U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ANDROSTANOLONE

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

HIDE SMILES / InChI
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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Neodrol

Approved Use

Anemia of chronic renal failure
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.8 nM
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

AUC

ValueDoseCo-administeredAnalytePopulation
44.8 nM × h
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

T1/2

ValueDoseCo-administeredAnalytePopulation
12 day
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

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
unknown, unknown
STANOLONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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]
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical 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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Patents
Name Type Language
ANDROSTANOLONE
INN   MART.   WHO-DD  
INN  
Official Name English
DIHYDROTESTOSTERONE
Common Name English
17.BETA.-HYDROXY-5.ALPHA.-ANDROSTAN-3-ONE
Systematic Name English
STANOLONE [MI]
Common Name English
ANDROSTANOLONE [WHO-DD]
Common Name English
STANOLONE
MI  
Common Name English
ANDRACTIM
Brand Name English
ANABOLEX
Brand Name English
ANDROSTANOLONE [INN]
Common Name English
4-DIHYDROTESTOSTERONE
Common Name English
TESTOSTERONE IMPURITY F [EP]
Common Name English
17.BETA.-HYDROXY-5.ALPHA.-ANDROSTANE-3-ONE
Systematic Name English
NSC-10972
Code English
ANDROSTANOLONE [MART.]
Common Name English
5ALPHA-DIHYDROTESTOSTERONE
Common Name English
DIHYDROTESTOSTERONE (DHT)
Common Name English
NEODROL
Brand Name English
Classification Tree Code System Code
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Code System Code Type Description
EPA CompTox
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
CAS
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
NCI_THESAURUS
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
PRIMARY
DRUG CENTRAL
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
PRIMARY
ChEMBL
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
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
ECHA (EC/EINECS)
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
PRIMARY
DRUG BANK
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
PRIMARY
EVMPD
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
PRIMARY
PUBCHEM
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
PRIMARY
MESH
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
PRIMARY
INN
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
PRIMARY
FDA UNII
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
PRIMARY
WIKIPEDIA
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
PRIMARY