Jump to content

Boldenone: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous editNext edit →
Content deleted Content added
VisualWikitext
Rescuing 1 sources and tagging 0 as dead.) #IABot (v2.0.1
consistent citation formatting; templated cites
Line 25: Line 25:
| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| elimination_half-life = [[Intramuscular injection|Intramuscular]]: 14 days (as [[boldenone undecylenate]])<ref name="RuizStrain2011">{{cite book|author1=Pedro Ruiz|author2=Eric C. Strain|title=Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook|url=https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358|year=2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-60547-277-5|pages=358–}}</ref>
| elimination_half-life = [[Intramuscular injection|Intramuscular]]: 14 days (as [[boldenone undecylenate]])<ref name="RuizStrain2011">{{cite book| first1 = Pedro | last1 = Ruiz | first2 = Eric C. | last2 = Strain | name-list-format = vanc |title=Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook|url=https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358|year=2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-60547-277-5|pages=358–}}</ref>
| excretion =
| excretion =


Line 58: Line 58:
}}
}}


'''Boldenone''' (developmental code name '''RU-18761'''), is a [[natural product|naturally occurring]] [[anabolic–androgenic steroid]] (AAS) and the 1(2)-[[dehydrogenated]] [[structural analog|analogue]] of [[testosterone]].<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=640–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA131|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=131–}}</ref><ref name="MortonHall2012">{{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA52|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=52–}}</ref><ref name="Drugs.com">{{cite web|title=Boldenone international brand names|url=https://www.drugs.com/international/boldenone.html|publisher=Drugs.com|accessdate=28 April 2017}}</ref><ref name="Llewellyn2011">{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT483|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=483–490}}</ref> Boldenone itself has never been marketed; as a [[pharmaceutical drug]], it is used as [[boldenone undecylenate]], the [[undecylic acid|undecylenate]] [[ester]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />
'''Boldenone''' (developmental code name '''RU-18761'''), is a [[natural product|naturally occurring]] [[anabolic–androgenic steroid]] (AAS) and the 1(2)-[[dehydrogenated]] [[structural analog|analogue]] of [[testosterone]].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=640–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA131|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=131–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA52|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=52–}}</ref><ref name="Drugs.com">{{cite web|title=Boldenone international brand names|url=https://www.drugs.com/international/boldenone.html|publisher=Drugs.com|accessdate=28 April 2017}}</ref><ref name="Llewellyn2011">{{cite book| first = William | last = Llewellyn | name-list-format = vanc |title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT483|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=483–490}}</ref> Boldenone itself has never been marketed; as a [[pharmaceutical drug]], it is used as [[boldenone undecylenate]], the [[undecylic acid|undecylenate]] [[ester]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />


{{TOC limit|3}}
{{TOC limit|3}}
Line 68: Line 68:


===Pharmacodynamics===
===Pharmacodynamics===
Like other AAS, boldenone is an [[agonist]] of the [[androgen receptor]] (AR).<ref name="Llewellyn2011" /> The activity of boldenone is mainly [[anabolic]], with a low [[androgenic]] potency. Boldenone will increase [[nitrogen]] retention, protein synthesis, increases appetite and stimulates the release of [[erythropoietin]] in the kidneys.<ref>Forbes GB (1985) The effect of anabolic steroids on lean body mass the dose response curve. Metab Clin Exp 34(6) 571–573</ref> Boldenone was synthesized in an attempt to create a long-acting injectable [[metandienone]], for androgen deficiency disorders. Boldenone acts similar to metandienone with fewer adverse androgenic effects.{{Medcn|date=September 2015}} Although commonly compared to [[nandrolone]], boldenone lacks [[progesterone receptor]] interaction and associated [[progestogen]]ic side effects.
Like other AAS, boldenone is an [[agonist]] of the [[androgen receptor]] (AR).<ref name="Llewellyn2011" /> The activity of boldenone is mainly [[anabolic]], with a low [[androgenic]] potency. Boldenone will increase [[nitrogen]] retention, protein synthesis, increases appetite and stimulates the release of [[erythropoietin]] in the kidneys.<ref name="Forbes_1985">{{cite journal | vauthors = Forbes GB | title = The effect of anabolic steroids on lean body mass: the dose response curve | journal = Metabolism: Clinical and Experimental | volume = 34 | issue = 6 | pages = 571–3 | date = June 1985 | pmid = 3999979 | doi = 10.1016/0026-0495(85)90196-9 }}</ref> Boldenone was synthesized in an attempt to create a long-acting injectable [[metandienone]], for androgen deficiency disorders. Boldenone acts similar to metandienone with fewer adverse androgenic effects.{{Medcn|date=September 2015}} Although commonly compared to [[nandrolone]], boldenone lacks [[progesterone receptor]] interaction and associated [[progestogen]]ic side effects.


==Chemistry==
==Chemistry==

Revision as of 20:12, 27 July 2020

Not to be confused with 1-Testosterone.
Boldenone
Clinical data
Other namesΔ1-Testosterone; 1-Dehydrotestosterone; RU-18761; Androsta-1,4-dien-17β-ol-3-one
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-lifeIntramuscular: 14 days (as boldenone undecylenate)[1]
Identifiers
  • (8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.011.533 Edit this at Wikidata
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
Melting point165 °C (329 °F)
  • O=C\1\C=C/[C@]4(/C(=C/1)CC[C@@H]2[C@@H]4CC[C@@]3([C@@H](O)CC[C@@H]23)C)C
  • InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-17,21H,3-6,8,10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1 checkY
  • Key:RSIHSRDYCUFFLA-DYKIIFRCSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Boldenone (developmental code name RU-18761), is a naturally occurring anabolic–androgenic steroid (AAS) and the 1(2)-dehydrogenated analogue of testosterone.[2][3][4][5][6] Boldenone itself has never been marketed; as a pharmaceutical drug, it is used as boldenone undecylenate, the undecylenate ester.[2][3][6]

Side effects

See also: Anabolic steroid § Adverse effects

Pharmacology

Pharmacodynamics

Like other AAS, boldenone is an agonist of the androgen receptor (AR).[6] The activity of boldenone is mainly anabolic, with a low androgenic potency. Boldenone will increase nitrogen retention, protein synthesis, increases appetite and stimulates the release of erythropoietin in the kidneys.[7] Boldenone was synthesized in an attempt to create a long-acting injectable metandienone, for androgen deficiency disorders. Boldenone acts similar to metandienone with fewer adverse androgenic effects.[medical citation needed] Although commonly compared to nandrolone, boldenone lacks progesterone receptor interaction and associated progestogenic side effects.

Chemistry

See also: List of androgens/anabolic steroids

Boldenone, also known as Δ1-testosterone, 1-dehydrotestosterone, or androsta-1,4-dien-17β-ol-3-one, is a naturally occurring androstane steroid and a derivative of testosterone.[2][3][6] It is specifically testosterone with a double bond between the C1 and C2 positions.[2][3][6] A related compound is quinbolone, the 17-cyclopentenyl enol ether of boldenone.[2][3]

Sources

Boldenone occurs naturally in the scent gland of Ilybius fenestratus, a species of aquatic beetle.[2]

History

Ciba reportedly patented boldenone in 1949.[6] It subsequently developed several experimental esters of the drug in the 1950s and 1960s.[6] One of these was boldenone undecylenate, which was introduced for clinical use under the brand name Parenabol and saw some use in the late 1960s and early 1970s.[6] However, it was discontinued before the end of the 1970s.[6] Subsequently, boldenone undecylenate was introduced by Squibb under the brand name Equipose for veterinary use, most commonly in horses.[6]

Society and culture

Generic names

Boldenone is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.[2][3][4][5]

Brand names

Boldenone is marketed as veterinary drug as boldenone undecylenate (a derivative of boldenone) under the following brand names: Boldebal H, Equipoise, and Sybolin.[5] It is marketed as a veterinary combination drug with methandriol under the brand name Drive.[5]

In the Ukraine, it is marketed for human consumption as the injectable steroid Boldenol.[8]

Doping in sports

See also: List of doping in sport cases § Boldenone undecylenate

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

References

  1. ^ Ruiz, Pedro; Strain, Eric C. (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  2. ^ a b c d e f g 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. ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 131–. ISBN 978-3-88763-075-1.
  4. ^ a b 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. ^ a b c d "Boldenone international brand names". Drugs.com. Retrieved 28 April 2017.
  6. ^ a b c d e f g h i j Llewellyn, William (2011). Anabolics. Molecular Nutrition Llc. pp. 483–490. ISBN 978-0-9828280-1-4. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  7. ^ Forbes GB (June 1985). "The effect of anabolic steroids on lean body mass: the dose response curve". Metabolism: Clinical and Experimental. 34 (6): 571–3. doi:10.1016/0026-0495(85)90196-9. PMID 3999979.
  8. ^ Lyka Labs. "Boldenol 200 (boldenone undecylenate)". Retrieved 15 January 2020.
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Boldenone&oldid=969859093"