Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H30O2 |
Molecular Weight | 290.441 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]12CCC(=O)C[C@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@@]([H])([C@@]4(C)CC[C@@]31[H])O
InChI
InChIKey=NVKAWKQGWWIWPM-ABEVXSGRSA-N
InChI=1S/C19H30O2/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/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
STANOLONE, also known as dihydrotestosterone, is a potent androgenic metabolite of testosterone and anabolic agent for systemic use. It may be used as a replacement of male sex steroids in men who have androgen deficiency, for example as a result of the loss of both testes, and also the treatment of certain rare forms of aplastic anemia which are or may be responsive to anabolic androgens.
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.8 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9709942/ |
16 mg single, topical dose: 16 mg route of administration: Topical experiment type: SINGLE co-administered: |
STANOLONE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
44.8 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9709942/ |
16 mg single, topical dose: 16 mg route of administration: Topical experiment type: SINGLE co-administered: |
STANOLONE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9709942/ |
16 mg single, topical dose: 16 mg route of administration: Topical experiment type: SINGLE co-administered: |
STANOLONE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1778174/ |
unknown, unknown |
STANOLONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
250 mg 1 times / day multiple, transdermal Highest studied dose Dose: 250 mg, 1 times / day Route: transdermal Route: multiple Dose: 250 mg, 1 times / day Sources: |
healthy, 58 years (range: 50-70 years) n = 60 Health Status: healthy Age Group: 58 years (range: 50-70 years) Sex: M Population Size: 60 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [Activation 15.8489 uM] | ||||
no [Activation >15.8489 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/ |
yes | |||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
major [Km 5.7 uM] | ||||
major | ||||
minor [Km 382.3 uM] | ||||
minor [Km 78.9 uM] | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak [Km 676.4 uM] | ||||
weak | ||||
yes [Km 2.6 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18599551/ |
||||
PubMed
Title | Date | PubMed |
---|---|---|
Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
|
Ultrastructural and quantitative immunohistochemical changes induced by nonsteroid antiandrogens on pituitary gonadotroph population of prepubertal male rats. | 2001 |
|
Testosterone, corticosterone, and photoperiod interact to regulate plasma levels of binding globulin and free steroid hormone in dark-eyed juncos, Junco hyemalis. | 2001 Apr |
|
Antitumor effect of an HER2-specific antibody-toxin fusion protein on human prostate cancer cells. | 2001 Apr |
|
Regional variations of insulin-like growth factor I (IGF-I), IGF-II, and receptor type I in benign prostatic hyperplasia tissue and their correlation with intraprostatic androgens. | 2001 Apr |
|
Evaluation of the male pubertal onset assay to detect testosterone and steroid biosynthesis inhibitors in CD rats. | 2001 Apr |
|
Androgen receptor stabilization in recurrent prostate cancer is associated with hypersensitivity to low androgen. | 2001 Apr 1 |
|
Effects of finasteride on size of the prostate gland and semen quality in dogs with benign prostatic hypertrophy. | 2001 Apr 15 |
|
Caveolin-1 interacts with androgen receptor. A positive modulator of androgen receptor mediated transactivation. | 2001 Apr 20 |
|
Cross-talk between signal transducer and activator of transcription 3 and androgen receptor signaling in prostate carcinoma cells. | 2001 Apr 27 |
|
Paracrine regulation of apoptosis by steroid hormones in the male and female reproductive system. | 2001 Feb |
|
Oral contraceptives in the treatment of acne. | 2001 Feb |
|
Gonadal dysgenesis and bone metabolism. | 2001 Feb |
|
Role of androgens in the growth of endometrial carcinoma: an in vivo animal model. | 2001 Feb |
|
Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts. | 2001 Feb |
|
Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members. | 2001 Feb |
|
Messenger ribonucleic acid levels of steroid 5 alpha-reductase 2 in human prostate predict the enzyme activity. | 2001 Feb |
|
Testosterone inhibits osteoclast formation stimulated by parathyroid hormone through androgen receptor. | 2001 Feb 23 |
|
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol. | 2001 Feb 28 |
|
Androstanolone treatment for congenital penile curvature. | 2001 Jan |
|
[7alpha-18F]fluoro-17alpha-methyl-5alpha-dihydrotestosterone: a ligand for androgen receptor-mediated imaging of prostate cancer. | 2001 Jan |
|
Biochemical roles of testosterone and epitestosterone to 5 alpha-reductase as indicators of male-pattern baldness. | 2001 Jan |
|
Maternal steroids and contaminants in common tern eggs: a mechanism of endocrine disruption? | 2001 Jan |
|
Social influences on androgen levels in the southern leopard frog, Rana sphenocephala. | 2001 Jan |
|
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase. | 2001 Jan 22 |
|
Compounded percutaneous testosterone gel: use and effects in hypogonadal men. | 2001 Jan-Feb |
|
Suppression of spermatogenesis with desogestrel and testosterone pellets is not enhanced by addition of finasteride. | 2001 Jan-Feb |
|
Dihydrotestosterone enhances transforming growth factor-beta-induced apoptosis in hormone-sensitive prostate cancer cells. | 2001 Jun |
|
Androgen regulates the level and subcellular distribution of the AU-rich ribonucleic acid-binding protein HuR both in vitro and in vivo. | 2001 Jun |
|
Age and gender specific stimulation of creatine kinase specific activity by gonadal steroids in human bone-derived cells in culture. | 2001 Mar |
|
Induction of primer pheromone production by dihydrotestosterone in the male goat. | 2001 Mar |
|
Effects of indomethacin, luteinizing hormone (LH), prostaglandin E2 (PGE2), trilostane, mifepristone, ethamoxytriphetol (MER-25) on secretion of prostaglandin E (PGE), prostaglandin F2alpha (PGF2alpha) and progesterone by ovine corpora lutea of pregnancy or the estrous cycle. | 2001 Mar |
|
Phenotypic variation in a family with partial androgen insensitivity syndrome explained by differences in 5alpha dihydrotestosterone availability. | 2001 Mar |
|
Interrelationships among lipoprotein levels, sex hormones, anthropometric parameters, and age in hypogonadal men treated for 1 year with a permeation-enhanced testosterone transdermal system. | 2001 Mar |
|
Polymorphism of the androgen receptor gene is associated with male pattern baldness. | 2001 Mar |
|
Androgen receptor antagonism by the organophosphate insecticide fenitrothion. | 2001 Mar |
|
Negative feedback regulation of the secretion and actions of gonadotropin-releasing hormone in males. | 2001 Mar |
|
Androgen receptors in thymic epithelium modulate thymus size and thymocyte development. | 2001 Mar |
|
Differentiation-dependent expression of connective tissue growth factor and lysyl oxidase messenger ribonucleic acids in rat granulosa cells. | 2001 Mar |
|
Administration of tamoxifen but not flutamide to hormonally intact, adult male rats mimics the effects of short-term gonadectomy on the catecholamine innervation of the cerebral cortex. | 2001 Mar 19 |
|
Adrenal steroids in human prostatic cancer cell lines. | 2001 Mar-Apr |
|
5alpha-reductases in human breast carcinoma: possible modulator of in situ androgenic actions. | 2001 May |
|
The gonadotropin-releasing hormone antagonist abarelix depot versus luteinizing hormone releasing hormone agonists leuprolide or goserelin: initial results of endocrinological and biochemical efficacies in patients with prostate cancer. | 2001 May |
|
Tissue effects of saw palmetto and finasteride: use of biopsy cores for in situ quantification of prostatic androgens. | 2001 May |
|
Androgens alter corticotropin releasing hormone and arginine vasopressin mRNA within forebrain sites known to regulate activity in the hypothalamic-pituitary-adrenal axis. | 2001 May |
|
Behavioral and hormonal effects of exogenous vasotocin and corticosterone in the green treefrog. | 2001 May |
|
Effects of cyclic adenosine-monophosphate on growth and PSA secretion of human prostate cancer cell line. | 2001 May |
|
Impact of sex and gonadal steroids on prolongation of ventricular repolarization and arrhythmias induced by I(K)-blocking drugs. | 2001 May 1 |
|
Hypogonadism following prostate-bed radiation therapy for prostate carcinoma. | 2001 May 15 |
|
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction. | 2001 May 15 |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C2298
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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FDA ORPHAN DRUG |
93995
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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LOINC |
1849-9
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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DEA NO. |
4000
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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FDA ORPHAN DRUG |
747120
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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NCI_THESAURUS |
C243
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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LOINC |
43826-7
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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WHO-ATC |
G03BB02
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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LOINC |
15057-3
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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LOINC |
35189-0
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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LOINC |
6775-1
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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WHO-VATC |
QA14AA01
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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WHO-ATC |
A14AA01
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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LOINC |
1848-1
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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WHO-VATC |
QG03BB02
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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Code System | Code | Type | Description | ||
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521-18-6
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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521-18-6
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
|
PRIMARY | |||
|
C72098
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
|
3927
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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CHEMBL27769
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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M10190
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | Merck Index | ||
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208-307-3
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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DB02901
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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SUB05509MIG
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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10635
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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D013196
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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238
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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08J2K08A3Y
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY | |||
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DIHYDROTESTOSTERONE
Created by
admin on Sat Jun 26 07:04:37 UTC 2021 , Edited by admin on Sat Jun 26 07:04:37 UTC 2021
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PRIMARY |
ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)