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  #1  
Old 02-21-2011, 07:57 AM
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Steroid structural chemistry and biochemistry

It occurred to me that the average individual interested in anabolic steroids has little background in the basics of steroid structure and biochemistry. When someone refers to a 19-nor compound or a 5-alpha compound often the reference is not fully understood. I have written this article to help members better understand steroid compounds, there basic structure, the most abundant steroids that occur in the human body, their biochemistry and the nomenclature used to describe modifications to the basic testosterone structure to produce “better” compounds for anabolic purposes and the basic biochemistry surrounding their metabolism. I hope the following article helps some to better understand these compounds and approach use with a better understanding that will aid in their choice and safe use of this class of compounds.



All steroids are structurally based on the tetracyclic compound above, gonane.



Conventionally each ring is designated a letter A-D. Note that the above representation has 2 methyl groups. Most natural steroids start out with these methyl groups and this imparts chemical identity to them, which is important for recognition by processing enzymes and target molecules. Estranes are an exception to this rule but, as they originate from androgens, their precursors have these methyls.



Cholestane is the mother of most natural steroid compounds. Note the numbering pattern in the cholestane molecule. This numbering pattern assigns a numbered designation for each carbon in the molecule. These designations help us to identify and name each compound based on the substituent groups found on these carbon atoms. C5 is actually very important also because it determines the position of the A ring so you will often see the designation 5-a of 5-b
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Old 02-21-2011, 07:58 AM
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Cholestane is the mother of most natural steroid compounds. Note the numbering pattern in the cholestane molecule. This numbering pattern assigns a numbered designation for each carbon in the molecule. These designations help us to identify and name each compound based on the substituent groups found on these carbon atoms. C5 is actually very important also because it determines the position of the A ring so you will often see the designation 5-alpha of 5-beta
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Old 02-21-2011, 08:00 AM
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Steroids are classified by their basic structure and number of total carbons. There are 5 major classes including cholestanes (27 carbons), cholic acids (21 carbon), pregnanes (21 carbons), andranes (19 carbons) and estranges (18 carbons). When a double bond is found the name –ane is changed to –ene. Substituents are referred to in the name along with the carbon position for which they substitute. For instance testosterones IUPAC name is properly based on androstane. As it has the 19 carbon configuration, a C4 double bond, C3-one and 17beta-ol so the name would be 17beta-hydroxyandrost-4-en-3-one.
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Old 02-21-2011, 08:01 AM
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Anyway, when you see what seems to be gibberish for a name often this is the rational to designate a name for the compound.


Below are the most common steroid molecules found in humans.

Testosterone:

This is the major steroid that differentiates men from women. Men have roughly 200 times as much testosterone as women. Some of its major functions are skeletal muscle growth, bone metabolism, and neurological functions. It has a role in energy metabolism and nutrient partitioning. It interacts with HGH secretion and subsequent somatomedin secretion such as IGF-1. Low estosterone can lead to loss of memory function, low energy, depression, loss of sex drive, erectile dysfunction, gynecomastia, fat deposition, increased LDL and triglyceride with concomitant decrease in HDL. Testosterone is readily converted to estrogens and dihydrotestosterone. Estrogen is required for many feminization processes seen in women such as characteristic feminine fat distribution, ovulation and mammary tissue development. Estrogens have important roles in both genders. They are required for bone deposition and sealing of the epiphyseal centers of the long bones. Estrogens are also required in normal joint tissue development and maintenance. Estrogens have been shown to have neuroprotecive properties and are important in brain functions including memory function. So, it is important to have estrogen but too much can be detrimental leading to feminine fat distribution, gynecomastia, oily skin etc. Dihydrotestosterone is about 3 times as strong as testosterone meaning that it will bind to the androgen receptor more strongly. The problem lays in the distribution of androgen receptor and the 5-alpha reductase that coverts testosterone to dihydrotestosterone. The reductase is found in high concentration in prostate tissue and may contribute to benign prostate hyperplasia. DHT is also associated with the development of secondary sexual characteristics such as increased body hair and male sex organ maturation. DHT may have a role in benign prostate hyperplasia (BPH) and prostate cancer. The prostate has about 10 times the AR concentration as skeletal muscle so along with a high level of 5-a reductase in the prostate conversion of androgenic steroids and testosterone itself to the more potent C4/5 reduced forms in the prostate can have detrimental effects in theory. These characteristics of E and DHT are considered less desirable in the design of anabolic steroids and structural changes to the testosterone molecule are designed to remove these affects.
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Old 02-21-2011, 08:03 AM
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Dihydrotestosterone: Development of secondary sexual characteristics
[img]http://i728.photobucket.com/albums/ww283/glycomann/figureestriol.jpg[img]
Estriol: an estrogen that is seen to increase in pregnant women. It is only significanlt produced in the fetal liver using precursors suplied by the placenta. It can serve as a marker for some congenital diseases such as Down’s syndrome as it is reduced in this order in the fetus. Interestingly, pregnant women with multiple scerosis are relieved on disease symptoms and research is ongoing to study the effect of estriol on the disease.



Estradiol: the most abundant estrogen in humans. Roles in bone deposition, epiphyseal plate ossification, joint maintenance, neurological affects, neurotrotective. Extenisve roles in bone, joints, liver, brain, sexual development (female), cardiovascular system, fat structure and skin composition. Interestingly, estradiol is produced in the male testes and may be required to prevent apoptosis (an orderly kind of cell death) of the male germ cells.
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Old 02-21-2011, 08:04 AM
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Progesterone: important functions include thickening of the endometrial wall in preparation for implantation of the newly fertilized ovum. It also regulated the females immuns system in response to pregnancy. Other functions include a link to prolactin production and release during gestation. In its presence breast tissue can develop but is not sectreted. After delivery progesterone levels drop allowing lactation under the direction of prolactin among other factors. Progesterone is also a mineral corticoid receptor regulator. Therefore, for instance, it can affect cortisol and aldosterone signaling. Progesterone, like estrogen, does not cross the blood brain barrier, but can be synthesized there. It is found in high concentration in the brain and, like estrogen and testosterone, has neuroprotective properties.

Some major processing enzymes:

Processing enzymes:

Aromatase: this enzyme is among a family of cytochrome P450 enzymes. It catalyzes the formation of estrogens from testosterone via oxidation and elimination of C19 methyl group. It is found in high concentrations in male testes. Also found in adipose tissues and other tissues.

5-a reductase: Catalyzes the formation of dihydrotestosterone from testosterone by reduction of the C4-C5 double bond of testosterone. DHT is 3 times as potent as T. The enzyme is found in high concentration in prostate and other sexual tissues in men and lower concentration in skeletal muscle. It is also present in sabacious glands, liver and skin. There are two isozymes encoded from different genes. A disease state is caused by a deficiency of one enzyme. These enzymes are targeted by drugs such as Finasteride and dutasteride, the later of which inhibits both forms.

Catabolic enzymes:

Glucuranolsyltransferases: thesse enzymes make he steroid molecules more soluble and more readily available for excretion through urine and bile salts. Some attention is given to this class of enzymes in BPH and prostate cancer as one is expressed in high abundance on prostate and could therefore be targeted for increased removal of DHT from the target tissue.

Steroid oxidases: This family of enzymes, members of the CPY450 family introduce oxygen into the ring structures breaking the rings, increasing solubility and leading to the formation of bile salts. These enzymes can be upregulated through the Pregnane X receptor, which senses steroid concentrations. Speculating this may be once reason why we see increasing dosages required for continued anabolic effects.

Other catabolic enzymes: there are other more minor activities such as hydroxyltransferases, sulfotransferases, glutathione and glycosyltransferases all of which impart hydrophilic groups to aid in removal from the body through bile and urinary excretion.
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Old 02-21-2011, 08:05 AM
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Building better steroids:

Pharmaceutical companies have altered the basic testosterone molecule in attempts to reduce androgenic effect, reduce conversion to estrogens, impart chemical identity to increase bioavailabiliy and drug life time. The figure below summarizes the functional group changes that are used to enhance the testosterone anabolic activity thus giving us anabolic-androgenic steroids.
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Old 02-21-2011, 08:06 AM
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Structural modifications

Structural and pharmacokinetic properties of anabolic steroids have been reviewed extensively (Wilson, 1988,1996;Kuhn, 2002). Portions of the Wilson and Kuhn works are summarized or extracted from the original articles below.

1. 17 esters of testosterone: many esters are used on parenteral preparations. These include cypionate, propionate, phenyl propionate, caproate, isocaproate, enanthate,dacanoate, undeylanate and undecanoate. These are listed in order of increasing size. Esterification at this site renders the steroid more fat soluble and delays absorption into the circulation. The rule of thumb is the longer the ester the longer the drug will remain active. This relates to the partitioning of the compound from the depot site in its oil base into the blood plasma. Nandrolone 17 esters also exist.

2. 17 derivatives (e.g. methyltestosterone, methandrostenolone, norethandrolone,
fluoxymesterone, danazol, oxandrolone, stanozol). These derivatives resist
metabolism in the liver, so are orally active. This modification can be associated with
significant hepatic toxicities. Modifications at C1 can also have tis effect (i.e. msterolone).

3. Modifications of the A, B, or C rings (e.g. mesterolone, nortestosterone,
methenolone, fluoxymesterone, methandrostenolone, northandrolone, danazol,
nandrolone, stanozol). These modifications achieve a number of goals, including:
a) slower metabolism
b) enhanced affinity for the androgen receptor (19-nortestosterone);
c) resistance to aromatization to estradiol (fluoxymesterone, 19
nortestosterone)
d) decreased binding of metabolites to androgen receptor (5 reduced metabolites of 19-nortestosterone, 7 19 nortestosterone).

Structure:activity modifications that limit either conversion to DHT and/or to
estradiol partially target specific testosterone derivatives to specific activities.
Agents such as fluoxymesterone and 19 nortestosterone (nandrolone), for the most part, resist aromatization thus lack the feminizing side effects of testosterone.. 19 nortestosterone, or nandrolone, is thought to have this characteristic but recent evidence suggests that it may potentiate estrogen like effects through the androgen receptor. This could be possible by recruitment of a specific set of ancillary factors to the steroid receptor complex, a strategy that is currently targeted for development of steroid androgen receptor modulators (SARMS).

Below is a chart containing most steroids that have been produced by pharmaceutical companies. Hopefully after reading this, one should be able to better understand the structure of natural anabolic steroids, the general purpose and activities of them in the human body, and the general purposes of the modifications that synthetic androgens bear.



References

Kuhn CM. 2002 Anabolic steroids,Recent Prog Horm Res 57:411-34. Review.
Wilson JD 1988 Androgen abuse by athletes. Endocr Rev 9:181–191
Wilson JD 1996 Androgens. In Hardman JG, Limbird LE, Molinoff PB, Ruddon RW, Goodman
Gilman A, eds. Goodman Gilman’s Experimental Basis of Therapeutics. New York:
McGraw-Hill; 1441–1457

Acknowledgment
HenryV for proper referencing of Kuhn.
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Old 12-04-2011, 01:33 PM
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Good write up.
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Old 12-04-2011, 01:49 PM
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Quote:
Originally Posted by SHINE View Post
Good write up.
Glad to see you made it over here.
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