53-39-4 Usage
Description
Oxandrolone, also known as 17β-hydroxy-17-methyl-2-oxaandrostan-3-one, is a synthetic anabolic-androgenic steroid and a 17 alpha-methylated version of dihydrotestosterone (DHT). It is a white solid that is soluble in chloroform and slightly soluble in ethanol, acetone, and ether, with very slight solubility in water. Oxandrolone acts as an agonist of the androgen receptor, modulating related gene expression to increase protein synthesis, muscle growth, body mass, and bone mineral density. It is especially effective in the treatment of severe burns without causing obvious side effects. The brand name for Oxandrolone is Oxandrin (Savient).
Uses
Used in Medical Treatment:
Oxandrolone is used as a treatment for various disorders, including idiopathic short stature, body mass loss due to catabolic illness, severe burns, trauma, hereditary angioedema, and Turner syndrome. It is particularly effective in treating severe burns and is used to promote weight gain after weight loss following surgery, chronic infections, or severe trauma. It also offsets protein catabolism associated with long-term corticosteroid use and relieves bone pain accompanying osteoporosis.
Used in Pediatric Burn Care:
Oxandrolone is used as an anabolic agent for severely burned children, enhancing muscle protein anabolism and improving the efficiency of protein synthesis. It is used as an androgenic anabolic steroid to reverse catabolic tissue processes, promote the buildup of protein, and increase erythropoietin production. Oxandrolone administration decreases loss of body weight, improves healing of the donor site wound, and reduces the length of acute hospitalization. In a large clinical trial, 0.1 mg/kg oxandrolone administered twice daily sustained lean body mass and improved liver protein synthesis. Severely burned pediatric patients receiving oxandrolone for 1 year experienced improved growth, decreased cardiac work, and improved muscle strength. The treatment also improved lung function at rest and during exercise, with benefits maintained for up to 4 years after treatment ended.
Used in Treatment of Osteoporosis:
Oxandrolone is used as a treatment for osteoporosis, helping to promote muscle growth and combat involuntary weight loss. It has also been used to treat cases of alcoholic hepatitis and HIV wasting syndrome.
Used in Androgenic Anabolic Steroid Therapy:
Oxandrolone is used for the same indications as nandrolone, a synthetic anabolic steroid. It is used to promote muscle growth and combat involuntary weight loss, with its androgenic effect being less than its anabolic effect.
testosterone
Oxandrolone is an anabolic steroid, a testosterone analog with ten times the anabolic activity but one-tenth of the androgenic activity of testosterone. Research into its use in burn injury for preventing loss or restoring muscle mass has been going on since the mid-1990s. Demling found that patients in the rehabilitation phase on an exercise programme, oxan- drolone and a high protein diet gained more body weight than those on an exercise programme and normal or high protein diet. Oxandrolone was effective in older adults, over 60 years, as well as in younger adults. This is important in light of the difficulties older adults face due to loss of lean body mass.
In 2000 Demling used oxandrolone (20 mg/ day) in the acute phase on burn injury, beginning when patients reached a minimum of 75% of their energy and protein requirements. Twenty patients were studied in a double-blind randomised controlled trial. Patients on oxandrolone had an improved net nitrogen balance, decreased weight loss, faster healing of donor sites and a shorter length of stay. Oxandrolone did not decrease metabolic rate and there were no side effects. The use of oxandralone is being considered in burns in the UK.
Pharmacokinetics
Oxandrolone is administered orally and is rapidly absorbed. Oxandrolone is highly bound (9–97%) to plasma proteins and has a bioavailability of approximately 97%. Hepatic metabolism of oxandrolone is markedly slower than that of testosterone or other androgens due to the modification of ring A (lack of a 4-ene function) and 17alfa-alkylation. The elimination half-life for oxandrolone is approximately 9.4 h, and peak plasma concentrations are higher than methyltestosterone. Oxandrolone is excreted primarily in the urine as the unchanged parent drug (approximately 28%) and unconjugated product.
Side effects
No significant side effects have been reported in boys treated with oxandrolone for CDGD. Although oxandrolone has significantly fewer androgenic effects than testosterone, mild virilization has been reported in girls taking oxandrolone, including clitoromegaly. This is less of a concern at lower doses. There are also reports of a delay in breast development that improves upon higher estrogen dosing. Hepatic dysfunction has been reported with oxandrolone treatment, manifested by alterations in HDL cholesterol, and thus monitoring of lipids is suggested.
overdose
No symptoms or signs associated with overdosage have been reported. It is possible that sodium and water retention may occur.
The oral LD50 of oxandrolone in mice and dogs is greater than 5,000 mg/kg. No specific antidote is known, but gastric lavage may be used.
Related Articles
Oxandrolone is a man-made steroid, similar to the naturally occurring steroid testosterone. Oxandrolone is an "anabolic" steroid that promotes the growth of muscle tissue.
https://www.drugs.com/mtm/oxandrolone.html
Oxandrolone is a synthetic, orally active anabolic-androgenic steroid. Oxandrolones interact with androgen receptors in target tissues.
https://drugs.ncats.io/substance/7H6TM3CT4L
Oxandrolone is an anabolic steroid that has been used in catabolic situations such as hepatitis and AIDS patients and can be administered orally, thus eliminating one source of stress for children and families.
https://www.sciencedirect.com/topics/neuroscience/oxandrolone
Oxandrin (oxandrolone) is indicated as adjunctive therapy to promote weight gain after weight loss following extensive surgery, chronic infections, or severe trauma, and in some patients who without definite pathophysiologic reasons fail to gain or to maintain normal weight, to offset the protein catabolism associated with prolonged administration of corticosteroids, and for the relief of the bone pain frequently accompanying osteoporosis (See DOSAGE AND ADMINISTRATION).
https://www.rxlist.com/oxandrin-drug.htm#indications
Originator
Anavar,Searle,US,1964
Therapeutic Function
Androgen
Biochem/physiol Actions
Oxandrolone is a synthetic anabolic steroid. It is is a non-aromatizable androgen with no estrogenic effects and with mild androgenic activity. Clinical uses of oxandrolone include to promote weight gain after weight loss following extensive surgery or chronic infections or trauma, to offset the protein catabolism associated with prolonged administration of corticosteroids, to relieve bone pain frequently accompanying osteoporosis, and to treat Turner′s syndrome in girls.
Safety Profile
Moderately toxic by ingestion andintraperitoneal routes. Experimental reproductive effects.When heated to decomposition it emits acrid smoke andfumes.
Synthesis
Oxandrolone, 17β-hydroxy-17α-methyl-2-oxa-5-androstan-3-one (29.3.10),
is made by oxidation of the C1–C2 double bond of 17β-hydroxy-17α-methyl-1-androsten-
3-one by a mixture of lead tetraacetate and osmium tetroxide with an opening of the A ring
of the steroid system, which forms an aldehyde acid (29.3.9). Upon reducing the aldehyde
group with sodium borohydride, intramolecular cyclization takes place, directly forming a
lactone (29.3.10), which is the desired oxandrolone.
References
Li, H., et al. "The efficacy and safety of oxandrolone treatment for patients with severe burns: A systematic review and meta-analysis. " Burns Journal of the International Society for Burn Injuries 42.4(2016): 717.
Hart, D. W., et al. "Anabolic effects of oxandrolone after severe burn." Annals of Surgery 233.4(2001): 556-564.
Sheffieldmoore, M, et al. "Short-term oxandrolone administration stimulates net muscle protein synthesis in young men. " Journal of Clinical Endocrinology & Metabolism 84.8(1999): 2705-11.
https://en.wikipedia.org/wiki/Oxandrolone
Check Digit Verification of cas no
The CAS Registry Mumber 53-39-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 3 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 53-39:
(4*5)+(3*3)+(2*3)+(1*9)=44
44 % 10 = 4
So 53-39-4 is a valid CAS Registry Number.
InChI:InChI=1/C19H30O3/c1-17-11-22-16(20)10-12(17)4-5-13-14(17)6-8-18(2)15(13)7-9-19(18,3)21/h12-15,21H,4-11H2,1-3H3/t12-,13+,14-,15-,17-,18-,19-/m0/s1
53-39-4Relevant articles and documents
A facile method for the rapid and selective deprotection of methoxymethyl (MOM) ethers
Han, Jae Hyun,Kwon, Young Eun,Sohn, Jeong-Hun,Ryu, Do Hyun
experimental part, p. 1673 - 1677 (2010/04/04)
We describe a rapid and efficient method for selective deprotection of methoxymethyl (MOM) ethers using ZnBr2 and n-PrSH, which completely removed MOM from diverse MOM ethers of primary, secondary, and tertiary alcohols or phenol derivatives. The deprotection takes less than ten minutes with both high yield and selectivity in the presence of other protecting groups. In addition, the rapid deprotection of MOM ethers of tertiary hydroxyls in high yield with no epimerization allows MOM to be a suitable protecting group for tertiary alcohols.
PROCESS FOR THE PRODUCTION OF 2-OXA-3-ONE ANDROSTANE DERIVATIVES
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Page 6, (2008/06/13)
The present invention relates to processes for the production of 2-oxa-3-one androstane derivatives. The processes comprise reacting a 3-one androstane derivative with ozone to form a 2-oxa-3-one androstane derivative.
Process for the synthesis of 17β-hydroxy-17α-methyl-2-oxa-5α-androstane-3-one
-
, (2008/06/13)
The invention relates to a new process for the synthesis of 17β-hydroxy-17α-methyl-2-oxa-5α-androstane-3-one of formula (I). The process according to the invention is as follows: the 17β-hydroxy-17α-ethyl-1,3-seco-2-nor-5α-androstane-1,3-diacid of formula (III) is transformed into the ring-closed 17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-1,3-diacid anhydride of formula (II) in an inert solvent or without solvent with a C2-C3alkan acid anhydride or a substituted carbodiimide of formula R1—N═C═N—R2— wherein R1and R2independently are C1-C6alkyl group, C1-C6alkyl group substituted by tertiary or quaternary amino group or 1-3 phenyl group, C5-C6cycloalkyl group, aryl group substituted by 1-3 methoxy, tertiary amino, nitro, C1-C4alkyl group or 1-3 halogen atom—and the obtained compound of formula (II) is reduced regioselectively by a complex alkali metal hydride in an inert solvent The new 17β-hydroxy-17α-methyl-1,3-seco-2-nor-5α-androstane-1,3-diacid anhydride of formula (II) is also the subject of the invention.
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