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黄体酮
孕酮 · 助孕素 · 激孕酮 · 保孕素 · 黄体素 · 黄体酮 · 孕烯二酮 · 黄体激素
标识与物理属性
| CAS No. | 57-83-0 |
|---|---|
| 分子式 | C21H30O2 |
| 平均分子量 | 314.5 g/mol |
| 单同位素质量 | 314.2245802 g/mol |
| SMILES | CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C |
| InChIKey | RJKFOVLPORLFTN-LEKSSAKUSA-N |
| PubChem CID | 5994 |
| ChEMBL | CHEMBL103 |
| ChEBI | CHEBI:17026 |
| EC No. | 200-350-6 |
| DTXSID | DTXSID3022370 |
| 中文名 | 黄体酮 |
化学与物理性质
| XLogP | 3.9 |
|---|---|
| 极性表面积 | 34.1 |
| 氢键供体 | 0 |
| 氢键受体 | 2 |
| 可旋转键 | 1 |
| 重原子 | 23 |
| 形式电荷 | 0 |
| 复杂度 | 589 |
| 物质类别 | CarcinogensHormone |
| 药物 | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Steroids |
| 脂质 | Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203] |
| 化妆品 | Cosmetics ingredient -> Other (Specify) |
| SpringerMaterials Properties | Chemical shift |
| LogP（油水分配系数） | log Kow = 3.87 |
| 气味 | Odorless |
| 密度 | 1.171 at 68 °F (NTP, 1992) - Denser than waterwill sink1.166 g/cu cm at 23 °Cd23 1.166d20 1.171 |
| Color/Form | PrismsWhite crystalline powderExists in two crystalline forms |
| 溶解性 | less than 1 mg/mL at 66 °F (NTP, 1992)<0.1 g/100 mL at 19 ºCSol in alcohol, acetone, dioxane /beta-Progesterone/Soluble in alcohol, acetone, dioxane, concentrated sulfuric acidsparingly soluble in vegetable oilsIn double-distilled water, 9.12 mg/LIn water, 8.81 mg/L at 25 °CH2O: 25 mg/mL, may be clear to slightly hazy |
| Human Drugs | Breast FeedingLactationMilk, HumanHormonesProgesterone CongenersFDA approved drugs -> Active ingredient |
| Animal Drugs | Active Ingredients (Progesterone) -> FDA GreenbookPharmaceuticals -> UK Veterinary Medicines Directorate ListPharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| 熔点 | 128-132 °C (lit.) |
| 比旋光度 | 186 º (c=1, ethanol) |
| 沸点 | 394.13°C (rough estimate) |
| 折射率 | 182 ° (C=2, Dioxane) |
| 闪点 | 2℃ |
| 储存条件 | room temp |
| 形态 | powder |
| 颜色 | Yellow to yellow-brown |
| 生物来源 | synthetic (organic) |
| Merck | 7773 |
| BRN | 1915950 |
| 亨利常数 | 1.5×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| BCS Class | 4 |
| 稳定性 | Stable. Incompatible with strong oxidizing agents. |
| 主要应用 | pharmaceutical (small molecule) |
| 化妆品成分功效 | SKIN CONDITIONING |
| InChI | 1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 |
| InChIKey | RJKFOVLPORLFTN-LEKSSAKUSA-N |
| SMILES | CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C |
| LogP（油水分配系数） | 3.870 |
| CAS 数据库 | 57-83-0(CAS DataBase Reference) |
| NIST化学物质信息 | Progesterone(57-83-0) |
| EPA化学物质信息 | Progesterone (57-83-0) |
化学性质
白色粉末状固体
安全与法规
| GHS 分类 | DangerH350 (12.2%): May cause cancer [Danger Carcinogenicity]P203, P260, P263, P264, P270, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 271 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 法规信息 | Hazard Traits - CarcinogenicityDirective (EC) No 74/2003Status: Cease Manufacture Update: 21-07-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/12218Progesterone: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| 其他安全信息 | IMAP assessments - Pregn-4-ene-3,20-dione: Human health tier I assessment |
| 火灾危害 | Flash point data for this compound are not availablehowever, it is probably combustible. (NTP, 1992) |
| 健康危害 | ACUTE/CHRONIC HAZARDS: This chemical may be absorbed through the skin. (NTP, 1992) |
| FDA 要求 | No residues of progesterone are permitted in excess of the following increments above the concentrations of progesterone naturally present in untreated animals: (a) In uncooked edible tissues of steers and calves: (1) 3 parts per billion for muscle. (2) 12 parts per billion for fat. (3) 9 parts per billion for kidney. (4) 6 parts per billion for liver. (b) In uncooked edible tissues of lambs: (1) 3 parts per billion for muscle. (2) 15 parts per billion for fat, kidney, and liver.Progesterone and estradiol benzoate. Conditions of use in cattle. It is used for implantation as follows: (1) Suckling beef calves ... For increased rate of weight gain ... (2) Steers ... For increased rate of weight gain and improved feed efficiency ... (3) Steers fed in confinement for slaughter ... For additional improvement in rate of weight gain.Progesterone intravaginal inserts. ... (1) Cows ... (A) For synchronization of estrus in suckled beef cows and replacement beef and dairy heifersfor advancement of first postpartum estrus in suckled beef cowsand for advancement of first pubertal estrus in replacement beef heifers. (B) For synchronization of estrus in lactating dairy cows. (C) For synchronization of the return to estrus in lactating dairy cows inseminated at the immediately preceding estrus. ... (2) Ewes ... For induction of estrus in ewes (sheep) during seasonal anestrus.The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including progesterone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Progesterone is included on this list. |
| 反应性基团 | Ketones |
| Special Reports | National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Progesterone (57-83-0) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s152prog.pdf] |
| Reactivity Profile | PROGESTERONE is sensitive to light (NTP, 1992). |
| Air and Water Reactions | Insoluble in water. |
| Hazard Classes and Categories | Carc. 1B (12.2%)Carcinogens |
| Hazardous Reactivities and Incompatibilities | A carcinogen. |
| 消防 | Fires involving this material can be extinguished with a foam, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| 急救 | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| 储存条件 | Parenteral progesterone preparations, progesterone capsules, progesterone vaginal inserts, and progesterone vaginal gel should be stored at 15-30 °C. |
| 非火灾泄漏应对 | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| 处置方法 | SRP: 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.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash. |
| Allowable Tolerances | No residues of progesterone are permitted in excess of the following increments above the concentrations of progesterone naturally present in untreated animals: (a) In uncooked edible tissues of steers and calves: (1) 3 parts per billion for muscle. (2) 12 parts per billion for fat. (3) 9 parts per billion for kidney. (4) 6 parts per billion for liver. (b) In uncooked edible tissues of lambs: (1) 3 parts per billion for muscle. (2) 15 parts per billion for fat, kidney, and liver. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992) |
| 相互作用 | Progesterone has been shown to increase cocaine's cardiovascular toxicity in sheep and rats. To determine whether progesterone enhances the lethality of cocaine, 50 non-pregnant female rats were treated with 8 mg/kg/day im progesterone for 3 days, and 45 non-pregnant control rats were given im injections of vehicle (peanut oil, benzoylbenzoate, and phenol). A third group consisted of 21 untreated d16 pregnant rats. On day 3 of injections, rats received one ip injection of cocaine at a dose between 25-75 mg/kg, and were observed for seizures and/or death. Three dose-response curves were constructed using logistic regression analysis. All 51 rats who died did so within 17 minutes, and 49 of these deaths were preceded by sudden seizures. Mean time-to-seizure and time-to-death did not significantly differ among groups. Serum progesterone levels (ng/ml + or - standard error of measurement) were significantly different: 23 + or - 2.3 (control), 102 + or - 9.9 (progesterone treated), and 144 + or - 11.5 (untreated pregnant). Logistic regression dose/fatality curves for the three groups were not significantly different based on the chi-square and likelihood ratio test (p= 0.81). The LD50s in mg/kg ip (95% confidence interval) were (control) 54.8 (49.6-60.5) (progesterone treated) 56.5 (50.3-63.6), and (untreated pregnant) 51.8 (42.2-63.5). Curves of cocaine dose vs isolated seizures plus deaths were not different between control and progesterone treated groups. Though progesterone enhances cocaine's cardiac toxicity, it does not increase the risk of death from acute cocaine exposure in rats.The effects of progesterone treatment on bupivacaine arrhythmogenicity in beating rat heart myocyte cultures and on anesthetized rats were determined. After determining the bupivacaine AD50 (the concentration of bupivacaine that caused 50% of all beating rat heart myocyte cultures to become arrhythmic), the effect of 1 hr progesterone hydrogen chloride exposure on myocyte contractile rhythm was determined. Each concentration of progesterone (6.25, 12.5, 25, and 50 ug/ml) caused a significant and concentration dependent reduction in the AD50 for bupivacaine. Estradiol treatment also increased the arrhythmogenicity of bupivacaine in myocyte cultures, but was only one fourth as potent as progesterone. Neither progesterone nor estradiol effects on bupivacaine arrhythmogenicity were potentiated by epinephrine. Chronic progesterone pretreatment (5 mg/kg/day for 21 days) caused a significant increase in bupivacaine arrhythmogenicity in intact pentobarbital anesthetized rats. There was a significant decrease in the time to onset of arrhythmia as compared with control nonprogesterone treated rats (6.2 + or - 1.3 vs 30.8 + or - 2.5 min, mean + or - standard error). The results of this study indicate that progesterone can potentiate bupivacaine arrhythmogenicity both in vivo and in vitro. Potentiation of bupivacain arrhythmia in myocyte cultures suggests that this effect is at least partly mediated at the myocyte level.10 mg progesterone injected sc twice weekly into 52 rabbits exposed to vaginal strings containing 3-methylcholanthrene did not affect incidence of vaginal tumors occurring within 20 months, incidences being 5/23 in controls compared with 4/30 in treated animals.Decreased efficacy of some progestins, ... has been suggested to be caused by enhanced metabolism of the progestins by these drugs /hepatic enzyme inducing medications, such as: carbamazepine, phenobarbital, phenytoin, rifabutin, rifampin/. /Progestins/For more Interactions (Complete) data for PROGESTERONE (6 total), please visit the HSDB record page. |
| 健康影响 | Chronically high levels of progesterone are associated with at least 3 inborn errors of metabolism including: Congenital adrenal hyperplasia, Adrenal Hyperplasia Type 3 and Adrenal hyperplasia type 5. |
| 生态毒性数值 | EC50Species: Strongylocentrotus purpuratus (Purple Sea Urchin, age 1 hr postfertilization embryo)Conditions: saltwater, static, 17 °CConcentration: 546.6 ug/L for 95 hr (95% confidence interval: 363.1-745.9 ug/L)Effect: increased abnormal development /100% purity/ |
| 环境归趋 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2,800(SRC), determined from a log Kow of 3.87(2) and a regression-derived equation(3), indicates that progesterone is expected to have slight mobility in soil(SRC). Volatilization of progesterone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.5X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Progesterone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.6X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2011).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2,800(SRC), determined from a log Kow of 3,87(2) and a regression-derived equation(3), indicates that progesterone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 6.5X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 170(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Biodegradation data were not available(SRC, 2011).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), progesterone, which has an estimated vapor pressure of 3.6X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase progesterone 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 1.2 hrs(SRC), calculated from its rate constant of 1.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase progesterone may be removed from the air by wet or dry deposition(SRC). Progesterone exhibits a lambda max of 240 nm(4) and absorbs light at wavelengths of 290 nmtherefore it may be susceptible to direct photolysis by sunlight(SRC). |
| 暴露途径 | Progesterone absorption is prolonged with an absorption half-life of approximately 25-50 hours. |
| Milk Concentrations | Progestins are reportedly distributed into milk. The possible effects of progestins in milk on nursing infants have not been determined. /Progestins General Statement/EXPERIMENTAL: Women who received 6 subdermal implants containing 100 mg each of progesterone between days 30 to 35 postpartum for contraception had milk progesterone levels measured. Milk progesterone levels were 5.7 ug/L in 6 women at 3 to 4 months postpartum and 6.3 ug/L in 7 women at 9 to 12 months postpartum. By comparison, 9 women who received a Copper T intrauterine device had negligible progesterone levels. The authors estimated that infants would receive about 5 ug of progesterone daily through breastmilk |
| 毒性概述 | Progesterone shares the pharmacological actions of the progestins. Progesterone binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like Progesterone will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. In women who have adequate endogenous estrogen, progesterone transforms a proliferative endometrium into a secretory one. Progesterone is essential for the development of decidual tissue and is necessary to increase endometrial receptivity for implantation of an embryo. Once an embryo has been implanted, progesterone acts to maintain the pregnancy. Progesterone also stimulates the growth of mammary alveolar tissue and relaxes uterine smooth muscle. It has little estrogenic and androgenic activity. |
| Plant Concentrations | Previously, the presence of a wide variety of chemically diverse steroids has been identified in both flora and fauna. Despite the relatively small differences in chemical structures and large differences in physiological function of steroids, new discoveries indicate that plants and animals are more closely related than previously thought. In this regard, the present study gathers supporting evidence for shared phylogenetic roots of structurally similar steroids produced by these two eukaryotic taxa. Definitive proof for the presence of progesterone in a vascular plant, Juglans regia /Walnut tree/ is provided. Additional evidence is gleaned from the characterization of five new plant steroids from Adonis aleppica /Ranunculaceae/: three 3-O-sulfated pregnenolones, a sulfated H-5beta carbenolide, strophanthidin-3-O-sulfate, and spirophanthigenin, a novel C-18 oxygenated spirocyclic derivative of strophanthidin. The ab initio isolation and structure elucidation (NMR, MS) of these genuine minor plant steroids offers information on preparative metabolomic profiling at the ppm level and provides striking evidence for the conserved structural space of pregnanes and its congeners across the phylogenetic tree. |
| Effluent Concentrations | Progesterone was estimated as present at a concentration of 3 ng/L in runoff water from agricultural fields irrigated with treated wastewater. The fields are located in the Calleguas Creek watershed in coastal Ventura County, southern California and sampled from July 1990 - April 2000method detection limit = 203 ng/L. It was present in applied effluent at a concentration of <10 ng/L. Progesterone was not detected in nearby streams(1). The concentration in typical raw sewage ranges from 0-0.02 ug/L(2). Progesterone was detected in effluent from the Eysines Sewage Treatment Plant (northern suburbs, Bordeaux, France) at a mean concentrations of <9.0 ng/L in July 2003 (detection limit = 9.0 ng/L)(3). Progesterone was tested for but not detected (method detection limits = 2-100 ng/L) in effluent samples from sewage treatment plants in the vicinity of Barcelona, Spain, sampled from April to June, 1999(4). It was detected in a typical dairy waste disposal system for 2000 dairy cows in San Jacinto, CA (ug/kg dry weight) as followsfresh manure less than 2 hrs old, less than the limit of quantificationpiled manure at 2 weeks, 196not detected in 3 lagoon dams at 3 months(5). |
| Soil Adsorption/Mobility | The Koc of progesterone is estimated as 2,800(SRC), using a log Kow of 3.87(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that progesterone is expected to have slight mobility in soil. |
| Natural Pollution Sources | Progesterone is the mammalian female sex hormone secreted by the corpus luteum, by the adrenal cortex, or by the placenta during pregnancy. It is believed to be the precursor of the adrenal steroid hormones(1).PROGESTERONE IS SECRETED BY THE OVARY MAINLY FROM CORPUS LUTEUM DURING SECOND HALF OF MENSTRUAL CYCLE. ... THE FORMATION OF PROGESTERONE FROM STEROID PRECURSORS ... OCCURS IN THE OVARY, TESTIS, ADRENAL CORTEX, AND PLACENTA. |
| Human Toxicity Excerpts | /CASE REPORTS/ This paper presents the /a/ case of progesterone-induced cyclical erythema multiforme. The patient, 33 years of age, suffered from recurrent pruritic annular and target lesions on the hands, feet, and trunk and oral laceration from 1977-83. She had taken oral contraceptives in 1972 without adverse effects. The eruptions began in the 2nd half of the menstrual cycle, worsened through the luteal phase, and were at their most florid on days 2-4 of menstrution. There was no relationship to estrogen levelshowever, the postovulatory progesterone peak, as indicated by serial serum progesterone levels, corresponded to the initiation of eruptions. Erythema multiforme was induced within 48 hours by intramuscular injection of 10 mg progesterone or 10 mg medroxyprogesteronethis further evoked a rise in circulating immune complexes for 48 hours. There was no indication that the erythema multiforme was associated with menstrual-linked herpes simplex or the use of analgesics during menstruation. Autoimmune progesterone dermatitis is often associated with prior exposure to synthetic progesterones, as in this case. It has been suggested that the synthetic progesterone acts as a stimulus for antibodies which cross-react with natural progesterone. The antiestrogen tamoxifern was used successfully in this case and is a valuable alternative to treatment with oophorectomy./CASE REPORTS/ /The authors/ report a case of acquired sideroblastic anaemia precipitated by progesterone. On two separate occasions, over 15 years apart, the patient developed sideroblastic anaemia with iron overload shortly after the administration of progesterone. No other cause for sideroblastic anaemia was found, and treatment with folic acid, pyridoxine or androgens corrected the anaemia. In both instances removal of the progestational agent led to prompt disappearance of the anaemia as well as the ringed sideroblasts. Using a two-phase liquid culture procedure in which human peripheral blood-derived progenitor cells undergo erythroid proliferation and differentiation, /investigators/ demonstrated enhanced sensitivity of the patient's erythroid progenitors to progesterone./CASE REPORTS/ Micronized natural progesterone is often prescribed alone or in association with beta-agonists in the treatment of preterm labor in France. /The authors/ observed drug-induced hepatitis in 4 such patients. The main manifestation of liver disease was pruritus. After drug withdrawal, elevated transaminase levels continued to rise for one week then normalized within 10 to 30 days. The imputability of this undesirable effect was assessed and considered to be likely. The effectiveness of micronized natural progesterone in the prevention of premature delivery and in decreasing perinatal mortality and morbidity has not yet been proven. This drug should therefore be used with care, keeping in mind the risk of hepatitis, particularly in patients presenting with pruritus./CASE REPORTS/ /The authors/ present a case of autoimmune progesterone anaphylaxis (AIPA) observed in an adolescent female. The patient is an 18-year-old Caucasian female with no significant past medical history and no prior exogenous hormone use, who presented to her primary care physician complaining of cyclic skin eruptions with dyspnea, cough and respiratory distress. She noted that her symptoms occurred monthly, just prior to her menses. An intradermal skin test using 0.1 cml /(sic)/ of progesterone was performed. The patient developed a 15 mm wheal after 15 minutes, confirming the diagnosis of AIPA. The patient was started on a continuous regimen of an oral conjugated estrogen (0.625 mg). The skin eruptions and respiratory symptoms have not returned since the initiation of this therapy. Autoimmune progesterone dermatitis manifests via the occurrence of cyclic skin eruptions. Women with the disorder commonly present with dermatologic lesions in the luteal phase of the menstrual cycle, if there are any other organ involvement in addition to skin (e.g. lung, GI) the reaction should be called as autoimmune progesterone anaphylaxis. Diagnosis of AIPA is confirmed by performing a skin allergen test using progesterone.For more Human Toxicity Excerpts (Complete) data for PROGESTERONE (14 total), please visit the HSDB record page. |
| 水危害等级（WGK） | 3 |
| TSCA 清单状态 | TSCA listed |
| 毒性 | LD50 intraperitoneal in rat: 327mg/kg |
| RTECS 号 | TW0175000 |
| 储存类别 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 安全说明（S） | 36/37-45-53-16 |
| 海关编码 | 29372390 |
| 危险品标志 | Xn,T,F |
| 危险类别 | Carc. 2Lact.Repr. 1A |
| 危险类别码（R） | 40-45-62-36-20/21/22-11 |
| 毒害物质数据 | 57-83-0(Hazardous Substances Data) |
| 运输编号（UN） | UN 1648 3 / PGII |
用途与应用
简介
孕酮（英语：progesterone，亦被称为黄体酮、孕甾酮、黄体甾酮、助孕激素、助孕素、黄体素或助孕酮，其缩写为P4，也被称为(孕甾-4-烯-3,20-二酮)，是一种内源性类固醇和孕激素性激素，也是在体内的主要孕激素，由女性的卵巢分泌。黄体酮是由卵巢黄体细胞分泌的一种含有21个碳原子的类固醇激素，也是合成一切类固醇激素的中间产物，属于孕激素之一。有两种晶型，即α-型和β-型，两种晶型有相同的生理活性，α-型是从稀乙醇中析出，为正交晶系白色棱柱状结晶，β-型为正交晶系白色针状结晶，二者均不溶于水，溶于乙醇、乙醚、氯仿、丙酮、二氧六环及浓硫酸。
用途
黄体酮在体内对雌激素激发过的子宫内膜有显著形态学影响，为维持妊娠所必须。在月经后期与雌激素一起促进子宫内膜发育增生，使之由增殖期变为分泌期，为受精卵着床和胚胎发育创造条件；在行经期使子宫内膜全部脱落；在妊娠期抑制子宫的运动和对催产素的敏感性，有安胎作用，并与雌激素一起促使乳腺进一步发育，为产乳作好准备；大剂量则能通过下丘脑-垂体前叶-卵巢轴的反馈调节作用，抑制垂体前叶分泌黄体生成素，从而抑制排卵，起到避孕作用。黄体酮可用于习惯性流产、先兆流产、子宫功能性出血、血崩症、痛经、子宫内膜异位症、闭经、输尿管结石。前列腺增生症、睡眠呼吸暂停综合征和顽固性肝硬化腹水等。
制备与合成方法
生产方法
醋酸孕甾双烯醇酮经催化氢化，碱水解，异丙醇铝氧化制得。
生产方法
由妊烯醇酮氧化得到。将干燥的甲苯加入干燥的反应锅内，加入环已酮及妊烯醇酮，搅拌溶解，蒸甲苯脱水至尽，迅速加入异丙醇铝，于115℃氧化反应2h，冷却至80℃左右，在搅拌下加入5%稀硫酸，静置分层，分去水层，甲苯层用水洗至中性后进行水蒸气蒸馏，蒸出甲苯及环已酮。冷却，过滤，滤渣用石油醚搅成浆状，过滤，以石油醚洗涤，干燥得黄体酮粗品。粗品溶于乙醇，用活性炭脱色，重结晶成品，收率80%。