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HCID 441130Erstellt: 27. Oktober 2026

Meropenem

Meropenem · MEROPENEM WITH SODIUM CARBONATE · Meropenem (300 mg) · MEROPENEMTRIHYDRATE(3-[[5-[(DIMETHYLAMINO)CARBONYL]-3-PYRROLIDINYL]THIO]-6-(1-HYDROXYETHYL)-4-METHYL-7-OXO-1-AZABICYCLO[3,2,0]HEPT-2-ENE-2-CARBOXYLICACIDTRIHYDRATE) · Meropenem Sanshui · SM 7338 trihydrate · Meropenem 3-hydrate · Meropenem Trihydrat

https://huagongshe.com/de/chemical/441130

Molekülstruktur von Meropenem

Identifikatoren & physikalische Daten

CAS No.119478-56-7
SummenformelC17H25N3O5S
Durchschnittliche Molmasse383,5 g/mol
Monoisotopische Masse383,1514919 g/mol
SMILESC[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C(S[C@@H]3CN[C@H](C(=O)N(C)C)C3)[C@H](C)[C@H]12
InChIKeyDMJNNHOOLUXYBV-PQTSNVLCSA-N
PubChem CID441130
ChEMBLCHEMBL127
ChEBICHEBI:43968
EC No.641-424-1
DTXSIDDTXSID7045526

Chemische & physikalische Eigenschaften

XLogP-2,4
Polarare Oberfläche (TPSA)135
H-Brücken-Donoren3
H-Brücken-Akzeptoren7
Frei drehbare Bindungen5
Schwere Atome26
Formalladung0
Komplexität679
ArzneimittelPharmaceuticals -> Used in SwitzerlandPharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15
LogP (Verteilungskoeffizient)-0.6
LöslichkeitSparingly5.63e+00 g/LSoluble in aqueous solution at approximately 5mg/ml
Human DrugsBreast FeedingLactationAnti-Infective AgentsCarbapenemsFDA approved drugs -> Active ingredientAntituberculosis medicines
Physical DescriptionSolid
Stability/Shelf LifeSolutions of Meropenem (Meropenem concentrations ranging from 1 to 20 mg/mL) in Water for Injection or Sodium Chloride Injection 0.9% (for up to 4 hours) or in Dextrose Injection 5% (for up to 2 hours) at controlled room temperatures 15-25 °C (59-77 °F) are stable in plastic tubing and volume control devices of common intravenous infusion sets. Solutions of Meropenem (Meropenem concentrations ranging from 1 to 20 mg/mL) in Water for Injection or Sodium Chloride Injection 0.9% (for up to 48 hours) or in Dextrose Injection 5% (for up to 6 hours) are stable at 4 °C (39 °F) in plastic syringes.Freshly prepared solutions of Meropenem should be used whenever possible. However, constituted solutions of Meropenem maintain satisfactory potency at controlled room temperature 15-25 °C (59-77 °F) or under refrigeration at 4 °C (39 °F) ... . Solutions of intravenous Meropenem should not be frozen.Meropenem injection vials constituted with sterile Water for Injection for bolus administration (up to 50 mg/mL of Meropenem) may be stored for up to 2 hours at controlled room temperature 15-25 °C (59-77 °F) or for up to 12 hours at 4 °C (39 °F).Solutions of Meropenem (Meropenem concentrations ranging from 2.5 to 20 mg/mL) in Baxter Minibag Plus bags with Sodium Chloride Injection 0.9% may be stored for up to 4 hours at controlled room temperatures 15-25 °C (59-77 °F) or for up to 24 hours at 4 °C (39 °F). Solutions of Meropenem (Meropenem concentrations ranging from 2.5 to 20 mg/mL) in Baxter Minibag Plus bags with Dextrose Injection 5% may be stored up to 1 hour at controlled room temperatures 15-25 °C (59-77 °F) or for up to 6 hours at 4 °C (39 °F).Meropenem infusion vials constituted with Sodium Chloride Injection 0.9% (Meropenem concentrations ranging from 2.5 to 50 mg/mL) are stable for up to 2 hours at controlled room temperature 15-25 °C (59-77 °F) or for up to 18 hours at 4 °C (39 °F). Infusion vials of Meropenem constituted with Dextrose Injection 5% (Meropenem concentrations ranging from 2.5 to 50 mg/mL) are stable for up to 1 hour at controlled room temperature 15-25 °C (59-77 °F) or for up to 8 hours at 4 °C (39 °F).
Collision Cross Section192.42 Ų [M-H]-
Other Experimental PropertiesWhite to pale yellow crystalline powder. Sparingly soluble in watervery slightly soluble in hydrated ethanol /Meropenem trihydrate/The solution varies from colorless to yellow depending on the concentration. The pH of freshly constituted solutions is between 7.3 and 8.3. Meropenem is soluble in 5% monobasic potassium phosphate solution ... and practically insoluble in acetone or ether. /Meropenem trihydrate/
Schmelzpunkt>192°C (dec.)
Siedepunkt627℃
Flammpunkt>110°(230°F)
Lagerbedingungen-20°C
Aggregatzustandpowder
Farbewhite to off-white
Merck14,5900
Hauptanwendungenforensics and toxicologypharmaceutical (small molecule)
InChIKeyDMJNNHOOLUXYBV-PQTSNVLCSA-N
SMILESC(C1=C([C@H](C)[C@]2([H])[C@@]([H])([C@H](O)C)C(=O)N12)S[C@@H]1CN[C@H](C(=O)N(C)C)C1)(=O)O.O |&1:3,5,7,9,16,19,r|
CAS Datenbank119478-56-7(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-EinstufungDangerH315 (76.9%): Causes skin irritation [Warning Skin corrosion/irritation]P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 13 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
BrandpotenzialThis material is assumed to be combustible.
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including meropenem, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Hazard Classes and CategoriesSkin Irrit. 2 (76.9%)
BrandbekämpfungsverfahrenAs with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.Water spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials.
ReinigungsverfahrenSpill Response: Wear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labelled container for disposal. Wash spill site.
EntsorgungsverfahrenSRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

Anwendungen & Verwendung

Verwenden

Meropenem trihydrate is a carbapenem antibiotic with wide spectrum of antibacterial. It is an ultra-broad spectrum beta-lactam antibiotic and has antibacterial activity against Gram-negative and Gram-positive bacteria as well as anaerobic microorganisms such as Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, Enterobacter species, Serratia marcescens, Streptococcus pyogenes, Streptococcus agalactiae and Citrobacter sp. Meropenem trihydrate is indicated for the treatment of serious bacterial infection including complicated skin infections, complicated intra-abdominal infections, urinary tract infections, severe pneumonia, broncho-pulmonary infections and bacterial meningitis.

Preventive MeasuresSRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.Engineering controls such as exhaust ventilation are recommended.As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.
Personal Protective Equipment (PPE)Respiratory Protection: Use a NIOSH approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used. Gloves: Chemically compatible. Eye Protection: Safety Glasses. Protective Clothing: Protect exposed skin.
WechselwirkungenCase reports in the literature have shown that co-administration of carbapenems, including meropenem, to patients receiving valproic acid or divalproex sodium results in a reduction in valproic acid concentrations. The valproic acid concentrations may drop below the therapeutic range as a result of this interaction, therefore increasing the risk of breakthrough seizures. Although the mechanism of this interaction is unknown, data from in vitro and animal studies suggest that carbapenems may inhibit the hydrolysis of valproic acid's glucuronide metabolite (VPA-g) back to valproic acid, thus decreasing the serum concentrations of valproic acid. If administration of Meropenem for injection is necessary, then supplemental anti-convulsant therapy should be consideredProbenecid competes with meropenem for active tubular secretion, resulting in increased plasma concentrations of meropenem. Co-administration of probenecid with meropenem is not recommended.
HepatotoxicitySerum aminotransferase elevations have been reported in 1% to 6% of recipients of intravenous meropenem when given for up to 14 days. These elevations are usually transient, mild and asymptomaticand rarely require dose adjustment. Meropenem has also been linked to rare cases of cholestatic jaundice that usually arises after 1 to 3 weeks of therapy. Immunoallergic features may be present, but are rarely prominent. Autoantibodies are rare. Most cases are mild and self-limited, but at least one instance of vanishing bile duct syndrome related to meropenem therapy has been published (Case 1). Meropenem has not been reported to cause acute liver failure.
Human Toxicity Excerpts/CASE REPORTS/ A male patient was hospitalized as a case of pneumonia. He was diabetic, hypertensive and post Hepatitis "C". He reported skin eruption following administration of meropenem. Skin biopsy revealed acute generalized exanthematous pustulosis. ... The diagnosis was made after excluding all other possible causes. Dermatologists and clinicians must be aware of this .. unusual side effect./CASE REPORTS/ Vanishing bile duct syndrome is a rare and potentially life-threatening disorder in which progressive destruction and disappearance of small intrahepatic bile ducts occur, with resultant cholestasis. The mechanism by which biliary epithelial cells are damaged and intrahepatic bile ducts are lost has not been fully elucidated. However, many etiologies have been reported,and several drugs have been implicated. Meropenem is a widely used, well tolerated broad-spectrum carbapenem antibiotic indicated for the treatment of intraabdominal infections, complicated skin and skin structure infections, and pediatric bacterial meningitis. We describe what we believe is the first reported case of meropenem-induced vanishing bile duct syndrome. A 60-year-old woman was diagnosed with vanishing bile duct syndrome after being treated with meropenem for a left temporal lobe brain abscess. Three weeks after starting the drug, the patient developed mixed hepatocellular and cholestatic liver injury with jaundice and pruritus.Meropenem-induced liver injury was suspected, and the drug was discontinued. Diagnostic tests ruled out other causes of cholestasis, including infectious and immunologic conditions. A liver biopsy, performed due to persistent liver injury, demonstrated an absence of bile ducts, which, in conjunction with the patient's clinical course, was consistent with the diagnosis of vanishing bile duct syndrome. Several months after the cessation of meropenem, the patient's liver function test results improved. Use of the Naranjo adverse drug reaction probability scale indicated a probable relationship (score of 6) between the patient's development of vanishing bile duct syndrome and meropenem therapy. A high index of suspicion is necessary to diagnose vanishing bile duct syndrome and other types of drug induced liver injury. Clinicians should consider vanishing bile duct syndrome as a potential diagnosis in patients receiving meropenem who have prolonged cholestasis, especially after other more probable causes have been excluded./GENOTOXICITY/ Genetic toxicity studies were performed with meropenem using the ... cultured human lymphocytes cytogenic assay ... . There was no evidence of mutagenic potential found in /this test/.
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)MeropenemvLess-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ In mice and rats, large intravenous doses of meropenem (2200-4000 mg/kg) have been associated with ataxia, dyspnea, convulsions, and mortalities./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproductive studies were performed with meropenem in rats at doses up to 1000 mg/kg/day, and cynomolgus monkeys at doses up to 360 mg/kg/day (on the basis of AUC comparisons, approximately 1.8 times and 3.7 times, respectively, to the human exposure at the usual dose of 1 g every 8 hours). There was no reproductive toxicity seen/GENOTOXICITY/ Genetic toxicity studies were performed with meropenem using the bacterial reverse mutation test, the Chinese hamster ovary HGPRT assay, ... and the mouse micronucleus test. There was no evidence of mutagenic potential found in any of these tests.
Populations at Special RiskMeropenem for injection (IV) is contraindicated in patients with known hypersensitivity to any component of this product or to other drugs in the same class or in patients who have demonstrated anaphylactic reactions to beta-lactams.
Antidote and Emergency Treatment/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B//SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Wassergefährdungsklasse (WGK)3
Zollcode2941906000
R-Sätze (R)36/37/38
GefahrensymboleXi
Sicherheitshinweise (S)26
Lagerklasse11 - Combustible Solids
GefahrenklasseResp. Sens. 1Skin Sens. 1