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Clavulanic acid

 
Drug Info: Ticarcillin; Clavulanic Acid

Brand names: Timentin®

Chemical formula:





Clavulanate Potassium, Ticarcillin Disodium Solution for injection

What is this medicine?

TICARCILLIN, CLAVULANIC ACID (tye kar SILL in,  KLAV yoo la nate  AS id) is a penicillin 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:
•bleeding problems
•kidney disease
•salt restricted diet
•an unusual or allergic reaction to ticarcillin, clavulanic acid, penicillins or other antibiotics, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

This medicine is for infusion into a vein. 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. Special care may be needed.

Patients over 65 years old may have a stronger reaction and need a smaller dose.

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?

•aspirin and aspirin-like drugs
•certain antibiotics given by injection
•medicines that treat or prevent blood clots like warfarin, heparin, enoxaparin, and dalteparin
•methotrexate
•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 healthcare professional if your symptoms do not start to get better or if they get worse. 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.

This medicine can interfere with some urine protein tests. If you use such tests, talk with your health care professional.

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
•breathing problems
•dark urine
•fever or chills
•red spots on the skin
•redness, blistering, peeling or loosening of the skin, including inside the mouth
•seizures
•tense, stiff muscles
•unusual bleeding or bruising
•unusually weak or tired
•yellowing of eyes or skin

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•change in taste or smell
•diarrhea
•headache
•heartburn
•nausea, vomiting
•pain at site where injected
•sore mouth

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.

If you are using this medicine at home, 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.

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Wikipedia: Clavulanic acid
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Clavulanic acid
Systematic (IUPAC) name
(2R,5R,Z)-3-(2-hydroxyethylidene)-
7-oxo-4-oxa-1-aza-bicyclo[3.2.0]
heptane-2-carboxylic acid
Identifiers
CAS number 58001-44-8
ATC code J01CR (combinations with penicillins)
PubChem 5280980
DrugBank APRD00049
ChemSpider 4444466
Chemical data
Formula C8H9NO5 
Mol. mass 199.16
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability "well absorbed"
Metabolism hepatic (extensive)
Half life 1 hour
Excretion renal (30–40%)
Therapeutic considerations
Pregnancy cat.

B (USA)
B1 (Aust)

Legal status

Schedule 4 (Aust)

Routes oral, IV
 Yes check.svgY(what is this?)  (verify)

Clavulanic acid (rINN) (pronounced /klævjuːˌlænɨk ˈæsɨd/) is a beta-lactamase inhibitor (marketed by GlaxoSmithKline, formerly Beecham) combined with penicillin group antibiotics to overcome certain types of antibiotic resistance. It is used to overcome resistance in bacteria that secrete beta-lactamase, which otherwise inactivates most penicillins. In its most common form, the potassium salt potassium clavulanate is combined with amoxicillin (co-amoxiclav [brand name Augmentin] or the veterinary formulation Synulox from Pfizer, or [Clavulox]) or ticarcillin.

It is also under investigation as a NAALADase inhibitor with purported antidepressant and aphrodisiac properties, as in page 15 of this patent[1]. Clinical trials are underway on XR ("Serdaxin") and IR ("RX-10100", "Zoraxel") formulations by Rexahn in the US.[2]

Clavulanic acid is an example of a clavam.

Contents

Source

The name is derived from the Streptomyces clavuligerus, which produces clavulanic acid.[3][4]

Clavulanic acid is biosynthetically generated from the amino acid arginine and the sugar glyceraldehyde 3-phosphate.

History

Clavulanic acid was discovered around 1974/75 by British scientists working at the drug company Beecham. After several attempts, Beecham finally filed for US patent protection for the drug in 1981, and U.S. Patents 4,525,352, 4,529,720 and 4,560,552 were granted in 1985.

Mechanism of action

Clavulanic acid has negligible intrinsic antimicrobial activity, despite sharing the β-lactam ring that is characteristic of beta-lactam antibiotics. However, the similarity in chemical structure allows the molecule to act as a competitive inhibitor of beta-lactamases secreted by certain bacteria to confer resistance to beta-lactam antibiotics. This inhibition restores the antimicrobial activity of beta-lactam antibiotics against lactamase-secreting-resistant bacteria. Despite this, some bacterial strains that are even resistant to such combinations have emerged.

Adverse effects

The use of clavulanic acid with penicillins has been associated with an increased incidence of cholestatic jaundice and acute hepatitis during therapy or shortly after, particularly in men and those aged over 65 years. The associated jaundice is usually self-limiting and very rarely fatal.[5]

The UK Committee on Safety of Medicines (CSM) recommends that treatments such as amoxicillin/clavulanic acid preparations should be reserved for bacterial infections likely to be caused by amoxicillin-resistant β-lactamase-producing strains, and that treatment should not normally exceed 14 days.

Allergy has been reported.[6]

References

  1. ^ http://www.google.com/patents/pdf/Therapeutic_treatment_for_sexual_dysfunc.pdf?id=Lhl_AAAAEBAJ&output=pdf&sig=ACfU3U0ESWXC1lRCKxRbO4OD8h9FFa6LyQ
  2. ^ http://clinicaltrials.gov/ct2/results?term=rx-10100
  3. ^ Arulanantham H, Kershaw NJ, Hewitson KS, Hughes CE, Thirkettle JE, Schofield CJ (January 2006). "ORF17 from the clavulanic acid biosynthesis gene cluster catalyzes the ATP-dependent formation of N-glycyl-clavaminic acid". J. Biol. Chem. 281 (1): 279–87. doi:10.1074/jbc.M507711200. PMID 16251194. http://www.jbc.org/cgi/pmidlookup?view=long&pmid=16251194. 
  4. ^ Tahlan K, Park HU, Wong A, Beatty PH, Jensen SE (March 2004). "Two sets of paralogous genes encode the enzymes involved in the early stages of clavulanic acid and clavam metabolite biosynthesis in Streptomyces clavuligerus". Antimicrob. Agents Chemother. 48 (3): 930–9. PMID 14982786. PMC 353097. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=14982786. 
  5. ^ Joint Formulary Committee. British National Formulary, 47th edition. London: British Medical Association and Royal Pharmaceutical Society of Great Britain; 2004.
  6. ^ Tortajada Girbés M, Ferrer Franco A, Gracia Antequera M, Clement Paredes A, García Muñoz E, Tallón Guerola M (2008). "Hypersensitivity to clavulanic acid in children". Allergol Immunopathol (Madr) 36 (5): 308–10. PMID 19080805. http://www.elsevier.es/revistas/0301-0546/36/308. 

 
 

 

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