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HCID 6128생성일: 2026년 10월 27일

안드로스트-4-엔-3,17-다이온

안드로스트-4-엔-3,17-다이온 · 4-AD · 4-ANDROSTENE-3,17-DIONE · 4-ANDROSTENEDIONE · ANDROSTENDIONE · ANDROSTA-4-ENE-3,17-DIONE · Androstenedione (CRM) · skf2170

https://huagongshe.com/ko/chemical/6128

안드로스트-4-엔-3,17-다이온 분자 구조식

식별자 및 물리적 특성

CAS No.63-05-8
분자식C19H26O2
평균 분자량286.4 g/mol
단동위원소 질량286.19328007 g/mol
SMILESC[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
InChIKeyAEMFNILZOJDQLW-QAGGRKNESA-N
PubChem CID6128
ChEMBLCHEMBL274826
ChEBICHEBI:16422
EC No.200-554-5
DTXSIDDTXSID8024523
현지명안드로스트-4-엔-3,17-다이온

화학 및 물리적 성질

XLogP2.7
극성 표면적34.1
수소 결합 공여자 수0
수소 결합 수용자 수2
회전 가능 결합 수0
무거운 원자 수21
형식 전하0
복잡도546
물질 분류Hormone
의약품DEA Schedule III Controlled Substance -> Anabolic steroidsPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
지질Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]
SpringerMaterials PropertiesChemical shift
LogP(분배 계수)log Kow = 2.75
밀도1.18 g/cu cm at 20 °C (GLP compliance study)1.0655 (rough estimate)
Color/FormCrystals from hexane
용해도In water, 57.3 mg/L at 25 °C, pH 7.340 mg/L at 37 °C, pH 7.4In water, 66 mg/L at 20 °C, pH 6.5 (EU Method A.6, Water Solubility, flask method)0.0578 mg/mLChloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Sparingly)
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
끓는 점Decomposes at 200 °C before boiling368.77°C (rough estimate)
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
녹는점170-171 °C(lit.)
굴절률1.4709 (estimate)
인화점2℃
저장 조건Controlled Substance, -20°C Freezer
물리적 상태고체
색상아세톤에서 바늘 모양으로 또는 헥산에서 결정체로 결정화
용해도57.28mg/L(25℃)
Merck13,643
헨리 상수2.7×102 mol/(m3Pa) at 25℃, HSDB (2015)
InChI1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChIKeyAEMFNILZOJDQLW-QAGGRKNESA-N
SMILES[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)C(=O)CC[C@@]24[H]
NISTAndrost-4-ene-3,17-dione(63-05-8)
EPA4-Androstenedione (63-05-8)

화학적 성질

White to Off-White Solid

안전 및 규제

GHS 분류DangerH302 (97.9%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P263, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보Hazard Traits - CarcinogenicityDEA schedule III controlled substanceStatus: Active Update: 15-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13632Androstenedione: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
FDA 요건Schedule III shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Each drug or substance has been assigned the DEA Controlled Substances Code Number set forth opposite it. ... Anabolic Steroids. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture or preparation containing any quantity of the following substances, including its salts, esters and ethers. Anabolic steroids /including 4-androstenedione/, DEA Code 4000, is included on this list.
Hazard Classes and CategoriesAcute Tox. 4 (97.9%)
처리 방법SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
체내 부담In sixty random serum samples collected from male and female volunteers, androstenedione levels ranged from 0.15-4.78 nmol/L(1).
상호 작용Concentrations of intratesticular (IT) testosterone (T) are known to be 100-200 times those of serum Thowever, the IT concentrations of T's precursors, their testicular to serum gradients, gonadotropin dependence, and response to stimulation with human chorionic gonadotropin (hCG) have not been studied in detail. We hypothesized that serum and IT androstenedione (ADD) and IT dehydroepiandrosterone (DHEA) would be significantly suppressed by the administration of a GnRH antagonist and increased when stimulated by hCG, without a similar suppression of serum DHEA. We suppressed gonadotropins in 23 normal men with the GnRH antagonist acyline and randomly assigned them to one of four doses of hCG, 0, 15, 60, or 125 IU sc every other day for 10 d. Blood and IT fluid for the measurement of serum and IT hormones were obtained at baseline and after 10 d of treatment. Baseline IT ADD [median (25th, 75th percentile)] was 629 (308, 860) nmol/liter, and IT DHEA was 564 (411, 879) nmol/liter, which were 175 and 27 times higher than their respective serum concentrations. IT ADD and IT DHEA were suppressed by 98 and 82%, respectively, by acyline and significantly increased with hCG administration. Likewise, serum ADD was suppressed by 50%, but serum DHEA was unchanged. ADD and DHEA are highly concentrated within the human testes compared with serum. Serum and IT ADD and IT DHEA are markedly suppressed with GnRH administration and stimulated by hCG, but serum DHEA is not, suggesting that most circulating DHEA is not of testicular origin.

용도

개요

Androstenedione (CRM) (Item No. ISO60161) is a certified reference material categorized as an anabolic androgenic steroid. Androstenedione is a precursor of testosterone (Item Nos. ISO60154 | ISO00154 | 15645) and estrone . Androstenedione is regulated as a Schedule III compound in the United States. Androstenedione (CRM) (Item No. ISO60161) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.

용도

Testosterone precursor and metabolite with androgenic activity. Controlled substance (anabolic sterid)

Anticoagulant effects of coumarin- or indandione-derivative or anti-inflammatory analgesics, nonsteroidal or salicylates, in therapeutic doses may be increased during concurrent use with anabolic steroids, especially 17-alpha-alkylated compounds, because of decreased procoagulant factor concentration caused by alteration of procoagulant factor synthesis or catabolism and increased receptor affinity for the anticoagulant
anticoagulant dosage adjustment based on prothrombin time determinations may be required during and following concurrent use with anabolic steroids. /Anabolic Steroids/
Concurrent use of antidiabetic agents, sulfonylurea or insulin with anabolic steroids may decrease blood glucose concentration
diabetic patients should be closely monitored for signs of hypoglycemia ... /Anabolic Steroids/
Concurrent use of corticosteroids, glucocorticoid, especially with significant mineralocorticoid activity, prolonged therapeutic corticotropin or sodium-containing medications or foods with anabolic steroids may increase the possibility of edema
in addition, concurrent use of glucocorticoids or corticotropin with anabolic steroids may promote development of severe acne. /Anabolic Steroids/
For more Interactions (Complete) data for Androstenedione (7 total), please visit the HSDB record page.
건강 영향Androstenedione was legally defined as an anabolic steroid by the FDA in 2004. It poses significant health risks commonly associated with steroids. The side effects for men include breast development, behavioral changes, heart disease, and more. Side effects for women are similar to the side effects from anabolic steroids in that their voices will deepen and they may grow facial hair since both occur from an increase level of testosterone. Another side effect of androstenedione is male pattern baldness. The main psychological side effect of androstenedione is depression. Mood swings are also common. Chronically high levels of androstenedione are associated with male pseudohermaphrodism with gynecomastia, Adrenal Hyperplasia Type 3 and Aromatase deficiency.
환경 거동TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 6170(2) indicates that androstenedione is expected be immobile in soil(SRC). Volatilization of androstenedione from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.7X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Androstenedione is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 7.35X10-9 mm Hg at 20 °C(4). Using OECD Guideline 301B (CO2 Evolution Test) with a non-adapted activated sludge inoculum, androstenedione reached 79-95% degradation over a 28-day incubation period which classified the compound as readily biodegradable(4). Based on the results of soil column studies with various soils and sands(2), the estimated half-life of androstenedione ranged from 1.7 to 77 hours(SRC). Androstenedione absorbs at wavelenghts >290 nm(5), and direct photolysis tests in water(5) suggest that androstenedione is expected to be susceptible to photodegradation on soil surfaces exposed to sunlight(SRC).AQUATIC FATE: Based on a classification scheme(1), a Koc value of 6170(2) indicates that androstenedione is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.7X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 30(SRC), from a log Kow of 2.75(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). Using OECD Guideline 301B (CO2 Evolution Test) with a non-adapted activated sludge inoculum, androstenedione reached 79-95% degradation over a 28-day incubation period which classified the compound as readily biodegradable(7). Androstenedione absorbs at wavelenghts >290 nm(8), and, therefore, may be susceptible to direct photolysis at water surfaces exposed to sunlight(SRC). In photodegradation studies in aqueous solution, androstenedione underwent direct photolysis half-lives ranging from 3.7 to 10.8 hours in direct sunlight(8). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), androstenedione, which has an extrapolated vapor pressure of 7.35X10-9 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase androstenedione is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 3.5 hours(SRC), calculated from its rate constant of 1.1X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase androstenedione is also degraded in the atmosphere by reaction with ozone(SRC)the half-life for this reaction in air is estimated to be 1 day(SRC), calculated from its rate constant of 1.1X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase androstenedione may be removed from the air by wet and dry deposition(SRC). Androstenedione absorbs at wavelenghts >290 nm(4), and therefore, may be susceptible to direct photolysis(SRC). Androstenedione underwent direct photolysis half-lives ranging from 3.7 to 10.8 hours in aqueous solution via sunlight exposure(4).
노출 경로Endogenous, ingestion
독성 요약IDENTIFICATION AND USE: Androstenedione is a synthetic analog of androgens, formerly used as a dietary supplement. HUMAN STUDIES: There are cases of androstenedione-induced impotence and severe oligospermia. The effects of androstenedione supplementation on the hormonal profile of 10 males and its interaction with resistance exercise have been studied. Exercise elevated testosterone, with no difference between conditions. Exercise in the supplemented condition significantly elevated plasma estradiol by approximately 83% for 90 min. Androstenedione supplementation, thus, is unlikely to provide male athletes with any anabolic benefit and, with heavy resistance exercise, elevates estrogen. Other study suggested that oral androstenedione, when given in dosages of 300 mg/day, increased serum testosterone and estradiol concentrations in some healthy men. However, supplementation does result in significant increases in estrogen-related compounds, dehydroepiandrosterone sulfate concentrations, down-regulation in testosterone synthesis, and unfavorable alterations in blood lipid and coronary heart disease risk profiles of men aged 35 to 65 years. ANIMAL STUDIES: Androstenedione did not reveal a skin sensitization potential when tested in a guinea pig maximization test with a concentration of 5% for intradermal induction and 25% for epicutaneous induction and challenge following. Eye irritation was reported in rabbits. A single oral dose of androstenedione to male rats caused mortality at 1000 mg/kg, whereas animals survived at 500 mg/kg. Compound-related clinical signs were apathy, disturbance of gait and squatting position. At the lethal dose, additional signs included prone position, unconsciousness, disturbance in respiration and increased diuresis. The once daily oral administration of androstenedione to male and female rats over 4 weeks at doses of 0, 15, 50 and 150 mg/kg led to dose-dependent effects in females, such as increased body weight, atrophy of uterus, cervix, pituitary gland and adrenals, as well as increased numbers of erythrocytes and increased hemoglobin. For males alterations in thymus were reported. These effects were regarded to represent endocrine effects typical for a steroid hormone. Infusion of androstenedione to pregnant monkeys resulted in the premature occurrence of labor-type myometrial activity and increases in maternal plasma estrogen, oxytocin and amnion fibronectin concentrations similar to those measured at normal-term labor. In rats, androstenedione had no specific effect on the development of individual bones or soft tissues. Androstenedione did not show a mutagenic potential in a bacterial reverse mutation assay according to OECD TG 471 (Ames test in S. typhimurium TA98, TA1537, TA100, TA102, TA1535) when tested up to the highest recommended dose level of 5.0 mg/plate in the absence or presence of metabolic activation. ECOTOXICITY STUDIES: Exposure to androstenedione via water can cause masculinization of adult female mosquitofish in a relatively short period of time. Exogenous androstenedione, at environmentally relevant concentrations, can significantly modulate the reproductive physiology of the fathead minnows in a sex-specific manner.Androstenedione is converted to testosterone and estrogen, and when taken in sufficient quantities androstenedione can cause unwanted masculinizing and feminizing effects. Androstenedione is considered an androgenic steroid precursor because testosterone is an androgen or male hormone. In males, conversion of androstenedione to testosterone requires the enzyme 17β-hydroxysteroid dehydrogenase. In females, conversion of androstenedione to estrogen (e.g., estrone and estradiol) requires the enzyme aromatase.
생태독성 발췌/AQUATIC SPECIES/ In this study, ...the capacity of androstenedione to masculinize female mosquitofish /was investigated/. Previous studies have identified androstenedione in the water and sediment of the Fenholloway River, a Florida, USA, coastal river that receives paper mill effluent and contains masculinized eastern mosquitofish (Gambusia holbrooki). Females of the closely related western mosquitofish, Gambusia affinis, were exposed to androstenedione through both dietary and static renewal treatments. Morphological masculinization of female mosquitofish is characterized by the development of a male secondary sexual trait: an elongated and modified anal fin (gonopodium). Dietary exposure to 0.7, 7, 70, and 700 ug of androstenedione per gram of food failed to induce gonopodial development at any concentration within the six-week exposure period. Static renewal treatments used androstenedione concentrations of 0.14, 1.4, 14, 140, and 350 nM. Significant anal fin ray elongation was observed in all but the lowest exposure group. Fish growth during the static renewal exposure experiment was negatively correlated with androstenedione concentration. No significant effects were observed for gonadosomatic index, vitellogenin expression, or ovarian area in fish exposed to androstenedione via either the dietary or static renewal methods. These results indicate that exposure to androstenedione via water can cause masculinization of adult female mosquitofish in a relatively short period of time and that acute dietary exposure to androstenedione at the concentrations used is not sufficient to induce masculinization./AQUATIC SPECIES/ High concentrations (300 ng/L) of androstenedione (A4) were identified in snowmelt runoff from fields fertilized with manure from livestock feeding operations in Wisconsin, USA. In fishes, A4 is an active androgen and substrate for biosynthesis of functional androgens (e.g., testosterone and 11-ketotestosterone) and estrogens (e.g., estradiol-17beta). Thus, A4 has the potential to be a powerful endocrine disruptor. This hypothesis was tested by exposing reproductively mature fathead minnows to 0.0 ng/L, 4.5 ng/L, 74 ng/L, and 700 ng/L A4 for 26 days in a flow-through system. Various reproductive endpoints were measured including fecundity, fertilization success, secondary sexual characteristics, gonadosomatic index (GSI), and hepatic vitellogenin messenger RNA (mRNA) expression. In addition, fertilized embryos from the reproduction assay were used in an embryonic development assay to assess A4 effects on development and hatchability. In males, A4 significantly increased Vtg mRNA expression (estrogenic effect), significantly reduced GSI, and had no effect on tubercle expression (p=0.067). In females, A4 induced tubercle development (androgenic effect) with no effects on GSI. Fecundity was not significantly impacted. Exposure to A4 had no effect on fertilization, embryonic development, or hatchability. These data indicate that exogenous A4, at environmentally relevant concentrations, can significantly modulate the reproductive physiology of the fathead minnows in a sex-specific manner and that A4 should be monitored as an endocrine disruptor./AQUATIC SPECIES/ Standard reproductive assays with daphnids involve parthenogenetically reproducing females and exclude the assessment of effects on sexual reproduction. The goals of this study were to characterize sexual differentiation of male and female daphnids (Daphnia magna) and to evaluate whether exposure to putative endocrine-disrupting chemicals may perturb the development of sex characteristics. Anatomical sex differences that developed during maturation in males included elongated first antennae and morphologic alterations in the head capsule and carapace edge. Reproductive maturation in females was associated with the development of a brood chamber and abdominal process. Alterations in the growth rates of the first antennae of males and the abdominal process of females were used to evaluate the effects of chemical exposure on the development of these sex characteristics during maturation. Exposure of female daphnids to the nonsteroidal vertebrate estrogen diethylstilbesterol and the insect juvenile hormone analog methoprene at concentrations as low as 3.0 and 0.080 uM, respectively, stimulated development of the abdominal process. Exposure of males to the steroidal vertebrate androgen androstenedione (> or = 6.0 uM) stimulated development of the first antennae. These results demonstrate that the development of secondary sex characteristics in daphnids can be altered by chemical exposure.
Plant ConcentrationsAndrostenedione occurrence in plants(1).[Table#6924]
Signs and SymptomsBreast development (in men), behavioral changes, heart disease, male pattern baldness and depression. Side effects for women include a deepening and they may grow facial hair. In children or fetuses high levels of androstenedione (CAH) can lead to a number of changes. Females with congenital adrenal hyperplasia are born with an enlarged clitoris and normal internal reproductive tract structures. Males have normal genitals at birth. CAH causes abnormal growth for both sexespatients will be tall as children and short as adults. Females develop male characteristics, and males experience premature sexual development.
Ongoing Test StatusEPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of July 27, 2017: http://actor.epa.gov/dashboard/]The following link will take the user to the National Toxicology Program (NTP) Test Status of Agents Search page, which tabulates the results and current status of tests such as "Short-Term Toxicity Studies", "Long-term Carcinogenicity Studies", "Developmental Studies", "Genetic Toxicology Studies", etc., performed with this chemical. Testing status for androstenedione is available.[Available from, as of April 24, 2017: https://ntpsearch.niehs.nih.gov/?e=True&ContentType=Testing+Status]
Effluent ConcentrationsSampling at drinking water treatment plants in France during 2007-2008 detected androstenedione at concentrations of 0.1-2.1 ng/L in the influent waters (surface waters) and not detectable (0.04 ng/L)-2.8 ng/L in the effluent drinking water(1). Androstenedione was detected in STP (sewage treatment plant) effluents sampled from Beijing, China in 2006(2) and in 2008(3).
Soil Adsorption/MobilityThe Koc of androstenedione has been measured as log 3.79 (Koc of 6170) in Drummer soil, a silty clay sand soil, organic content of 2.91%(1). According to a classification scheme(2), this Koc value suggests that androstenedione is expected to be immobile in soil.
수질 위해 등급(WGK)3
RTECS 번호BV8150000
운송 번호(UN)UN 1648 3 / PGII
관세 코드29372900
위험 문구(R)40-64-52-22-61-60-36-20/21/22-11
위험 표시Xn,T,F
안전 문구(S)22-24/25-36-45-36/37-53-26-16
위험 등급Acute Tox. 4 OralCarc. 2Lact.Repr. 1A
저장 분류6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터63-05-8(Hazardous Substances Data)