Etiocholanolone, also known as 5β-androsterone, as well as 3α-hydroxy-5β-androstan-17-one or etiocholan-3α-ol-17-one, is an etiocholane (5β-androstane)

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

as well as an endogenous 17-ketosteroid that is produced from the

metabolism Metabolism (, from ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cellular processes; the co ...

testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...

. It causes

fever Fever or pyrexia in humans is a symptom of an anti-infection defense mechanism that appears with Human body temperature, body temperature exceeding the normal range caused by an increase in the body's temperature Human body temperature#Fever, s ...

, immunostimulation, and leukocytosis, and is used to evaluate adrenal cortex function, bone marrow performance, and in neoplastic disease to stimulate the

immune system The immune system is a network of biological systems that protects an organism from diseases. It detects and responds to a wide variety of pathogens, from viruses to bacteria, as well as Tumor immunology, cancer cells, Parasitic worm, parasitic ...

. Etiocholanolone is also known to be an

inhibitory An inhibitory postsynaptic potential (IPSP) is a kind of synaptic potential that makes a Chemical synapse, postsynaptic neuron less likely to generate an action potential.Purves et al. Neuroscience. 4th ed. Sunderland (MA): Sinauer Associates, Inc ...

androstane neurosteroid, acting as a positive allosteric modulator of the GABA_A receptor, and possesses

anticonvulsant Anticonvulsants (also known as antiepileptic drugs, antiseizure drugs, or anti-seizure medications (ASM)) are a diverse group of pharmacological agents used in the treatment of epileptic seizures. Anticonvulsants are also used in the treatme ...

effects. The unnatural enantiomer of etiocholanolone is more potent as a positive allosteric modulator of GABA_A receptors and as an anticonvulsant than the natural form. Etiocholanolone has been studied as a pyrogenic steroid in the so-called steroid fever (or etiocholanolone fever), a condition similar to familial mediterranean fever (FMF). Etiocholanolone (like pregnanolone) activates the pyrin inflammasome. It is not known whether these endogenous

steroids A steroid is an organic compound with four fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter mem ...

play a role in triggering FMF flares but they may make a link between stress,

menstrual cycle The menstrual cycle is a series of natural changes in hormone production and the structures of the uterus and ovaries of the female reproductive system that makes pregnancy possible. The ovarian cycle controls the production and release of eg ...

and disease flares. Etiocholanolone is produced from 5β-dihydrotestosterone, with 3α,5β-androstanediol as an intermediate.

Chemistry

References

{{GABAAR PAMs Etiocholanes Neurosteroids GABAA receptor positive allosteric modulators Human metabolites World Anti-Doping Agency prohibited substances

Chemistry

See also

References