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Wikipedia - Dihydrotestosterone

For other uses, see DHT (disambiguation).
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 This article may require copy editing for grammar, style, cohesion, tone or spelling. You can assist by editing it. (June 2010)
Dihydrotestosterone
Systematic (IUPAC) name
5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10
,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17
-tetradecahydrocyclopenta[a]phenanthren-3-one [citation needed]
Identifiers
CAS number 521-18-6
ATC code A14AA01
PubChem CID 10635
ChemSpider 10189
Chemical data
Formula C19H30O2 
Mol. mass 290.440 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability Oral 0-2%
Metabolism Hepatic
Excretion Renal
Therapeutic considerations
Pregnancy cat. X

u
Legal status Schedule III (US), Schedule IV (CA)
Routes Intramuscular, transdermal
 YesY(what is this?)  (verify)

Dihydrotestosterone (DHT) Full name: 5a-Dihydrotestosterone, abbreviating to 5a-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 5a-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. Androgens are part of the biology of gender by stimulating and controlling the development and maintenance of masculine characteristics.

Contents

[edit] Significance

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

DHT is a hormone produced in different amounts by both males and females, and is responsible for the formation of sex-specific characteristics in men. DHT has 3 times greater affinity for androgen receptors than testosterone and has 15-30 times greater affifinty than adrenal androgens.

DHT plays an important role in the development of male secondary sex characteristics.[1]

An illustration of the significance of DHT for the development of secondary sex characteristics is congenital 5-a-reductase (5-AR)deficiency which can result in pseudohermaphroditism, undeveloped male genitalia and prostate. These individuals are often raised as girls due to their lack of consipicuous male genitalia. When puberty occurs, although their DHT levels remain very low, their testosterone levels elevate normally. Their musculature develops like that of other adults, confirming that testosterone is the prominent contributor in the development of muscle mass. They end up with little or no pubic and body hair and no incidence of male pattern baldness (MPB).[2]

Unlike other androgens such as testosterone, DHT cannot be converted by the enzyme aromatase to estradiol. Therefore, it is frequently used in research settings to distinguish between effects of testosterone caused by binding to the androgen receptor and those caused by testosterone's conversion to estradiol and subsequent binding to estrogen receptors.[3]

[edit] Pathology

DHT is the primary contributing factor in male pattern baldness (MPB).[4][5] Female hair loss is more complex, and DHT is only one of several possible causes.[6] Women with increased levels of DHT may develop certain androgynous male secondary sex characteristics, including a deepened voice and facial hair. DHT plays a role in the development and exacerbation of benign prostatic hyperplasia (BPH), as well as prostate cancer, by enlarging the prostate gland.[7] Prostate growth and differentiation are highly dependent on sex steroid hormones, particularly DHT.[8]

[edit] Treatment

The drugs belonging to the group known as 5a-reductase inhibitors are finasteride and dutasteride. Dutasteride is approved for the treatment of BPH and is prescibed off-label for the treatment of MPB, whereas finasteride is approved for both conditions. Dutasteride is three times more potent than finasteride in inhibiting the Type II enzyme and 100 times more potent than finasteride in inhibiting the Type I form of the DHT-producing enzyme, which finasteride does not inhibit. Both Type I and Type II are found in the hair follicle, though a recent study has shown that Type I is also present in the human brain, but the function remains unclear.[9] Currently, DHT hormone replacement therapy does not exist as a treatment for DHT androgen deficiency.

[edit] See also

[edit] References

  1. ^ Principles of Orthomolecularism - Google books
  2. ^ DHT - Is It All Bad? - Mesomorphosis.com
  3. ^ Dihydrotestosterone: a rationale for its use as a non-aromatizable androgen replacement therapeutic agent
  4. ^ What Is DHT? What is its Role in Hair Loss? - Medical News TODAY
  5. ^ What is dihydrotesterone (DHT)? - PrimaMed
  6. ^ American Hair Loss Association - Women's Hair Loss / Causes of Hair Loss
  7. ^ Prostate Enlargement (Benign Prostatic Hyperplasia - ehealthMD
  8. ^ Prostate Size and Risk of High-Grade, Advanced Prostate Cancer and Biochemical Progression After Radical Prostatectomy: A Search Database Study - Journal of Clinical Oncology
  9. ^ Update on Dutasteride | IAHRS Hair Transplant & Hair Loss Info Center
v • d • e
Anabolic steroids (A14) (tradename in brackets)
Androstane (carbon 19 present)
Androisoxazole • Bolasterone (Myagen) • Bolazine • Boldione • Boldenone undecylenate (Equipoise) • 4-Chlordehydromethyltestosterone (Turinabol) • 4-Hydroxytestosterone • Calusterone • Clostebol • Danazol • Desoxymethyltestosterone (Madol) • DHT • Drostanolone (Masteron) • Enestebol • Epitiostanol • Fluoxymesterone (Halotestin) • Formebolone • Furazabol (Miotolan) • Hydroxystenozole • Mebolazine • Mesabolone • Mestanolone • Mesterolone (Proviron) • Methandriol • Methandrostenolone (Dianabol) • Methenolone • Methenolone enanthate (Primobolan) • Methasterone • Methyltestosterone • Oxandrolone (Anavar) • Oxymetholone (Anadrol) • Oxymesterone • Prostanozol • Quinbolone (Anabolicum Vister) • Roxibolone • Silandrone • Stanozolol (Strombafort, Winstrol) • Stenbolone • Testosterone`s (Sustamed, Sustanon) • 1-Testosterone • Thiomesterone • Trestolone
Estrene (carbon 19 absent)
Prohormones
v • d • e
Cholesterol and steroid metabolic intermediates
Mevalonate pathway
Geranyl-
Non-mevalonate pathway
DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP
To Cholesterol
Steroid
Androgens
(C19 androstane)
Estrogens
(C18 estrane)
Nonhuman

M: MET

mt, a/u/y/n/h, r/g/c/p/i, f/s/l/o, m, e, t

au/y/n/h, rgcp/i, f/s/l/o, m, epon

meds(A16, C10),intm(a/u/y/n/h, r/g/c/p/i, f/s/o, e, t)
Retrieved from "http://en.wikipedia.org/wiki/Dihydrotestosterone"

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dihydrotestosterone".

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