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Mecillinam

Mecillinam structure

CAS No:
32887-01-7
Formula:
C15H23N3O3S
Chemical Name:
Mecillinam
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-,(2S,5R,6R)-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-,[2S-(2α,5α,6β)]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-,(+)-;(2S,5R,6R)-6-[[(Hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6β-[(Hexahydro-1H-azepin-1-yl)methyleneamino]penicillanic acid;FL 1060;6-[[(Hexahydro-1H-azepin-1-yl)methylene]amino]penicillanic acid;Mecillinam;Penicillin Hx;Hexacillin;Amdinocillin;Hexapen;Coactin;51556-89-9;70178-27-7;73937-07-2;79580-20-4
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

White Solid

Solid

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.|Amidinopenicillanic acid derivative with broad spectrum antibacterial action. It is poorly absorbed if given orally and is used in urinary infections and typhus. Amdinocillin is not available in the United States.|Amdinocillin is a semisynthetic, broad spectrum beta-lactam penicillin with antibacterial activity. Amdinocillin specifically binds to and inactivates penicillin-binding protein 2 (PBP 2) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall and causes cell lysis. Given the fact that most beta-lactam penicillins bind almost exclusively to PBPs 1 and 3, amdinocillin is able to synergize with other penicillins in the treatment against bacterial infections.|An amidinopenicillanic acid derivative with broad spectrum antibacterial action.

Mecillinam Basic Attributes

Molecular Weight：

325.43

Exact Mass：

325.43

EC Number：

251-277-1

UNII：

V10579P3QZ

DSSTox ID：

DTXSID3022584

NCI Thesaurus Code：

C65229

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

98.5

XLogP3：

1.3

Appearance：

White solid

Density：

1.3±0.1 g/cm3

Melting Point：

156 °C (decomp)

Boiling Point：

551℃

Flash Point：

>110°(230°F)

Refractive Index：

1.604

Water Solubility：

soluble in water at approximately 1mg/ml

Storage Conditions：

Store at 0-5°C

Specific rotation：

D20 +285° (c = 1 in 0.1N HCl)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

RTECS Number：

XI0185000

Marks：

Drug Information

Drug Indication：

Used in the treatment of urinary tract infections caused by some strains of E. coli and klebsiella and enterobacter species. Used mainly against Gram negative organisms.

Pharmacology：

Amdinocillin is a novel, semisynthetic penicillin effective against many gram-negative bacteria. The antibacterial activity of amdinocillin is derived from its ability to bind specifically and avidly to Penicillin Binding Protein-2 (PBP 2). Amdinocillin is active alone against many gram-negative organisms. Pseudomonas and non-fermenting gram-negative bacteria, however, are usually resistant. Amdinocillin, in combination with many beta-lactams, exhibits marked synergy against many enterobacteriaceae. No such synergy can be demonstrated for gram-positive organisms or pseudomonas species. Amdinocillin is not beta-lactamase stable. Organisms which produce high levels of plasma-mediated beta-lactamase are resistant to the drug. Co-administration of probenecid results in markedly elevated plasma levels of amdinocillin and delays its excretion.

MeSH：

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Absorption：

Poorly absorbed if given orally.

Biological Half-Life：

Approximately 1 hour in patients with normal renal function. Increases to 3 to 6 hours in anephric patients.

Mechanism of Action：

Amdinocillin is a stong and specific antagonist of Penicillin Binding Protein-2 (PBP 2). It is active against gram negative bacteria, preventing cell wall synthesis by inhibiting the activity of PBP2. PBP2 is a peptidoglycan elongation initiating enzyme. Peptidoglycan is a polymer of sugars and amino acids that is the main component of bacterial cell walls.

MeSH Entry Terms：

Amdinocillin

Mecillinam Use and Manufacturing

Methods of Manufacturing

Method 1: The action of aza leather and trichloroacetaldehyde introduces a formyl group on the nitrogen to form an acetal under the action of dimethyl sulfate, and reacts with 6-APA to form a Schiff'S base at the 6-amino group on 6-APA. That is mecillin. Method 2: 6-APA reacts with hexamethylsilane to form a trimethylsilyl group on the 6-APA 6-position amino group, and then reacts with N-formylaza leather in the presence of triethylamine to obtain mecillin.

Uses

Active antibacterial against gram-negative bacteria

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:325.4
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:325.14601278
Monoisotopic Mass:325.14601278
Topological Polar Surface Area:98.5
Heavy Atom Count:22
Complexity:500
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

6-Aminopenicillanic acid

Recommended Suppliers of Mecillinam

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Mecillinam

CAS No.: 32887-01-7

Content: 99.00%

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