Showing Compound Stanozolol (FDB023109)

Record Information

Version

1.0

Creation date

2011-09-21 00:24:48 UTC

Update date

2018-05-28 18:35:17 UTC

Primary ID

FDB023109

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Stanozolol

Description

Stanozolol was first synthesized by Clinton et al. in 1959, as a heterocyclic anabolic androgenic steroid. The structure of Stan differs from endogenous steroid hormones and most commercially available anabolic steroids. It most closely resembles methyl testosterone. Instead of the 3-ketogroup in methyltestosterone, there is a pyrazole ring fused to the androstane ring system. This slightly different structure has the disadvantage of making extraction and isolation of the molecule from matrices more difficult. Like most other anabolic steroids, Stan has poor gas chromatographic behavior and is difficult to detect in urine, because of renal clearance and low urinary excretion. This is due to the rapid metabolization, leading to low concentration levels of the parent compound found in urine. Therefore, most research studies had focused on the detection of urinary metabolites. Androgens are drugs, derived from the natural male sex hormone testosterone, with high anabolic potential and minimized androgenic activity. Anabolic steroids stimulate protein synthesis, resulting in an acceleration of the food conversion rate and increasing muscle growth, body mass and enhanced performance. Androgens can be used as therapeutics, because they accelerate the recovery of protein deficiency and protein-wasting disorders (e.g. osteoporosis), but they are also widely abused in doping, as well in animals as in men. (PMID: 10404632, 10435307, 11175645, 11284331, 12064656, 12580506, 1448813, 14698206, 15013688, 15458725, 15631866, 15664350, 16040239, 16259046, 16288903, 1640693, 17066372, 17146762, 2306548, 2362445, 2625454, 2663904, 6539197, 9001957, 9300863, 9580049) [HMDB]

CAS Number

10418-03-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Androstanazole	ChEBI
Estanozolol	ChEBI
Stanozololum	ChEBI
Stromba	ChEBI
Strombaject	ChEBI
Winstrol	ChEBI
(5a,17b)-17-Methyl-2'H-androst-2-eno[3,2-c]pyrazol-17-ol	HMDB
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	HMDB
17-Methyl-5a-androstano[3,2-c]pyrazol-17b-ol	HMDB
17-Methyl-pyrazolo[4',3':2,3]-5a-androstan-17b-ol	HMDB
17a-Methyl-17b-hydroxy-5a-androstano(3,2-c)pyrazole	HMDB
17b-Hydroxy-17-methyl-5a-androstano[3,2-c]pyrazole	HMDB
17b-Hydroxy-17a-methyl-5a-androstano[3,2-c]pyrazole	HMDB
2'H-5a-Androst-2-eno[3,2-c]pyrazol-17b-ol, 17-methyl- (8ci)	HMDB
Anabol	HMDB
Androstanazol	HMDB, MeSH
Androstanazolestanazol	HMDB
Cyclopenta[7,8]phenanthro[2,3-c]pyrazole, 2'H-androst-2-eno[3,2-c]pyrazol-17-ol deriv.	HMDB
Estazol	HMDB
Stanazolol	HMDB, MeSH
Tevabolin	HMDB
Win 14833	HMDB
Winstroid	HMDB
Winstrol depot	HMDB
Winstrol V	HMDB
Sanofi winthrop brand OF stanozolol	MeSH, HMDB
Zambon brand OF stanozolol	MeSH, HMDB
Methylstanazol	MeSH, HMDB
Sanofi-synthelabo brand OF stanozolol	MeSH, HMDB
(5a,17b)-17-methyl-2'H-Androst-2-eno[3,2-c]pyrazol-17-ol	hmdb
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	hmdb
2'H-5a-Androst-2-eno[3,2-c]pyrazol-17b-ol, 17-methyl- (8CI)	hmdb
Winstrol Depot	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	4.33	ALOGPS
logP	3.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	16.23	ChemAxon
pKa (Strongest Basic)	2.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.91 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	96.8 m³·mol⁻¹	ChemAxon
Polarizability	39.22 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C21H32N2O

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-4,7-dien-17-ol

InChI Identifier

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

InChI Key

LKAJKIOFIWVMDJ-IYRCEVNGSA-N

Isomeric SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=NNC=C3C[C@]12C

Average Molecular Weight

328.4916

Monoisotopic Molecular Weight

328.251463656

Classification

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Azole
Cyclic alcohol
Pyrazole
Tertiary alcohol
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary alcohol (CHEBI:9249 )
organic heteropentacyclic compound (CHEBI:9249 )
17beta-hydroxy steroid (CHEBI:9249 )
anabolic androgenic steroid (CHEBI:9249 )
Androstane and derivatives (C07311 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

System process:

Reproduction

Cellular process:

Cell signaling

Role

Biological role:

Molecular messenger:

Signaling molecule

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Stanozolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ika-1698000000-3f8c35eb18e311ca156b	Spectrum
Predicted GC-MS	Stanozolol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0079-3249000000-250fe7ac2a107a020916	Spectrum
Predicted GC-MS	Stanozolol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-0009000000-092e853c1b3ea4cea476	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-0009000000-e44e17759e6628cd979d	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-0092000000-fb2af0d825cd4939b25f	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udj-9870000000-8e6ba7db421ffbe6d4d4	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-f62def968e0fcaf5ad8b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0096000000-6c72948a57cb2e8a7683	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03xr-6198000000-d225125a553d5bedac3e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0009000000-507d1b76f5fbab2cd617	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0009000000-507d1b76f5fbab2cd617	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0039000000-a11542c5a5960f8c2e3a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0019000000-e17ed5d1d401678c0a12	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2963000000-c456325d88b698b6ee3e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-1790000000-56ae15e8bf663dc1ee84	2021-09-24	View Spectrum