Boldenone undecylenate

Last updated
Boldenone undecylenate
Boldenone undecylenate.svg
Boldenone undecylenate molecule ball.png
Clinical data
Trade names Boldane, Equipoise, Parenabol, others
Other namesBoldenone undecenoate; Ba 29038; Boldenone 17β-undec-10-enoate; Δ1-Testosterone 17β-undec-10-enoate; 1-Dehydrotestosterone 17β-undec-10-enoate; Androsta-1,4-dien-17β-ol-3-one 17β-undec-10-enoate
Pregnancy
category
  • AU:X (High risk)
Routes of
administration 		Intramuscular injection
Drug class Androgen; Anabolic steroid; Androgen ester
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-life Intramuscular: 14 days [1]
Identifiers
  • [(8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] undec-10-enoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.032.734 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C30H44O3
Molar mass 452.679 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCCCCCCCC=C)CCC4=CC(=O)C=C[C@]34C
  • InChI=1S/C30H44O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h4,17,19,21,24-27H,1,5-16,18,20H2,2-3H3/t24-,25-,26-,27-,29-,30-/m0/s1
  • Key:AHMMSNQYOPMLSX-CNQKSJKFSA-N

Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. [2] [3] [4] [5] [6] It was formerly used in humans as well. [6] It is given by injection into muscle. [6]

Contents

Side effects of boldenone undecylenate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. [6] The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). [6] [7] It has strong anabolic effects and moderate androgenic effects, weak estrogenic effects, and no risk of liver damage. [6] [7] Boldenone undecylenate is an androgen ester and a long-lasting prodrug of boldenone in the body. [6]

Boldenone undecylenate was introduced for medical use in the 1960s. [6] In addition to its medical use, boldenone undecylenate is used to improve physique and performance. [6] The drug is a controlled substance in the United States and its use is generally illicit. [6] It remains marketed for veterinary use in Australia and the United States. [6] [5]

Uses

Veterinary

Boldenone undecylenate is used in veterinary medicine, mainly in horses. [6] [5]

Clinical

Boldenone undecylenate was formerly used in clinical medicine in humans, but was discontinued. [6] The drug is currently not approved by Food and Drug Administration. [8] [9] It is also classified as DEA Schedule III controlled substance. [10]

Side effects

Pharmacology

Pharmacodynamics

Boldenone undecylenate is a prodrug of boldenone, and hence is an agonist of the androgen receptor. [6] Boldenone has strong anabolic effects and moderate androgenic effects. [6] It also has low estrogenic activity [11] and has little or no progestogenic activity. [6] In relation to the fact that it is not 17α-alkylated, boldenone and boldenone undecylenate have little or no risk of hepatotoxicity. [6]

Pharmacokinetics

Boldenone undecylenate is a prodrug of boldenone. [6] When administered via intramuscular injection, a depot is formed from which boldenone undecylenate is slowly released into the body and then transformed into boldenone. [6] The drug possess a biological half-life of 14 days when administered by intramuscular injection. [1] Boldenone is a substrate for 5α-reductase and may be converted by this enzyme into 1-testosterone (δ1-dihydrotestosterone, δ1-DHT, dihydroboldenone) in tissues that express it such as the skin, hair follicles, and prostate gland. [6] However, its affinity for this enzyme is said to be extremely low. [6]

Chemistry

Boldenone undecylenate, or boldenone 17β-undec-10-enoate, is a synthetic androstane steroid and a derivative of testosterone. [2] [3] [6] It is the C17β undecylenate (undecenoate) ester of boldenone (δ1-testosterone, 1-dehydrotestosterone, or androsta-1,4-dien-17β-ol-3-one), which itself is the C1(2) dehydrogenated analogue of testosterone and a naturally occurring androgen found in the scent gland of Ilybius fenestratus (a species of aquatic beetle). [2] [3] [6] Boldenone is the non-17α-alkylated variant of metandienone (17α-methyl-δ1-testosterone). [2] [3] [6] An AAS related to boldenone undecylenate is quinbolone (δ1-testosterone 17β-cyclopentenyl enol ether). [2] [3]

Structural properties of major anabolic steroid esters
Anabolic steroidStructureEsterRelative
mol. weight		Relative
AAS contentb		Durationc
PositionMoietyTypeLengtha
Boldenone undecylenate
Boldenone undecylenate.svg
C17β Undecylenic acid Straight-chain fatty acid111.580.63Long
Drostanolone propionate
Drostanolone propionate.svg
C17β Propanoic acid Straight-chain fatty acid31.180.84Short
Metenolone acetate
Metenolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid21.140.88Short
Metenolone enanthate
Metenolone enanthate.png
C17β Heptanoic acid Straight-chain fatty acid71.370.73Long
Nandrolone decanoate
Nandrolone decanoate.svg
C17β Decanoic acid Straight-chain fatty acid101.560.64Long
Nandrolone phenylpropionate
Nandrolone phenylpropionate.svg
C17β Phenylpropanoic acid Aromatic fatty acid– (~6–7)1.480.67Long
Trenbolone acetate
Trenbolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid21.160.87Short
Trenbolone enanthate d
Trenbolone enanthate.svg
C17β Heptanoic acid Straight-chain fatty acid71.410.71Long
Footnotes:a = Length of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative androgen/anabolic steroid content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution. d = Never marketed. Sources: See individual articles.

History

Boldenone was reportedly patented by Ciba in 1949, and esters of the compound were developed by the company in the 1950s and 1960s. [6] One such ester, boldenone undecylenate, was introduced for clinical use as an injectable AAS under the brand name Parenabol in the 1960s. [6] However, it was discontinued for use in humans in the late 1970s. [6] Squibb introduced boldenone undecylenate for veterinary use under the brand name Equipoise. [6] The medication has been used much more widely in veterinary medicine, in which it has been used mainly in horses, and remains in use today. [6] [5]

Society and culture

Generic names

Boldenone undecylenate is the generic name of the drug and its USAN, while boldenone undecenoate is its BANM. [2] [3] [5]

Brand names

Boldenone undecylenate is or has been marketed under a number of brand names including Boldane, Equipoise, Parenabol, and Vebonol among others. [2] [3] [5] [6]

Availability

Boldenone undecylenate remains marketed for veterinary use in Australia and the United States. [6] [5]

Doping in sports

There are many known cases of doping in sports with boldenone undecylenate by professional athletes.

Related Research Articles

<span class="mw-page-title-main">Nandrolone</span> Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

<span class="mw-page-title-main">Metenolone</span> Chemical compound

Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate and metenolone enanthate. Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure. Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.

<span class="mw-page-title-main">Nandrolone decanoate</span> Anabolic steroid

Nandrolone decanoate, sold under the brand name ROLON among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemias and wasting syndromes, as well as osteoporosis in menopausal women. It is given by injection into muscle or fat once every one to four weeks.

<span class="mw-page-title-main">Oxymetholone</span> Androgen and anabolic steroid

Oxymetholone, sold under the brand names Anadrol and Anapolon among others, is an androgen and anabolic steroid (AAS) medication which is used primarily in the treatment of anemia. It is also used to treat osteoporosis, HIV/AIDS wasting syndrome, and to promote weight gain and muscle growth in certain situations. It is taken by mouth.

<span class="mw-page-title-main">Quinbolone</span> Chemical compound

Quinbolone, sold under the brand names Anabolicum and Anabolvis, is an androgen and anabolic steroid (AAS) which was previously marketed in Italy. It was developed by Parke-Davis as a viable orally administered AAS with little or no liver toxicity.

<span class="mw-page-title-main">Boldenone</span> Chemical compound

Boldenone, is a naturally occurring anabolic–androgenic steroid (AAS) and the 1(2)-dehydrogenated analogue of testosterone. Boldenone itself has never been marketed; as a pharmaceutical drug, it is used as boldenone undecylenate, the undecylenate ester.

<span class="mw-page-title-main">Metenolone enanthate</span> Chemical compound

Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market. A related drug, metenolone acetate, is taken by mouth.

<span class="mw-page-title-main">Ethylestrenol</span> Chemical compound

Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.

<span class="mw-page-title-main">Mesterolone</span> Chemical compound

Mesterolone, sold under the brand name Proviron among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels. It has also been used to treat male infertility, although this use is controversial. It is taken by mouth.

<span class="mw-page-title-main">Drostanolone propionate</span> Chemical compound

Drostanolone propionate, or dromostanolone propionate, sold under the brand names Drolban, Masteril, and Masteron among others, is an androgen and anabolic steroid (AAS) medication which was used to treat breast cancer in women but is now no longer marketed. It is given by injection into muscle.

<span class="mw-page-title-main">Mestanolone</span> Chemical compound

Mestanolone, also known as methylandrostanolone and sold under the brand names Androstalone and Ermalone among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer used. It is still available for use in Japan however. It is taken by mouth.

<span class="mw-page-title-main">1-Testosterone</span> Chemical compound

1-Testosterone, also known as δ1-dihydrotestosterone (δ1-DHT), as well as dihydroboldenone, is a synthetic anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of boldenone (Δ1-testosterone). It differs from testosterone by having a 1(2)-double bond instead of a 4(5)-double bond in its A ring. It was legally sold online in the United States until 2005, when it was reclassified as a Schedule III drug.

<span class="mw-page-title-main">Stenbolone</span> Chemical compound

Stenbolone is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. A C17β ester prodrug of stenbolone, stenbolone acetate, is used as an AAS for depot intramuscular injection under the brand names Anatrofin and Stenobolone.

<span class="mw-page-title-main">Methylstenbolone</span> Chemical compound

Methylstenbolone, known by the nicknames M-Sten, Methyl-Sten, and Ultradrol, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-methylated derivative of dihydrotestosterone (DHT) which was never introduced for medical use. It is a designer steroid and has been sold via the internet marketed as a dietary/nutritional supplement.

<span class="mw-page-title-main">Nandrolone phenylpropionate</span> Anabolic steroid

Nandrolone phenylpropionate (NPP), or nandrolone phenpropionate, sold under the brand name Durabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used primarily in the treatment of breast cancer and osteoporosis in women. It is given by injection into muscle once every week. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.

<span class="mw-page-title-main">Metenolone acetate</span> Chemical compound

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is taken by mouth. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone enanthate, is given by injection into muscle.

<span class="mw-page-title-main">Androstanolone</span> Androgenic and anabolic steroid medication

Androstanolone, or stanolone, also known as dihydrotestosterone (DHT) and sold under the brand name Andractim among others, is an androgen and anabolic steroid (AAS) medication and hormone which is used mainly in the treatment of low testosterone levels in men. It is also used to treat breast development and small penis in males. Compared to testosterone, androstanolone (DHT) is less likely to aromatize into estrogen, and therefore it shows less pronounced estrogenic side effects, such as gynecomastia and water retention. On the other hand, androstanolone (DHT) show more significant androgenic side effects, such as acne, hair loss and prostate enlargement.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

References

  1. 1 2 Westreich LM (2011). "Anabolic-Androgenic Steroids". In Ruiz P, Strain EC (eds.). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN   978-1-60547-277-5.
  2. 1 2 3 4 5 6 7 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 640–. ISBN   978-1-4757-2085-3.
  3. 1 2 3 4 5 6 7 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 131–. ISBN   978-3-88763-075-1.
  4. ↑ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 52–. ISBN   978-94-011-4439-1.
  5. 1 2 3 4 5 6 7 "Boldenone". Drugs.com. Retrieved 28 April 2017.
  6. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 483–490. ISBN   978-0-9828280-1-4.
  7. 1 2 Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC   2439524 . PMID   18500378.
  8. ↑ "CFR - Code of Federal Regulations Title 21". www.accessdata.fda.gov. Retrieved 2021-02-22.
  9. ↑ "5 Things Athletes Should Know About Boldenone". www.usada.org. 9 April 2020. Archived from the original on 2020-12-05. Retrieved 2021-02-22.
  10. ↑ "Boldenone undecylenate". PubChem. U.S. National Libbrary of Medicine. Retrieved 2021-02-22.
  11. ↑ "Boldenone Undecylenate - Equipoise: Injections, Dosages and Administration". workoutmag.net. 29 August 2020. Archived from the original on 2020-10-23. Retrieved 2021-02-22.
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