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

Molecular Formula C19H30O2
Molecular Weight 290.441
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Morphometric analysis of cortical bone upon the exposure to sustained delivery of anabolic promoting agents using adult male rats as a model.
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
Androgen metabolism in the brain of the green anole lizard (Anolis carolinensis): effects of sex and season.
2001 Apr
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
2001 Apr
Antitumor effect of an HER2-specific antibody-toxin fusion protein on human prostate cancer cells.
2001 Apr
Evaluation of the male pubertal onset assay to detect testosterone and steroid biosynthesis inhibitors in CD rats.
2001 Apr
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
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
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
Fetal androgen exposure inhibits fetal rat lung fibroblast lipid uptake and release.
2001 Jan - Feb
Finasteride cream in hirsutism.
2001 Jan-Feb
Compounded percutaneous testosterone gel: use and effects in hypogonadal men.
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
Impact of genetic polymorphisms of 17-hydroxylase cytochrome P-450 (CYP17) and steroid 5alpha-reductase type II (SRD5A2) genes on prostate-cancer risk among the Japanese population.
2001 Jun 1
Brain aromatase is neuroprotective.
2001 Jun 15
N-cadherin is regulated by gonadal steroids in adult sexually dimorphic spinal motoneurons.
2001 Jun 15
Characterization of a novel type of human microsomal 3alpha -hydroxysteroid dehydrogenase: unique tissue distribution and catalytic properties.
2001 Jun 22
3alpha-Hydroxysteroid dehydrogenase in animal and human tissues.
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
Covariate measurement error adjustment for matched case-control studies.
2001 Mar
Proliferation and differentiation of prostatic stromal cells.
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
Long-term exposure of tumor necrosis factor alpha causes hypersensitivity to androgen and anti-androgen withdrawal phenomenon in LNCaP prostate cancer cells.
2001 Mar 1
Sex-dependent regulation by dexamethasone of murine hydroxysteroid sulfotransferase gene expression.
2001 Mar 8
Adrenal steroids in human prostatic cancer cell lines.
2001 Mar-Apr
Structural and functional alterations in the androgen receptor in spinal bulbar muscular atrophy.
2001 May
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
The hormonal milieu in early stages of bone cell differentiation modifies the subsequent sex-specific responsiveness of the developing bone to gonadal steroids.
2001 May
Tissue effects of saw palmetto and finasteride: use of biopsy cores for in situ quantification of prostatic androgens.
2001 May
Are serum hormones associated with the risk of prostate cancer? Prospective results from the Massachusetts Male Aging Study.
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
Effects of cyclic adenosine-monophosphate on growth and PSA secretion of human prostate cancer cell line.
2001 May
Nongenomic effect of testosterone on chloride secretion in cultured rat efferent duct epithelia.
2001 May
Initial induction and subsequent reduction of alpha(2u)-globulin in urine and serum of mature male rats after repeated intraperitoneal injections of (anti)estrogen.
2001 May 11
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
A missense substitution A49T in the steroid 5-alpha-reductase gene (SRD5A2) is not associated with prostate cancer in Finland.
2001 May 18
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:04:36 UTC 2021
Edited
by admin
on Sat Jun 26 07:04:36 UTC 2021
Record UNII
08J2K08A3Y
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
PARENT -> METABOLITE ACTIVE
DHT binds with greater affinity to SHBG than does testosterone
MAJOR
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP
Related Record Type Details
ACTIVE MOIETY