Norclostebol

Norclostebol
Clinical data
Trade names	Lentabol
Other names	SKF-6611; CP-73; 4-Chloroestr-4-en-17β-ol-3-one
Identifiers
	IUPAC name (8R,9S,10R,13S,14S,17S)-4-Chloro-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one;
CAS Number	13583-21-6 ;
PubChem CID	166576 ;
ChemSpider	145769 ;
UNII	VI1001O2DI ;
CompTox Dashboard (EPA)	DTXSID401016377 ;
Chemical and physical data
Formula	C18H25ClO2
Molar mass	308.85 g·mol−1
3D model (JSmol)	Interactive image ;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C(C(=O)CC[C@H]34)Cl;
	InChI InChI=1S/C18H25ClO2/c1-18-9-8-11-10-4-6-15(20)17(19)13(10)3-2-12(11)14(18)5-7-16(18)21/h10-12,14,16,21H,2-9H2,1H3/t10-,11-,12-,14+,16+,18+/m1/s1 ; Key:OZDDFAQVVGFDJP-YGRHGMIBSA-N ;
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Last updated June 17, 2024

Norclostebol (INN Tooltip International Nonproprietary Name; brand name Lentabol; former developmental code names SKF-6611, CP-73) is a synthetic androgen and anabolic steroid (AAS) that was derived from nandrolone.^[1]^[2]^[3] It was described in the literature in 1957.^[1] Norclostebol is also used as an ester, norclostebol acetate (brand name Anabol 4-19).

Norclostebol is a 4-chloro derivative of testosterone. It works out to be significantly stronger than pure testosterone. It is approximately 6.6 times as anabolic while only 40% as androgenic. This may not be a particularly fair or valid comparison however. It is more appropriate to compare norclostebol to testosterone propionate due to the use of an ester. In this case they are fairly even in anabolic potency at 112% but only 20–25% as androgenic. In practice this means norclostebol is a potent anabolic compound with minimal tendency towards side effects.^[4]

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 now used by oral administration or 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">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.

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.

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.

Oxabolone cipionate, or oxabolone cypionate, also known as 4-hydroxy-19-nortestosterone 17β-cypionate or estr-4-en-4,17β-diol-3-one 17β-cypionate, is synthetic and injected anabolic–androgenic steroid (AAS) and derivative of nandrolone (19-nortestosterone) which has been marketed in Europe. It is the C17β cypionate ester and a prodrug of oxabolone (4-hydroxy-19-nortestosterone).

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

<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">Cloxotestosterone</span> Chemical compound

Cloxotestosterone, also known as 17β-chloral hemiacetal testosterone, is a synthetic anabolic–androgenic steroid (AAS) and an androgen ether – specifically, the 17β-trichloro hemiacetal ether of testosterone – which was never marketed. The O-acetate ester of cloxotestosterone, cloxotestosterone acetate, in contrast to cloxotestosterone, has been marketed.

Cloxotestosterone acetate, also known as testosterone 17β-chloral hemiacetal O-acetate, is a synthetic, injected anabolic–androgenic steroid (AAS) and an androgen ether and ester – specifically, the O-acetate ester of cloxotestosterone, the 17β-trichloro hemiacetal ether of testosterone. It is administered via intramuscular injection, as a 100 mg, 2 mL aqueous suspension and lasts 4 to 6 weeks with a single administration. The drug was first marketed in the early 1960s.

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.

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).

Norclostebol acetate, or norchlorotestosterone acetate (NClTA), also known as 4-chloro-19-nortestosterone 17β-acetate or as 4-chloroestr-4-en-17β-ol-3-one, is a synthetic, injectable anabolic-androgenic steroid (AAS) and derivative of 19-nortestosterone (nandrolone). It is an androgen ester – specifically, the C17β acetate ester of norclostebol (4-chloro-19-nortestosterone).

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. It was formerly used in humans as well. It is given by injection into muscle.

Stenbolone acetate, also known as 2-methyl-4,5α-dihydro-δ¹-testosterone 17β-acetate or as 2-methyl-5α-androst-1-en-17β-ol-3-one 17β-acetate, is a synthetic, injected anabolic–androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT) which has been marketed in Spain.

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.

Clostebol acetate is a synthetic, injected anabolic-androgenic steroid (AAS) and a derivative of testosterone that is marketed in Germany and Italy. It is an androgen ester – specifically, the C17β acetate ester of clostebol (4-chlorotestosterone) – and acts as a prodrug of clostebol in the body. Clostebol acetate is administered via intramuscular injection.

Clostebol caproate, also known as clostebol hexanoate or chlorotestosterone caproate (JAN), as well as 4-chlorotestosterone 17β-caproate or as 4-chloroandrost-4-en-17β-ol-3-one 17β-caproate, is a synthetic, injected anabolic-androgenic steroid (AAS) and a derivative of testosterone. It is an androgen ester – specifically, the C17β caproate ester of clostebol (4-chlorotestosterone) – and acts as a prodrug of clostebol in the body. Clostebol acetate is administered via intramuscular injection.

Clostebol propionate, also known as 4-chlorotestosterone 17β-propionate or as 4-chloroandrost-4-en-17β-ol-3-one 17β-propionate, is a synthetic, injected anabolic-androgenic steroid (AAS) and a derivative of testosterone. It is an androgen ester – specifically, the C17β propionate ester of clostebol (4-chlorotestosterone) – and acts as a prodrug of clostebol in the body. Clostebol acetate is administered via intramuscular injection.

References

1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 168–. ISBN 978-1-4757-2085-3.
↑ Karch SB (9 October 2007). Pathology, Toxicogenetics, and Criminalistics of Drug Abuse. CRC Press. pp. 67–. ISBN 978-1-4200-5456-9.
↑ Wright JE (1982). Anabolic Steroids and Sports: A Comprehensive, Up-to-date Summary and Discussion of the Scientific Findings about the Controversial Drugs Widely Used to Increase Muscle Size and Strength. Sports Science Consultants. ISBN 978-0-9609306-0-9.
↑ Le Bizec B, Van Hoof N, Courtheyn D, Gaudin I, Van De Wiele M, Bichon E, et al. (January 2006). "New anabolic steroid illegally used in cattle-structure elucidation of 19-norchlorotestosterone acetate metabolites in bovine urine". The Journal of Steroid Biochemistry and Molecular Biology. 98 (1): 78–89. doi:10.1016/j.jsbmb.2005.07.008. PMID 16216493.

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[Elks2014-1] 1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 168–. ISBN 978-1-4757-2085-3.

[FFFLM2007-2] Karch SB (9 October 2007). Pathology, Toxicogenetics, and Criminalistics of Drug Abuse. CRC Press. pp. 67–. ISBN 978-1-4200-5456-9.

[Wright1982-3] Wright JE (1982). Anabolic Steroids and Sports: A Comprehensive, Up-to-date Summary and Discussion of the Scientific Findings about the Controversial Drugs Widely Used to Increase Muscle Size and Strength. Sports Science Consultants. ISBN 978-0-9609306-0-9.

[4] Le Bizec B, Van Hoof N, Courtheyn D, Gaudin I, Van De Wiele M, Bichon E, et al. (January 2006). "New anabolic steroid illegally used in cattle-structure elucidation of 19-norchlorotestosterone acetate metabolites in bovine urine". The Journal of Steroid Biochemistry and Molecular Biology. 98 (1): 78–89. doi:10.1016/j.jsbmb.2005.07.008. PMID 16216493.

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