Androgen and anabolic steroid
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Pharmaceutical compound
Oxymetholone Clinical data Trade names Anadrol, Anapolon, others Other names CI-406; NSC-26198; 2-Hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone; 2-Hydroxymethylene-17α-methyl-DHT; 2-Hydroxymethylene-17α-methyl-5α-androstan-17β-ol-3-one AHFS /Drugs.com Consumer Drug Information Pregnancy Dependence Moderate[ 1] Addiction Moderate[ 1] Routes of By mouth Drug class Androgen ;Anabolic steroid ATC code Legal status Legal status Pharmacokinetic dataBioavailability Well-absorbed[ 3] Metabolism Liver [ 3] [ 4] Eliminationhalf-life Unknown[ 4] Excretion Urine [ 3] [ 4] Identifiers (2Z ,5S ,8R ,9S ,10S ,13S ,14S ,17S )-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a ]phenanthren-3-one
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA) ECHA InfoCard 100.006.454 Chemical and physical data Formula C 21 H 32 O 3 Molar mass −1 3D model (JSmol ) InChI=1S/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12-/t14-,15+,16-,17-,19-,20-,21-/m0/s1
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Oxymetholone , sold under the brand namesAnadrol andAnapolon among others, is anandrogen andanabolic steroid (AAS) medication which is used primarily in the treatment ofanemia .[ 5] [ 6] osteoporosis ,HIV/AIDS wasting syndrome , and to promoteweight gain [ 7] muscle growth in certain situations.[ 5] by mouth .[ 5] [ 6]
Side effects of oxymetholone include increasedsexual desire as well assymptoms ofmasculinization likeacne ,increased hair growth , andvoice changes .[ 5] liver damage .[ 5] [ 6] synthetic androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).[ 5] [ 8] anabolic effects and weakandrogenic effects.[ 5]
Oxymetholone was first prescribed in 1959 and was introduced for medical use but was discontinued in 1961 due its high lipid toxicity.[ 5] [ 9] [ 10] [ 11] United States .[ 5] [ 12] improve physique and performance .[ 5] controlled substance in many countries and so non-medical use is generally illicit.[ 5]
The primary clinical applications of oxymetholone include treatment ofanemia andosteoporosis , as well as stimulatingmuscle growth in malnourished or underdeveloped patients.[ 5] United States , the only remainingFDA Tooltip Food and Drug Administration -approved indication is the treatment ofanemia .[ 5] [ 13]
Following the introduction of oxymetholone,nonsteroidal drugs such asepoetin alfa were developed and shown to be more effective as a treatment foranemia andosteoporosis without theside effects of oxymetholone.[ 5] HIV/AIDS wasting syndrome .[ 5]
Presented most commonly as a 50 mgtablet , oxymetholone has been said to be one of the "strongest" and "most powerful" AAS available for medical use.[ 5] [ 14] side effects .[ 15] [ 16] [ 5] bodybuilders andathletes .[ 5]
Oxymetholone is used forphysique- and performance-enhancing purposes bycompetitive athletes ,bodybuilders , andpowerlifters .[ 5]
The commonside effects of oxymetholone includedepression ,lethargy ,headache ,swelling , fast and excessiveweight gain ,priapism , changes in skin color, urination problems,nausea ,vomiting ,stomach pain (if taken on an empty stomach),loss of appetite ,jaundice ,breast swelling in men, feeling restless or excited,insomnia , anddiarrhea .[ 15] acne , changes inmenstrual periods ,voice deepening ,hair growth on the chin or chest ,pattern hair loss ,enlarged clitoris , and changes inlibido .[ 5] [ 15] hepatotoxic .[ 5] hepatitis ,liver cancer , andcirrhosis ; therefore periodicliver function tests are recommended for those taking oxymetholone.[ 16]
Like other AAS, oxymetholone is anagonist of theandrogen receptor (AR).[ 5] 5α-reductase (as it is already 5α-reduced) and is a poor substrate for3α-hydroxysteroid dehydrogenase (3α-HSD), and therefore shows a high ratio ofanabolic toandrogenic activity.[ 5]
As a DHT derivative, oxymetholone is not asubstrate foraromatase and hence cannot be aromatized intoestrogenic metabolites .[ 5] gynecomastia (rarely) andwater retention .[ 5] [ 17] [ 18] [ 19] estrogen receptor by oxymetholone.[ 5] progestogenic activity.[ 5]
There is limited information available on thepharmacokinetics of oxymetholone.[ 6] well-absorbed withoral administration .[ 6] affinity for human serumsex hormone-binding globulin (SHBG), less than 5% of that of testosterone and less than 1% of that of DHT.[ 3] metabolized in theliver byoxidation at the C2 position,reduction at the C3 position,hydroxylation at the C17 position, andconjugation .[ 6] [ 4] cleaved to formmestanolone (17α-methyl-DHT), which may contribute to the effects of oxymetholone.[ 5] elimination half-life of oxymetholone is unknown.[ 4] metabolites areeliminated in theurine .[ 3] [ 4]
Oxymetholone, also known as 2-hydroxymethylene-17α-methyl-4,5α-dihydrotestosterone (2-hydroxymethylene-17α-methyl-DHT) or as 2-hydroxymethylene-17α-methyl-5α-androstan-17β-ol-3-one, is asynthetic androstane steroid and a17α-alkylated derivative of DHT.[ 20] [ 21] [ 5]
Oxymetholone was first described in a 1959 paper by scientists fromSyntex .[ 5] [ 9] Syntex andImperial Chemical Industries in theUnited Kingdom under the brand name Anapolon by 1961.[ 10] [ 11] Parke-Davis ) by 1961 and Anadrol (Syntex) by 1962.[ 22] [ 23] [ 24] United States in the early 1960s.[ 5]
Society and culture [ edit ] Oxymetholone is thegeneric name of the drug and itsINN Tooltip International Nonproprietary Name ,USAN Tooltip United States Adopted Name ,USP Tooltip United States Pharmacopeia ,BAN Tooltip British Approved Name , andJAN Tooltip Japanese Accepted Name , whileoxymétholone is itsDCF Tooltip Dénomination Commune Française .[ 20] [ 21] [ 25] [ 12]
Oxymetholone has been marketed under a variety of brand names including Anadrol, Anadroyd, Anapolon, Anasterona, Anasteronal, Anasterone, Androlic, Androyd, Hemogenin, Nastenon, Oxitoland, Oxitosona, Oxyanabolic, Oxybolone, Protanabol, Roboral, Synasterobe, Synasteron, and Zenalosyn.[ 20] [ 21] [ 12] [ 5] [ 26]
Oxymetholone is one of the few AAS that remains available for medical use in theUnited States .[ 27] testosterone ,testosterone cypionate ,testosterone enanthate ,testosterone undecanoate ,methyltestosterone ,fluoxymesterone , andnandrolone [ 27]
The availability of oxymetholone is fairly limited and seems to be scattered into isolated markets inEurope ,Asia , andNorth andSouth America .[ 5] Turkey ,Greece ,Moldova ,Iran ,Thailand ,Brazil , andParaguay .[ 5] [ 12] Canada , theUnited Kingdom ,Belgium , theNetherlands ,Spain ,Poland , TheUAE ,Israel ,Hong Kong , andIndia .[ 21]
Oxymetholone, along with other AAS, is aschedule III controlled substance in theUnited States under theControlled Substances Act .[ 28]
^a b "Anabolic steroid misuse" .nhs.uk . 2022-11-04. Retrieved2024-07-12 .^ Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-15 .^a b c d e Saartok T, Dahlberg E, Gustafsson JA (June 1984). "Relative binding affinity of anabolic-androgenic steroids: comparison of the binding to the androgen receptors in skeletal muscle and in prostate, as well as to sex hormone-binding globulin".Endocrinology .114 (6):2100– 6.doi :10.1210/endo-114-6-2100 .PMID 6539197 . ^a b c d e f Hochadel M (1 April 2015).Mosby's Drug Reference for Health Professions ISBN 978-0-323-31103-8 ^a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae af ag ah William Llewellyn (2011).Anabolics 323– 334.ISBN 978-0-9828280-1-4 ^a b c d e f Pavlatos AM, Fultz O, Monberg MJ, Vootkur A (June 2001). "Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid".Clinical Therapeutics .23 (6):789– 801, discussion 771.doi :10.1016/s0149-2918(01)80070-9 .PMID 11440282 . ^ "Oxymetholone Powder Uses" .aea.ltd . Retrieved2022-12-17 .^ Kicman AT (June 2008)."Pharmacology of anabolic steroids" .British Journal of Pharmacology .154 (3):502– 21.doi :10.1038/bjp.2008.165 .PMC 2439524 PMID 18500378 . ^a b Zderic JA, Carpio H, Ringold HJ (January 1959). "Steroids. CVI. Synthesis of 7β-Methyl Hormone Analogs".Journal of the American Chemical Society .81 (2):432– 436.Bibcode :1959JAChS..81..432Z .doi :10.1021/ja01511a041 . ^a b "Advertisements" .Proceedings of the Royal Society of Medicine .54 (3): XLI. 1961.PMC 1870224 ^a b "Advertisements" .British Medical Journal .1 (5224). 1961.PMC 1953122 ^a b c d "Oxymetholone" .^ "Oxymetholone" .AdisInsight . Springer Nature Switzerland AG.^ "Anadrol-50" (PDF) . Meda Pharmaceuticals. December 2006. Archived fromthe original (PDF) on 11 June 2014. Retrieved8 January 2012 .^a b c "Oxymetholone Side Effects" . drugs.com.^a b "Anadrol Official FDA Information, Side Effects and Uses" . drugs.com.^ Hengge UR, Stocks K, Wiehler H, Faulkner S, Esser S, Lorenz C, et al. (March 2003)."Double-blind, randomized, placebo-controlled phase III trial of oxymetholone for the treatment of HIV wasting" .AIDS .17 (5):699– 710.doi :10.1097/00002030-200303280-00008 PMID 12646793 .S2CID 29998317 . ^ Cortesgallegos V, Castaneda G, Alonso R, Perezpasten E, Reyeslugo V, Barron C, Mondragon L, Villalpando S (January 1982). "Spontaneous and Oxymetholone-Induced Gynecomastia".Journal of Andrology .3 (1). C/O Allen Press, Inc Po Box 368, Lawrence, Ks 66044: Amer Soc Andrology, Inc.: 33. ^ Villalpando S, Mondragon L, Barron C, Reyeslugo U, Perezpasten E, Alonso R, Castaneda G, Gallegos V (January 1982). "5-Alpha Reductase Blockade May Be Responsible for Spontaneous and Oxymetholone-Induced Gynecomastia".Archivos de Investigacion Medica .13 (2). Social Apdo Postal 73-032, Mexico Df 03020, Mexico: Inst Mexicano Seguro.: s13. ^a b c Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^a b c d Index Nominum 2000: International Drug Directory ISBN 978-3-88763-075-1 ^ Locum R (1961)."Latest Pharmaceutical Preparations" (PDF) .The Central African Journal of Medicine .7 (11):443– 444. ^ Clark GM (August 1962). "New drugs in rheumatic disease".Arthritis and Rheumatism .5 (4):415– 8.doi :10.1002/art.1780050411 .PMID 13879693 . ^ Matusow PD (1962)."If - Then; C.A.M.S.I.; In the future" (PDF) .Dalhousie Medical Journal .15 (1). ^ Morton IK, Hall JM (6 December 2012).Concise Dictionary of Pharmacological Agents: Properties and Synonyms ISBN 978-94-011-4439-1 ^ Kochakian CD (6 December 2012).Anabolic-Androgenic Steroids ISBN 978-3-642-66353-6 ^a b "Drugs@FDA: FDA Approved Drug Products" . United States Food and Drug Administration. Retrieved17 December 2016 .^ Karch SB (21 December 2006).Drug Abuse Handbook, Second Edition ISBN 978-1-4200-0346-8 Pavlatos AM, Fultz O, Monberg MJ, Vootkur A (June 2001). "Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid".Clinical Therapeutics .23 (6):789– 801, discussion 771.doi :10.1016/s0149-2918(01)80070-9 .PMID 11440282 .
Androgens AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor antagonists Steroidogenesis
Antigonadotropins D2 receptor antagonists (prolactin releasers ) (e.g.,domperidone ,metoclopramide ,risperidone ,haloperidol ,chlorpromazine ,sulpiride )Estrogens (e.g.,bifluranol ,diethylstilbestrol ,estradiol ,estradiol esters ,ethinylestradiol ,ethinylestradiol sulfonate ,paroxypropione )GnRH agonists (e.g.,leuprorelin )GnRH antagonists (e.g.,cetrorelix )Progestogens (incl.,chlormadinone acetate ,cyproterone acetate ,hydroxyprogesterone caproate ,gestonorone caproate ,medroxyprogesterone acetate ,megestrol acetate )Others
ER Tooltip Estrogen receptor
Agonists Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g.,testosterone andesters ,methyltestosterone ,metandienone (methandrostenolone) ,nandrolone andesters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estrofurate Estrogenic substances Estromustine Estrone Etamestrol (eptamestrol) Ethinylandrostenediol Ethinylestradiol Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g.,anethole ,anol ,dianethole ,dianol ,photoanethole )Chalconoids (e.g.,isoliquiritigenin ,phloretin ,phlorizin (phloridzin) ,wedelolactone )Coumestans (e.g.,coumestrol ,psoralidin )Flavonoids (incl.7,8-DHF ,8-prenylnaringenin ,apigenin ,baicalein ,baicalin ,biochanin A ,calycosin ,catechin ,daidzein ,daidzin ,ECG ,EGCG ,epicatechin ,equol ,formononetin ,glabrene ,glabridin ,genistein ,genistin ,glycitein ,kaempferol ,liquiritigenin ,mirificin ,myricetin ,naringenin ,penduletin ,pinocembrin ,prunetin ,puerarin ,quercetin ,tectoridin ,tectorigenin )Lavender oil Lignans (e.g.,enterodiol ,enterolactone ,nyasol (cis -hinokiresinol) )Metalloestrogens (e.g.,cadmium )Pesticides (e.g.,alternariol ,dieldrin ,endosulfan ,fenarimol ,HPTE ,methiocarb ,methoxychlor ,triclocarban ,triclosan )Phytosteroids (e.g.,digitoxin (digitalis ),diosgenin ,guggulsterone )Phytosterols (e.g.,β-sitosterol ,campesterol ,stigmasterol )Resorcylic acid lactones (e.g.,zearalanone ,α-zearalenol ,β-zearalenol ,zearalenone ,zeranol (α-zearalanol) ,taleranol (teranol, β-zearalanol) )Steroid -like (e.g.,deoxymiroestrol ,miroestrol )Stilbenoids (e.g.,resveratrol ,rhaponticin )Synthetic xenoestrogens (e.g.,alkylphenols ,bisphenols (e.g.,BPA ,BPF ,BPS ),DDT ,parabens ,PBBs ,PHBA ,phthalates ,PCBs )Others (e.g.,agnuside ,rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
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