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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H36
Molecular Weight 288.5105
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PREGNANE

SMILES

CC[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4CCCC[C@]4(C)[C@H]3CC[C@]12C

InChI

InChIKey=JWMFYGXQPXQEEM-NUNROCCHSA-N
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

HIDE SMILES / InChI

Molecular Formula C21H36
Molecular Weight 288.5105
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Putative role of the orphan nuclear receptor SXR (steroid and xenobiotic receptor) in the mechanism of CYP3A4 inhibition by xenobiotics.
2002-09-06
Glucocorticoid-mediated induction of CYP3A4 is decreased by disruption of a protein: DNA interaction distinct from the pregnane X receptor response element.
2002-09
Effects of dexamethasone on aryl (SULT1A1)- and hydroxysteroid (SULT2A1)-sulfotransferase gene expression in primary cultured human hepatocytes.
2002-09
Insights from a three-dimensional model into ligand binding to constitutive active receptor.
2002-09
Cholesterol and bile acids regulate xenosensor signaling in drug-mediated induction of cytochromes P450.
2002-08-16
In vitro studies of tibolone in breast cells.
2002-08
Expression and induction of CYP2C P450 enzymes in primary cultures of human hepatocytes.
2002-08
Modulation of mouse and human phenobarbital-responsive enhancer module by nuclear receptors.
2002-08
Transcriptional regulation of the human CYP3A4 gene by the constitutive androstane receptor.
2002-08
Hepatic cytochrome P450 3A drug metabolism is reduced in cancer patients who have an acute-phase response.
2002-07-29
Expression of CYP3A4, CYP2B6, and CYP2C9 is regulated by the vitamin D receptor pathway in primary human hepatocytes.
2002-07-12
Molecular mechanisms of polymorphic CYP3A7 expression in adult human liver and intestine.
2002-07-05
Tissue distribution and chemical induction of multiple drug resistance genes in rats.
2002-07
The effect of cyclophosphamide with and without dexamethasone on cytochrome P450 3A4 and 2B6 in human hepatocytes.
2002-07
CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes.
2002-07
Ectopic expression of MHC class II genes (RT1.B(I) beta/alpha) in rat hepatocytes in vivo and in culture can be elicited by treatment with the pregnane X receptor agonists pregnenolone 16 alpha-carbonitrile and dexamethasone.
2002-06-07
Redundant pathways for negative feedback regulation of bile acid production.
2002-06
Human organic anion transporting polypeptide 8 promoter is transactivated by the farnesoid X receptor/bile acid receptor.
2002-06
A natural product that lowers cholesterol as an antagonist ligand for FXR.
2002-05-31
Cross-repression, a functional consequence of the physical interaction of non-liganded nuclear receptors and POU domain transcription factors.
2002-05-24
Vitamin D receptor as an intestinal bile acid sensor.
2002-05-17
Pharmaceutical use of mouse models humanized for the xenobiotic receptor.
2002-05-01
Pregnane X receptor (PXR), constitutive androstane receptor (CAR), and benzoate X receptor (BXR) define three pharmacologically distinct classes of nuclear receptors.
2002-05
Tissue expression, ontogeny, and inducibility of rat organic anion transporting polypeptide 4.
2002-05
Induction of cytochrome P450 3A4 in primary human hepatocytes and activation of the human pregnane X receptor by tamoxifen and 4-hydroxytamoxifen.
2002-05
Induction of CYP3A expression by dehydroepiandrosterone: involvement of the pregnane X receptor.
2002-05
Reduction in cytochrome P-450 enzyme expression is associated with repression of CAR (constitutive androstane receptor) and PXR (pregnane X receptor) in mouse liver during the acute phase response.
2002-04-26
How to calculate the dose of chemotherapy.
2002-04-22
PXR, CAR and drug metabolism.
2002-04
Induction of rat organic anion transporting polypeptide 2 by pregnenolone-16alpha-carbonitrile is via interaction with pregnane X receptor.
2002-04
Regulation of xenobiotic and bile acid metabolism by the nuclear pregnane X receptor.
2002-03
Organic anion transporting polypeptides, cholestasis, and nuclear receptors.
2002-03
Postnatal expression and induction by pregnenolone-16alpha-carbonitrile of the organic anion-transporting polypeptide 2 in rat liver.
2002-03
Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression.
2002-02-28
Steroid hormone receptors and dietary ligands: a selected review.
2002-02
The PXR crystal structure: the end of the beginning.
2002-02
The role of hepatocyte RXR alpha in xenobiotic-sensing nuclear receptor-mediated pathways.
2002-02
[Regulation of cytochrome P-450 (CYP) genes by nuclear receptors].
2002-01
Structural insights into the promiscuity and function of the human pregnane X receptor.
2002-01
Synthesis and pharmacological evaluation of new 16-methyl pregnane derivatives.
2002-01
[Analysis of the mechanisms of the drug-drug interaction from a view of pharmacogenomics].
2002-01
BAREing it all: the adoption of LXR and FXR and their roles in lipid homeostasis.
2002-01
Nuclear xeno-sensors as receptors for cholestatic bile acids: the second line of defense.
2002-01
Specific and overlapping functions of the nuclear hormone receptors CAR and PXR in xenobiotic response.
2002
Regulation of hepatic drug metabolism: role of the nuclear receptors PXR and CAR.
2002
Orphan nuclear receptor binding site in the human inducible nitric oxide synthase promoter mediates responsiveness to steroid and xenobiotic ligands.
2002
Regulation of cyp3a gene transcription by the pregnane x receptor.
2002
Faecal oestrogens and progesterone metabolites in mares of different breeds during the last trimester of pregnancy.
2001-10
Regulation of drug transport by new xenobiotic receptors.
2001
Cycloartanes, protolimonoids, a pregnane and a new ergostane from Trichilia reticulata.
2001
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:10:58 GMT 2025
Edited
by admin
on Mon Mar 31 22:10:58 GMT 2025
Record UNII
10Z78HHV4C
Record Status Validated (UNII)
Record Version
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Name Type Language
17.BETA.-ETHYLETIOCHOLANE
Preferred Name English
PREGNANE
MI  
Systematic Name English
5.BETA.-PREGNANE
Systematic Name English
PREGNANE [MI]
Common Name English
PREGNANE, (5.BETA.)-
Systematic Name English
Code System Code Type Description
MERCK INDEX
m9114
Created by admin on Mon Mar 31 22:10:58 GMT 2025 , Edited by admin on Mon Mar 31 22:10:58 GMT 2025
PRIMARY Merck Index
PUBCHEM
439513
Created by admin on Mon Mar 31 22:10:58 GMT 2025 , Edited by admin on Mon Mar 31 22:10:58 GMT 2025
PRIMARY
CHEBI
8386
Created by admin on Mon Mar 31 22:10:58 GMT 2025 , Edited by admin on Mon Mar 31 22:10:58 GMT 2025
PRIMARY
CAS
481-26-5
Created by admin on Mon Mar 31 22:10:58 GMT 2025 , Edited by admin on Mon Mar 31 22:10:58 GMT 2025
PRIMARY
FDA UNII
10Z78HHV4C
Created by admin on Mon Mar 31 22:10:58 GMT 2025 , Edited by admin on Mon Mar 31 22:10:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID80331420
Created by admin on Mon Mar 31 22:10:58 GMT 2025 , Edited by admin on Mon Mar 31 22:10:58 GMT 2025
PRIMARY
WIKIPEDIA
Pregnane
Created by admin on Mon Mar 31 22:10:58 GMT 2025 , Edited by admin on Mon Mar 31 22:10:58 GMT 2025
PRIMARY