Nandrolone Laurate

Administered via intramuscular injection, this nandrolone ester combines the male sex hormone with a chemical compound to offer a unique therapeutic approach, particularly in the supportive management of chronic renal failure in cats and dogs ^[1][2].

Its formulation as a light-yellow oily solution, containing 25 mg/ml of the active ingredient, makes it accessible to animal health professionals, farmers, pet owners, and horse owners, emphasizing the importance of responsible medication use ^[2]. Nandrolone Laurate

This exploration into what nandrolone is and how it works delves into the compound’s chemical structure and properties, its historical context, and clinical applications. By understanding its mechanism of action and comparative advantages over other androgenic steroids, alongside a critical analysis of its adverse effects and legal status, this article aims to provide comprehensive insights into the evolving role of nandrolone laurate.

Offering a significant contribution to various medical fields, nandrolone’s operations extend beyond veterinary uses, touching on pivotal issues like anemia, bodybuilding, and the management of conditions related to testosterone, hypertension, and more ^[1][2][3].

Chemical Structure and Properties

Nandrolone Laurate, known chemically as [(8 R ,9 S ,10 R ,13 S ,14 S ,17 S )-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1 H -cyclopenta[ a ]phenanthren-17-yl] dodecanoate, is a compound with significant medical and scientific interest. Its structural and physical characteristics are vital for understanding its function and application in medical treatments. Below is a detailed breakdown of its chemical identifiers and physical properties:

Chemical Identifiers:

• IUPAC Name: (8 R ,9 S ,10 R ,13 S ,14 S ,17 S )-13-methyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1 H -cyclopenta[ a ]phenanthren-17-yl] dodecanoate ^[1]
• CAS Number: 26490-31-3 ^[1]
• PubChem CID: 94371 ^[1]
• ChemSpider: 85167 ^[1]
• UNII: WVJ22FFN83 ^[1]
• CompTox Dashboard (EPA): DTXSID80949362 ^[1]
• ECHA InfoCard: 100.043.384 ^[1]

Physical Properties:

• Molecular Formula: C30H48O3 ^[1]
• Molecular Weight: 456.711 g·mol−1 ^[1]
• SMILES and InChI Keys: Providing a detailed representation of the molecule’s structure ^[1]
• Solubility and Melting Points: Soluble in ether, chloroform, and alcohol; with melting points varying by ester ^[1]

Biological Activity:

• Androgen Receptor Agonist: Nandrolone decanoate acts as an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and DHT, which explains its strong anabolic effects and weak androgenic effects ^[6].
• Anabolic to Androgenic Ratio: Nandrolone esters, including nandrolone laurate, are thought to have the highest ratio of anabolic to androgenic effects of any AAS. This characteristic, along with its low androgenicity due to inactivation by 5α-reductase, makes it especially suitable for use in demographics sensitive to androgenic effects, such as women and children ^{[6] [8]}.

Understanding these chemical and physical properties, alongside the biological activity, is crucial for comprehending how nandrolone laurate functions within the body and its potential therapeutic applications. The compound’s structure directly influences its interaction with biological systems, contributing to its efficacy and safety profile in medical and veterinary contexts.

Historical Context and Initial Approval

The historical development and initial approval of Nandrolone, particularly its decanoate form, mark significant milestones in medical and pharmaceutical sciences. This section outlines the key events and approvals that have shaped the trajectory of Nandrolone’s use in medicine.

• Discovery and Development:
• 1. Synthesis of Synthetic Nandrolone: The synthetic version of nandrolone was developed in the 1950s, aiming to create a compound with enhanced anabolic properties compared to testosterone ^[7].
  2. First Described: Nandrolone esters, including Nandrolone Laurate, were first described in scientific literature in 1960, highlighting their potential medical applications ^[6].
  3. Nandrolone for Sale: Although developed in the 1950s, nandrolone only became available for sale in 1962 in the form of Nandrolone Decanoate under the trade name Deca-Durabolin by the Organon company ^[7].
• Medical Approval and Uses:
• 1. Initial Approval: Nandrolone Decanoate was first approved for medical use in the United States in 1959, marking its entry into the pharmaceutical market for therapeutic applications ^[7].
  2. Clinical Applications: It has been utilized in the treatment of various conditions, including anemias, cachexia, osteoporosis, breast cancer, among other indications, showcasing its versatility in medical treatments ^[4].
• Global Impact and Usage:
• 1. Widespread Adoption: Nandrolone Decanoate, among other esters, quickly became one of the most widely used anabolic androgenic steroids (AAS) worldwide, owing to its favorable anabolic to androgenic effects ^[6].
  2. Significance in Medical Fields: Its adoption across various medical fields underscores the compound’s significance and the pivotal role it has played in advancing treatment options for several chronic and acute conditions ^[4].

The historical context and initial approval of Nandrolone and its esters, particularly Nandrolone Decanoate, underscore the compound’s importance in the pharmaceutical and medical landscape. From its synthesis in the 1950s to becoming one of the most widely used anabolic steroids, Nandrolone’s journey reflects the evolving understanding and application of synthetic hormones in medicine.

Mechanism of Action

Nandrolone Laurate’s mechanism of action is multifaceted, affecting various aspects of metabolism and physiological functions. Below is a detailed breakdown of its primary mechanisms:

• Metabolic Enhancements:
• 1. Promotes positive effects on nitrogen, calcium, and phosphorus metabolism, crucial for maintaining the balance of these elements in the body, which is essential for bone health and muscle function ^[2].
  2. Contributes to the normalization of tissue water/electrolyte balance, ensuring proper hydration and electrolyte levels within tissues, vital for cellular function and overall health ^[2].
• Muscle Recovery and Growth:
• 1. Increases the rate of muscle glycogen repletion after exercise, aiding in quicker recovery and preparation for subsequent physical activities ^[11].
  2. This increase is attributed to enhanced glucose output by the liver, elevated plasma insulin concentration, and improved insulin-independent glucose transport, facilitating efficient energy storage and utilization in muscles ^[11].
• Hormonal Effects:
• 1. Suppresses the gonadotropic functions of the pituitary gland and may have a direct impact on the testis, influencing testosterone production and overall hormonal balance ^[7].
  2. Acts as a progestogen with a relative affinity for the progesterone receptor of 20% and for the androgen receptor of 154-155%, indicating its significant anabolic effects and minimal androgenic effects ^[1].
  3. Metabolized by the enzyme 5α-reductase into metabolites like 5α-dihydronandrolone, which are detectable in urine and act as long-lasting prodrugs in the body, contributing to its sustained anabolic activity ^{[3] [4]}.
• Immunomodulatory Actions:
• 1. Reduces immune system activity, which can be beneficial in conditions where inflammation and tissue damage are concerns, such as in the healing of burns, allergic reactions, and certain types of cancers ^[12].

Nandrolone Laurate’s comprehensive mechanism of action, from metabolic enhancements to hormonal effects and immunomodulatory actions, underscores its utility in both clinical and illicit contexts. Its ability to promote muscle growth and recovery while managing hormonal and immune functions makes it a compound of interest in various medical and athletic settings.

Clinical Uses

Nandrolone Decanoate, marketed under the name Deca-Durabolin among others, has a broad spectrum of clinical applications, leveraging its anabolic effects with reduced androgenic effects for therapeutic purposes ^[3]. The clinical uses of Nandrolone Decanoate and its variants, including Nandrolone Laurate, span across human and veterinary medicine, reflecting its versatility and efficacy in treating a range of conditions:

• Human Medicine:
• • Treatment of anemia associated with chronic kidney disease, enhancing hemoglobin and red cell mass ^[7].
  • Management of osteoporosis in postmenopausal women, contributing to bone density improvement ^[3].
  • Supportive care in inoperable breast cancer, long-term corticosteroid therapy, and HIV/AIDS associated wasting syndrome ^[3].
  • Recovery aid post-burns, radiation therapy, surgery, and trauma, facilitating healing and tissue repair ^[3].
  • Rheumatoid arthritis treatment in postmenopausal women, showing significant improvements in total body nitrogen and hemoglobin levels ^[16].
• Veterinary Medicine:
• • Muscle growth and appetite enhancement in animals, particularly in Austria, France, the Netherlands, and Switzerland ^[1].
  • Supportive management of chronic renal failure in dogs and cats, improving their quality of life ^[2].
  • Treatment of debilitated and anaemic horses, assisting in recovery from surgery, minor injuries, malnutrition, and physical exhaustion ^[14].

The administration of Nandrolone, whether in human or veterinary contexts, is typically via injection into muscle or fat, emphasizing the importance of professional supervision due to its potent effects and potential side effects ^[4][15].

Dosage varies significantly based on the condition being treated, with adults generally recommended to receive 50 to 100 mg per week for women and 100 to 200 mg per week for men, while children from 2 to 13 years of age may receive 25 to 50 mg every 3 to 4 weeks ^[7].

These applications underscore Nandrolone’s role as a critical therapeutic agent, offering benefits in muscle strength and size, red blood cell production, muscle endurance and healing, lean muscle mass growth, and increased bone density ^[15].

Adverse Effects and Warnings

While Nandrolone Decanoate presents numerous therapeutic benefits, it’s imperative to acknowledge its potential adverse effects and warnings associated with its use. These effects span across various physiological systems, underscoring the need for cautious administration:

Endocrine and Reproductive System:

• Virilization symptoms in females, including deepened voice and facial hair ^[3][17].
• Gynecomastia and hormonal disorders in males ^[3][17].
• Infertility issues due to alterations in genital function and suppression of gonadotropic functions ^[3][7][17].
• Inhibition of endogenous testosterone release and potential impact on spermatogenesis ^[17].

Cardiovascular and Hematologic Concerns:

• Vascular damage, coagulation disorders, and arteriosus hypertension ^[3].
• Fluid retention leading to edema, with or without congestive heart failure ^[17].
• Alterations in clotting factors and prolonged prothrombin time, affecting blood coagulation ^[17].

Metabolic and Hepatic Effects:

• Disturbances in electrolyte balance, nitrogen retention, and urinary calcium excretion ^[17].
• Hepatic abnormalities, including peliosis hepatis, hepatic neoplasms, and hepatocellular carcinomas ^[17].
• Osteolytic-induced hypercalcemia in immobilized patients or those with metastatic breast disease ^[17].

Dermatologic and Psychiatric Manifestations:

• Dermatologic issues such as acne, increased hair growth, and skin spots ^[3][17].
• Psychiatric effects including mood disorders, aggressiveness, and sleep disturbances ^[3][17].

Musculoskeletal and Gastrointestinal Reactions:

• Closure of epiphyseal growth centers, affecting bone growth ^[17].
• Gastrointestinal disturbances like nausea, vomiting, and diarrhea ^[17].

Special Considerations and Contraindications:

• Contraindicated in pregnant animals and those with hypercalcemia or androgen-dependent tumors ^[2].
• Caution advised in cases of hepatic impairment and known hypersensitivity to Nandrolone or any excipients ^[2].

Adverse Reactions in Animals:

• Behavioral changes and androgenic side effects, especially in female animals ^[2].
• Frequency of adverse reactions ranging from very common to very rare, emphasizing the importance of monitoring and professional guidance ^[2].

This comprehensive overview of potential adverse effects and warnings associated with Nandrolone Decanoate underscores the importance of careful consideration and professional oversight when utilizing this compound for therapeutic purposes.

Pharmacokinetics

Nandrolone Laurate, a long-acting ester of nandrolone, exhibits distinct pharmacokinetic properties that are crucial for its therapeutic application and efficacy. Understanding these properties provides insights into how the drug is processed within the body, including its absorption, distribution, metabolism, and excretion:

• Absorption and Duration of Action:
• • Once administered via intramuscular injection, Nandrolone Laurate demonstrates a half-life (T1/2) of approximately 243 hours ^[2]. This extended half-life reflects its duration of action, which ranges from 3 to 4 weeks, allowing for less frequent dosing schedules ^[2].
  • The laurate ester specifically influences the duration of action, with the phenylpropionate ester acting for 1 week, the decanoate for 2-3 weeks, and the laurate for 3-4 weeks, respectively ^[2].
• Metabolism and Excretion:
• • Nandrolone Laurate undergoes metabolism similarly to testosterone, with its conversion into 3-norandrosterone by the enzyme 5α-reductase ^[8]. This process is pivotal as it transforms Nandrolone Laurate into its active metabolite, nandrolone, which then exerts the desired therapeutic effects ^[1].
  • The compound exhibits ‘flip-flop’ pharmacokinetics, where the initial phase of the curve represents the disposition of nandrolone, and the descending part reflects the rate-limiting process of nandrolone decanoate’s release from the muscle into the general circulation ^[8]. This unique pharmacokinetic profile ensures a sustained release and prolonged action.
• Detection in Biological Fluids:
• • Following administration, nandrolone metabolites such as 19-norandrosterone (19-NA) and 19-noretiocholanolone (19-NE) can be detected in urine. In a study, these metabolites were identifiable in a significant proportion of subjects, with detection times extending up to 6 months post-injection in some cases, depending on the dosage administered ^[8]. This extended detectability is particularly relevant in the context of doping control and therapeutic monitoring.

These pharmacokinetic characteristics of Nandrolone Laurate underline its utility in clinical settings, offering a balance between efficacy and convenience with its long-acting nature. However, the extended presence of its metabolites in biological fluids also necessitates careful consideration in scenarios where doping control is a concern.

Comparative Analysis with Other Androgenic Steroids

Nandrolone Laurate demonstrates a unique profile when compared to other androgenic steroids, particularly in terms of its anabolic and androgenic effects, as well as its influence on muscle composition and performance. A comparative analysis reveals the following distinctions:

• Anabolic vs. Androgenic Effects:
• • Nandrolone Laurate: Known for its strong anabolic effects but weak androgenic effects, making it preferable for use in populations sensitive to androgenic side effects, such as women and children ^[3][4].
  • Other Androgenic Steroids: Typically exhibit a more balanced ratio of anabolic to androgenic effects, which may lead to more pronounced androgenic side effects, including virilization in females and gynecomastia in males.
• Influence on Muscle Composition and Performance:
• • Positive Nitrogen Balance: Both Nandrolone Laurate and other anabolic steroids promote a positive nitrogen balance, crucial for muscle growth and recovery ^[14].
  • Muscle Fiber Composition: An interesting aspect of Nandrolone Laurate is its potential to affect muscle composition by increasing the proportion of Type I fibers, which are known for endurance, while decreasing the proportion of Type II fibers, associated with strength and speed ^[14]. This contrasts with some steroids that do not significantly alter muscle fiber composition.
  • Performance Metrics: Unlike other anabolic steroids, Nandrolone Laurate does not affect peak heart rate, V200 (velocity at which VO2 max occurs), or VLa4 (velocity at lactate threshold), indicating its effects on performance may be mediated through mechanisms other than cardiovascular efficiency ^[14].
• Behavioral and Metabolic Effects:
• • Behavioral Changes: Anabolic steroids, including Nandrolone Laurate, have been shown to increase stallion-like behavior in treated individuals, potentially indirectly enhancing muscle performance ^[14]. This is a unique consideration not often discussed in the context of other androgenic steroids.
  • Metabolic Considerations: Elevated plasma urea levels suggest that the nitrogen retention benefits of anabolic steroids, including Nandrolone Laurate, might be due to higher blood nitrogen levels rather than a direct anabolic effect on muscle tissues ^[14]. This insight provides a nuanced understanding of how these compounds might exert their effects on the body.

This comparative analysis underscores the unique properties of Nandrolone Laurate, especially its favorable anabolic to androgenic ratio and specific effects on muscle composition and metabolic processes. These distinctions are critical for clinicians and researchers in tailoring therapeutic applications and anticipating outcomes from treatment with anabolic steroids.

Legal Status and Control Measures

Nandrolone Laurate and its variants, including Nandrolone Decanoate, are subject to strict regulatory measures and legal classifications across various jurisdictions due to their potent anabolic properties and potential for abuse. The legal status and control measures surrounding these compounds are outlined as follows:

• Controlled Substance Classification:
• • In the United States, Nandrolone Decanoate is classified as a Schedule III controlled substance under the Anabolic Steroids Control Act of 1990, indicating its potential for abuse and dependence, but also its acceptance for medical use with a prescription ^{[3] [15]}.
  • The drug’s classification as a controlled substance is echoed in many countries, underscoring the global consensus on the need for regulation to prevent misuse ^{[1] [6]}.
• Banned by Sports Organizations:
• • Nandrolone and its esters, including Nandrolone Laurate, are prohibited by most sports organizations. They are listed on the World Anti-Doping Agency (WADA) Prohibited List, making their non-medical use banned in competitive sports ^[3].
  • Additionally, the National Collegiate Athletic Association (NCAA) prohibits the use of Nandrolone, reinforcing the commitment to maintaining fairness and health in athletic competitions ^[15].
• Environmental and Health Safety Regulations:
• • Nandrolone Laurate is classified under several hazardous categories including Carcinogenicity Category 1B, Reproductive toxicity Category 1A, and Effects on or via lactation Category Yes, indicating significant health risks associated with exposure ^[19].
  • The compound is also identified as toxic to aquatic life with long-lasting effects, prompting regulations around its disposal and handling to mitigate environmental impact ^[19].
  • Guidelines for handling Nandrolone Laurate stress the importance of good industrial hygiene and safety practices. It should be stored only in the original receptacle, and disposed of in accordance with local environmental legislation and regulations ^[19].

These regulatory measures and classifications reflect the dual nature of Nandrolone and its esters as valuable medical treatments on one hand, and substances with potential for abuse and environmental harm on the other. The strict controls are designed to ensure that while the therapeutic benefits of Nandrolone can be harnessed, the risks associated with its misuse and environmental impact are minimized.

Recent Research and Future Directions

Recent advancements in research have highlighted innovative methods and significant findings in the realm of nandrolone decanoate and its implications:

• Innovations in Detection Techniques:
• • A groundbreaking approach involves the use of dried blood spots (DBSs) for detecting anabolic steroid esters, including testosterone, nandrolone, and boldenone, offering a less invasive and more stable alternative to traditional urine testing ^[20].
  • The development of a simultaneous liquid chromatography–tandem mass spectrometry method capable of detecting 28 steroid esters in DBS samples marks a significant advancement in steroid detection technology. This method boasts limits of detection for testosterone, nandrolone, and boldenone esters at impressively low concentrations of less than 0.1-0.9 ng/mL ^[20].
  • A trial demonstrated the efficacy of this method, where testosterone enanthate was identifiable in DBS samples from upper arms and fingertips for up to 144 and 216 hours, respectively, showcasing the potential for long-term detection ^[20].
• Clinical Implications and Therapeutic Applications:
• • Research has shown that nandrolone decanoate treatment can affect sarcoplasmic reticulum Ca(2+) ATPase function in skinned rat slow- and fast-twitch fibers, suggesting a nuanced impact on muscle physiology ^[21].
  • A study highlighted the beneficial effects of long-term nandrolone decanoate treatment in women with joint diseases, noting significant improvements in intestinal calcium absorption and bone mineral content, which points to its potential in treating osteoporosis and other bone-related conditions ^[21].
  • The reversal of nandrolone decanoate-induced perturbations in sperm characteristics through taurine supplementation offers insights into mitigating some of the adverse effects associated with nandrolone use, providing a pathway for addressing fertility concerns ^[21].
• Understanding Metabolic and Molecular Mechanisms:
• • The role of PDE7B in nandrolone decanoate hydrolysis in liver cytosol and its androgen-induced transcription up-regulation in HepG2 cells reveal complex interactions at the molecular level that could inform future drug development and therapeutic strategies ^[21].
  • Observations from administering a 150 mg dose of nandrolone decanoate showed that 19-norandrosterone concentrations were 2-8 times higher than 19-noretiocholanolone for up to nine months, highlighting the long-lasting presence and potential for monitoring use or abuse of nandrolone ^[21].
  • The combination of anabolic steroid nandrolone decanoate with strength training in Wistar rats led to improved outcomes but also raised concerns over potential adverse effects on heart and kidney health, as well as metabolic disruptions, underscoring the importance of balanced and monitored use in therapeutic and athletic contexts ^[21].

These recent research endeavors provide valuable insights into the detection, clinical applications, and underlying mechanisms of nandrolone decanoate, paving the way for future investigations and the development of more effective and safer therapeutic approaches.

Conclusion

Throughout this article, we unraveled the complex nature of Nandrolone Laurate, shedding light on its vital contributions to both medical and veterinary fields. From its significant role in therapeutic interventions to its potential implications in bodybuilding and athletic performance enhancement, the discussion underscored the intricate balance between its benefits and the need for cautious use.

Emphasizing responsible administration and awareness of its adverse effects, we highlighted the critical importance of professional oversight when employing this potent anabolic steroid.

As we delve into the future of Nandrolone Laurate’s applications, it’s imperative to consider the evolving landscape of medical research and regulatory frameworks. Recent studies offer promising insights that could lead to more refined and safer use, though it’s crucial to remain vigilant about the ethical considerations and potential for abuse.

By fostering ongoing discourse on its clinical benefits, side effects, and legal status, the medical community can better navigate the complex terrain of Nandrolone Laurate, ensuring that its potential is maximized while minimizing risks.

FAQs

How Does Nandrolone Function in the Body?

Nandrolone operates by binding to androgen receptors without being convert into DHT (dihydrotestosterone) in the body. This action inhibits the production of testosterone by providing negative feedback to the hypothalamic-pituitary-gonadal (HPG) axis, leading to reduced levels of testosterone and DHT. This reduction can adversely affect erectile function.

Can Nandrolone Affect Your Skin?

Yes, nandrolone can cause allergic reactions manifesting as skin issues. These may include symptoms such as rashes, hives, itching, redness, swelling, blisters, or peeling of the skin, possibly accompanied by fever. Other severe reactions can include wheezing, chest tightness, difficulty breathing or swallowing, unusual hoarseness, and swelling of the mouth, face, lips, tongue, or throat.

What Are the Overall Effects of Nandrolone?

Nandrolone and its esters can have several side effects, including masculinization. In women, the use of nandrolone may lead to increased libido, acne, growth of facial and body hair, changes in voice, and clitoral enlargement, among other effects.

What Does It Feel Like to Use Nandrolone?

Using nandrolone, even in medically prescribed doses (approximately 0.4 milligrams per kilogram of body weight daily for treating illnesses or injuries), can lead to side effects. These may include headaches, bloating, diarrhea, abdominal pain, jaundice, high blood pressure, and alterations in the menstrual cycle.