Ciclotic acid

Last updated
Ciclotic acid
Ciclotic acid.png
Names
IUPAC name
4-Methylbicyclo[2.2.2]oct-2-ene-1-carboxylic acid
Other names
Ciclotic acid, ciclotate, cyclotate
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C10H14O2/c1-9-2-5-10(6-3-9,7-4-9)8(11)12/h2,5H,3-4,6-7H2,1H3,(H,11,12)/t9-,10-
    Key: AMMPLVWPWSYRDR-MGCOHNPYSA-N
  • C[C@@]12C=C[C@@](CC1)(CC2)C(=O)O
Properties
C10H14O2
Molar mass 166.220 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ciclotic acid, or cyclotic acid, systematic name 4-methylbicyclo[2.2.2]oct-2-ene-1-carboxylic acid, is a bicyclic carboxylic acid. [1] The salts and esters of ciclotic acid are known as ciclotates (cyclotates). An example is nandrolone cyclotate, a long-acting ester prodrug of the anabolic-androgenic steroid nandrolone. [2] [3] [4]

See also

Related Research Articles

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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 now used by oral administration or instead are given by injection into muscle or fat.

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

Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed. Trenbolone ester prodrugs, including trenbolone acetate and trenbolone hexahydrobenzylcarbonate, are or have been marketed for veterinary and clinical use. Trenbolone acetate is used in veterinary medicine in livestock to increase muscle growth and appetite, while trenbolone hexahydrobenzylcarbonate was formerly used clinically in humans but is now no longer marketed. In addition, although it is not approved for clinical or veterinary use, trenbolone enanthate is sometimes sold on the black market under the nickname Trenabol.

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

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

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<span class="mw-page-title-main">Nandrolone caproate</span> Synthetic androgen and anabolic steroid

Nandrolone caproate, or nandrolone hexanoate, also known as 19-nortestosterone 17β-hexanoate, is a synthetic androgen and anabolic steroid and a nandrolone ester.

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

Nandrolone cypionate, or nandrolone cipionate, also known as 19-nortestosterone 17β-cyclopentanepropionate, is a synthetic androgen and anabolic steroid and a nandrolone ester.

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

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

Nandrolone cyclotate, or nandrolone ciclotate, also known as 19-nortestosterone 17β-ciclotate, is a synthetic and injected anabolic–androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group which was never marketed. It is an androgen ester – specifically, the C17β ciclotate (4-methylbicyclo[2.2.2]oct-2-ene-1-carboxylate) ester of nandrolone. Nandrolone cyclotate has potent and prolonged activity as an AAS when administered by intramuscular injection and is reported to have a similar duration of action to that of nandrolone decanoate via this route.

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

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

Nandrolone hexyloxyphenylpropionate, also known as 19-nortestosterone 17β-(3- phenyl)propionate, is a synthetic androgen and anabolic steroid and a nandrolone ester that is marketed in France, Denmark, Austria, Luxembourg, and Turkey. It has been studied as a potential long-acting injectable male contraceptive, though it has not been marketed for this indication. Approximately 70% of men became azoospermic, while the remaining men all became oligospermic. NHPP has a mean residence time in the body of 29.1 days and an elimination half-life in the body of 20.1 days.

<span class="mw-page-title-main">Nandrolone hydrogen succinate</span> Chemical compound

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

Nandrolone laurate, or nandrolone dodecanoate, also known as 19-nortestosterone 17β-laurate, is a synthetic androgen and anabolic steroid and a nandrolone ester. It is used in veterinary medicine in Austria, France, the Netherlands, and Switzerland.

<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">Nandrolone propionate</span> Chemical compound

Nandrolone propionate, or nandrolone propanoate, also known as 19-nortestosterone 17β-propionate, is a synthetic androgen and anabolic steroid and nandrolone ester that is or has been marketed in Spain.

<span class="mw-page-title-main">Nandrolone sulfate</span> Synthetic androgen and anabolic steroid

Nandrolone sulfate, also known as 19-nortestosterone 17β-sulfate and used medically as the sodium salt nandrolone sodium sulfate, is a synthetic androgen and anabolic steroid and a nandrolone ester which is or has been used as an ophthalmic drug in the form of eye drops in Spain, Denmark, Switzerland, France, Portugal, and Belgium.

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

Nandrolone undecanoate (NU), also known as nandrolone undecylate, and sold under the brand names Dynabolon, Dynabolin, and Psychobolan, is an androgen and anabolic steroid medication and a nandrolone ester. It was developed in the 1960s, and was previously marketed in France, Germany, Italy, and Monaco, but has since been discontinued and is now no longer known to be available. The pharmacokinetics of nandrolone undecanoate alone (Dynabolon) and in combination with other steroid esters (Trophobolene) have been studied and compared.

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

Bolandiol dipropionate (USAN), or bolandiol propionate (JAN), also known as norpropandrolate or 19-nor-4-androstenediol dipropionate, as well as estr-4-ene-3β,17β-diol 3,17-dipropionate, is a synthetic anabolic-androgenic steroid (AAS) and derivative of 19-nortestosterone (nandrolone). It is an androgen ester – specifically, the 3,17-dipropionate ester of bolandiol (19-nor-4-androstenediol).

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

Androstenediol dipropionate, or 5-androstenediol 3β,17β-dipropionate, also known as androst-5-ene-3β,17β-diol 3β,17β-dipropionate, is a synthetic anabolic–androgenic steroid and an androgen ester – specifically, the dipropionate diester of 5-androstenediol (androst-5-ene-3β,17β-diol) – which has been marketed in Europe, including in Spain, Italy, and Austria.

References

  1. "Archived copy" (PDF). apps.who.int. Archived from the original (PDF) on 23 November 2016. Retrieved 17 January 2022.{{cite web}}: CS1 maint: archived copy as title (link)
  2. "Bicyclo(2.2.2)octane and oct-2-ene-1-carboxylates of selected 17beta-hydroxy steroids fused to a heterocyclic ring".
  3. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 660–. ISBN   978-1-4757-2085-3.
  4. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1473–. ISBN   978-3-88763-075-1.