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58-22-0 molecular structure
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(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

ChemBase ID: 506
Molecular Formular: C19H28O2
Molecular Mass: 288.42442
Monoisotopic Mass: 288.20893014
SMILES and InChIs

SMILES:
O[C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)CC3)C)CC2)CC1)C
Canonical SMILES:
O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C)C
InChI:
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
InChIKey:
MUMGGOZAMZWBJJ-DYKIIFRCSA-N

Cite this record

CBID:506 http://www.chembase.cn/molecule-506.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
IUPAC Traditional name
testosterone
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one
Brand Name
Andriol
Andro
Andro 100
Andro L.A. 200
Androderm
Androgel
Android 10
Android 25
Android 5
Androlin
Andronaq
Andronate 100
Andronate 200
Andropatch
Andropository 200
Andrusol
Andryl 200
Beta Testosterone
CDB 111C
Cristerona T
Cristerone T
Delatest
Delatestryl
Depo-Testosterone
Depo-Testosterone Cypionate
Depotest
Everone 200
Geno-Cristaux Gremy
Homosteron
Homosterone
Libigel
Malerone
Malestrone
Malogen in Oil
Malogen, Aquaspension Injection
Mertestate
Metandren
Methyltestosterone
Neo-Hombreol F
Neo-Testis
Neotestis
Oreton
Oreton F
Oreton Methyl
Oreton-F
Orquisteron
Perandren
Percutacrine Androgenique
Primotest
Primoteston
Relibra
Scheinpharm Testone-Cyp
Striant
Sustanon
Sustanone
Sustason 250
Synandrol F
T-Cypionate
Teslen
Testamone 100
Testandrone
Testaqua
Testiculosterone
Testim
Testobase
Testoderm
Testoderm Tts
Testogel
Testoject-50
Testolin
Testopel Pellets
Testopropon
Testosteroid
Testoviron
Testoviron Schering
Testoviron T
Testred
Testred Cypionate 200
Testrin-P.A
Testro Aq
Testrone
Testryl
Virilon
Virilon IM
Virormone
Virosterone
Androsorb
Androderm, Delatestryl
Synonyms
Testosterona [INN-Spanish]
Testosteronum [INN-Latin]
TES
Testosterone Hydrate
Testosterone Enanthate
Testosterone Cypionate
Testostosterone
Testosteron
Trans-Testosterone
Dea No. 4000
testosterone
Testosterone
Testosterone solution
(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
Andropatch
Atmos
(17β)-17-Ηydroxyandrost-4-en-3-one
AndroGel
Androderm
Androlin
(+)-Testosterone
Testoderm
Testogel
Testolin
Testro AQ
Testrone
Virosterone
Testosterone
17β-Hydroxy-3-oxo-4-androstene
17β-Hydroxy-4-androsten-3-one
4-Androsten-17β-ol-3-one
睾酮 溶液
17β-羟基-3-氧代-4-雄甾烯
17β-羟基-4-雄甾烯-3-酮
4-雄甾烯-17β-醇-3-酮
反式-睾酮
睾酮
CAS Number
58-22-0
EC Number
200-370-5
MDL Number
MFCD00003654
Beilstein Number
1915399
PubChem SID
24900279
24899970
160963969
46505691
24870573
PubChem CID
6013
CHEBI ID
17347
ATC CODE
G03BA03
CHEMBL
386630
Chemspider ID
5791
DrugBank ID
DB00624
IUPHAR ligand ID
2858
KEGG ID
D00075
Unique Ingredient Identifier
3XMK78S47O
Wikipedia Title
Testosterone

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 19.08686  H Acceptors
H Donor LogD (pH = 5.5) 3.3654232 
LogD (pH = 7.4) 3.3654232  Log P 3.3654232 
Molar Refractivity 84.4298 cm3 Polarizability 33.260063 Å3
Polar Surface Area 37.3 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.99  LOG S -3.94 
Solubility (Water) 3.33e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
23.4 mg/L expand Show data source
DMSO expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
146-148°C expand Show data source
155°C (311°F) expand Show data source
Flash Point
41 °F expand Show data source
5 °C expand Show data source
Optical Rotation
+110.2° expand Show data source
Hydrophobicity(logP)
3.6 expand Show data source
Sec Combustion
-11080 kJ/mol expand Show data source
Storage Condition
-20°C expand Show data source
Controlled Substance, -20°C Freezer expand Show data source
RTECS
XA3030000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Toxic Toxic (T) expand Show data source
UN Number
2252 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
45-60-61-11-19-20 expand Show data source
45-63 expand Show data source
Safety Statements
53-16-45 expand Show data source
53-36/37-45 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H225-H332-H350-H360FD expand Show data source
H350-H361 expand Show data source
GHS Precautionary statements
P201-P210-P308 + P313 expand Show data source
P201-P281-P308 + P313 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Eyeshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2252 3/PG 2 expand Show data source
Supplemental Hazard Statements
May form explosive peroxides. expand Show data source
Drug Control
Home Office Schedule 4.2 expand Show data source
USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Intramuscular injection, transdermal (cream, gel, or patch), sub-'Q' pellet expand Show data source
Bioavailability
low (due to extensive first pass metabolism) expand Show data source
Excretion
Urine (90%), feces (6%) expand Show data source
Half Life
2–4 h expand Show data source
Metabolism
Liver, Testis and Prostate expand Show data source
Legal Status
Schedule III (USA)
Schedule IV (Canada)
expand Show data source
Pregnancy Category
X (USA), Teratogenic effects expand Show data source
Gene Information
human ... AR(367), EBP(10682), ESR1(2099), PGR(5241), SERPINA6(866), SHBG(6462)mouse ... Esr1(13982)rat ... Ar(24208), Esr1(24890), Nr3c1(24413), Nr3c2(25672), Pgr(25154) expand Show data source
Mechanism of Action
Activity in many tissues appears to depend on reduction to dihydrotestosterone which binds to cytosolic receptor proteins expand Show data source
Androgen expand Show data source
Exogenous administration inhibits endogenous release via feedback inhibition of pituitary ICSH expand Show data source
FSH antagonist. expand Show data source
Gonadotropin antagonist expand Show data source
High dose: spermatogenesis inhibitor expand Show data source
ICSH antagonist expand Show data source
The steroid receptor complex is transported to the nucleus where it initiates transcription events and cellular changes related to androgen action expand Show data source
Purity
≥98% expand Show data source
98% expand Show data source
Concentration
1.0 mg/mL±2% in 1,2-dimethoxyethane expand Show data source
Grade
drug standard expand Show data source
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
cell culture tested expand Show data source
Biological Source
Constit. of human urine expand Show data source
Sterility
γ-irradiated expand Show data source
Application(s)
Used in the treatment of male hypogonadism (transdermal administration) expand Show data source
Empirical Formula (Hill Notation)
C19H28O2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00624 external link
Item Information
Drug Groups approved; investigational
Description Testosterone is a steroid sex hormone found in both men and women. In men, testosterone is produced primarily by the Leydig (interstitial) cells of the testes when stimulated by luteinizing hormone (LH). It functions to stimulate spermatogenesis, promote physical and functional maturation of spermatozoa, maintain accessory organs of the male reproductive tract, support development of secondary sexual characteristics, stimulate growth and metabolism throughout the body and influence brain development by stimulating sexual behaviors and sexual drive. In women, testosterone is produced by the ovaries (25%), adrenals (25%) and via peripheral conversion from androstenedione (50%). Testerone in women functions to maintain libido and general wellbeing. Testosterone exerts a negative feedback mechanism on pituitary release of LH and follicle-stimulating hormone (FSH). Testosterone may be further converted to dihydrotestosterone or estradiol depending on the tissue.
Indication To be used as hormone replacement or substitution of diminished or absent endogenous testosterone. Use in males: For management of congenital or acquired hypogonadism, hypogonadism associated with HIV infection, and male climacteric (andopause). Use in females: For palliative treatment of androgen-responsive, advanced, inoperable, metastatis (skeletal) carcinoma of the breast in women who are 1-5 years postmenopausal; testosterone esters may be used in combination with estrogens in the management of moderate to severe vasomotor symptoms associated with menopause in women who do not respond to adequately to estrogen therapy alone.
Pharmacology Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does.
Toxicity Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
Affected Organisms
Humans and other mammals
Biotransformation Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).
Absorption Approximately 10% of the testosterone dose applied on the skin surface is absorbed into systemic circulation
Half Life 10-100 minutes
Protein Binding 40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.
Elimination About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites; about 6% of a dose is excreted in the feces, mostly in the unconjugated form.
References
Freeman ER, Bloom DA, McGuire EJ: A brief history of testosterone. J Urol. 2001 Feb;165(2):371-3. [Pubmed]
Hoberman JM, Yesalis CE: The history of synthetic testosterone. Sci Am. 1995 Feb;272(2):76-81. [Pubmed]
Contraceptive efficacy of testosterone-induced azoospermia in normal men. World Health Organization Task Force on methods for the regulation of male fertility. Lancet. 1990 Oct 20;336(8721):955-9. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Selleck Chemicals - S2033 external link
Related research area: Endocrinology
Sigma Aldrich - T1268 external link
Biochem/physiol Actions
Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.
Sigma Aldrich - T6147 external link
Biochem/physiol Actions
睾丸分泌的睾酮在具有协调多种睾酮生物作用的目标组织中被转化为双氢睾酮。雄激素在胚胎形成过程中以及青春期引导男性表型的发育。
Sigma Aldrich - T1500 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.
Sigma Aldrich - T5641 external link
Biochem/physiol Actions
Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.
Sigma Aldrich - 46923 external link
Biochem/physiol Actions
Testosterone secreted by the testis is converted to dihydrotestosterone in the target tissues where it appears to mediate many of the biological actions of testosterone. Androgens direct the development of the male phenotype during embryogenesis and at puberty.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Toronto Research Chemicals - T155000 external link
Testosterone, Principal hormone of the testes, produced by the interstitial cells. Major circulating androgen; converted by 5α-reductase in androgen-dependent target tissues to 5α-dehydrotestosterone which is required for normal male sexual differentiatio

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Freeman ER, Bloom DA, McGuire EJ: A brief history of testosterone. J Urol. 2001 Feb;165(2):371-3. Pubmed
  • • Hoberman JM, Yesalis CE: The history of synthetic testosterone. Sci Am. 1995 Feb;272(2):76-81. Pubmed
  • • Contraceptive efficacy of testosterone-induced azoospermia in normal men. World Health Organization Task Force on methods for the regulation of male fertility. Lancet. 1990 Oct 20;336(8721):955-9. Pubmed
  • •  http://en.wikipedia.org/wiki/Testosterone
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