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Boldenone undecylenate

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]

Boldenone undecylenate
Boldenone undecylenate.svg
Boldenone undecylenate molecule ball.png
Clinical data
Trade namesBoldane, Equipoise, Parenabol, Vebonol, 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)
  • US: X (Contraindicated)
Routes of
administration
Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-lifeIntramuscular: 14 days[1]
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.032.734 Edit this at Wikidata
Chemical and physical data
FormulaC30H44O3
Molar mass452.679 g/mol g·mol−1
3D model (JSmol)

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 many countries and so non-medical use is generally illicit.[6] It remains marketed for veterinary use in Australia and the United States.[6][5]

UsesEdit

VeterinaryEdit

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

ClinicalEdit

Boldenone undecylenate was formerly used in clinical medicine in humans, but was discontinued.[6]

Side effectsEdit

PharmacologyEdit

PharmacodynamicsEdit

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 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]

PharmacokineticsEdit

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] Boldenone undecylenate is reported to 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-testosterone1-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]

ChemistryEdit

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 boldenone1-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 quinbolone1-testosterone 17β-cyclopentenyl enol ether).[2][3]

Structural properties of major anabolic steroid esters

Anabolic steroid Structure Ester Relative
mol. weight
Relative
AAS contentb
Durationc
Position Moiety Type Lengtha
Boldenone undecylenate
 
C17β Undecylenic acid Straight-chain fatty acid 11 1.58 0.63 Long
Drostanolone propionate
 
C17β Propanoic acid Straight-chain fatty acid 3 1.18 0.84 Short
Metenolone acetate
 
C17β Ethanoic acid Straight-chain fatty acid 2 1.14 0.88 Short
Metenolone enanthate
 
C17β Heptanoic acid Straight-chain fatty acid 7 1.37 0.73 Long
Nandrolone decanoate
 
C17β Decanoic acid Straight-chain fatty acid 10 1.56 0.64 Long
Nandrolone phenylpropionate
 
C17β Phenylpropanoic acid Aromatic fatty acid – (~6–7) 1.48 0.67 Long
Trenbolone acetate
 
C17β Ethanoic acid Straight-chain fatty acid 2 1.16 0.87 Short
Trenbolone enanthated
 
C17β Heptanoic acid Straight-chain fatty acid 7 1.41 0.71 Long
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.

HistoryEdit

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 cultureEdit

Generic namesEdit

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

Brand namesEdit

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]

AvailabilityEdit

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

Doping in sportsEdit

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

ReferencesEdit

  1. ^ a b Pedro Ruiz; Eric C. Strain (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5.
  2. ^ a b c d e f g J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 640–. ISBN 978-1-4757-2085-3.
  3. ^ a b c d e f g Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 131–. ISBN 978-3-88763-075-1.
  4. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 52–. ISBN 978-94-011-4439-1.
  5. ^ a b c d e f g "Boldenone - Drugs.com". Drugs.com. Retrieved 28 April 2017.
  6. ^ a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab ac ad ae William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 483–490. ISBN 978-0-9828280-1-4.
  7. ^ a b Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.

External linksEdit