ANDROSTANE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H32
Molecular Weight	260.4574
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12CCC[C@H]1[C@@H]3CC[C@H]4CCCC[C@]4(C)[C@H]3CC2

InChI

InChIKey=QZLYKIGBANMMBK-UGCZWRCOSA-N

InChI=1S/C19H32/c1-18-11-5-7-16(18)15-9-8-14-6-3-4-12-19(14,2)17(15)10-13-18/h14-17H,3-13H2,1-2H3/t14-,15+,16+,17+,18+,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H32
Molecular Weight	260.4574
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
androgen receptor signaling pathway 1 Target ID: GO:0030521 Sources: https://academic.oup.com/endo/article-abstract/67/6/887/2783161	Activator 1447

PubMed

Title	Date	PubMed
Genetic profiling defines the xenobiotic gene network controlled by the nuclear receptor pregnane X receptor.	2003-07	12663745
Sex difference in the proliferative response of mouse hepatocytes to treatment with the CAR ligand, TCPOBOP.	2003-06	12807759
Cloning of a functional vitamin D receptor from the lamprey (Petromyzon marinus), an ancient vertebrate lacking a calcified skeleton and teeth.	2003-06	12746335
Identification of a novel human constitutive androstane receptor (CAR) agonist and its use in the identification of CAR target genes.	2003-05-09	12611900
Nuclear receptors orchestrate detoxification pathways.	2003-05	12737794
Quantitation of CYP2B6, constitutive androstane receptor, and pregnane X receptor mRNA levels.	2003-05	12718301
Glucocorticoid receptor enhancement of pregnane X receptor-mediated CYP2B6 regulation in primary human hepatocytes.	2003-05	12695351
Regulation of drug transporter gene expression by nuclear receptors.	2003-05	12695338
A novel distal enhancer module regulated by pregnane X receptor/constitutive androstane receptor is essential for the maximal induction of CYP2B6 gene expression.	2003-04-18	12571232
Induction of bilirubin clearance by the constitutive androstane receptor (CAR).	2003-04-01	12644704
Control of steroid, heme, and carcinogen metabolism by nuclear pregnane X receptor and constitutive androstane receptor.	2003-04-01	12644700
Sequence diversity and functional characterization of the 5'-regulatory region of human CYP2C19.	2003-04	12668916
Activation of orphan nuclear constitutive androstane receptor requires subnuclear targeting by peroxisome proliferator-activated receptor gamma coactivator-1 alpha. A possible link between xenobiotic response and nutritional state.	2003-03-28	12551939
Repression of farnesoid X receptor during the acute phase response.	2003-03-14	12519762
Use of dominant negative nuclear receptors to study xenobiotic-inducible gene expression in primary cultured hepatocytes.	2003-03-12	12628309
Assessment of porcine and human 16-ene-synthase, a third activity of P450c17, in the formation of an androstenol precursor. Role of recombinant cytochrome b5 and P450 reductase.	2003-03	12631293
Predicting inductive drug-drug interactions.	2003-03	12605548
Transcriptional analysis in vivo of the hepatic genes, Cyp2b9 and Cyp2b10, by intravenous administration of plasmid DNA in mice.	2003-02-17	12573485
The expression of CYP2B6, CYP2C9 and CYP3A4 genes: a tangle of networks of nuclear and steroid receptors.	2003-02-17	12573484
Phenobarbital induction of drug/steroid-metabolizing enzymes and nuclear receptor CAR.	2003-02-17	12573483
Functional and structural comparison of PXR and CAR.	2003-02-17	12573482
Regulation of P450 genes by liver-enriched transcription factors and nuclear receptors.	2003-02-17	12573481
Homology modelling of the nuclear receptors: human oestrogen receptorbeta (hERbeta), the human pregnane-X-receptor (PXR), the Ah receptor (AhR) and the constitutive androstane receptor (CAR) ligand binding domains from the human oestrogen receptor alpha (hERalpha) crystal structure, and the human peroxisome proliferator activated receptor alpha (PPARalpha) ligand binding domain from the human PPARgamma crystal structure.	2003-02	12710995
The critical role of carboxy-terminal amino acids in ligand-dependent and -independent transactivation of the constitutive androstane receptor.	2003-02	12554751
The orphan nuclear receptor HNF4alpha determines PXR- and CAR-mediated xenobiotic induction of CYP3A4.	2003-02	12514743
The role of the nuclear receptor CAR as a coordinate regulator of hepatic gene expression in defense against chemical toxicity.	2003-01-01	12464260
Comparative urinary androstanes in the great apes.	2003-01	12535626
Transcriptional analysis of the orphan nuclear receptor constitutive androstane receptor (NR1I3) gene promoter: identification of a distal glucocorticoid response element.	2003-01	12511605
Constitutive androstane receptor and pregnane X receptor gene expression in human liver: interindividual variability and correlation with CYP2B6 mRNA levels.	2003-01	12485946
In vivo activation of the constitutive androstane receptor beta (CARbeta) by treatment with dehydroepiandrosterone (DHEA) or DHEA sulfate (DHEA-S).	2002-12-18	12482595
A ligand-based approach to understanding selectivity of nuclear hormone receptors PXR, CAR, FXR, LXRalpha, and LXRbeta.	2002-12	12523656
Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives.	2002-11	12446049
Squalestatin 1-inducible expression of rat CYP2B: evidence that an endogenous isoprenoid is an activator of the constitutive androstane receptor.	2002-11	12391282
Dietary effects of arachidonate-rich fungal oil and fish oil on murine hepatic and hippocampal gene expression.	2002-10-21	12617750
Modulation of acetaminophen-induced hepatotoxicity by the xenobiotic receptor CAR.	2002-10-11	12376703
Toxicology. Protecting liver from painkiller's lethal dose.	2002-10-11	12376675
Pharmacogenomics, regulation and signaling pathways of phase I and II drug metabolizing enzymes.	2002-10	12369894
Regulation of human CYP2C9 by the constitutive androstane receptor: discovery of a new distal binding site.	2002-09	12181452
Nuclear pregnane x receptor and constitutive androstane receptor regulate overlapping but distinct sets of genes involved in xenobiotic detoxification.	2002-09	12181440
Glucocorticoid-mediated induction of CYP3A4 is decreased by disruption of a protein: DNA interaction distinct from the pregnane X receptor response element.	2002-09	12167569
Insights from a three-dimensional model into ligand binding to constitutive active receptor.	2002-09	12167558
A genome-wide linkage scan for steroids and SHBG levels in black and white families: the HERITAGE Family Study.	2002-08	12161500
Expression and induction of CYP2C P450 enzymes in primary cultures of human hepatocytes.	2002-08	12130704
Modulation of mouse and human phenobarbital-responsive enhancer module by nuclear receptors.	2002-08	12130690
Transcriptional regulation of the human CYP3A4 gene by the constitutive androstane receptor.	2002-08	12130689
Receptor-mediated hepatocarcinogenesis: role of hepatocyte proliferation and apoptosis.	2002-07	12193254
[The role of nuclear receptors in cytochrome P-450 induction by xenochemicals].	2002	12664659
[Investigation of neuromuscular blocking agents at Richter Ltd].	2002	12426786
Direct expression of fluorescent protein-tagged nuclear receptor CAR in mouse liver.	2002	12424912
[Progress in the study of orphan nuclear receptor].	2001-04	12545897

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:04:14 GMT 2025` Edited by `admin` on `Mon Mar 31 22:04:14 GMT 2025`
Record UNII	KT649U81FE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANDROSTANE

Systematic Name

English

NSC-49000

Preferred Name

English

AETIOALLOCHOLANE

Common Name

English

ETIOALLOCHOLANE

Common Name

English

5.ALPHA.-ANDROSTAN

Systematic Name

English

ANDROSTANE, (5.ALPHA.)-

Systematic Name

English

ANDROSTANE [MI]

Common Name

English

5.ALPHA.-ANDROSTANE

Systematic Name

English

Code System Code Type Description

CHEBI

28859