Ertapenem

Brand names: Invanz®

Chemical formula:

Español:
• Ertapenem Sódico, Solución para inyección

Ertapenem Sodium Solution for injection

What is this medicine?

ERTAPENEM (er ta PEN em) is a carbapenem antibiotic. It is used to treat certain kinds of bacterial infections. It will not work for colds, flu, or other viral infections.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
•brain tumor, lesion
•kidney disease
•seizure disorder
•an unusual or allergic reaction to ertapenem, other antibiotics, amide local anesthetics like lidocaine, or other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

This medicine is infused into a vein or injected deep into a muscle. It is usually given by a health care professional in a hospital or clinic setting.

If you get this medicine at home, you will be taught how to prepare and give this medicine. Use exactly as directed. Take your medicine at regular intervals. Do not take your medicine more often than directed.

It is important that you put your used needles and syringes in a special sharps container. Do not put them in a trash can. If you do not have a sharps container, call your pharmacist or healthcare provider to get one.

Talk to your pediatrician regarding the use of this medicine in children. While this drug may be prescribed for children as young as 3 months old for selected conditions, precautions do apply.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

•probenecid

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Tell your doctor or health care professional if your symptoms do not improve or if you get new symptoms. Your doctor will monitor your condition and blood work as needed.

Do not treat diarrhea with over the counter products. Contact your doctor if you have diarrhea that lasts more than 2 days or if it is severe and watery.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•anxiety, confusion, dizzy
•chest pain
•difficulty breathing, wheezing
•edema, swelling
•fever
•irregular heart rate, blood pressure
•pain or difficulty passing urine
•seizures
•unusually weak or tired
•white or red patches in mouth

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•constipation or diarrhea
•difficulty sleeping
•headache
•nausea, vomiting
•pain, swelling or irritation where injected
•stomach upset
•vaginal itch, irritation

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

You will be instructed on how to store this medicine. Throw away any unused medicine after the expiration date on the label.

Last updated: 7/1/2002

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

Ertapenem
Systematic (IUPAC) name
(4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl] pyrrolidin-3-yl]sulfanyl-6-(1-hydroxyethyl)-4-methyl-7- oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Identifiers
CAS number	153832-46-3
ATC code	J01DH03
PubChem	150610
DrugBank	APRD00952
Chemical data
Formula	C22H25N3O7S
Mol. mass	475.516 g/mol
Pharmacokinetic data
Bioavailability	90% (intramuscular)
Protein binding	Inversely proportional to concentration; 85 to 95%
Metabolism	Minor hydrolysis of beta-lactam ring, CYP not involved
Half life	4 hours
Excretion	Renal (80%) and fecal (10%)
Therapeutic considerations
Pregnancy cat.	B3(AU) B(US)
Legal status	℞ Prescription only
Routes	Intramuscular, intravenous

Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz. It is structurally very similar to meropenem in that it possess a 1-β-methyl group.

Contents 1 Indications 2 Dosage 3 Pharmacology 3.1 Resistance 4 Side effects 5 References

Indications

Ertapenem has been designed to be effective against Gram negative bacteria. It is not active against MRSA, ampicillin-resistant enterococci, Pseudomonas aeruginosa or Acinetobacter species. Ertapenem also has clinically useful activity against anaerobic bacteria.

Ertapenem is marketed by Merck as a first-line treatment for community-acquired infections. It should not be used as empirical treatment for hospital-acquired infections because of its lack of activity against Pseudomonas aeruginosa. In practice, it is reserved primarily for use against Extended spectrum beta-lactamase (ESBL)-producing and high level AmpC-producing Gram-negative bacteria.

Dosage

Ertapenem is dosed as 1g given by intravenous injection over 30 minutes, or 1g diluted with 3.2ml of 1% lidocaine given intramuscularly. There is no oral preparation of ertapenem available. Ertapenem cannot be mixed with glucose.

The marketing slogan for ertapenem is "The Power of One", because the dose is one gram, once a day.

Pharmacology

Unlike imipenem and meropenem, ertapenem is highly protein bound, which explains its long half life (4 hours).

Ertapenem is excreted primarily (80%) by the kidneys. Metabolism by the liver is not clinically important and does not affect dosing.

Patients on haemodialysis should be given ertapenem at least 6 hours before dialysis. If it is given less than six hours before dialysis, then the patient should be given an additional dose of 150 mg IV after dialysis. Ideally, patients on haemodialysis should be given ertapenem immediately following dialysis.

Resistance

Acquired resistance to ertapenem is usually mediated by up-regulation of efflux mechanisms and by the selection of porin-deficient mutants. Organisms that produce a metallo-β-lactamase are innately immune to ertapenem (as well as all carbapenems).^{[citation needed]}

Side effects

There are few adverse effects of ertapenem. The only absolute contra-indication is a previous anaphylactic reaction to ertapenem or other β-lactam antibiotic. There are no studies done in pregnant women, so the manufacturers cannot comment on its safety in pregnancy. In 2006, Ertapenem is now approved for pediatric use in certain infections. Ertapenem is not recommended for children under 3 months of age and children with meningitis.

Use of all antibiotics is associated with increased rates of resistance (although carbapenem resistance is currently rare). There is particular worry that although ertapenem has no clinically useful activity against Pseudomonas aeruginosa, widespread use of ertapenem could still lead to increased carbapenem resistance in Pseudomonas.^[1]

Like many antibiotics, Clostridium difficile colitis has been associated with its use.

References

1. ^ Livermore DM, Mushtaq S, Warner M (2005). "Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems". J Antimicrob Chemother 55 (3): 306–311. doi:10.1093/jac/dki009. PMID 15705643. 

v • d • e Antibacterials: cell envelope antibiotics (J01C-J01D) Internal to membrane/ (inhibit peptidoglycan subunit synthesis and transport) NAM synthesis inhibition (Fosfomycin) · DADAL/AR inhibitors (Cycloserine) · bactoprenol inhibitors (Bacitracin) Glycopeptide/ (inhibit PG chain elongation) Vancomycin# (Oritavancin, Telavancin) · Teicoplanin (Dalbavancin) · Ramoplanin β-lactams/ (inhibit cross-links with PBP) Penicillins/ (penams) Extended sp. aminopenicillins: Amoxicillin#  · Ampicillin# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) · Epicillin carboxypenicillins: Carbenicillin (Carindacillin) · Ticarcillin · Temocillin ureidopenicillins: Azlocillin · Piperacillin · Mezlocillin other: Mecillinam (Pivmecillinam) · Sulbenicillin Narrow sp. β-lactamase sensitive Benzylpenicillin (G)#: Clometocillin · Benzathine benzylpenicillin#  · Procaine benzylpenicillin# · Azidocillin · Penamecillin Phenoxymethylpenicillin (V)#: Propicillin · Benzathine phenoxymethylpenicillin · Pheneticillin β-lactamase resistant Cloxacillin# (Dicloxacillin, Flucloxacillin) · Oxacillin · Meticillin · Nafcillin Penems Faropenem Carbapenems Biapenem · Doripenem · Ertapenem · Imipenem · Meropenem · Panipenem Cephalosporins/ (cephems) 1st (PEcK) Cefazolin# · Cefacetrile · Cefadroxil · Cefalexin · Cefaloglycin · Cefalonium · Cefaloridine · Cefalotin · Cefapirin · Cefatrizine · Cefazedone · Cefazaflur · Cefradine · Cefroxadine · Ceftezole 2nd (HEN) Cefaclor · Cefamandole · Cefminox · Cefonicid · Ceforanide · Cefotiam · Cefprozil · Cefbuperazone · Cefuroxime · Cefuzonam · cephamycin (Cefoxitin, Cefotetan, Cefmetazole) · carbacephem (Loracarbef) 3rd Cefixime# · Ceftazidime# · Ceftriaxone# · Cefcapene · Cefdaloxime · Cefdinir · Cefditoren · Cefetamet · Cefmenoxime · Cefodizime · Cefoperazone · Cefotaxime · Cefpimizole · Cefpiramide · Cefpodoxime · Cefsulodin · Cefteram · Ceftibuten · Ceftiolene · Ceftizoxime · oxacephem (Flomoxef, Latamoxef ‡) 4th Cefepime · Cefozopran · Cefpirome · Cefquinome 5th Ceftobiprole Veterinary Ceftiofur · Cefquinome · Cefovecin Monobactams Aztreonam · Tigemonam β-lactamase inhibitors penam (Sulbactam, Tazobactam) · clavam (Clavulanic acid) Combinations Co-amoxiclav (Amoxicillin/clavulanic acid)# · Imipenem/cilastatin# · Ampicillin/sulbactam (Sultamicillin) · Piperacillin/tazobactam Other polymyxins/detergent (Colistin, Polymyxin B) · depolarizing (Daptomycin) · hydrolyze NAM-NAG (Lysozyme) #WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III

v • d • e Merck & Co., Inc. Corporate directors: Richard Clark · Johnnetta Cole · William Harrison · William Kelley · Rochelle Lazarus · Thomas Shenk · Anne Tatlock · Samuel Thier · Wendell Weeks · Peter Wendell Products: Alendronate · Aprepitant · Ertapenem · Ezetimibe · Ezetimibe/simvastatin · Finasteride · Fosaprepitant · Indinavir · Losartan · Lovastatin · Montelukast · Raltegravir · Rizatriptan · Rofecoxib · Simvastatin · Sitagliptin · Vorinostat Publications: The Merck Manuals (Index · Manual · Veterinary · Geriatrics) Annual Revenue: $22.9 billion USD (▲2% FY 2004) · Employees: 63,000 · Stock Symbol: NYSE: MRK · Website: www.merck.com

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