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Trenbolone acetate

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Trenbolone acetate
Clinical data
Trade namesFinajet, Finaplix, others
Other namesRU-1697; Trenbolone 17β-acetate; 19-Nor-δ9,11-testosterone 17β-acetate; Estra-4,9,11-trien-17β-ol-3-one 17β-acetate
Routes of
administration
Intramuscular
Drug classAndrogen;Anabolic steroid;Androgen ester;Progestogen
Legal status
Legal status
Pharmacokinetic data
Eliminationhalf-lifeIMTooltip Intramuscular injection: 3 days[1]
Identifiers
  • [(8S,13S,14S,17S)-13-Methyl-3-oxo-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.030.380Edit this at Wikidata
Chemical and physical data
FormulaC20H24O3
Molar mass312.409 g·mol−1
3D model (JSmol)
  • CC(=O)O[C@H]1CC[C@@H]2[C@@]1(C=CC3=C4CCC(=O)C=C4CC[C@@H]23)C
  • InChI=1S/C20H24O3/c1-12(21)23-19-8-7-18-17-5-3-13-11-14(22)4-6-15(13)16(17)9-10-20(18,19)2/h9-11,17-19H,3-8H2,1-2H3/t17-,18+,19+,20+/m1/s1
  • Key:CMRJPMODSSEAPL-FYQPLNBISA-N

Trenbolone acetate, sold under brand names such asFinajet andFinaplix among others, is anandrogen andanabolic steroid (AAS) medication used inveterinary medicine, specifically to increase the profitability oflivestock by promotingmuscle growth incattle.[2][3][4][5] It is given byinjection into muscle.[5][2]

Side effects of trenbolone acetate includesymptoms ofmasculinization likeacne,increased body hair growth,scalp hair loss,voice changes, and increasedsexual desire.[5] The drug is asynthetic androgen and anabolic steroid[6] and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).[5][2][7] It has stronganabolic effects and highlyandrogenic effects, as well as potentprogestogenic effects, and weakglucocorticoid effects.[5][2][7][8][9] Trenbolone acetate is anandrogen ester and a short-lastingprodrug oftrenbolone in the body.

Trenbolone acetate was discovered in 1963 and was introduced for veterinary use in the early 1970s.[5][10][11] In addition to its veterinary use, trenbolone acetate is used toimprove physique and performance, for which purpose it is purchased fromblack market suppliers.[5] The drug is acontrolled substance in many countries and so non-veterinary use is generallyillicit.[5]

Uses

[edit]

Veterinary uses

[edit]
A single cartridge of Finaplix-H containing 10 implants. Each implant contains 10 small yellow pellets. (Image Adapted from Medi-Vet Animal Health, LLC (https://www.medi-vet.com/Finaplix-H-p/16301.html)).

In the livestock industry, trenbolone acetate is more often called Finaplix. It was intentionally developed to promoteandrogen and gain muscle mass incattle. Due to its properties, this allowslivestock to grow as much muscle as possible before they are transported to aslaughterhouse.

Methyl cellulose and yellow dye are usually present in pellets given tolivestock. A single dosage generally consists of ten pellets, and a package of Finaplix usually consists of one cartridge containing one hundred pellets. The medication is administered bysubcutaneous injection into theposterior ear using an implanter gun. Finaplix is consistently implanted until the animal is ready to beslaughtered. There is no withholding period.[clarification needed] Due to the common practice of trenbolone acetate use inveterinary medicine, it is quite common to find traces oftrenbolonemetabolites in cattle worldwide.[10][12]

Image showing the general area of the implantation of Finaplix-H pellets displayed on bovine ear.

Non-medical uses

[edit]

Bodybuilding

[edit]

Trenbolone acetate has never been approved for use in humans and therefore guidelines for human consumption do not exist.[5] However, athletes and bodybuilders have been using trenbolone acetate as aphysique- and performance-enhancing drug for decades. Some argue there are many benefits for bodybuilder's using trenbolone acetate as an AAS. Unlike exogenous testosterone, trenbolone acetate does not causefluid retention,[10] so bodybuilders appear leaner; therefore, it is more commonly used during preparation for competitive events. Trenbolone acetate does notconvert into anestrogenicmetabolite;[10] thus there are no estrogenic side effects.[5]Trenbolone enanthate is a commonly used AAS and lasts much longer than trenbolone acetate withintramuscular injection.[5]

Medical uses

[edit]

Trenbolone acetate was never approved for use in humans and hence has no medical uses.[5] However, as an AAS, it would be expected to be effective for treating indications in which other AAS are useful, such asandrogen deficiency,wasting syndromes,muscle atrophy, and certain types ofanemia.[5][13]

Trenbolone hexahydrobenzylcarbonate was previously produced for human use by Negma Pharmaceuticals of France in 1.5 ml ampoules containing 76.5 mg of the steroid.[citation needed]

Side effects

[edit]

Trenbolone acetate, like any other AAS, has manyside effects.[7][14][15] Its strongandrogenic properties stimulatevirilization,[7] making it unsuitable for women pursuing physique or performance enhancement.[5] The side effects of trenbolone acetate are similar to other AAS; however, the negative side effects specific to trenbolone acetate are as follows:

Androgenic

[edit]

Trenbolone acetate has androgenic activity.[16][17][18] Common side effects includeoily skin,acne,seborrhea,increased facial or body hair growth, and acceleratedscalp hair loss.[5][7][19] Severity of these side effects varies based on an individual's genetics. Men susceptible to hair loss have a higher chance of becoming permanently bald.[7] In women,voice deepening,hirsutism,clitoral enlargement, and generalvirilization may occur.[5]

Hypogonadism

[edit]

Trenbolone acetate contributes greatly to development of muscle mass andfeed efficiency; however, administration of any AAS suppresses naturaltestosterone production and therefore has the potential to causehypogonadism.[5][14][19]

Cardiovascular

[edit]

Administration of any AAS can lead to cardiovascular issues.[20] Trenbolone acetate can have a strongly negative impact on cholesterol levels by suppressinghigh-density lipoprotein (HDL) cholesterol production and stimulatinglow-density lipoprotein (LDL) cholesterol production.[21] When compared to oral AAS, trenbolone acetate exerts a stronger negative effect on cholesterol levels.[22]

"Tren cough"

[edit]

The exact mechanisms underlying "tren cough" are not known; however, trenbolone acetate's androgenic effect activates a variety of lipid-like active compounds calledprostaglandins,[23] many of which areinflammatory andvasoconstrictive. Prostaglandins act on two signaling pathways:cyclooxygenase (COX) (also known asprostaglandin-endoperoxide synthase) andlipoxygenase (LOX) (EC 1.13.11.34,EC 1.13.11.33, etc.).[24] The bradykinin peptide is well known to promote a cough reaction associated withACE inhibitors prescribed forhypertension.[25][relevant?]

Estrogenic and progestogenic

[edit]

Trenbolone is notestrogenic;[5] therefore, use does not lead to excessfluid retention.[5] However, due to trenbolone's potentprogestogenic activity (it binds with high affinity to theprogesterone receptor),[10][18]gynecomastia, characterized by development and swelling of breast tissue,[26] may occur.[citation needed]

Pharmacology

[edit]

Pharmacodynamics

[edit]
The administration of the trenbolone hormone promotes a direct anabolic effect on Androgen Receptor (AR) activity. AR activity facilitated by trenbolone contributes to an increase in IGF-1 and IGF-1R levels, which then enhances skeletal muscle protein accretion. Activation and proliferation of satellite cells then facilitate an increase in skeletal muscle growth.[27]

Trenbolone acetate is aprodrug oftrenbolone.[2][5] Like other AAS, trenbolone is anagonist of theandrogen receptor (AR) and hence hasanabolic andandrogenic activity as well asantigonadotropic activity.[5][2][8][17] The potency of Trenbolone is not known, although it's often falsely believed to be five times higher thantestosterone.[28][29] This is based on a book by William Llewellyn but has not been definitively proven. Trenbolone was never approved for human use, and therefore limited data on the subject exists. The relevant literature, is usually done in rats, which makes the 500/100 potency number inaccurate. Rats respond differently to androgens and are less sensitive to androgens. While some literature report a 5 fold higher potency, two other scientific reviews report a 3 fold higher potency, which makes it unclear as to how large the relative potency actually is.[30][31] Trenbolone is anagonist of theprogesterone receptor (PR), and in relation to this, has moderate to strongprogestogenic activity.[5][8][17] Conversely, trenbolone acetate is not asubstrate foraromatase and hence lacksestrogenic activity.[5][2][8] The compound also has weakglucocorticoid activity.[8][9]

Similar to many other AAS, trenbolone acetate has the capability to produceinsulin-like growth factor-1 (IGF-1).[32][33] This naturally produced protein-based hormone affects every cell in the body of an organism and plays a large role in muscle recovery and rejuvenation. Extreme muscle growth and cell splitting compared is facilitated through trenbolone acetate administration when compared to other AAS.[32] The facilitation of IGF-1 plays a significant role in the functions and properties of thecentral nervous system,pulmonary system,muscle tissue,ligaments,cartilage, andtendons.[33]

Trenbolone acetate also has the ability to increase red blood cell count. With a larger amount ofred blood cells,blood oxygenation is enhanced. This allows for enhancedmuscular endurance and therefore promotes a faster rate of recovery. Trenbolone acetate is capable of inhibitingglucocorticoids such ascortisol.[citation needed] The properties of glucocorticoid are the opposite of androgens as muscle tissue depletion and fat gain is promoted.[34] Administration of trenbolone acetate aims at decreasing the production ofglucocorticoid hormones. Trenbolone acetate’s contribution to feed efficiency, also known as nutrient efficiency is what makes it an attractive AAS used for agricultural purposes. Food is one of the mostanabolic substances that any living organism can consume, and therefore with the administration of trenbolone acetate, everynutrient in the body becomes a lot more valuable.[35] This facilitates an organism's body that is exposed to the AAS to make better use of the nutrients already consumed.[10][35]

Pharmacokinetics

[edit]

Theacetate ester of trenbolone acetate allows for slow release post injection. This ester gives trenbolone an activatedelimination half-life of about 3 days.[1]

Chemistry

[edit]
See also:Androgen ester andList of androgen esters § Trenbolone esters

Trenbolone acetate, or trenbolone 17β-acetate, is asyntheticestranesteroid and aderivative ofnandrolone (19-nortestosterone).[5][36][37] It is the C17βacetateester oftrenbolone, which itself is δ9,11-19-nortestosterone (δ9,11-19-NT) or estra-4,9,11-trien-17β-ol-3-one.[5][36][37] Othertrenbolone esters includetrenbolone enanthate,trenbolone hexahydrobenzylcarbonate, andtrenbolone undecanoate.[5][36][37]

Structural properties of major anabolic steroid esters
Anabolic steroidStructureEsterRelative
mol. weight
Relative
AAS contentb
Durationc
PositionMoietyTypeLengtha
Boldenone undecylenate
C17βUndecylenic acidStraight-chain fatty acid111.580.63Long
Drostanolone propionate
C17βPropanoic acidStraight-chain fatty acid31.180.84Short
Metenolone acetate
C17βEthanoic acidStraight-chain fatty acid21.140.88Short
Metenolone enanthate
C17βHeptanoic acidStraight-chain fatty acid71.370.73Long
Nandrolone decanoate
C17βDecanoic acidStraight-chain fatty acid101.560.64Long
Nandrolone phenylpropionate
C17βPhenylpropanoic acidAromatic fatty acid– (~6–7)1.480.67Long
Trenbolone acetate
C17βEthanoic acidStraight-chain fatty acid21.160.87Short
Trenbolone enanthated
C17βHeptanoic acidStraight-chain fatty acid71.410.71Long
Footnotes:a = Length ofester incarbonatoms forstraight-chain fatty acids or approximate length of ester in carbon atoms foraromatic fatty acids.b = Relative androgen/anabolic steroid content by weight (i.e., relativeandrogenic/anabolicpotency).c =Duration byintramuscular orsubcutaneous injection inoil solution.d = Never marketed.Sources: See individual articles.

Structure–activity relationships

[edit]

Trenbolone acetate is a modified form of nandrolone.[16] The structure of trenbolone acetate is a 19-nor classification, which represents a structural change of thetestosterone hormone. Trenbolone acetate lacks acarbon atom at the 19 position and carries a double bond atcarbons 9 and 11. The position of these carbons slows its metabolism, which greatly increases its binding affinity to the AR, and inhibits it from undergoing aromatization into the corresponding estrogenic metabolite. Trenbolone acetate contains trenbolone modified with the addition of acarboxylic acid ester (acetic acid) at the 17β-hydroxyl group.[10] This facilitates the slow release of the AAS from the area of injection.

History

[edit]

Trenbolone acetate was first synthesized in 1963 and approved by thelivestock industry as a growth promoter for beef cattle in the early 1970s.[5][10][11] During this period of its first administration, trenbolone acetate was sold under the names Finajet and Finaject. The original manufacturer of trenbolone acetate discontinued during the late 1980s and administered the synthesis of subcutaneous pellets called Finaplix. These pellets aimed to increase muscle mass and lean tissue of cattle prior to slaughter to increase the profitability of livestock when measured in total pounds of meat sold.[10]

The drug appears to have been an early development project ofRoussel Uclaf, a French pharmaceutical company, and by the early 1970s, it was being sold as aninjectable.[18] There are a number oftrenbolone esters but trenbolone acetate is the only one known to be produced in veterinary AAS manufacturers.

Trenbolone acetate became popular among bodybuilders and athletes during the early 1980s. During this period, the AAS was transported illegally from Europe in large quantities. Although trenbolone acetate was very popular for a short amount of time, the large amounts of supplies were discontinued in 1987.[10] This decision was based upon the public concern ofsports doping and its negative effects on athletes.[5]

Society and culture

[edit]

Generic names

[edit]

Trenbolone acetate is thegeneric name of the drug and itsUSANTooltip United States Adopted Name,USPTooltip United States Pharmacopeia, andBANMTooltip British Approved Name.[3][4][36][37]

Brand names

[edit]

Trenbolone acetate is or has been sold alone for veterinary use under the brand names Component TH, Component TS, Finaject, Finajet, Finaplix-H, and Finaplix-S.[3][4][5][36][37] It is or has also been sold in combination withestradiol orestradiol benzoate for veterinary use under the brand names Revalor and Synovex.[3][4][5][36][37]

Distribution and regulation

[edit]

Trenbolone acetate, specifically referred to as Finaplix in the livestock industry, is available to purchase in veterinary drug markets.[5] A typical cartridge usually comes in the form of 20 mg pellets. It generally comes in the form of implant pellets containing 20 mg of trenbolone acetate each.[36] Preparations containing trenbolone acetate remain rare since its decline in production after the 1980s. Using AAS for any other purpose, or without a doctor's prescription, is illegal in most countries. Major sporting andbodybuilding organizations ban the use of controlled AAS, and the possession or sale of drugs can lead to arrest and conviction ofdrug-trafficking in many countries, including theUnited States andAustralia. However, in theUnited Kingdom andCanada, owning AAS for personal use as a bodybuilding supplement is not illegal, but selling the AAS without a valid medical license or reason is still against the law.[38][39]

Doping in sports

[edit]
See also:List of doping in sport cases § Trenbolone esters

Regardless of their legality, AAS are still banned by most sporting leagues in the country, who routinely conduct drug tests to find the users of any AAS. There are known cases of doping in sports with trenbolone acetate byprofessionalathletes.

References

[edit]
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Further reading

[edit]

External links

[edit]
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PRTooltip Progesterone receptoragonists
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