(2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Mecillinam
CAS: 32887-01-7
Molecular Formula: C15H23N3O3S
(2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Names and Identifiers
(2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Physico-chemical Properties
| Molecular Formula | C15H23N3O3S |
| Molar Mass | 325.43 |
| Density | 1.44±0.1 g/cm3(Predicted) |
| Melting Point | 156°C |
| Boling Point | 551℃ |
| Specific Rotation(α) | D20 +285° (c = 1 in 0.1N HCl) |
| Flash Point | >110°(230°F) |
| Water Solubility | Soluble in water at approximately 1mg/ml |
| Solubility | Methanol (Slightly), Water (Slightly) |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | neat |
| Color | White to Off-White |
| pKa | pKa 3.40 (Uncertain) |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.686 |
| MDL | MFCD00056869 |
| Physical and Chemical Properties | Colorless crystal, odorless and tasteless. Soluble in water, slightly soluble in ethanol, acetone-soluble, insoluble in ether or isopropanol. Melting point 156 °c (decomposition). [a]D20 285 °(C = 1,0.1mol/L hydrochloric acid). |
| Use | Mainly used for the treatment of gram-negative bacteria caused by urinary tract infection and typhoid fever and other diseases |
(2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| RTECS | XI0185000 |
(2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Introduction
Dissolved in water, its hydrochloride dihydrate is a mixture of two epimers, colorless crystals. Easily soluble in water, methanol and ethanol, slightly soluble in ether and acetone.
Last Update：2022-10-16 17:24:38
(2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - Reference Information
| semi-synthetic penicillin | mexilin is an amphoteric compound with a molecular formula of C15H23N3O3S, white or white-like powder in appearance, easily soluble in water, clear aqueous solution, colorless to yellow. It was FrantzJLund by Danish Leo Pharmaceutical Factory and J.Tybring synthesized in the early 1970s. This product is the third generation of broad-spectrum semi-synthetic penicillin. It is a new compound found from semi-synthetic amidino semi-synthetic penicillins. This product is different from other penicillic acid in the C6 position of the parent nucleus of penicillic acid. The group replaces the usual phthalamine bond, thus giving it a unique antibacterial activity. It plays an antibacterial role by interfering with the biosynthesis of the bacterial cell wall. It mainly acts on the transpeptidase of bacteria. It has a particularly strong antibacterial effect on gram-blue-negative bacteria, especially Escherichia coli, Pneumobacteria, Enterobacter, Oak, Shigella and Salmonella. Melicillin has the strongest effect. The oral absorption of this product is poor, but it can be injected intramuscularly or intravenically. Fig. 1 is the structural formula |
| characteristics of mexilin | 1. it has strong effect on gram-blue negative bacteria, especially intestinal bacilli such as e. coli and salmonella are especially sensitive to this product. 2. The antibacterial mechanism is special, which mainly affects the penicillin binding protein 2 of bacteria, making bacteria become spheres. 3. Weak effect on Gram-positive bacteria. 4. It has synergistic antibacterial effect with penicillin, cephalosporins and aminoglycosides. 5. Intramuscular injection has fast absorption, high blood concentration, AUC is similar to that of intravenous injection, and bioavailability is 93.6%. 6. The protein binding rate is low, about 5-10%. 7. Strong stability to β-lactamase. 8. Less toxicity, less adverse reactions to liver and kidney. 9. High clinical efficacy, used for the treatment of urinary tract infection, typhoid fever, respiratory tract infection and sepsis. 10. The clinical dose is small and the patient is easy to tolerate. |
| pharmacokinetics | this product has poor oral absorption effect or even no absorption. After intravenous administration of 10mg per kilogram of body weight for 15min at intervals of 4h, the average steady-state blood drug concentration was 47-55 μg/ml at the highest, the lowest was 1.2-2.0 μg/ml, and the half-life was 51-55 min. 70% drugs are excreted in urine, and the concentration of active drugs in urine can reach 1 000 μg/ ml within 30min. Drugs are distributed in many organs and bile of body tissues, and rarely cross the blood-brain barrier. It can enter the amniotic fluid through the placenta. The binding rate of plasma protein is 15% ~ 25%, and the half-life of plasma is 1.2 hours. |
| medicinal properties and applications | this product is a new type of semi-synthetic penicillin, which has weak effect on g bacteria and strong effect on g-bacteria, such as Escherichia coli, Klebsiella, Enterobacter, Citrobacter, Shigella, Salmonella and some Serratia have good antibacterial activity. But for Pseudomonas, indole positive Proteus, Neisseria, anaerobic bacilli, Enterococcus and so on. The tolerance to β-lactamase is stronger than ampicillin. Combined application with other penicillins or cephalosporins has a synergistic effect. It can often become sensitive to the combined application of drug-resistant enterobacteria. It is also effective against some indole-positive Proteus and some Proweiten bacteria. This product mainly acts on PBP2 receptor on E. coli cell membrane. Oral absorption is not good, but its diester compound absorption is better. Intravenous administration has a high blood concentration and intramuscular injection is lower, but the bioavailability of the two is the same. The indications are similar to ampicillin and are mainly used for infections caused by sensitive bacteria such as Escherichia coli, Klebsiella, and Enterobacter, such as urinary tract infections and sepsis. In severe cases, other β-lactam antibiotics can be combined. (2016-01-22) |
| precautions | 1. penicillin skin test must be done before use, and those with positive reactions should not be used. 2. Pregnant women (within 3 months of pregnancy) should not be used, and those with renal insufficiency should be used with caution. 3. This product is injected immediately after dissolution, not for a long time. |
| dosage and usage | adults 4 times a day, 400~800 mg each time, dissolved with 2 mL of water for injection and intramuscular injection; It can also be slowly injected intravenously for 5~10 min after dissolution of 5% ~ 10% glucose injection 20 mL. Mild symptoms can also be taken 4 times a day, 200~400 mg each time. Children 30~60mg/kg daily, divided into 4 times of administration. |
| adverse reactions | occasionally can cause anaphylactic shock and other allergic reactions. There are eosinophils and thrombocytosis, elevated transaminases and alkaline phosphatase, neutrophils, leukopenia, dizziness, anemia, diarrhea, nausea, etc. There may be injection of local pain. A few patients developed rash and double infection. |
| use | semi-synthetic penicillin has little activity against gram-positive bacteria, but it has a strong bactericidal effect on gram-negative bacteria such as Escherichia coli, Pneumonia, Salmonella, Proteus, etc. It has a synergistic effect with other β-lactam antibiotics. It is clinically used for urinary system infection caused by sensitive bacteria, septicemia, typhoid fever, bacillary dysentery, etc. It is mainly used for the treatment of urinary tract infections and typhoid diseases caused by gram-negative bacteria The product is semi-synthetic penicillin. Mainly used for urinary tract infections and typhoid diseases caused by gram-negative bacteria. |
| Production method | Method 1: The action of azapanide and trichloroacetaldehyde, the formyl group is introduced on the nitrogen, and the acetal is formed under the action of dimethyl sulfate, and 6-APA The amino group at the 6 position on 6-APA forms Schiff'S base, which is mexicillin. Method 2:6-APA reacted with hexamethylsilane to form trimethylsilyl group on the amino group at the 6-APA6 position, and then reacted with N-formyl azapead in the presence of triethylamine to obtain mecillin. |
Last Update：2024-04-09 15:16:49
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(2S,5R,6R)-6-{[(E)-azepan-1-ylmethylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6-O-ALPHA-D-GALACTOPYRANOSYL-D-GLUCOPYRANOSYL-BETA-D-FRUCTOFURANOSIDE PENTAHYDRATE
TERT-BUTYL N-(2-AMINOETHYL)CARBAMATE HCL
4-PyriMidinecarboxylic acid, 6-aMino-5-chloro-, ethyl ester
ETHYL 4-[(3-CHLORO-2,2-DIMETHYLPROPANOYL)AMINO]BENZENECARBOXYLATE
1H-PYRROLO[2,3-B]PYRIDINE, 3-CHLORO-6-FLUORO-
2H-Indol-2-one, 1,3-dihydro-7-hydroxy-4-(3-piperidinyl)-, hydrobromide (1:1)
2-Propenoic acid, methyl ester, polymer with 1,1-dichloroethene and 2-propenenitrile
CBZ-D-ASP天冬
DOYLE DIRHODIUM CATALYST - RH2(5S-MEPY)4
6-O-ALPHA-D-GALACTOPYRANOSYL-D-GLUCOPYRANOSYL-BETA-D-FRUCTOFURANOSIDE PENTAHYDRATE
TERT-BUTYL N-(2-AMINOETHYL)CARBAMATE HCL
4-PyriMidinecarboxylic acid, 6-aMino-5-chloro-, ethyl ester
ETHYL 4-[(3-CHLORO-2,2-DIMETHYLPROPANOYL)AMINO]BENZENECARBOXYLATE
1H-PYRROLO[2,3-B]PYRIDINE, 3-CHLORO-6-FLUORO-
2H-Indol-2-one, 1,3-dihydro-7-hydroxy-4-(3-piperidinyl)-, hydrobromide (1:1)
2-Propenoic acid, methyl ester, polymer with 1,1-dichloroethene and 2-propenenitrile
CBZ-D-ASP天冬
DOYLE DIRHODIUM CATALYST - RH2(5S-MEPY)4