10418-03-8

Basic information

• Product Name: Stanozolol
• Synonyms: Stanozolol CIII (200 mg);Stanozolol Suspension (For Injection);WINSTROL (stanozolol);stanozolol--dea schedule;Stanozolol BP/USP (Winstrol);Stanozolol(Winstrol, Winstrol Depot);Stanozlol;2'H-Androst-2-eno[3,2-c]pyrazol-17-ol,17-Methyl-, (5a,17b)-
• CAS NO: 10418-03-8
• Molecular Formula: C₂₁H₃₂N₂O
• Molecular Weight: 328.49
• EINECS: 233-894-8
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone;Finished Steroid and Hormone;API;Pharmaceutical;Active Pharmaceutical Ingredients;Biochemistry;Steroids;Steroids (Others);pharmaceutical intermediate
• Mol File: 10418-03-8.mol

Chemical Properties

• Melting Point: 242 °C
• Boiling Point: 490.8 °C at 760 mmHg
• Flash Point: -2℃
• Appearance: white to light yellow/powder
• Density: 1.129 g/cm³
• Vapor Pressure: 1.89E-10mmHg at 25°C
• Refractive Index: 34 ° (C=0.4, CHCl3)
• Storage Temp.: 2-8°C
• Solubility: Practically insoluble in water, soluble in dimethylformamide, slightly soluble in ethanol (96 per cent), very slightly soluble in methylene chloride.
• PKA: 15.15±0.60(Predicted)
• Merck: 8794
• CAS DataBase Reference: Stanozolol(CAS DataBase Reference)
• NIST Chemistry Reference: Stanozolol(10418-03-8)
• EPA Substance Registry System: Stanozolol(10418-03-8)

Safety Data

• Hazard Codes: Xn,Xi,T,F
• Statements: 63-38-19-11-61-60
• Safety Statements: 53-22-36/37/39-36-26-45
• RIDADR: UN2252 - class 3 - PG 2 - 1,2-Dimethoxyethane solution
• WGK Germany: 3
• RTECS: BV8741000
• Hazardous Substances Data: 10418-03-8(Hazardous Substances Data)

Usage

Description

Stanozolol is a synthetic anabolic-androgenic steroids (AAS) belonging to the dihydrotestosterone group. It can be used for the treatment of wasting diseases, burn victims, osteroporosis, bone fractures, anemia and even obesity. It can stimulate fat loss without causing reduced lean body mass, inducing hemoglobin production and red blood cell formation. Stanozolol has the following physiological functions: (1) reduction of sex-hormone-binding-globulin; (2) inducing protein synthesis; (3) Maintain nitrogen retention; (4) Increase red blood cells; (5) inhibit glucocorticoids.

Description

Stanozolol (Item No. 21167) is an analytical reference standard that is categorized as a synthetic anabolic androgenic steroid. Stanozolol has low urinary excretion; therefore, its metabolites are usually used for detection. Formulations containing stanozolol are used as a treatment for hereditary angioedema. It has also been abused in athletics to improve performance. Stanozolol is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

Chemical Properties

White Solid

Originator

Winstrol,Winthrop,US,1961

Uses

androgen anabolic steroid

Uses

Anabolic steroid. Androgen. Controlled substance.

Definition

ChEBI: An organic heteropentacyclic compound resulting from the formal condensation of the 3-keto-aldehyde moiety of oxymetholone with hydrazine. Like oxymetholone, it is a synthetic anabolic steroid. It has both anabolic and androgenic properties, and has been u ed to treat hereditary angioedema and various vascular disorders. It has also been widely abused by professional athletes.

Manufacturing Process

To a stirred solution of 1.00 gram of 17β-hydroxy-17α-methyl-4- androsteno[3,2-c]pyrazole in 200 ml of tetrahydrofuran and 400 ml of liquid ammonia was added 2.12 grams of lithium wire during 5 minutes. The dark blue mixture was stirred for 45 minutes. A solution of 40 ml of tertiary-butyl alcohol in 160 ml of diethyl ether was added with stirring.After 15 minutes, 25 ml of ethanol was added with stirring. The mixture turned colorless after several hours, and the liquid ammonia was allowed to evaporate and the mixture was allowed to warm to room temperature over a period of about 15 hours.The solvent was evaporated to yield a colorless solid residue, which was taken up in ethyl acetate-ice water. The two layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, saturated sodium chloride solution and filtered through anhydrous sodium sulfate. The solvent was evaporated to yield 1.20 grams of light tan crystals, MP 151° to 155°C, ultraviolet maximum at 224 mμ (E = 4,095). Two recrystallizations from ethanol afforded: 1st crop, 0.619 grams (62%) of colorless crystals (dried at 120°C in vacuo for 17 hours), MP 232.8° to 238.0°C, ultraviolet maximum at 224 mμ (E = 4,840); 2nd crop, 0.142 gram (14%) of colorless crystals, MP 234° to 242°C.

Brand name

Winstrol (Ovation).

Therapeutic Function

Anabolic

Synthesis

Stanozol, 17α-methyl-5α-androstano[3,2-c]pyrazol-17β-ol (29.3.13), is made by reducing the double bond at C4–C5 in methyltestosterone, which has independent interest as an anabolic drug of mestanolone (29.3.11). Mestanolone undergoes formylation with ethylformate in the presence of sodium ethoxide, forming a 2-formyl (oxymethylene) derivative (29.3.12), which upon reaction with hydrazine easily cyclizes to the desired stanazole (29.3.13), which is a pyrazol-condensed steroid system.

Veterinary Drugs and Treatments

Labeled indications for the previously marketed veterinary stanozolol product Winstrol?-V (Winthrop/Upjohn) included “…to improve appetite, promote weight gain, and increase strength and vitality…” in dogs, cats and horses. The manufacturer also stated that: “Anabolic therapy is intended primarily as an adjunct to other specific and supportive therapy, including nutritional therapy.” Like nandrolone, stanozolol has been used to treat anemia of chronic disease. Because stanozolol has been demonstrated to enhance fibrinolysis after parenteral injection, it may be efficacious in the treatment of feline aortic thromboembolism or thrombosis in nephrotic syndrome; however, clinical studies and/or experience are apparently lacking for this indication at present.

References

https://www.steroid.com/Stanozolol.php https://pubchem.ncbi.nlm.nih.gov/compound/stanozolol https://en.wikipedia.org/wiki/Stanozolol

InChI:InChI=1/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

Synthetic route

17β-hydroxy-2-hydroxymethylene-17α-methyl-5α-androstan-3-one → stanozolol (10418-03-8)

Conditions	Yield
With hydrazine

stanozolol (10418-03-8) + 4-Nitrophenyl chloroformate (7693-46-1) → tanozolol-4-nitrophenyl-carbonate

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h; pH=8.5;	76.85%

stanozolol (10418-03-8) → 17,17-dimethyl-18-nor-5α-androst-13(14)-eno<3,2-c>pyrazole

Conditions	Yield
With hydrogenchloride for 0.25h; Ambient temperature;	66%

stanozolol (10418-03-8) + methanesulfonyl chloride (124-63-0) → (1S,3aS,3bR,5aS,10aS,10bS,12aS)-8-Methanesulfonyl-1,10a,12a-trimethyl-1,2,3,3a,3b,4,5,5a,6,8,10,10a,10b,11,12,12a-hexadecahydro-7,8-diaza-dicyclopenta[a,h]phenanthren-1-ol (107000-35-1)

Conditions	Yield
With pyridine at 0 - 20℃; for 1h;	56%

ethyl 5-bromovalerate (14660-52-7) + stanozolol (10418-03-8) → ethyl-5-{17β-hydroxy-17α-methylpyrazolo[3′,4′:3,2]-5α-androstan-1′-yl}pentanoate + ethyl 5-{17α-methyl-17β-hydroxypyrazolo[4′,5′:2,3]-5α-androstan-1′-yl}pentanoate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 5h; Microwave irradiation;	A 38% B 28%

stanozolol (10418-03-8) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → 2′‑[N‑(methyl 2,3,4‑tri‑O‑acetyl‑1‑deoxy‑β‑d‑glucuronosyluronate)]‑17α‑methyl‑5α‑androstano[3,2‑c]pyrazol‑17β‑ol + 1′‑[N‑(methyl 2,3,4‑tri‑O‑acetyl‑1‑deoxy‑β‑d‑glucuronosyluronate)]‑17α‑methyl‑5α‑androstano[3,2‑c]pyrazol‑17β‑ol

Conditions	Yield
With mercury(II) cyanide; mercury dibromide In nitromethane; benzene for 3h;	A 17% B 5%

pyridine (110-86-1) + stanozolol (10418-03-8) → stanozolol 17β-sulfate pyridinium salt

Conditions	Yield
With chlorosulfonic acid 1.) -5 deg C, 2.) RT, 3 h; Yield given. Multistep reaction;

stanozolol (10418-03-8) → Sulfuric acid mono-((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-hexadecahydro-7,8-diaza-dicyclopenta[a,h]phenanthren-1-yl) ester

Conditions	Yield
With sulfur trioxide pyridine complex In N,N-dimethyl-formamide for 2h; Ambient temperature;

stanozolol (10418-03-8) → 17-epistanozolol (145841-85-6, 125636-91-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfur trioxide pyridine complex / dimethylformamide / 2 h / Ambient temperature 2: K2CO3 / dimethylformamide; H2O / 72 h View Scheme

L-malic acid (2174-58-5) + stanozolol (10418-03-8) → ((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)*(S-methylsuccinic acid)

Conditions	Yield
In methanol Milling;

2-(R)-methylsuccinic acid (3641-51-8) + stanozolol (10418-03-8) → ((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)*2(R-methylsuccinic acid)

Conditions	Yield
In methanol Milling;

stanozolol (10418-03-8) → C21H30N2O

Conditions	Yield
With titanium(IV) oxide In water; acetonitrile Reagent/catalyst; UV-irradiation;

stanozolol (10418-03-8) → 1‑deoxy‑1‑(17β‑hydroxy‑17α‑methyl‑5α‑androstano[3,2‑c]pyrazol‑1′‑yl)‑β‑d‑glucopyranuronic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: mercury(II) cyanide; mercury dibromide / nitromethane; benzene / 3 h 2.1: lithium hydroxide monohydrate / methanol; water / 7 h / 20 °C 2.2: amberlite 120 ion resin / 0.25 h View Scheme

stanozolol (10418-03-8) → 1‑deoxy‑1‑(17β‑hydroxy‑17α‑methyl‑5α‑androstano[3,2‑c]pyrazol‑2′‑yl)‑β‑d‑glucopyranuronic acid

Conditions	Yield
Multi-step reaction with 2 steps 1.1: mercury(II) cyanide; mercury dibromide / nitromethane; benzene / 3 h 2.1: lithium hydroxide monohydrate / methanol; water / 6 h / 20 °C 2.2: amberlite 120 ion resin / 0.25 h View Scheme

stanozolol (10418-03-8) → C44H72N6O7S

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C / Microwave irradiation 2: sodium hydroxide; methanol / water / 1.5 h / 20 °C 3: benzotriazol-1-ol; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere View Scheme

stanozolol (10418-03-8) → C43H68N6O8S

Conditions

Yield

Multi-step reaction with 4 steps 1: sodium hydrogencarbonate / water; tetrahydrofuran / 20 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / chloroform / 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 100 °C / Microwave irradiation 4: benzotriazol-1-ol; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere View Scheme

stanozolol (10418-03-8) → C30H43N3O5

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C / Microwave irradiation 2: sodium hydroxide; methanol / water / 1.5 h / 20 °C 3: dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 20 °C View Scheme

stanozolol (10418-03-8) → C26H40N2O3

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C / Microwave irradiation 2: sodium hydroxide; methanol / water / 1.5 h / 20 °C View Scheme

stanozolol (10418-03-8) → C26H40N2O3

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C / Microwave irradiation 2: sodium hydroxide; methanol / water / 1.5 h / 20 °C View Scheme

stanozolol (10418-03-8) → 17α-methyl pyrazolo[3′,4′:3,2]-5α-androstane-17β-yl-hemisuccinate

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / water; tetrahydrofuran / 20 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / chloroform / 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 100 °C / Microwave irradiation View Scheme

stanozolol (10418-03-8) → C44H72N6O7S

Conditions	Yield
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 5 h / 80 °C / Microwave irradiation 2: sodium hydroxide; methanol / water / 1.5 h / 20 °C 3: benzotriazol-1-ol; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere View Scheme

di-tert-butyl dicarbonate (24424-99-5) + stanozolol (10418-03-8) → Boc-stanozolol + C26H40N2O3

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;

di-tert-butyl dicarbonate (24424-99-5) + stanozolol (10418-03-8) → C35H56N2O6Si

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / water; tetrahydrofuran / 20 °C 2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / chloroform / 20 °C View Scheme

stanozolol (10418-03-8) → C26H38N2O4

Conditions	Yield
Multi-step reaction with 2 steps 1: dmap / dichloromethane / 72 h 2: sodium hydroxide / methanol / 1 h / 20 °C View Scheme

stanozolol (10418-03-8) + succinic acid monomethylester chloride (1490-25-1) → C26H38N2O4 + C26H38N2O4

Conditions	Yield
With dmap In dichloromethane for 2h;

stanozolol (10418-03-8) + succinic acid monomethylester chloride (1490-25-1) → C31H44N2O7 + C31H44N2O7

Conditions	Yield
With dmap In dichloromethane for 72h; Overall yield = 90 percent;

Upstream product

• 10418-03-5 Stanozolol 
• 104180-33-8 PHE-LEU-GLU-GLU-VAL AMMONIUM 
• 104180-32-7 PHE-LEU-ARG-PHE AMIDE 
• 104180-31-6 PHE-LEU-GLU-GLU-ILE AMMONIUM 
• 104180-30-5 10-1-PYRENE-10-KETODECANOIC ACID 
• 104180-29-2 PRO-PHE-GLY-LYS 
• 104180-27-0 AC-ASP-ARG-VAL-TYR-ILE-HIS-PRO-PHE-HIS-LEU-VAL-ILE-HIS-ASN-OH 
• 104180-25-8 D-Trp-Ala-Trp-D-Phe amide 
• 104180-24-7 DES-ASP3-GASTRIN RELATED PEPTIDE 
• 104180-23-6 ASP-ARG-VAL-TYR-ILE-HIS-PRO-PHE-HIS-LEU-VAL-ILE-HIS-ASN 
• 104180-22-5 (VAL3)-BETA-CASOMORPHIN (1-4) AMIDE (BOVINE) ACETATE SALT 
• 104180-19-0 Z-GLY-GLY-LEU-BETANA 
• 104180-18-9 N-FORMYL-MET-LEU-PHE-LYS ACETATE SALT 
• 104-1-8 4-MethoxyPhenylAceticAcid 

Downstream Products

• 10418-09-4 pyruvic acid thiosemicarbazone 
• 10418-12-9 [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3R,4R)-2,3,4-trihydroxy-5-oxopentyl dihydrogen diphosphate (non-preferred name) 
• 104181-68-2 2-{[2-(methylamino)ethyl](thiophen-2-ylmethyl)amino}pyridin-3-ol 
• 104182-09-4 4,4-DiMethyl Retinoic Acid 
• 1041-82-3 3,4-dimethylhepta-1,5-diene 
• 104182-97-0 Neopentyl Glycol Dimethacrylate 
• 104182-98-1 PHENYL-D5-ACETIC ACID 
• 104183-45-1 (5Z)-5-(phenylmethylidene)-3-[({4-[(4-phenylpiperazin-1-yl)carbonyl]phenyl}amino)methyl]-2-thioxo-1,3-thiazolidin-4-one 
• 104183-46-2 (5Z)-5-benzylidene-3-[[[4-(piperidine-1-carbonyl)phenyl]amino]methyl]- 2-sulfanylidene-thiazolidin-4-one 
• 104183-47-3 (5Z)-3-({[4-(morpholin-4-ylcarbonyl)phenyl]amino}methyl)-5-(phenylmethylidene)-2-thioxo-1,3-thiazolidin-4-one 
• 104183-52-0 N,N-diethyl-4-[({(5Z)-5-[(4-methoxyphenyl)methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}methyl)amino]benzamide 
• 104183-59-7 4-[({(5Z)-5-[(4-chlorophenyl)methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl}methyl)amino]-N,N-diethylbenzamide 
• 104184-40-9 1,4,5,6-tetrahydropyrazine-2-carbonitrile 
• 104184-41-0 Pyrazinecarbonitrile, 1,4,5,6-tetrahydro-3-phenyl- (9CI)