Canonical SMILES:
CC12CCC3C(C1CCC2(C)O)CCC4C3(CC5=C(C4)NN=C5)C
Isomeric SMILES:
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(CC5=C(C4)NN=C5)C
Recent ClinicalTrials:
Hetrombopag for Low/Intermediate-1 Risk MDS With Thrombocytopenia
Chemical Composition and Structure
Stanozolol (Stan) is a heterocyclic anabolic androgenic steroid.
Chemical structure: 17β-hydroxy-17α-methyl-5α-androst-2-eno[3,2-c]-pyrazole.
History and Development
Synthesized in 1959 by Clinton et al.[1] and remains one of the most detected anabolic steroids in doping control samples[2].
Classified as an anabolic androgenic steroid.
Developed analytical methods focus on identifying and determining parent drug and/or metabolic products in urine samples.
Early research focused on gas chromatography–mass spectrometry (GC–MS) detection, but liquid chromatography–mass spectrometry (LC–MS) is now preferred.
Uses
Medical Applications:
Stanozolol has medical applications but is more commonly known for its illicit use in doping.
Doping Control:
Used for performance enhancement in athletics.
Animal Use:
Also used in veterinary medicine for performance enhancement and growth promotion.
Mechanism of Action
Acts as an androgen receptor agonist, promoting protein synthesis and muscle growth.
Pharmacokinetics
Stanozolol is rapidly metabolized in humans and animals.
Major phase-I metabolic products include 3′-hydroxy-stanozolol, 4β-hydroxy-stanozolol, 16β-hydroxy-stanozolol, and 4,16-dihydroxy-stanozolol.
Metabolites are excreted in urine mainly as glucuronide conjugates.[2]
Regulatory Status
The prohibition of the drugs by the International Olympic Committee (IOC) in 1974[1]. Illicit use of stanozolol is prohibited in most sports and is considered a controlled substance in many countries.
References
[1] Analytical possibilities for the detection of stanozolol and its metabolites (DOI 10.1016/S0003-2670(02)00672-4)
[2] Sensitive detection of 3′-hydroxy-stanozolol glucuronide by liquid chromatography–tandem mass spectrometry (DOI 10.1016/j.chroma.2013.01.001)