DOCSLIB.ORG

Use of Oral Contraceptives (OC) and Breast Cancer Risk Among Young Women by OC Formulation

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Use of Oral Contraceptives (OC) and Breast Cancer Risk Among Young Women by OC Formulation Use of oral contraceptives (OC) and breast cancer risk among young women by OC formulation and breast cancer subtype Elisabeth Frances Beaber A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy University of Washington 2012 Reading Committee: Christopher I. Li, Chair Diana S.M. Buist Kathleen E. Malone Program Authorized to Offer Degree: Epidemiology – Public Health University of Washington Abstract Use of oral contraceptives (OC) and breast cancer risk among young women by OC formulation and breast cancer subtype Elisabeth Frances Beaber Chair of the Supervisory Committee: Professor Christopher I. Li Epidemiology – Public Health Background: Many studies suggest a modest increased breast cancer risk is associated with recent oral contraceptive (OC) use, but risks associated with contemporary OCs and molecular subtypes of breast cancer are less well known. Estrogen and progestin doses have declined and new progestins have been used since OCs were introduced. Furthermore, the vast majority of studies have relied on self-reported OC use, rather than pharmacy data. Methods: Two studies examining invasive breast cancer risk were conducted in western Washington state. The first was a population-based interview case-control study among women ages 20-44 from 2004-2010 (985 cases, 882 controls). Logistic regression was used to estimate associations between lifetime OC use, overall risk, and breast cancer risk by subtype (estrogen receptor positive (ER+), ER-, and triple-negative (ER-/PR-/HER2-)). The second study was a nested case-control study among Group Health Cooperative health plan enrollees. Cases were ages 20-49 at diagnosis from 1990-2009 (n=1102) and controls were randomly selected (n=21952). Associations between recent OC use (within 1 year of reference date) by OC formulation and ER status were evaluated using conditional logistic regression. Results: In the first study, recent OC use for ≥5 years increased breast cancer risk (odds ratio (OR)=1.6), as well as lifetime duration of use for ≥15 years (OR=1.5). There was no statistically significant risk heterogeneity by OC formulation. ORs were generally greater among women ages 20-39. ER- cancer ORs were greater than ER+ ORs. Triple-negative breast cancer ORs were especially elevated. In the second study, recent OC use increased breast cancer risk (OR=1.6). Risk was greater for ER+ (OR=1.7) than ER- cancer (OR=1.3). Risk varied by OC formulation, with some OCs associated with an increased risk and others not associated with risk. Conclusions: We found that recent use of contemporary OCs increases breast cancer risk among women ages 20-49 and that long durations of use increases risk among ages 20-44. Risks may be greater among younger women and for triple-negative breast cancer. Risks may also vary by OC formulation. Continued monitoring of breast cancer risk is essential as OC formulations and use patterns continue to evolve. TABLE OF CONTENTS Page List of Tables.................................................................................................................................ii Chapter 1: Oral contraceptive use and breast cancer risk overall and by molecular subtype among women ages 20-44 Abstract...........................................................................................................................................1 Introduction.....................................................................................................................................2 Methods..........................................................................................................................................3 Results............................................................................................................................................7 Discussion.....................................................................................................................................10 Chapter 2: Recent oral contraceptive use by formulation and breast cancer risk among young women Abstract.........................................................................................................................................23 Introduction...................................................................................................................................24 Methods........................................................................................................................................25 Results .........................................................................................................................................31 Discussion.....................................................................................................................................34 Bibliography................................................................................................................................52 i LIST OF TABLES Table Number and Title Page 1.1 Selected characteristics of controls and cases.......................................................................16 1.2 Oral contraceptive (OC) use and risk of breast cancer...........................................................18 1.3 Risk of breast cancer associated with current use of specific combined oral contraceptive (OC) preparations for 5 years or longer........................................................................................19 1.4 Risk of breast cancer associated with ever or current use of specific combined oral contraceptive (OC) preparations...................................................................................................20 1.5 Duration of oral contraceptive (OC) use, recency of use, and risk of estrogen receptor positive (ER+), ER negative (ER-), and triple-negative (ER-/PR-/HER2-) breast cancer ............21 2.1 Descriptive characteristics of controls and cases...................................................................44 2.2 Additional descriptive characteristics among a subset of controls and cases ages 20-44 (reference years: 1995-2009).......................................................................................................45 2.3 Recent oral contraceptive (OC) use and invasive breast cancer risk by estrogen receptor (ER) status....................................................................................................................................46 2.4 Recent oral contraceptive (OC) use by number of scripts and pills and invasive breast cancer risk by estrogen receptor (ER) status................................................................................47 2.5 Recent oral contraceptive (OC) use and invasive breast cancer risk by age..........................48 2.6 Recent oral contraceptive (OC) use by estrogen dose and progestin type and invasive breast cancer risk, by all cases (left) and ER positive cases (right)..............................................49 2.7 Recent oral contraceptive (OC) use by monophasic formulations and invasive breast cancer risk, by all cases (left) and ER positive cases (right).....................................................................50 2.8 Recent oral contraceptive (OC) use by triphasic formulations and invasive breast cancer risk, by all cases (left) and ER positive cases (right).....................................................................51 ii ACKNOWLEDGEMENTS I would like to thank my dissertation chair, Chris Li, for his mentorship and support. His critical input, enthusiasm, and commitment to my research all have been integral to my experience as a graduate student at the University of Washington. I feel very fortunate to have worked with such an outstanding mentor. In addition, I would like to acknowledge Diana Buist for her contributions to the research conducted at Group Health Research Institute (GHRI) and her professional guidance. I also sincerely appreciate the expertise and assistance from Kathi Malone, Susan Reed, and Bill Barlow. This work could not have been completed without the support of numerous individuals in the Cancer Epidemiology Research Cooperative at the Fred Hutchinson Cancer Research Center, as well as the research team at GHRI. I especially would like to thank Mei Tang for her biostatistical support and the REACH study participants for donating their time. I would like to acknowledge the continual support and encouragement of my parents, siblings, and dear friends during my journey as a graduate student. In particular, thank you to Jed, Sara, Gaia, and Erin. iii DEDICATION To my dad, Larry Beaber. In memory of his constant love and support, good cheer, and commitment to lifelong learning. iv 1 CHAPTER 1: Oral contraceptive use and breast cancer risk overall and by molecular subtype among women ages 20-44 ABSTRACT Background: The majority of studies demonstrate recent oral contraceptive (OC) use is associated with a small increased breast cancer risk among young women; yet risks associated with modern OC formulations and by molecular subtype have not been well characterized. Methods: We conducted a population-based case-control study of invasive breast cancer among women ages 20-44 residing in the Seattle-Puget Sound area from 2004-2010 (985 cases and 882 controls). We collected detailed information on contraceptive use and participant characteristics via an in-person interview. Multivariable-adjusted logistic regression was used to calculate odds ratios (OR) and 95% confidence intervals (CI). Results: Current OC use
Load more

Recommended publications
  • UNITED STATES PATENT OFFICE 2,636,042 WATER-SOLUBLE HORMONE COMPOUNDS Ralph Salkin, Jackson Heights, N.Y., Assignor to S
    Patented Apr. 21, 1953 2,636,042 UNITED STATES PATENT OFFICE 2,636,042 WATER-SOLUBLE HORMONE COMPOUNDS Ralph Salkin, Jackson Heights, N.Y., assignor to S. B. Penick and Company, New York, N. Y., a corporation of Delaware No Drawing. Application July 8, 1949 Serial No. 103,759 5 Claims. (C. 260-39.4) 1. 2 My invention relates to an improvement in the ether, and the sulfate is then Salted out of the manufacture of water-soluble compounds of the aqueous solution by the addition of a, caustic estrane series, and in particular it is concerned solution under cooling. The liberated hormone With an improvement in the synthesis of alkali sulfate is extracted into a suitable Solvent, for and alkaline-earth metal salts of the sulfates of 5 instance butanol, pyridine being preferred how the estranes. ever. The hormone sulfate solution is exhaus The estranes to which my invention applies are tively extracted with ether to remove the solvent. steroids having a free hydroxyl group in the The resultant semicrystalline product is recrys 3-position and a hydroxy or keto group in the tallized from a dilute monohydric alcohol. Or 17-position of the molecule, such as estrone, O Water to give the pure sterol.ester. equilin, equilenin, estradiol and similar com In order to get pure ester Salts, I have found pounds. it essential that the tertiary amine-sulfur trioxide These products which are commonly known as adduct be absolutely pure when being reacted With conjugated estrogens can be obtained from nat the hormones. Improved yields and more readily ural sources such as the urine of pregnant mares purifiable light colored granular products result, or of stallions.
    [Show full text]
  • Labeling and Synthesis of Estrogens and Their Metabolites
    Labeling and Synthesis of Estrogens and Their Metabolites Paula Kiuru University of Helsinki Faculty of Science Department of Chemistry Laboratory of Organic Chemistry P.O. Box 55, 00014 University of Helsinki, Finland ACADEMIC DISSERTATION To be presented with the permission of the Faculty of Science of the University of Helsinki, for public criticism in Auditorium A110 of the Department of Chemistry, A. I. Virtasen Aukio 1, Helsinki, on June 18th, 2005 at 12 o'clock noon Helsinki 2005 ISBN 952-91-8812-9 (paperback) ISBN 952-10-2507-7 (PDF) Helsinki 2005 Valopaino Oy. 1 ABSTRACT 3 ACKNOWLEDGMENTS 4 LIST OF ORIGINAL PUBLICATIONS 5 LIST OF ABBREVIATIONS 6 1. INTRODUCTION 7 1.1 Nomenclature of estrogens 8 1.2 Estrogen biosynthesis 10 1.3 Estrogen metabolism and cancer 10 1.3.1 Estrogen metabolism 11 1.3.2 Ratio of 2-hydroxylation and 16α-hydroxylation 12 1.3.3 4-Hydroxyestrogens and cancer 12 1.3.4 2-Methoxyestradiol 13 1.4 Structural and quantitative analysis of estrogens 13 1.4.1 Structural elucidation 13 1.4.2 Analytical techniques 15 1.4.2.1 GC/MS 16 1.4.2.2 LC/MS 17 1.4.2.3 Immunoassays 18 1.4.3 Deuterium labeled internal standards for GC/MS and LC/MS 19 1.4.4 Isotopic purity 20 1.5 Labeling of estrogens with isotopes of hydrogen 20 1.5.1 Deuterium-labeling 21 1.5.1.1 Mineral acid catalysts 21 1.5.1.2 CF3COOD as deuterating reagent 22 1.5.1.3 Base-catalyzed deuterations 24 1.5.1.4 Transition metal-catalyzed deuterations 25 1.5.1.5 Deuteration without catalyst 27 1.5.1.6 Halogen-deuterium exchange 27 1.5.1.7 Multistep labelings 28 1.5.1.8 Summary of deuterations 30 1.5.2 Enhancement of deuteration 30 1.5.2.1 Microwave irradiation 30 1.5.2.2 Ultrasound 31 1.5.3 Tritium labeling 32 1.6 Deuteration estrogen fatty acid esters 34 1.7 Synthesis of 2-methoxyestradiol 35 1.7.1 Halogenation 35 1.7.2 Nitration of estrogens 37 1.7.3 Formylation 38 1.7.4 Fries rearrangement 39 1.7.5 Other syntheses of 2-methoxyestradiol 39 1.7.6 Synthesis of 4-methoxyestrone 40 1.8 Synthesis of 2- and 4-hydroxyestrogens 41 2.
    [Show full text]
  • REVIEW Steroid Sulfatase Inhibitors for Estrogen
    99 REVIEW Steroid sulfatase inhibitors for estrogen- and androgen-dependent cancers Atul Purohit and Paul A Foster1 Oncology Drug Discovery Group, Section of Investigative Medicine, Imperial College London, Hammersmith Hospital, London W12 0NN, UK 1School of Clinical and Experimental Medicine, Centre for Endocrinology, Diabetes and Metabolism, University of Birmingham, Birmingham B15 2TT, UK (Correspondence should be addressed to P A Foster; Email: [email protected]) Abstract Estrogens and androgens are instrumental in the maturation of in vivo and where we currently stand in regards to clinical trials many hormone-dependent cancers. Consequently,the enzymes for these drugs. STS inhibitors are likely to play an important involved in their synthesis are cancer therapy targets. One such future role in the treatment of hormone-dependent cancers. enzyme, steroid sulfatase (STS), hydrolyses estrone sulfate, Novel in vivo models have been developed that allow pre-clinical and dehydroepiandrosterone sulfate to estrone and dehydroe- testing of inhibitors and the identification of lead clinical piandrosterone respectively. These are the precursors to the candidates. Phase I/II clinical trials in postmenopausal women formation of biologically active estradiol and androstenediol. with breast cancer have been completed and other trials in This review focuses on three aspects of STS inhibitors: patients with hormone-dependent prostate and endometrial 1) chemical development, 2) biological activity, and 3) clinical cancer are currently active. Potent STS inhibitors should trials. The aim is to discuss the importance of estrogens and become therapeutically valuable in hormone-dependent androgens in many cancers, the developmental history of STS cancers and other non-oncological conditions.
    [Show full text]
  • University Microfilms, Inc., Ann Arbor, Michigan ADRENOCORTICAL STEROID PROFILE IN
    This dissertation has been Mic 61-2820 microfilmed exactly as received BESCH, Paige Keith. ADRENOCORTICAL STEROID PROFILE IN THE HYPERTENSIVE DOG. The Ohio State University, Ph.D., 1961 Chemistry, biological University Microfilms, Inc., Ann Arbor, Michigan ADRENOCORTICAL STEROID PROFILE IN THE HYPERTENSIVE DOG DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of the Ohio State University By Paige Keith Besch, B. S., M. S. The Ohio State University 1961 Approved by Katharine A. Brownell Department of Physiology DEDICATION This work is dedicated to my wife, Dr. Norma F. Besch. After having completed her graduate training, she was once again subjected to almost social isolation by the number of hours I spent away from home. It is with sincerest appreciation for her continual encouragement that I dedi­ cate this to her. ACKNOWLEDGMENTS I wish to acknowledge the assistance and encourage­ ment of my Professor, Doctor Katharine A. Brownell. Equally important to the development of this project are the experience and information obtained through the association with Doctor Frank A. Hartman, who over the years has, along with Doctor Brownell, devoted his life to the development of many of the techniques used in this study. It is also with extreme sincerity that I wish to ac­ knowledge the assistance of Mr. David J. Watson. He has never complained when asked to work long hours at night or weekends. Our association has been a fruitful one. I also wish to acknowledge the encouragement of my former Professor, employer and good friend, Doctor Joseph W.
    [Show full text]
  • Nomenclature of Steroids
    Pure&App/. Chern.,Vol. 61, No. 10, pp. 1783-1822,1989. Printed in Great Britain. @ 1989 IUPAC INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY and INTERNATIONAL UNION OF BIOCHEMISTRY JOINT COMMISSION ON BIOCHEMICAL NOMENCLATURE* NOMENCLATURE OF STEROIDS (Recommendations 1989) Prepared for publication by G. P. MOSS Queen Mary College, Mile End Road, London El 4NS, UK *Membership of the Commission (JCBN) during 1987-89 is as follows: Chairman: J. F. G. Vliegenthart (Netherlands); Secretary: A. Cornish-Bowden (UK); Members: J. R. Bull (RSA); M. A. Chester (Sweden); C. LiCbecq (Belgium, representing the IUB Committee of Editors of Biochemical Journals); J. Reedijk (Netherlands); P. Venetianer (Hungary); Associate Members: G. P. Moss (UK); J. C. Rigg (Netherlands). Additional contributors to the formulation of these recommendations: Nomenclature Committee of ZUB(NC-ZUB) (those additional to JCBN): H. Bielka (GDR); C. R. Cantor (USA); H. B. F. Dixon (UK); P. Karlson (FRG); K. L. Loening (USA); W. Saenger (FRG); N. Sharon (Israel); E. J. van Lenten (USA); S. F. Velick (USA); E. C. Webb (Australia). Membership of Expert Panel: P. Karlson (FRG, Convener); J. R. Bull (RSA); K. Engel (FRG); J. Fried (USA); H. W. Kircher (USA); K. L. Loening (USA); G. P. Moss (UK); G. Popjiik (USA); M. R. Uskokovic (USA). Correspondence on these recommendations should be addressed to Dr. G. P. Moss at the above address or to any member of the Commission. Republication of this report is permitted without the need for formal IUPAC permission on condition that an acknowledgement, with full reference together with IUPAC copyright symbol (01989 IUPAC), is printed.
    [Show full text]
  • Tailed Deer (Odocoileus Virginianus) by Immunoassay of Steroid Hormones Metabolytes in Feces
    Open Access Journal of Science Mini Review Open Access A study on reproductive endocrinology of white- tailed deer (Odocoileus virginianus) by immunoassay of steroid hormones metabolytes in feces Volume 2 Issue 4 - 2018 Summary The objective of this study was carried out a documentary review on studies about Rubén Cornelio Montes-Perez monitoring endocrine activity of white-tailed deer (Odocoileus virginianus) by Facultad de Medicina Veterinaria y Zootecnia, Universidad immunoassay of feces to diagnose ovarian cycle activity, sex allocation and pregnancy Autonoma de Yucatan, Mexico diagnostics was conducted. The results indicated that it is feasible to monitor reproductive endocrine activity by estimating gonadic steroid metabolytes in urine and Correspondence: Rubén Cornelio Montes Perez, Facultad feces, although the results are not consistent due to level variations of metabolytes in de Medicina Veterinaria y Zootecnia, Universidad Autonoma de feces and also due to the pregnancy and sex allocation diagnostics efficiency. Several Yucata, Carretera Mérida-Xmatkuil km 15.5, CP. 97315. Merida, factors determine this variability, therefore, it is necessary to optimize technologies Yucatan, Mexico, Tel 52 9992621918, and /or test strategies to standardize sampling methods, to obtain more reliable results. Email [email protected] Keywords: white-tailed deer, steroid metabolytes, endocrinology studies, non- Received: July 06, 2018 | Published: July 19, 2018 invasive methods Introduction ml to day 23 and undetectable values at day 26, which is the average time of the estrous cycle. They concluded that the levels, pattern of Reproduction of white-tailed deer (Odocoileus virgininianus) can changes and individual variation of blood progestin of the white tailed occur all year round in various South American countries; the highest female are similar to those reported for domestic sheep.
    [Show full text]
  • United States Patent Office Patented Aug
    3,338,926 United States Patent Office Patented Aug. 29, 1967 1. 2 3,338,926 Sult in an appreciable amount of by-product formation PROCESS FOR THE HYDROLYSIS OF CYCLIC through esterification of free hydroxyl groups on the ACETALS AND KETALS nucleus or in the side chains (producing, for example, 21 Francisco Alvarez, John B. Siddall, and Augusto Ruiz, formoxy steroids which, if they also contain a 17a-hy Palo Alto, Calif., assignors to Syntex Corporation, droxyl group and are later hydrolyzed, will in part un Panamaa, Panama, a corporation of Panama dergo D-homo rearrangement no matter how mild the No Drawing. Filled May 2, 1966, Ser. No. 546,602 base used, or 116-formoxy steroids, which can only be 10 Claims. (C. 260-397.4) hydrolyzed back to the free alcohols under relatively drastic conditions, thus giving rise, again in the case of the This is a continuation-in-part of copending application O 17a-hydroxypregnanes, to an even greater amount of D Ser. No. 460,462, filed June 1, 1965, now abandoned. homo rearrangement), degradation of a dihydroxy-ace This invention relates to a process for the preparation tone side chain, if present, or destruction of acid-sensi of cyclopentanophenanthrene derivatives. tive groups elsewhere in the steroid molecule, or all of More particularly, this invention relates to a novel these, leading to poor yields of free dihydroxy final prod method for the conversion, in good yields and with a 5 uct contaminated with relatively large amounts of un minimum of by-product formation, of cyclic acetal and wanted by-products.
    [Show full text]
  • Antiviral Drug
    Suraj Punj Journal For Multidisciplinary Research ISSN NO: 2394-2886 Vibrational spectra of 1- methylestin-3 thosomicarbozole (methisazole): Antiviral Drug Dr. DB Singh*, Kiran Pandey, Pragya Singh, Deepali Singh, Madhusmita Singh, DEEPIKA NISHAD Micro molecular and Bio physics Laboratory; Department Of Physics; DSMNR University; Lucknow. Abstract: 1-methylestin-3 thosomicarbozole (methisazole) is a chemical compound that shows the property of Antiviral Drug. A complete assignment of fundamental vibration frequencies has been made, and the spectra have been interpreted in detail. The non-planar frequencies have been calculated with the aid of force constants determined for related molecules. The fundamental vibrational frequencies and intensity of vibrational bands were evaluated using density functional theory (DFT) using standard B3LYP/6-31G methods and basis set combinations. The optimized geometric structure of 1- methylestin-3 thosomicarbozole (methisazole) has been studied by using Density Functional Theory (DFT). On the basis of ground and excited state geometries, the absorption spectra have been calculated using the DFT method. To understand the Non-Linear Optical properties of 1- methylestin-3 thosomicarbozole (methisazole), we computed dipole moment (μ) ,using B3LYP density functional theory method in conjunction with 6-31G basis set. Keywords: FTIR, FT-Raman, DFT, HOMO, LUMO, Vibrational spectra, antiviral. Volume 9, Issue 4, 2019 Page No: 31 Suraj Punj Journal For Multidisciplinary Research ISSN NO: 2394-2886 Introduction: 1-methylestin-3 thosomicarbozole (methisazole) is a chemical compound that shows the property of Antiviral Drug. The optimized geometrical compound of antiviral activity, this antiviral drug design is to identify viral proteins, or parts of proteins, that can be disabled.
    [Show full text]
  • Full Text (PDF)
    The Journal of Neuroscience, April 4, 2018 • 38(14):3377–3387 • 3377 Viewpoints Excreted Steroids in Vertebrate Social Communication Wayne I. Doyle and XJulian P. Meeks University of Texas Southwestern Medical Center, Dallas, Texas 75390-9111 Steroids play vital roles in animal physiology across species, and the production of specific steroids is associated with particular internal biological functions. The internal functions of steroids are, in most cases, quite clear. However, an important feature of many steroids (their chemical stability) allows these molecules to play secondary, external roles as chemical messengers after their excretion via urine, feces, or other shed substances. The presence of steroids in animal excretions has long been appreciated, but their capacity to serve as chemosignals has not received as much attention. In theory, the blend of steroids excreted by an animal contains a readout of its own biological state. Initial mechanistic evidence for external steroid chemosensation arose from studies of many species of fish. In sea lampreys and ray-finned fishes, bile salts were identified as potent olfactory cues and later found to serve as pheromones. Recently, we and others have discovered that neurons in amphibian and mammalian olfactory systems are also highly sensitive to excreted glucocor- ticoids, sex steroids, and bile acids, and some of these molecules have been confirmed as mammalian pheromones. Steroid chemosen- sation in olfactory systems, unlike steroid detection in most tissues, is performed by plasma membrane receptors, but the details remain largely unclear. In this review, we present a broad view of steroid detection by vertebrate olfactory systems, focusing on recent research in fishes, amphibians, and mammals.
    [Show full text]
  • Bp501t Medchem -Unit
    Bachelor of Pharmacy (B. Pharm) SEMESTER:5TH Subject: MEDICINAL CHEMISTRY-II CODE: BP501T UNIT:IV UNIT: IV 4. Drugs acting on Endocrine system 4.1. Introduction to steroids 4.1.1. Classification of Steroids 4.1.2. Nomenclature, 4.1.3. Stereochemistry 4.1.4. Metabolism of steroids 4.2. Sex hormones: 4.2.1. Testosterone, 4.2.2. Nandralone, 4.2.3. Progestrones, 4.2.4. Oestriol, 4.2.5. Oestradiol, 4.2.6. Oestrione, 4.2.7. Diethyl stilbestrol. 4.3. Drugs for erectile dysfunction 4.3.1. Sildenafil 4.3.2. Tadalafil 4.4. Oral contraceptives 4.4.1. Mifepristone 4.4.2. Norgestril 4.4.3. Levonorgestrol 4.5. Corticosteroids 4.5.1. Cortisone 4.5.2. Hydrocortisone 4.5.3. Prednisolone 4.5.4. Betamethasone 4.5.5. Dexamethasone 4.6. Thyroid and antithyroid drugs 4.6.1. L-Thyroxine 4.6.2. L-Thyronine 4.6.3. Propylthiouracil 4.6.4.Methimazole 4. Endocrine system The endocrine system helps to maintain internal homeostasis through the use of endogenous chemicals known as hormones. A hormone is typically regarded as a chemical messenger that is released into the bloodstream to exert an effect on target cells located some distance from the hormonal release site. The endocrine system is a series of glands that produce hormones which regulate respiration, metabolism, growth and development, tissue function, sexual function, reproduction etc. Endocrine glands are ductless glands of the endocrine system that secrete their products, hormones, directly into the blood. The major glands of the endocrine system include the pineal gland, pituitary gland, pancreas, ovaries, testes, thyroid gland, parathyroid gland, hypothalamus and adrenal glands (Fig.
    [Show full text]
  • Introduction (Pdf)
    Dictionary of Natural Products on CD-ROM This introduction screen gives access to (a) a general introduction to the scope and content of DNP on CD-ROM, followed by (b) an extensive review of the different types of natural product and the way in which they are organised and categorised in DNP. You may access the section of your choice by clicking on the appropriate line below, or you may scroll through the text forwards or backwards from any point. Introduction to the DNP database page 3 Data presentation and organisation 3 Derivatives and variants 3 Chemical names and synonyms 4 CAS Registry Numbers 6 Diagrams 7 Stereochemical conventions 7 Molecular formula and molecular weight 8 Source 9 Importance/use 9 Type of Compound 9 Physical Data 9 Hazard and toxicity information 10 Bibliographic References 11 Journal abbreviations 12 Entry under review 12 Description of Natural Product Structures 13 Aliphatic natural products 15 Semiochemicals 15 Lipids 22 Polyketides 29 Carbohydrates 35 Oxygen heterocycles 44 Simple aromatic natural products 45 Benzofuranoids 48 Benzopyranoids 49 1 Flavonoids page 51 Tannins 60 Lignans 64 Polycyclic aromatic natural products 68 Terpenoids 72 Monoterpenoids 73 Sesquiterpenoids 77 Diterpenoids 101 Sesterterpenoids 118 Triterpenoids 121 Tetraterpenoids 131 Miscellaneous terpenoids 133 Meroterpenoids 133 Steroids 135 The sterols 140 Aminoacids and peptides 148 Aminoacids 148 Peptides 150 β-Lactams 151 Glycopeptides 153 Alkaloids 154 Alkaloids derived from ornithine 154 Alkaloids derived from lysine 156 Alkaloids
    [Show full text]
  • United States Patent Office Patented May 5, 1970
    3,510,477 United States Patent Office Patented May 5, 1970. 1. 2 3,510,477 a carboxylic acyl group having from one to about twelve 22-ETHYLENE-3-OXO-STEROIDS carbon atoms. AND INTERMEDIATES When the 4'-hydroxyspirosteroid-2,4'-m-dioxan-3-one Andrew John Manson, Beaconsfield, Quebec, Canada, as or ester thereof is subjected to mild alkaline conditions signor to Sterling Drug Inc., New York, N.Y., a cor the dioxane ring is cleaved to produce a 2-methylene-3- poration of Delaware oxo-steroid (III). The mild alkaline conditions are pro No Drawing. Continuation-in-part of application Ser. No. duced by contacting the steroid with a weak inorganic 502,394, Oct. 22, 1965. This application Oct. 4, 1967, Ser. No. 672,713 base, for example, an alkali metal carbonate or aluminum Claims priority, application Great Britain, Oct. 17, 1966, oxide. 46,383/66 0 The 2-methylene-3-oxo-steroid reacts with diazometh Int. C. C07c 173/10, 169/22, 169/12 ane to give a spirosteroid-2,3'(2'o)-1-pyrazolin-3-one U.S. C. 260-239.5 39 Claims (IV-A). The latter may in part rearrange to the isomeric spirosteroid-2,3’ (2'oz) - 5 - pyrazolin - 3 - one (IV-B) under the reaction conditions and work-up procedures ABSTRACT OF THE DISCLOSURE 5 used. The pyrazolines (IV-A and IV-B) in acid medium, or by simple pyrolysis, lose nitrogen and are converted to 2,2-ethylene-3-oxo-steroids are prepared starting from a 2,2-ethylene-3-oxo-steroid (V).
    [Show full text]