Dihydrotestosterone
Systematic (IUPAC) name
?
Identifiers
CAS number	521-18-6
ATC code	A14ciAA01
PubChem	10635
Chemical data
Formula	C19H30O2
Mol. mass	290.440 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	? Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Legal status
Routes	?

Dihydrotestosterone (DHT) (Full name: 5α-Dihydrotestosterone, abbreviating to 5α-DHT; INN: androstanolone) is a biologically active metabolite of the hormone testosterone, formed primarily in the prostate gland, testes, hair follicles, and adrenal glands by the enzyme 5α-reductase by means of reducing the 4,5 double-bond. Dihydrotestosterone belongs to the class of compounds called androgens, also commonly called androgenic hormones or testoids. DHT is thought to be approximately 30 times more potent^{[citation needed]} than testosterone because of increased affinity for the androgen receptor. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... DHT may stand for: Distributed hash table, a type of distributed system that provides hash table-like functionality Dihydrotestosterone, a hormone commonly implicated in male baldness, produced from testosterone Discrete Hartley transform, a Fourier-related transform of discrete, periodic data similar to the discrete Fourier transform DHT may also refer... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... Norepinephrine A hormone (from Greek όρμή - to set in motion) is a chemical messenger from one cell (or group of cells) to another. ... Testosterone is a steroid hormone from the androgen group. ... The prostate is an exocrine gland of the male mammalian reproductive system. ... Human male anatomy The testicles, known medically as testes (singular testis), are the male generative glands in animals. ... A hair follicle is part of the skin that grows hair by packing old cells together. ... In mammals, the adrenal gland (also known as suprarenal glands) are the triangle-shaped endocrine glands that sit atop the kidneys; their name indicates that position (ad, near or at + renes, kidneys). They are chiefly responsible for regulating the stress response through the synthesis of corticosteroids and catecholamines, including cortisol... Ribbon diagram of the enzyme TIM, surrounded by the space-filling model of the protein. ... 5-alpha reductase is an enzyme (EC 1. ... Androgen is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of masculine characteristics in vertebrates. ...

Significance

Testosterone. Note the major difference -- the 4,5 double-bond on the A (leftmost) ring.

DHT is produced by males in utero and is responsible for the formation of male gender specific characteristics. DHT is also an important contributor to other characteristics generally attributed to males, including facial and body hair growth, and deepening of the voice. DHT has been shown to be deactivated in skeletal muscle through the actions of 3-alpha hydroxysteroid dehydrogenase and therefore does not have a significant effect on muscle hypertrophy. Image File history File links Testosterone_structure. ... Image File history File links Testosterone_structure. ... Testosterone is a steroid hormone from the androgen group. ... In Utero is the third and final studio album from the American grunge band Nirvana, released in September 1993 by Geffen Records. ... Steroid numbering. ... Bodybuilder Markus Rühl has marked hypertrophy of skeletal muscle. ...

Pathology

It is suspected that DHT is the primary contributing factor in most cases of male-pattern baldness. Women with increased levels of DHT may develop certain androgynous male secondary sex characteristics, including hair above the lip, a deepened voice, and increased muscular growth. DHT also seems to play a role in the development or exacerbation of benign prostatic hyperplasia, or BPH, and prostate cancer, though the exact reason for this is not known. This article or section does not adequately cite its references or sources. ... This article or section does not adequately cite its references or sources. ... For other uses of the acronym BPH, see BPH (disambiguation). ... Prostate cancer is a disease in which cancer develops in the prostate, a gland in the male reproductive system. ...

DHT is also known to participate in the development of acne.

Treatment

A natural substance known to control DHT is Zinc. However, xinc is also an aromatase inhibitor which indirectly increases testosterone. This can decrease the anti-dht effects. In fact, zinc is even reccomended for low testosterone levels.^{[citation needed]}

The drugs belonging to the group known as 5α-reductase inhibitors are used for treatment of problems stemming from DHT. This group includes finasteride (sold under the names Proscar for BPH and Propecia for androgenic alopecia as well as in generic formulation) and dutasteride (sold under the name Avodart). Currently, DHT supplementation is not used as a treatment for DHT/androgen deficiency. 5α-reductase inhibitors (or 5-alpha-reductase inhibitors) are a group of drugs with antiandrogenic activity, used in the treatment of benign prostatic hyperplasia and androgenic (or androgenetic) alopecia. ... Finasteride (marketed as Proscar, Propecia, Fincar, Finpecia, Finax, Finast, Finara, Finalo, Prosteride, Gefina, Finasterid IVAX) is an antiandrogen which acts by inhibiting 5-alpha reductase, the enzyme that converts testosterone to dihydrotestosterone. ... Dutasteride inhibits the conversion of testosterone into dihydrotestosterone. ...

Alternative treatments used to inhibit DHT include dietary supplementation with, or topically administered preparations of, saw palmetto berry extractives. Unlike most known 5-alpha-reductase inhibitors, saw palmetto induces its effects without interfering with the cellular capacity to secrete PSA. [1] Saw palmetto extract has been demonstrated to inhibit both isoforms of 5-alpha-reductase unlike finesteride which only inhibits the (predominant) type 2 isoenzyme of 5-alpha-reductase. [2] [3] [4] [5] [6] Binomial name Serenoa repens Hooker Saw Palmetto, Serenoa repens, is the sole species currently classified in the genus Serenoa. ... Prostate specific antigen (PSA) is a protein manufactured exclusively by the prostate gland; PSA is produced for the ejaculate where it liquifies the semen and allows sperm to swim freely. ...

Also, the chemical equol, derived by consuming foods rich in soy isoflavones by persons with certain digestive-tract bacterial flora, appears to have an androgen-inhibitive effect. Equol (4,7-isoflavandiol) is metabolized from Daidzein, a type of Isoflavone (common in Soy and other foods), by bacterial flora in the intestines. ... Binomial name Glycine max Soybeans (US) or soya beans (UK) (Glycine max) are a high-protein legume (Family Fabaceae) grown as food for both humans and livestock. ... Isoflavones are a class of organic compounds and biomolecules related to the flavonoids [1]. They are acting as phytoestrogens that are thought of by many [2] as useful in treating cancer. ... Escherichia coli, one of the many species of bacteria present in the human gut. ...