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57-83-0 分子结构
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(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

ChemBase编号:279
分子式:C21H30O2
平均质量:314.4617
单一同位素质量:314.2245802
SMILES和InChIs

SMILES:
O=C([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)CC3)C)CC2)CC1)C)C
Canonical SMILES:
O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C
InChI:
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

引用这个纪录

CBID:279 http://www.chembase.cn/molecule-279.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
IUPAC传统名
progesterone
商标名
Agolutin
Amen
Bio-Luton
Colprosterone
Corlutin
Corlutina
Corluvite
Corporin
Crinone
Curretab
Cyclogest
Cyclogesterin
Cycrin
Delalutin
Flavolutan
Fologenon
Gesterol
Gesterol 100
Gesterol 50
Gestiron
Gestone
Gestormone
Gestron
Glanducorpin
Gynlutin
Gynoluton
Gynolutone
Hormoflaveine
Hormoluton
Lingusorbs
Lipo-Lutin
Lucorteum
Lucorteum Sol
Luteal Hormone
Luteinique
Luteocrin Normale
Luteodyn
Luteogan
Luteohormone
Luteol
Luteopur
Luteosan
Luteostab
Luteovis
Lutex
Lutidon
Lutin
Lutociclina
Lutocuclin M
Lutocyclin
Lutocyclin M
Lutocylin
Lutocylol
Lutoform
Lutogyl
Lutren
Lutromone
Membrettes
Methylpregnone
Nalutron
Percutacrine
Percutacrine Luteinique
Piaponon
Pranone
Pregnenedione
Primolut
Prochieve
Progekan
Progestasert
Progesterol
Progestin
Progestogel
Progestol
Progeston
Progestone
Progestosol
Progestron
Progestronol
Projestaject
Prolets
Prolidon
Prolutin
Proluton
Prolutone
Prometrium
Protormone
Syngesterone
Syngestrets
Syntolutan
Thiuram E
Thiuranide
Utrogestan
Crinone, Endometrin
别名
孕烯二酮
孕酮
Prometrium
Agolutin
Corlutin
Progesterona [INN-Spanish]
Progesteronum
Progesteronum [INN-Latin]
Corpus Luteum Hormone
PROGESTERONE, γ-IRRADIATED
PREGANE-3,20-DIONE
Δ4-Pregnen-3,20-dione
Progesterone
(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
4-pregnene-3,20-dione
Progesterone: 2-hydroxypropyl-β-cyclodextrin complex
Progesterone: HBC complex
Progesterone-Water Soluble
Pregn-4-ene-3,20-dione
Δ4-Pregnene-3,20-dione
Bio-luton
CIDR
Corlutina
Corluvite
Corporin
Gestone
Progestan
Progestasert
Progestin
Progestogel
Progestol
Progeston
Utrogestan
Progesterone
Vitarrine
CAS号
57-83-0
EC号
200-350-6
MDL号
MFCD00003658
Beilstein号
1915950
PubChem SID
24898978
160963742
24899064
24898857
24898649
24898476
24278618
46508968
24870355
PubChem CID
5994
CHEBI ID
17026
ATC码
G03DA04
CHEMBL
103
Chemspider ID
5773
DrugBank ID
DB00396
IUPHAR配体索引
2377
KEGG ID
D00066
美国药典/FDA物质标识码
4G7DS2Q64Y
维基百科标题
Progesterone
Medline Plus
a604017

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 18.916313  质子受体
质子供体 LogD (pH = 5.5) 4.1486044 
LogD (pH = 7.4) 4.1486044  Log P 4.1486044 
摩尔折射率 92.7053 cm3 极化性 36.39888 Å3
极化表面积 34.14 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 3.58  LOG S -4.76 
溶解度 5.46e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
8.81 mg/L expand 查看数据来源
absolute ethanol: soluble1 mg/mL expand 查看数据来源
Acetone expand 查看数据来源
Chloroform expand 查看数据来源
Dioxane expand 查看数据来源
H2O: soluble25 mg/mL, clear to slightly hazy expand 查看数据来源
Methanol expand 查看数据来源
外观
powder expand 查看数据来源
White Solid expand 查看数据来源
熔点
126°C (258.8°F) expand 查看数据来源
127-128°C expand 查看数据来源
127-132°C expand 查看数据来源
128-132 °C expand 查看数据来源
128-132 °C(lit.) expand 查看数据来源
128-132°C expand 查看数据来源
比旋光度
[α]D expand 查看数据来源
[α]20/D +190±4°, c = 1% in ethanol expand 查看数据来源
[α]23/D +182°, c = 2 in dioxane expand 查看数据来源
疏水性(logP)
3.5 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
Room Temperature (15-30°C), Protect from light expand 查看数据来源
RTECS编号
TW0175000 expand 查看数据来源
欧盟危险性物质标志
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
40 expand 查看数据来源
40-62 expand 查看数据来源
R:45 expand 查看数据来源
安全公开号
36/37 expand 查看数据来源
S:28-36/37/39-45-53 expand 查看数据来源
GHS危险品标识
GHS08 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H351 expand 查看数据来源
H351-H361 expand 查看数据来源
GHS警示性声明
P281 expand 查看数据来源
个人保护装置
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand 查看数据来源
给药途径
oral, implant expand 查看数据来源
生物利用度
prolonged absorption, half-life approx 25-50 hours expand 查看数据来源
排泄
renal expand 查看数据来源
半衰期
34.8-55.13 hours expand 查看数据来源
代谢
hepatic to pregnanediols and pregnanolones expand 查看数据来源
蛋白结合率
96%-99% expand 查看数据来源
妊娠期药物分类
B (USA) expand 查看数据来源
相关基因信息
human ... ABCB1(5243), AR(367), CYP2C9(1559), EBP(10682), ESR1(2099), ESR2(2100), NR3C1(2908), NR3C2(4306), PGR(5241), SERPINA6(866)mouse ... Esr1(13982)rat ... Ar(24208), Nr3c1(24413), Pgr(25154) expand 查看数据来源
human ... ESR1(2099), PGR(5241) expand 查看数据来源
纯度
≥99% expand 查看数据来源
≥97.0% (HPLC) expand 查看数据来源
≥99% expand 查看数据来源
97% expand 查看数据来源
98% expand 查看数据来源
级别
certified reference material expand 查看数据来源
purum expand 查看数据来源
Sigma Reference Standard expand 查看数据来源
VETRANAL™, analytical standard expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
药效
0.1-20 ng/mL expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
包装
pkg of 1 g expand 查看数据来源
vial of 250 mg expand 查看数据来源
适用性
meets USP testing specifications expand 查看数据来源
suitable for cell culture expand 查看数据来源
简要说明
synthesized from materials derived from plant source expand 查看数据来源
无菌消毒
γ-irradiated expand 查看数据来源
干燥失重
≤0.5% loss on drying expand 查看数据来源
产品线
BioReagent expand 查看数据来源
Pharmacopeia Traceability
traceable to BP 449 expand 查看数据来源
traceable to PhEur P3300000 expand 查看数据来源
traceable to USP 1568007 expand 查看数据来源
Empirical Formula (Hill Notation)
C21H30O2 expand 查看数据来源

详细说明

详细说明

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals MP Biomedicals MP Biomedicals DrugBank DrugBank InterBioScreen InterBioScreen TRC TRC
Sigma Aldrich -  P9776 external link
Other Notes
由卵巢黄体产生的类固醇激素。
包装
Supplied in amber screw-cap vials
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
Sigma Aldrich -  850454 external link
Other Notes
由卵巢黄体产生的类固醇激素。
包装
5, 25 g in glass bottle
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
Sigma Aldrich -  PHR1142 external link
General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
由卵巢黄体产生的类固醇激素。
Values of analytes vary lot to lot.
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
Sigma Aldrich -  46665 external link
Other Notes
由卵巢黄体产生的类固醇激素。
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
Sigma Aldrich -  P7556 external link
Application
This product is not recommended for use in binding assays.
Other Notes
Contains approx. 70 mg progesterone per gram; balance 2-hydroxypropyl-β-cyclodextrin.
包装
Package size based on progesterone content
Sigma Aldrich -  81702 external link
Other Notes
由卵巢黄体产生的类固醇激素。
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
Sigma Aldrich -  P6149 external link
Application
用于细胞培养,研究细胞信号传导和基因表达的甾醇调控。
Other Notes
由卵巢黄体产生的类固醇激素。
Reconstitution
要制备 20μg/mL 的储存液,可加入 1mL 无水乙醇,温和搅拌使之溶解,再加入 49mL 无菌培养基。
Physical form
室温下为粉末状;分成小份冻存,以避免使用时反复冷冻/解冻
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
Sigma Aldrich -  P0130 external link
Other Notes
由卵巢黄体产生的类固醇激素。
包装
25, 100 g in poly bottle
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
Sigma Aldrich -  P8783 external link
Application
Use in cell culture applications to study sterol regulation of cell signaling and gene expression.
Other Notes
由卵巢黄体产生的类固醇激素。
Reconstitution
To prepare 20μg/ml stock solution, add 1ml absolute ethanol per mg progesterone, gently swirl to dissolve, add 49ml sterile medium per ml ethanol.
Physical form
powder-RT; stock-frozen in working aliquots, avoid repeated freeze/thaw
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
Sigma Aldrich -  P3972 external link
Other Notes
由卵巢黄体产生的类固醇激素。
Biochem/physiol Actions
诱导子宫内皮细胞的成熟和分泌活动;抑制排卵。孕酮与乳腺癌的病因有关。
Selleck Chemicals -  S1705 external link
Research Area: Endocrinology
Biological Activity:
Progesterone(Prometrium) is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestogens, and is the major naturally occurring human progestogen. [1]
MP Biomedicals -  02194570 external link
Cell Culture Reagent
γ-Irradiated
Purity: 99+%
Crystalline
MP Biomedicals -  02194571 external link
Cell Culture Reagent
Purity: 99+%
Crystalline
MP Biomedicals -  02102722 external link
Purity: 99+% Crystalline
MP Biomedicals -  05217145 external link
MP Biomedicals Rare Chemical collection
DrugBank -  DB00396 external link
Item Information
Drug Groups approved
Description The major progestational steroid that is secreted primarily by the corpus luteum and the placenta. Progesterone acts on the uterus, the mammary glands, and the brain. It is required in embryo implantation, pregnancy maintenance, and the development of mammary tissue for milk production. Progesterone, converted from pregnenolone, also serves as an intermediate in the biosynthesis of gonadal steroid hormones and adrenal corticosteroids. [PubChem]
Indication For progesterone supplementation or replacement as part of an Assisted Reproductive Technology (ART) treatment for infertile women with progesterone deficiency and for the treatment of secondary amenorrhea. Also used for the reduction of the incidence of endometrial hyperplasia and the attendant risk of endometrial carcinoma in postmenopausal women receiving estrogen replacement therapy, as well as treatment of abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology such as fibroids or uterine cancer.
Pharmacology Progesterone is a naturally occuring progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Progesterone tricks the body processes into thinking that ovulation has already occurred by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.
Affected Organisms
Humans and other mammals
Biotransformation Progesterone is metabolized primarily by the liver largely to pregnanediols and pregnanolones.
Absorption Progesterone absorption is prolonged with an absorption half-life of approximately 25-50 hours.
Half Life 34.8-55.13 hours
Protein Binding 96%-99%
Elimination The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites which are excreted in the bile may undergo enterohepatic recycling or may be excreted in the feces. Progesterone metabolites are excreted mainly by the kidneys.
Clearance * 2510 +/- 135 L/day [cycling women]
References
Allen WM: THE ISOLATION OF CRYSTALLINE PROGESTIN. Science. 1935 Aug 2;82(2118):89-93. [Pubmed]
Allen WM: Progesterone: how did the name originate? South Med J. 1970 Oct;63(10):1151-5. [Pubmed]
Schumacher M, Guennoun R, Robert F, Carelli C, Gago N, Ghoumari A, Gonzalez Deniselle MC, Gonzalez SL, Ibanez C, Labombarda F, Coirini H, Baulieu EE, De Nicola AF: Local synthesis and dual actions of progesterone in the nervous system: neuroprotection and myelination. Growth Horm IGF Res. 2004 Jun;14 Suppl A:S18-33. [Pubmed]
Hould FS, Fried GM, Fazekas AG, Tremblay S, Mersereau WA: Progesterone receptors regulate gallbladder motility. J Surg Res. 1988 Dec;45(6):505-12. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
InterBioScreen -  BB_NC-0185 external link
[a]20/D+192(c, 2 in dioxan)
Toronto Research Chemicals -  P755900 external link
Steroid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Anderson, E., et al.: Breast Cancer Res., 4, 197 (2002)
  • Lanari, C., et al.: Breast Cancer Res., 4, 240 (2002)
  • Albrecht, E.D., et al.: Front. Biosci., 8, 416 (2002)
  • Qiu, M., et al.: J. Steroid Biochem. Mol. Biol., 85, 147 (2002)
  • http://en.wikipedia.org/wiki/Progesterone
  • Allen WM: THE ISOLATION OF CRYSTALLINE PROGESTIN. Science. 1935 Aug 2;82(2118):89-93. Pubmed
  • Allen WM: Progesterone: how did the name originate? South Med J. 1970 Oct;63(10):1151-5. Pubmed
  • Schumacher M, Guennoun R, Robert F, Carelli C, Gago N, Ghoumari A, Gonzalez Deniselle MC, Gonzalez SL, Ibanez C, Labombarda F, Coirini H, Baulieu EE, De Nicola AF: Local synthesis and dual actions of progesterone in the nervous system: neuroprotection and myelination. Growth Horm IGF Res. 2004 Jun;14 Suppl A:S18-33. Pubmed
  • Hould FS, Fried GM, Fazekas AG, Tremblay S, Mersereau WA: Progesterone receptors regulate gallbladder motility. J Surg Res. 1988 Dec;45(6):505-12. Pubmed
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