TETRAHYDRODEOXYCORTICOSTERONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H34O3
Molecular Weight	334.4929
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TETRAHYDRODEOXYCORTICOSTERONE

Structure Search

SMILES

[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@]4([H])C[C@H](O)CC[C@]34C

InChI

InChIKey=CYKYBWRSLLXBOW-DATPGIFZSA-N

InChI=1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14-,15+,16+,17+,18-,20+,21+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22654809 | https://www.ncbi.nlm.nih.gov/pubmed/8603037 | https://www.ncbi.nlm.nih.gov/pubmed/15248811

Tetrahydrodeoxycorticosterone (THDOC) is a neuroactive steroid. Neurosteroids represent a class of endogenous steroids that are synthesized in the brain, the adrenals, and the gonads. It potentiates synaptic GABAA-receptor function. THDOC is extremely potent positive allosteric modulators of GABAA receptors with sedative, anxiolytic, and anticonvulsant properties. THDOC can regulate gene expression via the progesterone receptor. The induction of DNA-binding and transcriptional activation of the progesterone receptor requires intracellular oxidation of the neurosteroids into progesterone receptor-active 5 alpha-pregnane steroid. THDOC is involved in the pathophysiology of premenstrual syndrome, catamenial epilepsy, major depression, and stress-sensitive brain disorders.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2422758 \| https://www.ncbi.nlm.nih.gov/pubmed/17108970 \| https://www.ncbi.nlm.nih.gov/pubmed/22654809 \| https://www.ncbi.nlm.nih.gov/pubmed/25887256 \| https://www.ncbi.nlm.nih.gov/pubmed/11880484 \| https://www.ncbi.nlm.nih.gov/pubmed/11192636	Positive Allosteric Modulator 179
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8398145 \| https://www.ncbi.nlm.nih.gov/pubmed/10441302 \| https://www.ncbi.nlm.nih.gov/pubmed/8603037	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11978855 https://www.ncbi.nlm.nih.gov/pubmed/7932175 https://www.ncbi.nlm.nih.gov/pubmed/16325018	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Determination of urinary tetrahydro-11-deoxycortisol and tetrahydro-11-deoxycorticosterone by gas chromatography.	1971 Apr	5108103
Effect of a single oral dose of metyrapone on secretion of growth hormone and urinary tetrahydro-11-deoxycortisol and tetrahydro-11-deoxycorticosterone excretion in children.	1972 Jun	4644861
Incomplete virilization and subclinical mineralocorticoid excess in a boy with partial 17,20-desmolase/17 alpha-hydroxylase deficiency.	1990 Feb	2156398
Adrenal cortex, tumor, and peripheral production of deoxycorticosterone.	1992 Jan	1316648
The relationship between the effects of metyrapone treatment on depressed mood and urinary steroid profiles.	1996 Apr	8817726
Detection of beta-ureidopropionase deficiency with HPLC-electrospray tandem mass spectrometry and confirmation of the defect at the enzyme level.	2001 Dec	11804209
Membrane-initiated events account for progesterone's ability to regulate intracellular free calcium levels and inhibit rat granulosa cell mitosis.	2002 Aug	12135870
Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine.	2002 Sep	12271438
Chronic ethanol exposure produces tolerance to elevations in neuroactive steroids: mechanisms and reversal by exogenous ACTH.	2010 Oct	20633208

Patents

Sample Use Guides

In Vivo Use Guide

MIce: 1-20 mg/kg ip

Route of Administration: Other

In Vitro Use Guide

5 alpha-pregnane-3 alpha, 21-diol-20-one (5 alpha-tetrahydrodeoxycorticosterone; 5 alpha-THDOC) (10 microM) increased and prolonged the inhibitory postsynaptic potential (IPSP) in pyramidal neurons in an in vitro slice preparation of the adult rat frontal neocortex. At a concentration of 1 microM 5 alpha-THDOC increased only the early IPSP. Responses to the iontophoretically applied specific GABAA receptor agonist muscimol but not to the specific GABAB receptor agonist L-baclofen were enhanced by 5 alpha-THDOC (10 microM). In the giga-seal whole-cell configuration when the GABAB receptor-mediated IPSP component was absent due to intracellular perfusion, 5 alpha-THDOC (10 microM) increased IPSPs to a similar extent as in the conventional microelectrode recordings. Excitatory postsynaptic potentials, resting membrane potential, input resistance and action potential amplitude were not affected by 5 alpha-THDOC (10 microM).

Name

Type

Language

TETRAHYDRODEOXYCORTICOSTERONE

Common Name

English

5.BETA.-PREGNANE-3.ALPHA.,21-DIOL-20-ONE

Common Name

English

3.ALPHA.,21-DIHYDROXY-5.BETA.-PREGNAN-20-ONE

Systematic Name

English

5.BETA.-PREGNAN-20-ONE, 3.ALPHA.,21-DIHYDROXY-

Systematic Name

English

21-HYDROXYPREGNANOLONE

Common Name

English

CORTICOSTERONE, 11-DEOXYTETRAHYDRO-

Systematic Name

English

DEOXYTETRAHYDROCORTICOSTERONE

Common Name

English

PREGNAN-20-ONE, 3,21-DIHYDROXY-, (3.ALPHA.,5.BETA.)-

Systematic Name

English

TETRAHYDRO-11-DEOXYCORTICOSTERONE

Common Name

English

5.BETA.-PREGNAN-3.ALPHA.,21-DIOL-20-ONE

Common Name

English

CORTICOSTERONE, DEOXYTETRAHYDRO-

Systematic Name

English

3.ALPHA.,5.BETA.-TETRAHYDRODEOXYCORTICOSTERONE

Common Name

English

Code System Code Type Description

WIKIPEDIA

Tetrahydrodeoxycorticosterone