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Chemistry

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Also known as: Winstrol, Androstanazole, Androstanazol, 10418-03-8, Stromba, Stanazolol
Molecular Formula
C21H32N2O
Molecular Weight
328.5  g/mol
InChI Key
LKAJKIOFIWVMDJ-IYRCEVNGSA-N
FDA UNII
4R1VB9P8V3

Stanozolol
A synthetic steroid that has anabolic and androgenic properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1194)
1 2D Structure

Stanozolol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2S,10S,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol
2.1.2 InChI
InChI=1S/C21H32N2O/c1-19-11-13-12-22-23-18(13)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,24H,4-11H2,1-3H3,(H,22,23)/t14-,15+,16-,17-,19-,20-,21-/m0/s1
2.1.3 InChI Key
LKAJKIOFIWVMDJ-IYRCEVNGSA-N
2.1.4 Canonical SMILES
CC12CCC3C(C1CCC2(C)O)CCC4C3(CC5=C(C4)NN=C5)C
2.1.5 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
2.2 Other Identifiers
2.2.1 UNII
4R1VB9P8V3
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Androstanazol

2. Methylstanazol

3. Stanazolol

4. Stromba

5. Winstrol

2.3.2 Depositor-Supplied Synonyms

1. Winstrol

2. Androstanazole

3. Androstanazol

4. 10418-03-8

5. Stromba

6. Stanazolol

7. Tevabolin

8. Winstrol Depot

9. Strombaject

10. Estazol

11. Winstroid

12. Winstrol V

13. Estanozolol

14. Stanozololum

15. Win 14833

16. Anabol

17. Stanozolol Ciii

18. Androstanazolestanazol

19. Nsc-43193

20. Win-14833

21. Nsc 233046

22. 4r1vb9p8v3

23. Chebi:9249

24. 17-methyl-2'h-5alpha-androst-2-eno(3,2-c)pyrazol-17beta-ol

25. Nsc-233046

26. (1s,3as,3br,5as,10as,10bs,12as)-1,10a,12a-trimethyl-1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-hexadecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-ol

27. Cyclopenta(7,8)phenanthro(2,3-c)pyrazol-1-ol, 1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-hexadecahydro-1,10a,12a-trimethyl-

28. Stanozolo [dcit]

29. Androstanazole (van)

30. Stanozolo

31. Stanozolol (1'h Form)

32. Winstrol-v

33. Stanozololum [inn-latin]

34. Estanozolol [inn-spanish]

35. (1s,2s,10s,13r,14s,17s,18s)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5-dien-17-ol

36. Cyclopenta(7,8)phenanthro(2,3-c)pyrazol-1-ol, 1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydro-1,10a,12a-trimethyl-

37. Hsdb 3185

38. Sr-05000001522

39. Stanozolol (2'h Form)

40. 17?-methyl-5?-androstano[3,2-c]pyrazol-17?-ol

41. Einecs 233-894-8

42. Nsc 43193

43. Unii-4r1vb9p8v3

44. 17.beta.-hydroxy-17.alpha.-methyl-5.alpha.-androstano(3,2-c)pyrazole

45. Winstrol (tn)

46. 2'h-androst-2-eno(3,2-c)pyrazol-17-ol, 17-methyl-, (5alpha,17beta)-

47. 17-methyl-5alpha-androstano(3,2-c)pyrazol-17beta-ol

48. 302-96-5

49. Stanozolol [usan:usp:inn:ban:jan]

50. 17-beta-hydroxy-17-alpha-methylandrostano(3,2-c)pyrazole

51. 17beta-hydroxy-17alpha-methyl-androstano(3,2-c)pyrazole

52. 17-methyl-pyrazolo(4',3':2,3)-5alpha-androstan-17beta-ol

53. 17-methylpyrazolo(4',3':2,3)-5alpha-androstan-17beta-ol

54. 17beta-hydroxy-17-methyl-5alpha-androstano(3,2-c)pyrazole

55. Stanozolol [mi]

56. 17alpha-methyl-17beta-hydroxy-5alpha-androstano(3,2-c)pyrazole

57. Stanozolol [inn]

58. Stanozolol [jan]

59. 2'h-5alpha-androst-2-eno(3,2-c)pyrazol-17beta-ol, 17-methyl-

60. 2,3-(4',3'-pyrazolo)-5alpha-androstan-17beta-ol, 17-methyl-

61. Stanozolol [hsdb]

62. Stanozolol [usan]

63. Stanozolol [vandf]

64. Stanozolol [mart.]

65. Dsstox_cid_24128

66. Dsstox_rid_97564

67. Stanozolol [who-dd]

68. Stanozolol--dea Schedule Iii

69. Dsstox_gsid_44128

70. Schembl44099

71. Schembl44100

72. Stanozolol (jan/usp/inn)

73. 1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydro-1,10a,12a-trimethylcyclopenta(7,8)-phenanthro(2,3-c)pyrazol-1-ol

74. Mls001424321

75. 17-methyl-2'h-5.alpha.-androst-2-eno(3,2-c)pyrazol-17.beta.-ol

76. Stanozolol, Analytical Standard

77. Stanozolol [green Book]

78. Chembl2079587

79. Dtxsid3044128

80. Stanozolol [orange Book]

81. Gtpl10369

82. Stanozolol [ep Monograph]

83. Stanozolol Ciii [usp-rs]

84. Hms2052h11

85. Hms2090p03

86. Hms3713k06

87. Stanozolol [usp Monograph]

88. Bcp12548

89. Hy-b0899

90. Nsc43193

91. Win14833

92. Zinc4097376

93. Tox21_113993

94. 1'h-androstano(3,2-c)pyrazol-17-ol, 17-methyl-, (5-alpha,17-beta)-

95. Akos005067278

96. Stanozolol 1.0 Mg/ml In Acetonitrile

97. Am84316

98. Ccg-101186

99. Ccg-220452

100. Cs-4363

101. Db06718

102. Nc00436

103. Ncgc00344550-01

104. (1s,3as,3br,5as,10as,10bs,12as)-1,10a,12a-trimethyl-1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydrocyclopenta[5,6]naphtho[1,2-f]indazol-1-ol

105. Ac-16140

106. Ac-33164

107. As-35198

108. Cpd000058878

109. Smr000058878

110. Cas-10418-03-8

111. C07311

112. D00444

113. 17-methyl-5a-androstano[3,2-c]pyrazol-17b-ol

114. Ab00443942-03

115. Ab00443942-05

116. 418s038

117. Sr-05000001522-1

118. Sr-05000001522-2

119. W-108823

120. 17a-methyl-17b-hydroxy-5a-androstano(3,2-c)pyrazole

121. 17b-hydroxy-17-methyl-5a-androstano[3,2-c]pyrazole

122. 17b-hydroxy-17a-methyl-5a-androstano[3,2-c]pyrazole

123. Q63409446

124. 17-methyl-pyrazolo[4',3':2,3]-5a-androstan-17b-ol

125. Z1541662177

126. 17-methyl-1'h-5alpha-androstano[3,2-c]pyrazol-17beta-ol

127. Stanozolol, European Pharmacopoeia (ep) Reference Standard

128. (5a,17b)-17-methyl-2'h-androst-2-eno[3,2-c]pyrazol-17-ol

129. 2,3'-pyrazolo)-5.alpha.-androstan-17.beta.-ol, 17-methyl-

130. 5alpha-androstane-17alpha-methyl-17beta-ol-[3,2-c]pyrazole

131. 17-methyl-5.alpha.-androstano(3,2-c)pyrazol-17.beta.-ol

132. 2'h-5a-androst-2-eno[3,2-c]pyrazol-17b-ol, 17-methyl- (8ci)

133. 17alpha-methyl-17beta-hydroxy-5alpha-androst-2-eno(3,2-c)-pyrazole

134. 1'h-androstano(3,2-c)pyrazol-17-ol, 17-methyl-, (5.alpha.,17.beta.)-

135. 2'h-androst-2-eno(3,2-c)pyrazol-17-ol, 17-methyl-, (5.alpha.,17.beta.)

136. Cyclopenta[7,8]phenanthro[2,3-c]pyrazole, 2'h-androst-2-eno[3,2-c]pyrazol-17-ol Deriv.

137. (1s,2s,10s,13r,14s,17s,18s)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol

138. 1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b,11,12,12a-hexadecahydro-1,10a,12a-trimethyl-cyclopenta[7,8]phenanthro[2,3-c]pyrazol-1-ol

139. 17966-55-1

140. 875293-72-4

141. Cyclopenta[7,3-c]pyrazol-1-ol, 1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-hexadecahydro-1,10a,12a-trimethyl-

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 328.5 g/mol
Molecular Formula C21H32N2O
XLogP34.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass328.251463648 g/mol
Monoisotopic Mass328.251463648 g/mol
Topological Polar Surface Area48.9 Ų
Heavy Atom Count24
Formal Charge0
Complexity538
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Anabolic Steroids

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Stanozolol ... /is/ indicated in conditions such as chronic infections, extensive surgery, corticosteroid-induced myopathy, decubitus ulcers, burns, or severe trauma, which require reversal of catabolic processes or protein-sparing effects. /This agent is/ ... adjunct to, and not replacement for, conventional treatment of these disorders. /NOT included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140


Stanozolol is effective in raising hemoglobin concentrations in some cases of aplastic anemia (congenital or idiopathic). /NOT included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140


Stanozolol ... /is/ indicated in the prophylaxis of hereditary angioedema to decrease the frequency and severity of attacks. /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140


For more Therapeutic Uses (Complete) data for STANOZOLOL (10 total), please visit the HSDB record page.


4.2 Drug Warning

Vet: monitor benefits and need carefully in cardiac disease and nephritis.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 553


Use of anabolic steroids by athletes is not recommended. Objective evidence is conflicting and inconclusive as to whether these medications significantly increase athletic performance by increasing muscle strength. Weight gains reported by athletes are due in part to fluid retention, which is a potentially hazardous side effect of anabolic steroid therapy. The risk of other unwanted effects, such as testicular atrophy and suppression of spermatogenesis in males; menstrual disturbances and virilization, such as deepening of voice, development of acne, and unnatural growth of body hair in females; peliosis hepatis or other hepatotoxicity; and hepatic cancer outweigh and possible benefit received from anabolic steroids and make their use in athletes inappropriate. /Anabolic steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 140


Anabolic steroids are not recommended for use during pregnancy, since studies in animals have shown that anabolic steroids cause masculinization of the fetus. Risk-benefit must be carefully considered. /Anabolic steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


Contraindications: Hypersensitivity to anabolic steroids; male patients with prostate or breast carcinoma; carcinoma of the breast in females with hypercalcemia; nephrosis; the nephrotic phase of nephritis; pregnancy; to enhance physical appearance or athletic performance. /Anabolic steroids/

Novak, K.M. (ed.). Drug Facts and Comparisons 59th Edition 2005. Wolters Kluwer Health. St. Louis, Missouri 2005., p. 334


For more Drug Warnings (Complete) data for STANOZOLOL (17 total), please visit the HSDB record page.


4.3 Drug Indication

Stanozolol is a synthetic anabolic steroid with therapeutic uses in treating C1-inhibitor deficient hereditary angioedema. C1-inhibitor is a protease that inhibits the complement system (part of the innate immune system), a biochemical chain of reactions which assists the body in removing pathogens from the body. Stanozolol may help control attacks of hereditary angioedema. Stanozolol can be administered orally or intramuscularly.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Stanozolol is a synthetic anabolic-androgenic steroid (AAS), which promotes cell growth (anabolism) and development/maintenance of masculine characteristics (androgenism).


5.2 MeSH Pharmacological Classification

Androgens

Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power. (See all compounds classified as Androgens.)


Anabolic Agents

These compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power. (See all compounds classified as Anabolic Agents.)


5.3 ATC Code

A - Alimentary tract and metabolism

A14 - Anabolic agents for systemic use

A14A - Anabolic steroids

A14AA - Androstan derivatives

A14AA02 - Stanozolol


5.4 Absorption, Distribution and Excretion

It is not known whether anabolic steroids are distributed into breast milk. /Anabolic steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


5.5 Metabolism/Metabolites

Urinary metabolites of stanozolol (17 alpha-methyl-17 beta-hydroxy-5 alpha-androst-2-eno(3,2-c)-pyrazole) following oral administration were isolated by chromatography on XAD-2 and by preparative high-performance liquid chromatography (HPLC) and identified by gas chromatography-mass spectrometry (GC/MS) with electron impact (EI)-ionisation. Stanozolol is excreted as a conjugate but is metabolized to a large extent. All identified metabolites are hydroxylated, namely at C-3' of the pyrazole ring and at C-4 beta, C-16 alpha and C-16 beta of the steroid. Less than 5% of the metabolites are found in the unconjugated urine fraction: 3'-hydroxy-stanozolol (II) and 3'-hydroxy-17-epistanozolol (III). Conjugated excreted metabolites are 3'-hydroxystanozolol (II), stanozolol (I), 4 beta-hydroxy-stanozolol (IV), 16 beta-hydroxystanozolol (V), 16 alpha-hydroxystanozolol (VI), two isomers of 3',16-dihydroxystanozolol (VII, VIII), two isomers of 4 beta, 16-dihydroxystanozolol (IX, X) and a 3',?-dihydroxystanozolol (XI). 3'-Hydroxystanozolol, 4 alpha-hydroxystanozolol, 4 beta-hydroxystanozolol, 16 alpha-hydroxy-, 16 alpha-hydroxy-17-epi- and 16 beta-hydroxystanozolol were synthesised to confirm the structural assignment of the main metabolites.

PMID:2362445 Schanzer W et al; J Steroid Biochem 36 (1-2):153-74 (1990)


The equine phase I and phase II metabolism of the synthetic anabolic steroid stanozolol was investigated following its administration by intramuscular injection to a thoroughbred gelding. The major phase I biotransformations were hydroxylation at C16 and one other site, while phase II metabolism in the form of sulfate and beta-glucuronide conjugation was extensive.

PMID:15458725 McKinney AR et al; J Chromatogr B Analyt Technol Biomed Life Sci 811 (1): 75-83 (2004)


An analytical method has been developed in order to control the illegal use of stanozolol as growth promoter in livestock. ... Urinary metabolites were identified by mass spectrometry. Stanozolol and 16-hydroxystanozolol were detected after oral administration, while 16-hydroxystanozolol and 4,16-dihydroxystanozolol were found after subcutaneous administration.

PMID:9300863 Ferchaud V et al; J Chromatogr B Biomed Sci Appl 695 (2): 269-77 (1997)


5.6 Biological Half-Life

24 hours


5.7 Mechanism of Action

Stanozolol binds to androgen receptors, such as membrane bound receptor proteins LAGS and stanozolol-binding protein (STBP).


The anabolic steroid, stanozolol, is used therapeutically to treat a number of pathological conditions and its clinical effects suggest that it can modulate connective tissue breakdown. The ability of this compound to stimulate prostaglandin E2 (PGE2), collagenase, gelatinase and stromelysin production by human synovial and skin fibroblasts in vitro was examined. The results showed that stanozolol significantly stimulated, in a dose dependent manner, PGE2, collagenase and stromelysin production by skin fibroblasts. However, no stimulation was seen in the synovial cell lines. In contrast, no effect on gelatinase production was seen in either cell type, following exposure to stanozolol. The synovial and skin lines both exhibited a significant stimulation of PGE2 and all three metalloproteinases in response to interleukin-1 beta (IL-1 beta).

PMID:1529798 Ellis AJ et al; Agents Actions 35 (3-4): 232-7 (1992)


Steroid-binding proteins unrelated to the classical nuclear receptors have been proposed to play a role in non-genomic actions of the 17alpha-alkylated testosterone derivative (17alpha-AA) stanozolol (ST). We have previously reported that male rat liver endoplasmic reticulum contains two steroid-binding sites associated with high molecular mass oligomeric proteins: (1) the ST-binding protein (STBP); and (2) the low-affinity glucocorticoid-binding protein (LAGS). To further explore the role of LAGS on the mechanism of action of ST, we have now studied: (1) the interaction of ST and its hydroxylated metabolites with solubilized LAGS and the cytosolic glucocorticoid receptor (GR); and (2) the effects of hormones on the capability of STBP to bind ST. We found that, unlike 17alpha-methyltestosterone, neither ST nor its hydroxylated metabolites bind to GR. However, the 16beta-hydroxylation of ST significantly increases the capability of LAGS to bind ST. Interestingly, 3'-hydroxylation of ST abrogates the capability of LAGS to bind ST. ST (k(i)=30 nM) and 16beta-hydroxystanozolol (k(i)=13 nM) bind with high affinity to LAGS, and are capable of accelerating the rate of dissociation of previously bound dexamethasone from the LAGS. STBP and LAGS are strongly induced by ethinylestradiol. However, unlike STBP, LAGS is regulated by thyroid hormones and growth hormone, which proves that these steroid-binding activities are associated with different binding sites. These findings seem to suggest a novel mechanism for ST whereby membrane-associated glucocorticoid-binding activity is targeted by the 16beta-hydroxylated metabolite of ST. ST and its 16beta-hydroxylated metabolite modulate glucocorticoid activity in the liver through negative allosteric modulation of LAGS, with the result of this interaction an effective increase in classical GR-signaling by increasing glucocorticoid availability to the cytosolic GR.

PMID:14698206 Betancor-Hernandez E et al; J Steroid Biochem Mol Biol 87 (4-5): 253-64 (2003)


Reverses catabolic processes and negative nitrogen balance by promoting protein anabolism and stimulating appetite if there is concurrently a proper intake of calories and proteins. /Anabolic steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


Antianemic: Anemias due to bone marrow failure: Increases production and urinary excretion of erythropoietin. Anemias due to deficient red cell production : Stimulates erythropoietin production and may have a direct action on bone marrow. Anemias associated with renal disease: increases hemoglobin and red blood cell volume. /Anabolic steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


Angioedema (hereditary) prophylactic: Increases serum concentration of Cl esterase inhibitor and, as a result, C2 and C4 concentrations . /Anabolic steroids/

Thomson.Micromedex. Drug Information for the Health Care Professional. 25th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2005., p. 141


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18-Feb-2021
01-Oct-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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