プレグナン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/11/27 01:14:53」(JST)
[Wiki en表示]
Pregnane
|
|
Names |
IUPAC names
(8 S,9 S,10 S,13 R,14 S,17 S)-17-ethyl-
10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,
14,15,16,17-tetradecahydro-1H-
cyclopenta[a]phenanthrene
|
Identifiers |
CAS Number
|
24909-91-9 N |
ChEBI |
CHEBI:8386 Y |
ChemSpider |
5256760 Y |
InChI
-
InChI=1S/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1 Y
Key: JWMFYGXQPXQEEM-WZBAXQLOSA-N Y
-
InChI=1/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1
Key: JWMFYGXQPXQEEM-WZBAXQLOBZ
|
Jmol interactive 3D |
Image |
PubChem |
6857422 |
SMILES
-
C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)CC)CC4)C
|
Properties |
Chemical formula
|
C21H36 |
Molar mass |
288.511 g/mol |
Density |
0.926 g/ml |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
N verify (what is YN ?) |
Infobox references |
|
|
Pregnane is, indirectly, a parent of progesterone. It is a parent hydrocarbon for two series of steroids stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyletiocholane).
5β-Pregnane is the parent of the progesterones, pregnane alcohols, ketones, and several adrenocortical hormones and is found largely in urine as a metabolic product of 5β-pregnane compounds.
Contents
- 1 Pregnanes
- 2 Pregnenes
- 3 Pregnadienes
- 4 See also
- 5 References
- 6 External links
Pregnanes
Steroid nomenclature: Pregnanes have carbons 1 through 21.
Pregnanes are steroid derivatives with carbons present at positions 1 through 21.
Most biologically significant pregnane derivatives fall into one of two groups: pregnenes and pregnadienes. Another class is pregnatrienes.
Pregnenes
Main article: pregnene
Pregnenes have a double bond. Examples include:
- Cortisone
- Hydrocortisone
- Progesterone
Pregnadienes
Main article: Pregnadiene
Pregnadienes have two double bonds. Examples include:
- Cyproterone acetate
- Danazol
- Fluocinonide
See also
- Pregnanedione
- Pregnanediol
- Androstane
- Estrane
References
External links
- Pregnanes at the US National Library of Medicine Medical Subject Headings (MeSH)
- PubChem
- Diagram at qmul.ac.uk
- Definition of Pregnane
- Progesterone Chemistry
- Progesterone record in European Bioinformatics database
Steroid classification
|
|
C17 |
|
|
C18 |
|
|
C19 |
|
|
C21 |
|
|
C23 |
|
|
C24 |
|
|
C27 |
|
|
Functional group |
- 17-Ketosteroid
- Hydroxysteroid
- Halogenated steroid
|
|
Elements removed |
|
|
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Regulation of Human Cytosolic Sulfotransferases 1C2 and 1C3 by Nuclear Signaling Pathways in LS180 Colorectal Adenocarcinoma Cells.
- Rondini EA, Fang H, Runge-Morris M, Kocarek TA.Author information Institute of Environmental Health Sciences, Wayne State University, Detroit, Michigan.AbstractCytosolic sulfotransferases (SULTs) catalyze the sulfate conjugation of a myriad of endogenous and xenobiotic substrates. Among the 13 human SULTs, little is known regarding regulation of the SULT1C subfamily. We evaluated the effects of a panel of transcription factor activators on levels of SULT1C mRNA (1C2 and 1C3) and protein (1C2) in LS180 colorectal adenocarcinoma cells. Treatment with 3-[3-[N-(2-chloro-3-trifluoromethylbenzyl)-(2,2-diphenylethyl)amino]propyloxy]phenylacetic acid hydrochloride [GW3965, liver X receptor (LXR) activator], 3-(2,6-dichlorophenyl)-4-(3'-carboxy-2-chlorostilben-4-yl)oxymethyl-5-isopropylisoxazole [GW4064, farnesoid X receptor (FXR)], or rifampicin [pregnane X receptor (PXR)] moderately (≤2-fold) increased both SULT1C2 and SULT1C3 mRNA levels. 1α,25-Dihydroxyvitamin D3 [1,25(OH)2D3, vitamin D receptor (VDR)] selectively upregulated SULT1C2, whereas ciprofibrate [peroxisome proliferator-activated receptor α (PPARα)], rosiglitazone (PPARγ), and 2,3,7,8-tetrachlorodibenzo-p-dioxin [aryl hydrocarbon receptor (AhR)] selectively increased SULT1C3 mRNA levels. SULT1C2 protein content was strongly increased by 1,25(OH)2D3 treatment and moderately increased by GW3965, GW4064, and rifampicin. To evaluate SULT1C2 transcriptional regulation, treatment effects were determined on reporter activity from transfected constructs containing ∼10 kb of the SULT1C2 gene. Treatment with GW3965, GW4064, or 1,25(OH)2D3 increased reporter activity ∼2-, 5-, and 5.5-fold, respectively, from a construct containing mostly intron 1 of the SULT1C2 gene. Expression of AhR, LXRα, LXRβ, PPARα, PPARγ, PXR, and VDR was confirmed in LS180 cells using quantitative reverse-transcription polymerase chain reaction; however, FXR expression was negligible, suggesting that GW4064 increased SULT1C expression through an FXR-independent mechanism. Collectively, our findings are the first to characterize the regulation of human SULT1C2 and SULT1C3 expression by several transcription factor activators. Further, we determined that responsive regions for LXR and VDR are likely contained within intron 1 of the SULT1C2 gene.
- Drug metabolism and disposition: the biological fate of chemicals.Drug Metab Dispos.2014 Mar;42(3):361-8. doi: 10.1124/dmd.113.055673. Epub 2013 Dec 11.
- Cytosolic sulfotransferases (SULTs) catalyze the sulfate conjugation of a myriad of endogenous and xenobiotic substrates. Among the 13 human SULTs, little is known regarding regulation of the SULT1C subfamily. We evaluated the effects of a panel of transcription factor activators on levels of SULT1C
- PMID 24335393
- No activation of human pregnane x receptor by hyperforin-related phloroglucinols.
- Kandel BA, Ekins S, Leuner K, Thasler WE, Harteneck C, Zanger UM.Author information Dr. Margarete Fischer-Bosch Institute of Clinical Pharmacology, Stuttgart, Germany (B.A.K., U.M.Z.); University of Tübingen, Tübingen, Germany (B.A.K., U.M.Z.); Collaborations in Chemistry, Fuquay-Varina, North Carolina (S.E.); Department of Pharmaceutical Sciences, University of Maryland, Baltimore, Maryland (S.E.); Department of Pharmacology, Rutgers University-Robert Wood Johnson Medical School, Piscataway, New Jersey (S.E.); Division of Chemical Biology and Medicinal Chemistry, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina (S.E.); Molecular and Clinical Pharmacy, Friedrich-Alexander University, Erlangen-Nuremberg, Germany (K.L.); Department of Surgery, Grosshadern Hospital, Ludwig-Maximilians University, Munich, Germany (W.E.T.); and Institute of Pharmacology and Toxicology, Interfaculty Centre for Pharmacogenomics and Drug Research, University of Tübingen, Tübingen, Germany (C.H.).AbstractThe acylated phloroglucinol, hyperforin, the main active ingredient of St. John's Wort, exerts antidepressant properties via indirect inhibition of serotonin reuptake by selectively activating the canonical transient receptor potential channel 6 (TRPC6). Hyperforin treatment can lead to drug-drug interactions due to potent activation of the nuclear receptor PXR (NR1I2), a key transcriptional regulator of genes involved in drug metabolism and transport. It was previously shown that synthetic acylated phloroglucinol derivatives activate TRPC6 with similar potency as hyperforin. However, their interaction potential with PXR remained unknown. Here we investigated five synthetic TRPC6-activating phloroglucinol derivatives and four TRPC6-nonactivating compounds compared with hyperforin and rifampicin for their potential to activate PXR in silico and in vitro. Computational PXR pharmacophore modeling did not indicate potent agonist or antagonist interactions for the TRPC6-activating derivatives, whereas one of them was suggested by docking studies to show both agonist and antagonist interactions. Hyperforin and rifampicin treatment of HepG2 cells cotransfected with human PXR expression vector and a CYP3A4 promoter-reporter construct resulted in potent PXR-dependent induction, whereas all TRPC6-activating compounds failed to show any PXR activation or to antagonize rifampicin-mediated CYP3A4 promoter induction. Hyperforin and rifampicin treatment of primary human hepatocytes resulted in highly correlated induction of PXR target genes, whereas treatment with the phloroglucinol derivatives elicited moderate gene expression changes that were only weakly correlated with those of rifampicin and hyperforin treatment. These results show that TRPC6-activating phloroglucinols do not activate PXR and should therefore be promising new candidates for further drug development.
- The Journal of pharmacology and experimental therapeutics.J Pharmacol Exp Ther.2014 Mar;348(3):393-400. doi: 10.1124/jpet.113.209916. Epub 2013 Nov 20.
- The acylated phloroglucinol, hyperforin, the main active ingredient of St. John's Wort, exerts antidepressant properties via indirect inhibition of serotonin reuptake by selectively activating the canonical transient receptor potential channel 6 (TRPC6). Hyperforin treatment can lead to drug-drug in
- PMID 24259679
- Pregnane X receptor and hepatocyte nuclear factor 4α polymorphisms are cooperatively associated with carbamazepine autoinduction.
- Saruwatari J, Yoshida S, Tsuda Y, Okada Y, Ogusu N, Yoshida K, Oniki K, Yasui-Furukori N, Kaneko S, Ishitsu T, Nakagawa K.Author information aDivision of Pharmacology and Therapeutics, Graduate School of Pharmaceutical Sciences bCenter for Clinical Pharmaceutical Sciences, Kumamoto University, Kumamoto cDepartment of Neuropsychiatry, Hirosaki University School of Medicine, Hirosaki dKumamoto Saishunso National Hospital, Koshi, Japan.AbstractOBJECTIVE: We attempted to clarify the influence of polymorphisms of nuclear receptors on carbamazepine therapy.
- Pharmacogenetics and genomics.Pharmacogenet Genomics.2014 Mar;24(3):162-71. doi: 10.1097/FPC.0000000000000030.
- OBJECTIVE: We attempted to clarify the influence of polymorphisms of nuclear receptors on carbamazepine therapy.PARTICIPANTS AND METHODS: The common polymorphisms of nuclear receptors - a tentative pregnane X receptor (PXR)*1B, hepatocyte nuclear factor 4α (HNF4α) rs2071197 (c.115+308G>A), and
- PMID 24384557
Japanese Journal
- Resveratrol Suppresses the Inducible Expression of CYP3A4 Through the Pregnane X Receptor
- Deng Rongrong,Xu Chenshu,Chen Xiao [他]
- Journal of pharmacological sciences 126(2), 146-154, 2014-10
- NAID 40020237640
- ビタミンKと骨代謝(<特集>第65回大会シンポジウム「臨床とビタミンUp-Date」)
- 柴 祥子,井上 聡
- ビタミン 88(1), 18-24, 2014-01-25
- … On the other hand, VK_2 also regulates the transcription of bone-related genes in osteoblasts through activating steroid X receptor (SXR)/pregnane X receptor (PXR), as well as enhancing the phosphorylation of protein kinase A (PKA). …
- NAID 110009767428
- Roles of Xenobiotic Receptors in Vascular Pathophysiology
- Xiao Lei,Zhang Zihui,Luo Xiaoqin
- Circulation Journal 78(7), 1520-1530, 2014
- … The pregnane X receptor (PXR) and constitutive androstane receptor (CAR), 2 closely related and liver-enriched members of the nuclear receptor superfamily, and aryl hydrocarbon receptor (AhR), a nonnuclear receptor transcription factor (TF), are major receptors/TFs regulating the expression of genes for the clearance and detoxification of xenobiotics. …
- NAID 130004926969
Related Links
- pregnane.com Home About Contact Resource Hemp and Cannabis News and Information Seed, the Most Nutritionally Complete Food Source Seeds of the plant cannabis sativa – also known as hemp seed, contain all the ...
- pregnane [preg´nān] a crystalline saturated steroid hydrocarbon; β-pregnane is the form from which several hormones, including progesterone, are derived; α-pregnane is the form excreted in the urine. preg·nane (preg'nān), Parent ...
Related Pictures
![Pregnane](https://1mg.info/0/a/9/0490.jpg)
![FMPMC-PS - Pharmacologie - DCEM1](https://1mg.info/0/a/9/0491.jpg)
![Pregnane](https://1mg.info/0/a/9/0492.jpg)
![Description Pregnane.png](https://1mg.info/0/a/9/0493.jpg)
![3α, 6α,17-TRIHYDROXY-5β-PREGNANE-20-ONE](https://1mg.info/0/a/9/0494.jpg)
★リンクテーブル★
[★]
- 英
- pregnane
- 同
- 5β-プレグナン 5β-pregnane、17β-エチルエチオコラン 17β-ethyletiocholane
- 関
- ステロイド
[★]
テトラヒドロ-11-デオキシコルチゾール。5β-プレグナン-3β,17α,21-トリオール-20-オン