U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H30O2
Molecular Weight 290.4403
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANDROSTANOLONE

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@H]4CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O

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 290.4403
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)
Health Status: healthy
Age Group: 58 years (range: 50-70 years)
Sex: M
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
Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha.
1999 Oct
Examination of selected food additives and organochlorine food contaminants for androgenic activity in vitro.
2000 Feb
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.
2000 Jan
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
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
Androgen receptor stabilization in recurrent prostate cancer is associated with hypersensitivity to low androgen.
2001 Apr 1
Estradiol-17beta stimulates gonadotropin II expression and release in the protandrous male black porgy Acanthopagrus schlegeli Bleeker: a possible role in sex change.
2001 Feb
Regulation of the gap junction connexin 43 gene by androgens in the prostate.
2001 Feb
Messenger ribonucleic acid levels of steroid 5 alpha-reductase 2 in human prostate predict the enzyme activity.
2001 Feb
Human types 1 and 3 3 alpha-hydroxysteroid dehydrogenases: differential lability and tissue distribution.
2001 Feb
Estrogen and androgen elicit growth hormone release via dissimilar patterns of hypothalamic neuropeptide secretion.
2001 Feb
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
Androgens and isolation from adult tutors differentially affect the development of songbird neurons critical to vocal plasticity.
2001 Jan
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.
2001 Jan
Mutations at the boundary of the hinge and ligand binding domain of the androgen receptor confer increased transactivation function.
2001 Jan
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.
2001 Jan
Manipulation of androgens causes different energetic responses to cold in 60- and 40-day-old male rats.
2001 Jan
Sex steroid hormones enhance immune function in male and female Siberian hamsters.
2001 Jan
Effects of hyperprolactinemia on rat prostate growth: evidence of androgeno-dependence.
2001 Jan
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.
2001 Jan 22
Fetal androgen exposure inhibits fetal rat lung fibroblast lipid uptake and release.
2001 Jan-Feb
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
Proliferation and differentiation of prostatic stromal cells.
2001 Mar
Differentiation-dependent expression of connective tissue growth factor and lysyl oxidase messenger ribonucleic acids in rat granulosa cells.
2001 Mar
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
Nongenomic effect of testosterone on chloride secretion in cultured rat efferent duct epithelia.
2001 May
Patents
Substance Class Chemical
Created
by admin
on Wed Apr 02 07:02:29 GMT 2025
Edited
by admin
on Wed Apr 02 07:02:29 GMT 2025
Record UNII
08J2K08A3Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
STANOLONE
MI  
Preferred Name English
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
ANDRACTIM
Brand Name English
ANABOLEX
Brand Name English
androstanolone [INN]
Common Name English
4-DIHYDROTESTOSTERONE
Common Name English
17.BETA.-HYDROXY-5.ALPHA.-ANDROSTANE-3-ONE
Systematic Name English
NSC-10972
Code English
TESTOSTERONE IMPURITY F [EP IMPURITY]
Common Name English
Androstanolone [WHO-DD]
Common Name 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 Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
FDA ORPHAN DRUG 93995
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
LOINC 1849-9
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
DEA NO. 4000
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
FDA ORPHAN DRUG 747120
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
NCI_THESAURUS C243
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
LOINC 43826-7
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
WIKIPEDIA Designer-drugs-Dihydrotestosterone
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
WHO-ATC G03BB02
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
LOINC 15057-3
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
LOINC 35189-0
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
LOINC 6775-1
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
WHO-VATC QA14AA01
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
WHO-ATC A14AA01
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
LOINC 1848-1
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
WHO-VATC QG03BB02
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID9022364
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
SMS_ID
100000086923
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
CAS
521-18-6
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
NCI_THESAURUS
C72098
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
DRUG CENTRAL
3927
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
ChEMBL
CHEMBL27769
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
CHEBI
16330
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
CHEBI
85278
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
MERCK INDEX
m10190
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
208-307-3
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
DRUG BANK
DB02901
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
EVMPD
SUB05509MIG
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
PUBCHEM
10635
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
MESH
D013196
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
NSC
10972
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
INN
238
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
FDA UNII
08J2K08A3Y
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
WIKIPEDIA
DIHYDROTESTOSTERONE
Created by admin on Wed Apr 02 07:02:29 GMT 2025 , Edited by admin on Wed Apr 02 07:02:29 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
PARENT -> METABOLITE ACTIVE
PRODRUG -> METABOLITE ACTIVE
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP
Related Record Type Details
ACTIVE MOIETY