Capecitabine | APOLLO | +9191 46 950 950
Capecitabine | APOLLO | +9191 46 950 950
Capecitabine
CAS Number : 154361-50-9
Molecular Weight : 359.35 g/mol
Molecular Formula : C15H22FN3O6
Systematic (IUPAC) : pentyl[1-(3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)- 5-fluoro-2-oxo-1H-
pyrimidin- 4-yl]aminomethanoate
DRUG DESCRIPTION
Capecitabine CAS No. 154361-50-9
Description
Name: Capecitabine
Synonyms: Penty [1-(3,4-dihydroxyl-5-methyl-oxolan-2-yl)-5-fluoro-2-oxo-pyrimidin-4-yl] aminoformate,
Xeloda
Molecular Formula: C15H22FN3O6
Molecular Weight: 359.35
CAS: 154361-50-9
Capecitabine is FDA-approved for:
* Adjuvant in colorectal cancer Stage III Dukes' C - used as first-line monotherapy.
* Metastatic colorectal cancer - used as first-line monotherapy, if appropriate.
* Metastatic breast cancer - used in combination with docetaxel, after failure of anthracycline-based treatment. Also as monotherapy, if the patient has failed paclitaxel-based treatment, and if anthracycline-based treatment
has either failed or cannot be continued for other reasons (i.e., the patient has already received the
maximum lifetime dose of an anthracycline).
DOSAGE
Capecitabine CAS No. 154361-50-9
Your doctor may want you to take a combination of 500mg and 150mg tablets. You need to make sure that
you are taking the right dose.
The tablets should be swallowed whole with a glass of water, within half an hour of the end of a meal, as capecitabine works best if it is broken down in the
stomach with food. You should take them in the morning after breakfast, and then again after your
evening meal, so that the doses are spaced at least eight hours apart.
If you have trouble swallowing capecitabine tablets, they can be dissolved in a 200ml glass of warm water. The
mixture should be stirred with a spoon until the tablets are completely dissolved and drunk immediately. The glass and spoon should be washed and kept separate
from your other crockery and cooking utensils.
Capecitabine tablets are usually taken for a number of days, followed by a rest period in which no tablets are
taken. This can vary depending upon the type of cancer you have. It is important to follow the instructions
carefully and take the tablets as directed by your doctor, nurse or pharmacist.
You should only get the tablets from your hospital. You can't get a repeat prescription from your GP.
* For mild renal dysfunction (creatinine clearance 30-50 mL/min), it is recommended to reduce dose by 25%.
* For severe renal dysfunction (creatinine clearance <30 mL/min), treatment is not recommended.
* There is no recommendation for hepatic dysfunction.
* For elderly patients, lower doses may be required due to higher incidences of serious adverse reactions.
OVERDOSE
Capecitabine CAS No. 154361-50-9
When used in combination with anticoagulants ('blood thinners') such as warfarin (Coumadin), capecitabine
can cause serious bleeding and death. Tell your doctor if you are taking warfarin or phenprocoumon. Keep all
appointments with your doctor and the laboratory. Your doctor will order certain lab tests to check your response to capecitabine. If you experience any unusual bleeding
or bruising, call your doctor immediately.
SIDE EFFECTS
Capecitabine CAS No. 154361-50-9
Side effects from capecitabine are common and include:
* diarrhea
* nausea
* vomiting
* stomach pain
* constipation
* weakness
* tiredness
* dizziness
* headache
* sleeplessness
* dry or itching skin
* dehydration
If you experience any of the following symptoms or the one listed in the IMPORTANT WARNING section, call
your doctor immediately:
* severe diarrhea (more than four bowel movements each day or diarrhea at night)
* decreased appetite (complete loss of appetite or only able to eat occasionally)
* severe vomiting (more than one time in a 24-hour period)
* tingling, numbness, pain, redness, or swelling of the hands or feet
* sores or pain in the mouth or throat
* fever or infection (a temperature of 100.5 degrees F or greater)
* chills
* sore throat
* chest pain
* rash
PRECAUTIONS
Capecitabine CAS No. 154361-50-9
Before taking capecitabine,
* tell your doctor and pharmacist if you are allergic to a capecitabine, fluorouracil, or any other drugs.
* tell your doctor and pharmacist what prescription and nonprescription medications you are taking, especially
those listed in the IMPORTANT WARNING section, antacids, folic acid, leucovorin, phenytoin (Dilantin),
and vitamins.
* tell your doctor if you have or have ever had heart, liver, or kidney disease.
* women who are pregnant or breast-feeding should tell their doctors before they begin taking this drug. You
should not plan to have children while receiving chemotherapy or for a while after treatments. (Talk to
your doctor for further details.) Use a reliable method of birth control to prevent pregnancy.
* tell your doctor if you are breast-feeding. Capecitabine can cause serious side effects in nursing infants.
* do not have any vaccinations (e.g., measles or flu shots) without talking to your doctor.
INTERACTIONS
Capecitabine CAS No. 154361-50-9
* May interact with warfarin and increase bleeding risk.
* May inhibit cytochrome CYP2C9 enzyme, and therefore increase levels of substrates such as phenytoin
and other substrates of CYP2C9.
* Much as fluorouracil, the concomitant use of leucovorin may increase both the efficacy and the
toxicity of capecitabine.
ACTION
Capecitabine CAS No. 154361-50-9
Your doctor has ordered the drug capecitabine to help treat your illness. The drug is taken by mouth with
tablets. Take capecitabine with water within 30 minutes after eating a meal.
This medication is used to treat:
* metastatic colorectal cancer
* metastatic breast cancer
This medication is sometimes prescribed for other uses; ask your doctor or pharmacist for information.
Capecitabine is in a class of drugs known as antimetabolites. Capecitabine resembles a normal cell
nutrient needed by cancer cells to grow. The cancer cells take up the capecitabine, which then interferes with
their growth. The length of treatment depends on the types of drugs you are taking, how well your body
responds to them, and the type of cancer you have.
PATIANT INFORMATION
Capecitabine CAS No. 154361-50-9
Things to remember about capecitabine tablets
* It is important to take your tablets at the right times. You must take them as directed by your doctor,
specialist nurse or pharmacist.
* Keep the tablets in the original packaging and store them at room temperature, away from heat and direct
sunlight.
* Keep the tablets in a safe place where children cannot reach them, as capecitabine could harm them.
* If your doctor decides to stop the treatment, return any remaining tablets to the pharmacist. Do not flush them
down the toilet or throw them away.
* If you are sick just after taking the tablets let your doctor know as you may need to take another dose. Do not take another tablet without first telling your doctor.
* If you forget to take a tablet, do not take a double dose. Inform your doctor and keep to your regular dose
schedule.
Type
small molecule
Description
Capecitabine is an orally-administered chemotherapeutic agent used in the treatment of
metastatic breast and colorectal cancers. Capecitabine is a prodrug, that is enzymatically converted to fluorouracil
(antimetabolite) in the tumor, where it inhibits DNA synthesis and slows growth of tumor tissue.
Categories
Antineoplastic Agents
Antimetabolites
Prodrugs
Antimetabolites, Antineoplastic
Taxonomy
Kingdom Organic
Classes
Glycerol and Derivatives
Carbamates and Derivatives
Pyrimidines and Derivatives
Substructures
Glycerol and Derivatives
Hydroxy Compounds
Carbamates and Derivatives
Ethers
Pyrimidines and Derivatives
Alcohols and Polyols
Heterocyclic compounds
Aromatic compounds
Furans
Cyanamides
Aryl Halides
Pharmacology
Indication
For the treatment of patients with metastatic breast cancer resistant to both paclitaxel and an anthracycline-containing chemotherapy regimen. May also be used in
combination with docetaxel for the treatment of metastatic breast cancer in patients who have failed to respond to, or recurred or relasped during or following
anthracycline-containing chemotherapy. Capecitabine is used alone as an adjuvant therapy following the
complete resection of primary tumor in patients with stage III colon cancer when monotherapy with
fluroprymidine is preferred. The use or capecitabine in combination regimens for advanced gastric cancer is
currently being investigated.
Pharmacodynamics
Capecitabine is a fluoropyrimidine carbamate with antineoplastic activity indicated for the treatment of
metastatic breast cancer and colon cancer. It is an orally administered systemic prodrug that has little pharmacologic activity until it is converted to
fluorouracil by enzymes that are expressed in higher concentrations in many tumors. Fluorouracil it then
metabolized both normal and tumor cells to 5-fluoro-2′-deoxyuridine 5′-monophosphate (FdUMP) and 5-
fluorouridine triphosphate (FUTP).
Mechanism of Action
Capecitabine is a prodrug that is selectively tumour-activated to its cytotoxic moiety, fluorouracil, by
thymidine phosphorylase, an enzyme found in higher concentrations in many tumors compared to normal
tissues or plasma. Fluorouracil is further metabolized to two active metabolites, 5-fluoro-2'-deoxyuridine 5'-
monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP), within normal and tumour cells.
These metabolites cause cell injury by two different mechanisms. First, FdUMP and the folate cofactor, N5-
10-methylenetetrahydrofolate, bind to thymidylate synthase (TS) to form a covalently bound ternary complex. This binding inhibits the formation of
thymidylate from 2'-deaxyuridylate. Thymidylate is the necessary precursor of thymidine triphosphate, which is essential for the synthesis of DNA, therefore a deficiency
of this compound can inhibit cell division. Secondly, nuclear transcriptional enzymes can mistakenly
incorporate FUTP in place of uridine triphosphate (UTP) during the synthesis of RNA. This metabolic error can interfere with RNA processing and protein synthesis
through the production of fraudulent RNA.
Absorption
Readily absorbed through the GI tract (~70%)
Metabolism
Metabolized by thymidine phosphorylase to fluoruracil.
Route of Elimination
Capecitabine and its metabolites are predominantly excreted in urine; 95.5% of administered capecitabine dose is recovered in urine. Fecal excretion is minimal
(2.6%). The major metabolite excreted in urine is FBAL which represents 57% of the administered dose.About
3% of the administered dose is excreted in urine as unchanged drug.
Affected Organisms
Humans and other mammals
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