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Mecillinam

Product Name
Mecillinam
CAS No.
32887-01-7
Chemical Name
Mecillinam
Synonyms
AMDINOCILLIN;Coactin;Selexidin;Mecillinam (technical product);fl1060;Hexapen;FL10606;ro10-9070;Mecill·Nam;MECILLINAM
CBNumber
CB7203891
Molecular Formula
C15H23N3O3S
Formula Weight
325.43
MOL File
32887-01-7.mol
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Mecillinam Property

Melting point:
156°C
Boiling point:
551℃
alpha 
D20 +285° (c = 1 in 0.1N HCl)
Density 
1.44±0.1 g/cm3(Predicted)
Flash point:
>110°(230°F)
storage temp. 
Sealed in dry,2-8°C
solubility 
Methanol (Slightly), Water (Slightly)
pka
pKa 3.40 (Uncertain)
form 
Solid
color 
White to Off-White
Water Solubility 
Soluble in water at approximately 1mg/ml
CAS DataBase Reference
32887-01-7(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
2
RTECS 
XI0185000
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
33447
Product name
Mecillinam
Purity
VETRANAL
Packaging
100mg
Price
$201
Updated
2024/03/01
Alfa Aesar
Product number
J66774
Product name
Mecillinam, 95%
Packaging
100mg
Price
$158
Updated
2023/06/20
Cayman Chemical
Product number
9002008
Product name
Mecillinam
Purity
≥95%
Packaging
100 mg
Price
$79
Updated
2024/03/01
Cayman Chemical
Product number
9002008
Product name
Mecillinam
Packaging
1g
Price
$315
Updated
2024/03/01
Cayman Chemical
Product number
9002008
Product name
Mecillinam
Packaging
10g
Price
$1351
Updated
2023/01/06
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Mecillinam Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Selexidin,Leo,UK,1979

Uses

Effective against Gram-negative bacteria

Uses

Active antibacterial against gram-negative bacteria

Uses

Mecillinam (amidinocillin) is a penicillin nucleus (6 APA) derivative, active in vitro against most aerobic and anaerobic Gram-negative bacilli, including E. coli and B. fraglis, but not active against Staphylococcus aureus, Enterococcus, or Pseudomonas. Mecillinam is synergistic with other beta-lactam drugs and therefore can be used in combination to treat severe Gram-negative infections. Although its in vitro efficacy is convincing, there are not enough clinical trials to support its use for intra-abdominal infections.

Definition

ChEBI: Mecillinam is a penicillin in which the 6beta substituent is [(azepan-1-yl)methylidene]amino; an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria. It has a role as an antibacterial drug and an antiinfective agent.

Manufacturing Process

The starting material N-formylhexamethyleneimine was prepared from hexamethyleneimine and chloral.
12.7 g of N-formylhexamethyleneimine were dissolved in 250 ml of dry ether. While stirring and cooling, 8.5 ml of oxalyl chloride in 50 ml of dry ether were added dropwise, whereafter the mixture was stirred overnight at room temperature. The precipitated amide chloride was filtered off and washed with dry ether, and was placed in an exsiccator.
A solution of the amide chloride (4.6 g) in dry, alcohol-free chloroform (20 ml) was added slowly to a solution of trimethylsilyl 6-amino-penicillanate (7.2 g) and triethylamine (3.5 ml) in dry, alcohol-free chloroform (50 ml) with stirring and cooling to -70°C. The temperature was raised to 0°C during 1.5 hours. The solution was evaporated to dryness in vacuo and the residue was triturated with dry ether (200 ml). The precipitate was filtered off and washed with dry ether. The filtrate was diluted with ether (200 ml). 2-Butanol (2.8 ml) was added dropwise with stirring and cooling to 0°C. The stirring was continued for 1/4 hour at 0°C, whereupon the precipitate was filtered off, washed with ether and dried. It was a white, amorphous powder, soluble in water.

brand name

Coactin (Roche).

Therapeutic Function

Antibacterial

Antimicrobial activity

The antibacterial spectrum differs greatly from that of the aminopenicillins in that the compound displays high activity against many Gram-negative bacteria but limited activity against Gram-positive organisms. Mecillinam is active against many Enterobacteriaceae due to its selective binding to PBP 2, although the susceptibility of Proteus and Providencia spp. is variable. H. influenzae is less susceptible than enteric bacilli, and Acinetobacter spp., B. fragilis and Ps. aeruginosa are resistant.
It is readily inactivated by many β-lactamases, although it is more stable than ampicillin.

Acquired resistance

Intrinsic resistance in susceptible species of enterobacteria is uncommon and many ampicillin-resistant strains are susceptible. Bacteria that are resistant to both ampicillin and mecillinam are usually those producing large amounts of β-lactamase, most commonly plasmid-mediated enzymes.

Pharmacokinetics

Oral absorption (pivmecillinam): c. 75%
Cmax 200 mg intravenous infusion: 12 mg/L end infusion
200 mg intramuscular: c. 6 mg/L after 45 min
400 mg oral (pivmecillinam): 2–5 mg/L after c. 1 h
Plasma half-life: 50 min
Volume of distribution: 0.2–0.4 L/kg
Plasma protein binding: 5–10%
Absorption
Oral absorption is very poor, with conventional doses producing plasma levels of <1 mg/L and recovery of only about 5% in the urine. A 400 mg dose of the pivaloyl ester is equivalent to 273 mg mecillinam. It is relatively well absorbed and rapidly liberates the parent compound. Metabolism and excretion
The amidino side chain undergoes spontaneous aqueous hydrolysis to the N-formyl derivative, which retains some antibacterial activity. Hydrolysis of the β-lactam ring also occurs.
Approximately 60% is excreted unchanged in the urine in the first 6 h, achieving concentrations exceeding 1 g/L. The concentration in bile can reach 40 or 50 mg/L in patients with normally functioning gallbladders treated with 800 mg intramuscularly.

Clinical Use

Urinary tract infection (pivmecillinam)
Other infections with susceptible Gram-negative bacilli (usually in combination with other agents)

Side effects

It is generally well tolerated, and serious anaphylactic responses are said to be rare. Nausea and vomiting, which may be persistent, occur with diarrhea in some patients treated with pivmecillinam.

Mecillinam Preparation Products And Raw materials

Raw materials

Preparation Products

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Mecillinam Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Sichuan Kulinan Technology Co., Ltd
Tel
400-1166-196 18981987031
Fax
028-84555506 800101999
Email
cdhxsj@163.com
Country
China
ProdList
11707
Advantage
57
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
14055
Advantage
65
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
Advantage
58
UHN Shanghai Research & Development Co., Ltd.
Tel
021-58958002 18930822973
Fax
+86 (21) 5895-8628
Email
SALES@UHNSHANGHAI.COM
Country
China
ProdList
977
Advantage
58
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-400-6206333 18521732826
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
Advantage
55
Shanghai JONLN Reagent Co., Ltd.
Tel
400-0066400 13621662912
Fax
021-55660885
Email
422131432@qq.com
Country
China
ProdList
9978
Advantage
55
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View Lastest Price from Mecillinam manufacturers

Career Henan Chemical Co
Product
mecillinam 32887-01-7
Price
US $1.00/KG
Min. Order
1KG
Purity
98% HPLC
Supply Ability
10 tons/month
Release date
2020-01-09

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