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LETROZOLE- AN ANTI BREAST CANCER DRUG LOC HUA CHEMISTRY 12B- SEMINAR # 11 AN OVERVIEW OF BREAST CANCER 1. What is breast cancer? A single cell in a tissue undergoes transformation which converts a normal cell to a cancer cell. The cell evades destruction, it proliferates to form a tumor, a mass of abnormal cells within otherwise normal tissue. If the abnormal cell remain at the original site, the lump is called a begin tumor. A malignant tumor becomes invasive enough to impair the functions of one or more organs. At this point the tumor is cancer. AN OVERVIEW OF BREAST CANCER 2. What factors can cause breast cancer? Women over 40 have higher risks of breast cancer Native Americans, Hispanics, and Asians have lower rates of breast cancer than Caucasians and African Americans Genetic factor and family history Because growth of breast tissue is highly sensitive to estrogens, the more a women is exposed to estrogen over her lifetime, the higher the risk for breast cancer Pregnancy appears to increase the risk of breast cancer for up to 15 years following the first birth, particularly in older women AN OVERVIEW OF BREAST CANCER 3. Stages of Breast Cancer Stage 0: This means that paitient either have DCIS which is an early age of breast cancer or LCIS which is not a cancer but increase the chance to have breast cancer. Stage I: cancer is less than 1 inch across. The cancer is only in the breast and has not spread out. Stage II: cancer is about 1 to 2 inches or larger and has spread to the lymph nodes under arm Stage III: cancer has spread to tissues near the breast (skin or chest wall, including the ribs and the muscles in the chest). cancer has spread to lymph nodes inside the chest wall along the breast bone. Stage IV: This stage is defined by either of the following: the cancer has spread to other organs of the body, most often the bones, lungs, liver, or brain. the tumor has spread locally to the skin and lymph nodes inside the neck, near the collarbone. Recurrent: In this stage, the cancer has come back (recurred) after treatment. It may come back in the breast, in the soft tissues of the chest (the chest wall), or in another part of the body. AN OVERVIEW OF BREAST CANCER 4. Statistics of Breast Cancer Structure and Synthesis Letrozole 1. Pharmacology of Letrozole A type of drug called an aromatase inhibitor which work by limiting the ability of an enzyme called aromatase to create estrogen. Letrozole comes in pill form and is taken once a day. It’s also called Femara. Letrozole is a drug for patients that have been taking Tamoxifen for five years. Structure and Synthesis Letrozole 2. Synthesis Letrolzole Structure and Synthesis Letrozole structure Structure and Synthesis Letrozole FT -IR of Letrozole Show the amine group Show the nitriles group Show the aromatic ring Structure and Synthesis Letrozole 1H NMR 13C NMR Structure and Synthesis Letrozole Carbon Chemical Shift (ppm) 66.36 Proton Chemical Shift (ppm) 6.81 (singlet) Atom Number and Notes 1 (alkyl methine) 113.29 1,1' (benzene rings) 117.82 19, 21 (benzene rings) 128.9 7.70, 7.72 (doublet) 3, 5, 3', 5' (benzene rings) 132.91 7.28, 7.30 (doublet) 2, 6, 2', 6' (benzene rings) 141.76 4, 4' (benzene rings) 143.68 8.09 (singlet) 5 (triazole ring) 153.05 8.07 (singlet) 3 (triazole ring) Comparison between Tamoxifen and Letrozole Tamoxifen Letrozole 1. Long term working After 5 years the drug becomes ineffective 2. Effect no effect on the production of estrogen 3. Physical effect Effect on women sexual function, memory loss, stroke 4. Pregnancy affect on the fetus Continue after 5 years treatment A very powerful aromatase inhibitor, suppresses the production of estrogen hot flashes, sweating, edema, sore muscles and fatigue cause fetal harm when administered to pregnant women Reference http://www.cancer.gov/newscenter/pressreleases/letrozoleQand A http://www.drugs.com/pdr/Femara_Tablets.html http://www.usdoj.gov/dea/programs/forensicsci/microgram/journ al071203/mj071203_pg6.html http://www.fda.gov/cder/foi/label/2003/20726se8008_Femara_l bl.pdf#search='synthesis%20letrozole‘ http://www.sante.univnantes.fr/pharma/biocit/publispdf/p34.pdf http://www.reutershealth.com/wellconnected/doc06.html