5S2
Formula Weight
462.5
MOL File
34444-01-4.mol
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Cefamandole Property

Melting point:
107-109oC
Density 
1.3806 (rough estimate)
refractive index 
1.7000 (estimate)
storage temp. 
Refrigerator
solubility 
Chloroform (Sparingly), Methanol (Slightly)
pka
pKa 2.6–2.9 (Uncertain)
form 
Oil
color 
Off-White
CAS DataBase Reference
34444-01-4(CAS DataBase Reference)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC
Product number
F405774
Product name
Florfenicol-d3Amine
Packaging
1mg
Price
$175
Updated
2021/12/16
Usbiological
Product number
241501
Product name
R
Packaging
1g
Price
$184
Updated
2021/12/16
Usbiological
Product number
B1078-04
Product name
R-
Packaging
25mg
Price
$389
Updated
2021/12/16
Usbiological
Product number
008235
Product name
R-
Packaging
100mg
Price
$403
Updated
2021/12/16
Usbiological
Product number
A1377-91
Product name
R-
Packaging
100mg
Price
$418
Updated
2021/12/16
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Cefamandole Chemical Properties,Usage,Production

Description

Cefamandole is also known as cephamandole. It is a parenterally administered broad-spectrum cephalosporin antibiotic. The pharmacological action and indications for use of cefamandole is analogous to that of cefuroxime and cefamandole. Synonyms of this drug are mandoxef, kefandol, kefadol, and many others.

Chemical Properties

Off-White Foam

Originator

Mandokef,Lilly,W. Germany,1977

Uses

Intermediate for the oreparation of Phenylephrine Glucuronide.

Uses

Cefamandole is a second-generation cephalosporin antibiotic with antibacterial activity. It is a labelled metabolite of Deprenyl (D288641) (Selegiline).

Application

Cefamandole was synthesized by Eli Lilly & Co. in 1972. It shows strong activity against Proteus (indole-positive) species, Enterobacter, and Citrobacter, against which the earlier cephalosporins, such as cephalothin and cefazolin, are inactive. The nafate (sodium salt of the O-formyl ester) has been used in the United States and Europe, and the sodium salt of cefamandole has been used in Japan by injection.

Definition

ChEBI: Cefamandole is a cephalosporin compound having (R)-mandelamido and N-methylthiotetrazole side-groups. It has a role as an antibacterial drug. It is a cephalosporin and a semisynthetic derivative. It is a conjugate acid of a cefamandole(1-).

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

Antimicrobial activity

A semisynthetic cephalosporin supplied as the nafate, an antibacterially inactive ester hydrolyzed in the body to cefamandole. It is active against common pathogenic bacteria , but there is considerable strain variation in susceptibility. It is somewhat more stable than other group 1 agents to enterobacterial β-lactamases. Acinetobacter, Serratia and Pseudomonas spp. are often resistant. Some anaerobic Gram-negative rods are susceptible but B. fragilis is resistant.
A 1 g intramuscular dose achieves a plasma concentration of 20–35 mg/L after 1 h. It is widely distributed in body tissues. CSF levels are poor in the absence of meningeal inflammation. Therapeutically effective concentrations (c. 9 mg/kg) are found in bone after an intravenous dose of 2 g. Protein binding is 65–80%.
Renal excretion with a plasma half-life of around 50 min is mainly by both glomerular and tubular routes. A small amount is excreted in the bile and concentrations around 150–250 mg/L are found in T-tube bile following a 1 g intravenous dose. Only about 5% is removed by hemodialysis.
Cefamandole is one of the analogs containing the methylthiotetrazole side chain associated with bleeding . Rare renal damage or enhancement of existing renal damage has been described. Thrombophlebitis on intravenous administration is relatively common.
Experience in the treatment of a variety of infections and for surgical prophylaxis has been mixed and it is no longer recommended.

General Description

Cefamandole is a semisynthetic second-generation, β-lactam, wide-spectrum cephalosporin antibiotic with bactericidal activity. It is active against many strains resistant to other cephalosporins, such as Enterobacter species and indole-positive Proteus species. It is used for the treatment of serious infections caused by susceptible strains of microorganisms. In pharmaceutical products, cefamandole may be employed as cefamandole sodium (CAS number 30034-03-8, EC number 250-009-0, molecular formula C18H 17N6NaO5S2) or (when used parenterally) the formate ester prodrug cefamandole nafate (CAS number 42540-40-9, EC number 255-877-4, molecular formula C19H17N6NaO6S2).

Synthesis

Cefamandole, 7-D-mandelamido-3-[[(1-methyl-1H-tetrazol-5-yl)thio] methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.25), is synthesized from 7-aminocephalosporanic acid.
Protecting free amino group in 7-aminocephalosporanic acid by formylation with formic acid in the presence of acetic anhydride produces 7-formamidocephalosporanic acid (32.1.2.23). The acetoxy group of this compound is replaced by a reaction with 1-methyl- 1,2,3,4-tetrazol-5-thiol, after which the N-formyl protection is removed by hydrochloric acid, giving 7-amino-3-(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl-3-cefem-4-carboxylic acid (32.1.2.24). Reacting this with a mixed anhydride synthesized from mandelic acid and phosgene gives the desired cefamandole (32.1.2.25).

Cefamandole Preparation Products And Raw materials

Raw materials

Preparation Products

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Cefamandole Suppliers

Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
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58
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
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58
Nanjing Sunlida Biological Technology Co., Ltd.
Tel
025-57798810
Fax
025-57019371
Email
sales@sunlidabio.com
Country
China
ProdList
3239
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55
Alta Scientific Co., Ltd.
Tel
022-6537-8550 15522853686
Fax
022-2532-9655
Email
sales@altasci.com.cn
Country
China
ProdList
4511
Advantage
55
Zhengzhou Acme Chemical Co., Ltd.
Tel
0371-0371-55629727 13323845623
Fax
037155629727
Email
2885676761@qq.com
Country
China
ProdList
9996
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58
Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
Country
United States
ProdList
4660
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60
PI & PI BIOTECH INC.
Tel
020-81716320 17788709170
Fax
020-81716319
Email
Sales@pipitech.com
Country
China
ProdList
2649
Advantage
58
Nanjing Haolv Biotechnology Co.,Ltd
Tel
025-84622273 17361806303
Email
3004208264@qq.com
Country
China
ProdList
3021
Advantage
58
Hubei Dibai Chemical Co., Ltd.
Tel
027-87058617 15872383390
Fax
027-87058617
Email
hbdibo@163.com
Country
China
ProdList
885
Advantage
58
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View Lastest Price from Cefamandole manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
cefamandole 34444-01-4
Price
US $1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10mt
Release date
2024-11-11
Hebei Henghe Import and Export Trading Co. LTD
Product
cefamandole 34444-01-4
Price
US $280.00/KG
Min. Order
10KG
Purity
99%
Supply Ability
10
Release date
2020-12-09
Hebei Henghe Import and Export Trading Co. LTD
Product
cefamandole 34444-01-4
Price
US $260.00/KG
Min. Order
100KG
Purity
99%
Supply Ability
50
Release date
2020-11-24

34444-01-4, CefamandoleRelated Search:


  • Florfenicol AMine-d3 Discontinued See F405774
  • Florfenicol-d3 AMine
  • R-(-)-N-DeMethyl Deprenyl-d5
  • N-[(8-Hydroxy-3-Methyl-1-oxo-7-isochroManyl)carbonyl]-3- (phenyl-d5)-L-alanine
  • N-[[(3R)-3,4-Dihydro-8-hydroxy-3-Methyl-1-oxo-1H-2-benzopyran-7-yl]carbonyl]-L-(phenyl-d5)alanine
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-hydroxyphenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7R)-
  • 7-[(2-Hydroxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-7-[(R)-Hydroxyphenylacetylamino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-7α-[(R)-Hydroxy(phenyl)acetylamino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Compound-83405
  • 3-(1-Methyltetrazol-5-ylthiomethyl)-7-D-mandelamido-3-cephem-4-carboxylic acid
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(hydroxyphenylacetyl)amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-[6α,7β(R*)]]-
  • cefadole
  • cefamandol
  • cephadole
  • cephamandole
  • l-cefamandole
  • CEFAMANDOLE
  • (r*)))-
  • 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylicacid,7-((hydroxyphenylacetyl)
  • amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-,(6r-(6-alpha,7-beta
  • Vortioxetine Hydrobromide impurity R
  • Mosapride R isomer
  • Lifitegrast impurity R
  • ApreMilast R isomers
  • R hidalgoense
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7R)-
  • Cefamandole USP/EP/BP
  • Cefamandole Nafate EP Impurity B
  • (6R,7R)-7-((R)-2-Hydroxy-2-phenylacetamido)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (Cefmandole Sodium Impurity)
  • 34444-01-4
  • 4444-01-4
  • C18H18N6O5S2
  • Chiral Reagents
  • Glucuronides
  • Heterocycles