Megestrol Acetate 醋酸孕甾酮

CAS 595-33-5 MFCD00056470

化学结构图

595-33-5
SMILES: CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C

化学属性

Mol. FormulaC24H32O4
Mol. Weight385
Appearance White to off-white solid powder 白色或微黄色结晶性粉末（甲醇），无嗅无味。熔点214-216℃ 。溶于丙酮，微溶于乙醇、乙醚，不溶于水。
Melting Point214
Refractive index11 ° (C=2, CHCl3)
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical NameMegestrol Acetate
Synonym 17α-羟基-6-甲基-6-去氢孕酮 17-乙酸酯 17-alpha-Acetoxy-6-dehydro-6-methylprogesterone 17-alpha-Acetoxy-6-methyl-4,6-pregnadiene-3,20-dione 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione acet 17ALPHA-HYDROXY-6-METHYL-4,6-PRE 17alpha-acetoxy-6-methylpregna-4,6-diene-3,20-d 17α-Acetoxy-6-methyl-4,6-pregnadiene-3,20-dione 17α-乙酰氧基-6-甲基孕甾-4,6-二烯-3,20-二酮 17α-羟基-6-甲基-6-去氢孕酮 17-乙酸酯 17α-羟基-6-甲基孕甾-4,6-二烯-3,20-二酮 17-乙酸酯 甲地孕酮 17-乙酸酯 4,6-PREGNADIEN-6-METHYL-17-OL-3,20-DIONE ACETATE 6-Dehydro-6-methyl-17alpha-acetoxyprogesterone 6-dehydro-6-methyl-17-alpha-acetoxyprogesterone 6-dien 6-methyl-17-alpha-hydroxy-delta(sup6)-progesteroneacetate 6-甲基孕甾-4,6-二烯-17α-醇-3,20-二酮-17-醋酸酯 BDH 1298; BDH1298; BDH-1298; Megace; Ovaban; Pallace. Maygace; Megestil; Niagestin. DMAP MEGESTROL
MDL NumberMFCD00056470
PubChem Substance ID87560201
Beilstein Registry Number1917291
CAS Number595-33-5
EC Number209-864-5
Chemical Name Translation醋酸孕甾酮
Reaxys-RN1917291
Merck Number5805
Wiswesser Line NotationL E5 B666 OV KU MUTJ A1 E1 FV1 FOV1 L1
LabNetwork Molecule IDLN01299023
FormulaC24H32O4
IUPAC Name(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate
InChIKeyRQZAXGRLVPAYTJ-GQFGMJRRSA-N
InChIInChI=1S/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h12-13,18-20H,6-11H2,1-5H3/t18-,19+,20+,22-,23+,24+/m1/s1
Canonical SMILESCC(O[C@]1(C(C)=O)CC[C@@]2([H])[C@]3([H])C=C(C)C4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O)=O
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分类

  • {SNA} Analytical Standards, Chromatography, Pharmaceutical Standards, Pharmacopeia Standards, USP Standards, USP Standards L - M, 分析/色谱
  • {SNA} Additional Standards, Analytical Standards, Chemical Structure, Chromatography, Drugs & Metabolites, Drugs of Abuse, Forensic and Veterinary Standards, Neat Compounds, Steroid, 分析/色谱
  • {SNA} Alphabetical Index of Analytical Standards, Analytical Standards, Chemical Structure, Chromatography, Drugs & Metabolites, Drugs of Abuse,
  • {SNA} Analytical Standards, Pharmacopeia Metrological Institutes Standards, USP Standards,

产品应用

  • Megestrol acetate is the acetate ester of megestrol, a synthetic derivative of the naturally occurring female sex hormone progesterone, with progestogenic, antiestrogenic, and antineoplastic activities. Mimicking the action of progesterone, megestrol binds to and activates nuclear progesterone receptors (PRs) in the reproductive system and pituitary; ligand-receptor complexes are translocated to the nucleus where they bind to progesterone response elements (PREs) located on target genes.

相关文献及参考

  • Merck 14 ,5805

安全信息

RTECSTU4075000
GHS Symbol
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P308+P313
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H351 Suspected of causing cancer 怀疑致癌
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
Hazard Codes Xn
WGK Germany3
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
Signal word Warning
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
Risk Statements
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
  • R48 Danger of serious damage to health by prolonged exposure 长期接触有严重损害健康的危险
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : 256 mg/kg/7Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Skin and Appendages - tumors
   Endocrine - diabetes mellitus
REFERENCE :
   JTEHD6 Journal of Toxicology and Environmental Health.  (Hemisphere Pub.,
   1025 Vermont Ave., NW, Washington, DC 20005)  V.1-    1975/76-
   Volume(issue)/page/year: 3,167,1977

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Mammal - dog
DOSE/DURATION           : 182 mg/kg/2Y-C
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Skin and Appendages - tumors
REFERENCE :
   JAMAAP JAMA, Journal of the American Medical Association.  (AMA, 535 N.
   Dearborn St., Chicago, IL 60610)  V.1-    1883-  Volume(issue)/page/year:
   219,1601,1972

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 56 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems
   Laboratory, NIOSH Exchange Chemicals.  (Aberdeen Proving Ground, MD 21010)
   Volume(issue)/page/year: NX#00931

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 30 umol/L
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 16,1483,1995

TYPE OF TEST            : Unscheduled DNA synthesis
ROUTE OF EXPOSURE       : Subcutaneous
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 200 mg/kg
REFERENCE :
   JOENAK Journal of Endocrinology.  (Biochemical Soc. Book Depot, POB 32,
   Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1939-
   Volume(issue)/page/year: 60,167,1974

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Human Liver
DOSE/DURATION           : 20 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 395,179,1997

TYPE OF TEST            : DNA inhibition
ROUTE OF EXPOSURE       : Subcutaneous
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 200 mg/kg
REFERENCE :
   JOENAK Journal of Endocrinology.  (Biochemical Soc. Book Depot, POB 32,
   Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1939-
   Volume(issue)/page/year: 60,167,1974

TYPE OF TEST            : DNA adduct
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 100 mg/kg
REFERENCE :
   CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House,
   Southfield Road, Eynsham, Oxford OX8 1JJ, UK)  V.1-    1980-
   Volume(issue)/page/year: 16,1483,1995

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Mammal - dog
DOSE                    : 16800 ug/kg
SEX/DURATION            : female 21 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - female fertility index (e.g. # females pregnant
   per # sperm positive females; # females pregnant per # females mated)
REFERENCE :
   JRPFA4 Journal of Reproduction and Fertility.  (Biochemical Soc. Book Depot,
   POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1960-
   Volume(issue)/page/year: 5,331,1963

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 625 ug/kg
SEX/DURATION            : female 1 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - mating performance (e.g. # sperm positive females
   per # females mated; # copulations per # estrus cycles)
REFERENCE :
   ACEDAB Acta Endocrinologica, Supplementum (Copenhagen).  (Periodica,
   Skolegade 12 E, DK-2500 Valby, Denmark)  No.1-    1948-
   Volume(issue)/page/year: 73,17,1963

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Primate - monkey
DOSE                    : 100 ug/kg
SEX/DURATION            : female 5 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - other measures of fertility
REFERENCE :
   JRPFA4 Journal of Reproduction and Fertility.  (Biochemical Soc. Book Depot,
   POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK)  V.1-    1960-
   Volume(issue)/page/year: 25,99,1971

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 15 mg/kg
SEX/DURATION            : female 30 day(s) pre-mating
TOXIC EFFECTS :
   Re

Storage condition Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

其他信息

  • MOL 文件:595-33-5.mol
  • Sigma Aldrich:595-33-5(sigmaaldrich)
  • TCI Shanghai:甲地孕酮乙酸酯 Megestrol Acetate,>;96.0%(LC)(595-33-5)
  • 用途一:安宫黄体酮（甲孕酮）的中间体。
  • 下游产品:6Β-甲基孕甾-4-烯-17Α-醇-3,20-二酮-17-醋酸酯
  • 醋酸甲地孕酮价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/04/16 M1949 醋酸甲地孕酮 Megestrol Acetate 5G 1700元 2011/04/16 M1949 醋酸甲地孕酮 Megestrol Acetate 1G 560元
  • 方法一:可用16,17α-环氧黄体酮经溴化氢开环及镍催化还原脱溴，生成17α-羟基黄体酮，再经乙酰化及酸水解生成17α-乙酰氧基黄体酮，然后以原甲酸三乙酯醚化及Vilsmeier反应得3-乙氧基-6-甲酰基-17α-乙酰氧基孕甾-2,5-二烯-20-酮，最后以硼氢化钾还原，酸水解、脱水并转位制得该品。
  • 上游原料:硼氢化钾 --> 16,17-环氧黄体酮 --> 羟孕酮
  • 醋酸甲地孕酮价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 M1949 醋酸甲地孕酮 Megestrol Acetate 5G 989元 2014/06/02 M1949 醋酸甲地孕酮 Megestrol Acetate 1G 332元

系列性分类

  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Forensic and Veterinary Standards - Chromatography
  5. Drugs & Metabolites - Forensic and Veterinary Standards
  6. Neat Compounds - Drugs & Metabolites
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Market Segments - Analytical Standards
  4. Standards for Pharma Clinical Forensic & Veterinary Analysis - Market Segments
  5. Neats and Solutions - Standards for Pharma Clinical Forensic & Veterinary Analysis
  6. Hormones - Neats and Solutions
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. M - Alphabetic
  5. MEA - MES - M
  1. Medical Research Areas
  2. Microbiology
  3. HIV Protease

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