mesterolone profile

Mesterolone, also known as Proviron, is an orally active synthetic androgen that was initially developed in the 1960s. It is a derivative of dihydrotestosterone (DHT) and exhibits a high binding affinity for the androgen receptor. Mesterolone's synthesis involves a multi-step process starting with the modification of a steroid precursor molecule. It is primarily used for the treatment of hypogonadism and other conditions associated with androgen deficiency, although its use has declined in recent years due to the availability of other, more potent and safer androgen replacement therapies. Research into mesterolone focuses on its potential therapeutic applications, including its effects on muscle growth, bone density, and libido. Despite its historical use, ongoing research is limited, and its long-term safety and efficacy in various conditions remain to be fully elucidated.'

Mesterolone: 17 beta-Hydroxy-1 alpha-methyl-5 alpha-androstan-3-one. A synthetic steroid with anabolic and androgenic activities. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	15020
CHEMBL ID	258918
CHEBI ID	135293
SCHEMBL ID	148260
MeSH ID	M0013486

Synonym
mesterolonum
ec 215-836-3
0srq75x9i9 ,
unii-0srq75x9i9
mesterolona
mesterolonum [inn-latin]
5alpha-androstan-3-one, 17beta-hydroxy-1alpha-methyl-
einecs 215-836-3
testosterone, 4,5alpha-dihydro-1alpha-methyl-
17beta-hydroxy-1alpha-methyl-5alpha-androstan-3-one
1-alpha-methyl-5-alpha-androstan-17-beta-ol-3-one
sh 60723
mesterolona [inn-spanish]
5-alpha-androstan-3-one, 17-beta-hydroxy-1-alpha-methyl-
mesterolone [usan:inn:ban]
androstan-3-one, 17-hydroxy-1-methyl-, (1alpha,5alpha,17beta)-
1alpha-methyl-5alpha-dihydrotestosterone
1-alpha-methyl-17-beta-hydroxy-5-alpha-androstan-3-one
androstan-3-one, 17-hydroxy-1-methyl-, (1-alpha,5-alpha,17-beta)-
17-beta-hydroxy-1-alpha-methyl-5-alpha-androstan-3-one
nsc75054
proviron
testosterone,5.alpha.-dihydro-1.alpha.-methyl-
androviron
17-hydroxy-1-methyl-5-androstane-3 one
testiwop
pro-viron
nsc-75054
mestoranum
1.alpha.-methyl-5.alpha.-dihydrotestosterone
sh-60723
mesterolone
1424-00-6
androstan-3-one, (1.alpha.,5.alpha.,17.beta.)-
sh 723
mesteranum
mesterolone (usan/inn)
D04947
CHEBI:135293
sh-723
CHEMBL258918
(1s,5s,8r,9s,10s,13s,14s,17s)-17-hydroxy-1,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
LMST02020107
1a-methyl-5a-dihydrotestosterone
S3946
provirone 25
AKOS015894889
bdbm50423551
SCHEMBL148260
androstan-3-one, 17-hydroxy-1-methyl-, (1.alpha.,5.alpha.,17.beta.)-
mesterolone [ep monograph]
mesterolone [mi]
mesterolone [usan]
mesterolone [inn]
mesterolone [ep impurity]
mesterolone [who-dd]
mesterolone [mart.]
androstan-3-one, 17-hydroxy-1-methyl-, (1a,5a,17b)-
1a-methyl-5a-androstan-17b-ol-3-one
17b-hydroxy-1a-methyl-5a-androstan-3-one
1a-methyl-17b-hydroxy-5a-androstan-3-one
(1a,5a,17b)-17-hydroxy-1-methyl-androstan-3-one
mesterolone, analytical standard
mesterolone, european pharmacopoeia (ep) reference standard
mesterolone, 1.0 mg/ml in 1,2-dimethoxyethane
mesterolone 1.0 mg/ml in acetonitrile
DB13587
Q4291328
(1s,5s,8r,9s,10s,13s,14s,17s)-17-hydroxy-1,10,13-trimethylhexadecahydro-3h-cyclopenta[a]phenanthren-3-one
CCG-267514
DTXSID90878533

Excerpt	Reference	Relevance
"Mesterolone is a synthetic androgenic steroid indicating a weak anabolic activity. "	( A Validated TLC-Densitometric Method for the Determination of Mesterolone in Bulk Material and in Tablets. Dołowy, M; Filip, K; Pyka-Pająk, A; Zagrodzka, J, 2015)	2.1
"Mesterolone is a synthetic oral anabolic androgenic steroid used to treat hypogonadism. "	( Influence of mesterolone on satellite cell distribution and fiber morphology within maturing chicken pectoralis muscle. Aldirawi, MH; Allouh, MZ, 2012)	2.19

Excerpt	Reference	Relevance
"Mesterolone has probably modulated the autonomic innervation of the vesical musculature with correction of the defective neural mechanism which is believed to be implicated in the pathogenesis of nocturnal enuresis."	( Treatment of primary nocturnal enuresis by oral androgen mesterolone. A clinical and cystometric study. Abdel-Rahman, M; el-Barnachawy, R; el-Sadr, A; Koraitim, M; Sabry, AA, 1990)	1.25

Excerpt	Reference	Relevance
"Mesterolone treatment significantly decreased both plasma testosterone and protein bound testosterone levels."	( The effects of mesterolone, a male sex hormone in depressed patients (a double blind controlled study). Itil, KZ; Itil, TM; Michael, ST; Shapiro, DM, 1984)	1.34
"Treatment with mesterolone increased total cholesterol, triglyceride, low-density lipoprotein cholesterol (LDL-c) and very LDL-c (VLDL-c) plasma levels."	( Adverse effect of the anabolic-androgenic steroid mesterolone on cardiac remodelling and lipoprotein profile is attenuated by aerobicz exercise training. da Cruz-Höfling, MA; Fontana, K; Leonardo, MB; Mandarim-de-Lacerda, CA; Oliveira, HC, 2008)	0.94

Excerpt	Reference	Relevance
"Abuse of anabolic-androgenic steroids (AAS) for improving physical performance is associated with serious, sometimes fatal, adverse effects."	( Adverse effect of the anabolic-androgenic steroid mesterolone on cardiac remodelling and lipoprotein profile is attenuated by aerobicz exercise training. da Cruz-Höfling, MA; Fontana, K; Leonardo, MB; Mandarim-de-Lacerda, CA; Oliveira, HC, 2008)	0.6

Excerpt	Relevance	Reference
" They also indicate that the topical administration of effective dosage levels of L-651,580 causes few, if any, systemic effects."	( Topical anti-androgenicity of a new 4-azasteroid in the hamster. Berman, C; Brooks, JR; Krupa, DA; Primka, RL; Rasmusson, GH; Reynolds, GF, 1991)	0.28
" The stimulatory androgens used are mesterolone and testosterone undecanoate which, it is postulated, in a form and dosage that does not influence pituitary gonadotrophin secretion, either have a direct stimulatory effect on spermatogenesis or influence sperm transport and maturation though an effect on the epididymis, ductus deferens and seminal vesicles."	( Androgens versus placebo or no treatment for idiopathic oligo/asthenospermia. Hughes, E; Lilford, R; Vail, A; Vandekerckhove, P, 2000)	0.58
" The stimulatory androgens used are mesterolone and testosterone undecanoate which, it is postulated, in a form and dosage that does not influence pituitary gonadotrophin secretion, either have a direct stimulatory effect on spermatogenesis or influence sperm transport and maturation though an effect on the epididymis, ductus deferens and seminal vesicles."	( WITHDRAWN: Androgens versus placebo or no treatment for idiopathic oligo/asthenospermia. Hughes, E; Lilford, R; Vail, A; Vandekerckhove, P, 2007)	0.61

Class	Description
3-oxo-5alpha-steroid	A 3-oxo steroid that has alpha configuration at position 5.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Androgen receptor	Rattus norvegicus (Norway rat)	IC50 (µMol)	18.2800	0.0010	1.9794	14.1600	AID1489052
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Sex hormone-binding globulin	Homo sapiens (human)	Kd	0.0003	0.0002	0.3496	4.7863	AID318680
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
androgen binding	Sex hormone-binding globulin	Homo sapiens (human)
protein binding	Sex hormone-binding globulin	Homo sapiens (human)
steroid binding	Sex hormone-binding globulin	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
extracellular region	Sex hormone-binding globulin	Homo sapiens (human)
extracellular exosome	Sex hormone-binding globulin	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	77 (62.10)	18.7374
1990's	14 (11.29)	18.2507
2000's	13 (10.48)	29.6817
2010's	15 (12.10)	24.3611
2020's	5 (4.03)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	21 (15.33%)	5.53%
Reviews	7 (5.11%)	6.00%
Case Studies	15 (10.95%)	4.05%
Observational	0 (0.00%)	0.25%
Other	94 (68.61%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
betaine glycine betaine : The amino acid betaine derived from glycine.	2.31	1	0	amino-acid betaine; glycine derivative	fundamental metabolite
thiamine thiamine(1+) : A primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively.	1.95	1	0	primary alcohol; vitamin B1	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
4-nonylphenol 4-nonylphenol: structure in first source; see also record for nonylphenol. 4-nonylphenol : A member of the class of phenols that is phenol which is para-substituted with a nonyl group.	2.04	1	0	phenols	environmental contaminant
amitriptyline Amitriptyline: Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.. amitriptyline : An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.	9.31	2	2	carbotricyclic compound; tertiary amine	adrenergic uptake inhibitor; antidepressant; environmental contaminant; tropomyosin-related kinase B receptor agonist; xenobiotic
chlordiazepoxide Chlordiazepoxide: An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal.. chlordiazepoxide : A benzodiazepine that is 3H-1,4-benzodiazepine 4-oxide substituted by a chloro group at position 7, a phenyl group at position 5 and a methylamino group at position 2.	3.33	1	1	benzodiazepine
chlorpromazine Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.	3.33	1	1	organochlorine compound; phenothiazines; tertiary amine	anticoronaviral agent; antiemetic; dopaminergic antagonist; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; phenothiazine antipsychotic drug
flutamide Flutamide: An antiandrogen with about the same potency as cyproterone in rodent and canine species.	2.15	1	0	(trifluoromethyl)benzenes; monocarboxylic acid amide	androgen antagonist; antineoplastic agent
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group.	3.33	1	1	beta-amino acid ester; methyl ester; piperidines
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties.	1.95	1	0	aromatic amine
pentoxifylline [no description available]	8.35	1	1	oxopurine
theobromine Theobromine: 3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than THEOPHYLLINE and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9). theobromine : A dimethylxanthine having the two methyl groups located at positions 3 and 7. A purine alkaloid derived from the cacao plant, it is found in chocolate, as well as in a number of other foods, and is a vasodilator, diuretic and heart stimulator.	3.35	1	1	dimethylxanthine	adenosine receptor antagonist; bronchodilator agent; food component; human blood serum metabolite; mouse metabolite; plant metabolite; vasodilator agent
corticosterone [no description available]	2.38	2	0	11beta-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
estriol hormonin: estrogen replacement; each tablet contains 600 ug micronized 17beta-estradiol, 270 ug estriol and 1.4 mg estrone. chlorapatite : A phosphate mineral with the formula Ca5(PO4)3Cl.	2.04	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-hydroxy steroid	estrogen; human metabolite; human xenobiotic metabolite; mouse metabolite
reserpine Reserpine: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria. Reserpine inhibits the uptake of norepinephrine into storage vesicles resulting in depletion of catecholamines and serotonin from central and peripheral axon terminals. It has been used as an antihypertensive and an antipsychotic as well as a research tool, but its adverse effects limit its clinical use.. reserpine : An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.	1.96	1	0	alkaloid ester; methyl ester; yohimban alkaloid	adrenergic uptake inhibitor; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; environmental contaminant; first generation antipsychotic; plant metabolite; xenobiotic
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	2.05	1	0	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
aldosterone [no description available]	2.04	1	0	11beta-hydroxy steroid; 18-oxo steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid hormone; mineralocorticoid; primary alpha-hydroxy ketone; steroid aldehyde	human metabolite; mouse metabolite
prednisone Prednisone: A synthetic anti-inflammatory glucocorticoid derived from CORTISONE. It is biologically inert and converted to PREDNISOLONE in the liver.. prednisone : A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead of the oxo group at position 11), which is the active drug and also a steroid.	2	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(1),Delta(4)-steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	adrenergic agent; anti-inflammatory drug; antineoplastic agent; immunosuppressive agent; prodrug
estrone Hydroxyestrones: Estrone derivatives substituted with one or more hydroxyl groups in any position. They are important metabolites of estrone and other estrogens.	2.04	1	0	17-oxo steroid; 3-hydroxy steroid; phenolic steroid; phenols	antineoplastic agent; bone density conservation agent; estrogen; human metabolite; mouse metabolite
androsterone [no description available]	2.77	3	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid; C19-steroid	androgen; anticonvulsant; human blood serum metabolite; human metabolite; human urinary metabolite; mouse metabolite; pheromone
etiocholanolone Etiocholanolone: The 5-beta-reduced isomer of ANDROSTERONE. Etiocholanolone is a major metabolite of TESTOSTERONE and ANDROSTENEDIONE in many mammalian species including humans. It is excreted in the URINE.. 3alpha-hydroxy-5beta-androstan-17-one : An androstanoid that is 5beta-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals.	2.39	2	0	17-oxo steroid; 3alpha-hydroxy steroid; androstanoid	human metabolite; mouse metabolite
dehydroepiandrosterone Dehydroepiandrosterone: A major C19 steroid produced by the ADRENAL CORTEX. It is also produced in small quantities in the TESTIS and the OVARY. Dehydroepiandrosterone (DHEA) can be converted to TESTOSTERONE; ANDROSTENEDIONE; ESTRADIOL; and ESTRONE. Most of DHEA is sulfated (DEHYDROEPIANDROSTERONE SULFATE) before secretion.. dehydroepiandrosterone : An androstanoid that is androst-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It is a naturally occurring steroid hormone produced by the adrenal glands.	2.67	3	0	17-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; androstanoid	androgen; human metabolite; mouse metabolite
17-desoxyestradiol estra-1,3,5(10)-trien-3-ol : A 3-hydroxy steroid resulting from deoxygenation at position 17 of estradiol or estrone.	2.04	1	0	3-hydroxy steroid; phenolic steroid; phenols	estrogen
ethinyl estradiol Ethinyl Estradiol: A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.. 17alpha-ethynylestradiol : A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.	2.04	1	0	17-hydroxy steroid; 3-hydroxy steroid; terminal acetylenic compound	xenoestrogen
methyltestosterone Methyltestosterone: A synthetic hormone used for androgen replacement therapy and as an hormonal antineoplastic agent (ANTINEOPLASTIC AGENTS, HORMONAL).. methyltestosterone : A 17beta-hydroxy steroid that is testosterone bearing a methyl group at the 17alpha position.	7.7	3	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; enone	anabolic agent; androgen; antineoplastic agent
dromostanolone dromostanolone: synthetic anabolic androgenic steroid used to lower plasma cholesterol & as antineoplastic agent in advanced breast neoplasms; major descriptor (66-86); on-line search ANDROSTANOLS (80-86); ANDROSTANES (68-86); INDEX MEDICUS search DROMOSTANOLONE (66-86); RN given refers to (2alpha,5alpha,17beta)-isomer	1.98	1	0	17beta-hydroxy steroid; 3-oxo-5alpha-steroid; anabolic androgenic steroid	anabolic agent; antineoplastic agent
levodopa Levodopa: The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.. L-dopa : An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease	2.36	2	0	amino acid zwitterion; dopa; L-tyrosine derivative; non-proteinogenic L-alpha-amino acid	allelochemical; antidyskinesia agent; antiparkinson drug; dopaminergic agent; hapten; human metabolite; mouse metabolite; neurotoxin; plant growth retardant; plant metabolite; prodrug
androstenedione Androstenedione: A delta-4 C19 steroid that is produced not only in the TESTIS, but also in the OVARY and the ADRENAL CORTEX. Depending on the tissue type, androstenedione can serve as a precursor to TESTOSTERONE as well as ESTRONE and ESTRADIOL.. androst-4-ene-3,17-dione : A 3-oxo Delta(4)-steroid that is androst-4-ene substituted by oxo groups at positions 3 and 17. It is a steroid hormone synthesized in the adrenal glands and gonads.	2.38	2	0	17-oxo steroid; 3-oxo-Delta(4) steroid; androstanoid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE	2.04	1	0	20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone	human metabolite; mouse metabolite
norethindrone Norethindrone: A synthetic progestational hormone with actions similar to those of PROGESTERONE but functioning as a more potent inhibitor of ovulation. It has weak estrogenic and androgenic properties. The hormone has been used in treating amenorrhea, functional uterine bleeding, endometriosis, and for CONTRACEPTION.. norethisterone : A 17beta-hydroxy steroid that is testosterone in which the hydrogen at position 17 is replaced by an ethynyl group and in which the methyl group attached to position 10 is replaced by hydrogen.	2.04	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	progestin; synthetic oral contraceptive
17-alpha-hydroxyprogesterone 17alpha-hydroxyprogesterone : A 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone.	2.04	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; tertiary alpha-hydroxy ketone	human metabolite; metabolite; mouse metabolite; progestin
medroxyprogesterone acetate [no description available]	2.04	1	0	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; corticosteroid; steroid ester	adjuvant; androgen; antineoplastic agent; antioxidant; female contraceptive drug; inhibitor; progestin; synthetic oral contraceptive
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	2.36	2	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
fluoxymesterone Fluoxymesterone: An anabolic steroid that has been used in the treatment of male HYPOGONADISM, delayed puberty in males, and in the treatment of breast neoplasms in women.	3.06	5	0	11beta-hydroxy steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; anabolic androgenic steroid; fluorinated steroid	anabolic agent; antineoplastic agent
4-tert-octylphenol 4-tert-octylphenol: structure given in first source	2.04	1	0	alkylbenzene
pregnenolone [no description available]	2.38	2	0	20-oxo steroid; 3beta-hydroxy-Delta(5)-steroid; C21-steroid	human metabolite; mouse metabolite
20-alpha-dihydroprogesterone 20-alpha-Dihydroprogesterone: A biologically active 20-alpha-reduced metabolite of PROGESTERONE. It is converted from progesterone to 20-alpha-hydroxypregn-4-en-3-one by the 20-ALPHA-HYDROXYSTEROID DEHYDROGENASE in the CORPUS LUTEUM and the PLACENTA.	1.96	1	0	20-hydroxypregn-4-en-3-one	human metabolite; mouse metabolite
testosterone enanthate [no description available]	6.86	4	4	heptanoate ester; sterol ester	androgen
cyproterone acetate [no description available]	2.66	3	0	20-oxo steroid; 3-oxo-Delta(4) steroid; acetate ester; chlorinated steroid; steroid ester	androgen antagonist; geroprotector; progestin
nandrolone Nandrolone: C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of ESTRADIOL to resemble TESTOSTERONE but less one carbon at the 19 position.. nandrolone : A 3-oxo Delta(4)-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.	2.69	3	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; anabolic androgenic steroid	human metabolite
mestanolone mestanolone: non-virilizing androgenic steroid; RN given refers to (5alpha,17beta)-isomer; structure	2.04	1	0	3-oxo-5alpha-steroid
androstenediol Androstenediol: An intermediate in TESTOSTERONE biosynthesis, found in the TESTIS or the ADRENAL GLANDS. Androstenediol, derived from DEHYDROEPIANDROSTERONE by the reduction of the 17-keto group (17-HYDROXYSTEROID DEHYDROGENASES), is converted to TESTOSTERONE by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-HYDROXYSTEROID DEHYDROGENASES).. androst-5-ene-3beta,17beta-diol : A 3beta-hydroxy-Delta(5)-steroid that is 3beta-hydroxyandrost-5-ene carrying an additional hydroxy group at position 17beta.	2.04	1	0	17beta-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid	androgen; human metabolite; mouse metabolite; radiation protective agent
dihydrotestosterone Dihydrotestosterone: A potent androgenic metabolite of TESTOSTERONE. It is produced by the action of the enzyme 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE.. 17beta-hydroxyandrostan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4-5 double bond has been reduced to a single bond with unspecified configuration at position 5.. 17beta-hydroxy-5alpha-androstan-3-one : A 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5.	10.53	53	16	17beta-hydroxy steroid; 17beta-hydroxyandrostan-3-one; 3-oxo-5alpha-steroid	androgen; Daphnia magna metabolite; human metabolite; mouse metabolite
lithium carbonate Lithium Carbonate: A lithium salt, classified as a mood-stabilizing agent. Lithium ion alters the metabolism of BIOGENIC MONOAMINES in the CENTRAL NERVOUS SYSTEM, and affects multiple neurotransmission systems.	4.44	1	1	carbonate salt; lithium salt	antimanic drug
glycerylphosphorylcholine Glycerylphosphorylcholine: A component of PHOSPHATIDYLCHOLINES or LECITHINS, in which the two hydroxy groups of GLYCEROL are esterified with fatty acids. (From Stedman, 26th ed)	3.74	2	1	glycerophosphocholine
c.i. 42510 Rosaniline Dyes: Compounds that contain the triphenylmethane aniline structure found in rosaniline. Many of them have a characteristic magenta color and are used as COLORING AGENTS.. basic fuchsin : A four-component mixture of chemically related dyes comprising pararosanilin, rosanilin, magenta II and new fuchsin in varying amounts. rosanilin : A hydrochloride that is the monohydrochloride of 4-[(4-aminophenyl)(4-iminocyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline. One of the major constituents of Basic fuchsin, together with pararosanilin, magenta II and new fuchsin.	2.04	1	0
levonorgestrel Levonorgestrel: A synthetic progestational hormone with actions similar to those of PROGESTERONE and about twice as potent as its racemic or (+-)-isomer (NORGESTREL). It is used for contraception, control of menstrual disorders, and treatment of endometriosis.	2.39	2	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound	contraceptive drug; female contraceptive drug; progestin; synthetic oral contraceptive
dihydrotestosterone propionate dihydrotestosterone propionate: RN given refers to (5alpha,17beta)-isomer; structure	1.97	1	0
ethylestrenol Ethylestrenol: An anabolic steroid with some progestational activity and little androgenic effect.. ethylestrenol : A 17beta-hydroxy steroid that is estrane containing a double bond between positions 4 and 5 and substituted by an ethyl group and a hydroxy group at the 17alpha and 17beta positions, respectively. It is an anabolic steroid that has little androgenic effect and only slight progestational activity. It has been used to promote growth in boys with delayed bone growth.	2.04	1	0	17beta-hydroxy steroid; tertiary alcohol	anabolic agent
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	1.95	1	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
5 alpha-androstane-3 alpha,17 beta-diol 5alpha-androstane-3alpha,17beta-diol : The 5alpha-stereoisomer of androstane-3alpha,17beta-diol.	2.04	1	0	androstane-3alpha,17beta-diol	Daphnia magna metabolite; human metabolite
stanozolol Stanozolol: A synthetic steroid that has anabolic and androgenic properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1194). stanozolol : An organic heteropentacyclic compound resulting from the formal condensation of the 3-keto-aldehyde moiety of oxymetholone with hydrazine. Like oxymetholone, it is a synthetic anabolic steroid. It has both anabolic and androgenic properties, and has been used to treat hereditary angioedema and various vascular disorders. It has also been widely abused by professional athletes.	1.95	1	0	17beta-hydroxy steroid; anabolic androgenic steroid; organic heteropentacyclic compound; tertiary alcohol	anabolic agent; androgen
gestrinone Gestrinone: A non-estrogenic contraceptive which is a weak progestin with strong anti-progesterone properties. It is effective if used once a week orally or can also be used in intravaginal devices.	2.04	1	0	oxo steroid
danazol Danazol: A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders.	2.68	3	0	17beta-hydroxy steroid; terminal acetylenic compound	anti-estrogen; estrogen antagonist; geroprotector
bromocriptine Bromocriptine: A semisynthetic ergotamine alkaloid that is a dopamine D2 agonist. It suppresses prolactin secretion.	1.95	1	0	indole alkaloid	antidyskinesia agent; antiparkinson drug; dopamine agonist; hormone antagonist
androstane-3,17-diol Androstane-3,17-diol: The unspecified form of the steroid, normally a major metabolite of TESTOSTERONE with androgenic activity. It has been implicated as a regulator of gonadotropin secretion.	1.95	1	0	17-hydroxy steroid; 3-hydroxy steroid; androstanoid
desogestrel Desogestrel: A synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents (ORAL CONTRACEPTIVES, COMBINED).	2.04	1	0	17beta-hydroxy steroid; terminal acetylenic compound	contraceptive drug; progestin; synthetic oral contraceptive
finasteride Finasteride: An orally active 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE inhibitor. It is used as a surgical alternative for treatment of benign PROSTATIC HYPERPLASIA.. finasteride : An aza-steroid that is a synthetic drug for the treatment of benign prostatic hyperplasia.	2.15	1	0	3-oxo steroid; aza-steroid; delta-lactam	androgen antagonist; antihyperplasia drug; EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor
testosterone undecanoate [no description available]	6.38	3	3	steroid ester
16-hydroxytestosterone 16-hydroxytestosterone: RN given refers to (16alpha,17beta)-isomer. 16alpha-hydroxytestosterone : A C19-steroid that is testosterone in which the hydrogen at the 16alpha position has been replaced by a hydroxy group.	2.04	1	0	16alpha-hydroxy steroid; 17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; androstanoid; C19-steroid; diol; secondary alcohol	androgen
2-methoxyestradiol 2-methoxy-17beta-estradiol : A 17beta-hydroxy steroid, being 17beta-estradiol methoxylated at C-2.	2.04	1	0	17beta-hydroxy steroid; 3-hydroxy steroid	angiogenesis modulating agent; antimitotic; antineoplastic agent; human metabolite; metabolite; mouse metabolite
girard's reagent t Girard's reagent T: used for separating ketosteroids; RN given refers to chloride	7.82	2	0
2-iodoestradiol 2-iodoestradiol: RN given refers to unlabeled cpd	2.04	1	0
17-propylmesterolone 17-propylmesterolone: under investigation as a topical anti-androgen for treatment of acne & seborrhea	4.86	11	0
17-alpha-hydroxypregnenolone 17-alpha-Hydroxypregnenolone: A 21-carbon steroid that is converted from PREGNENOLONE by STEROID 17-ALPHA-HYDROXYLASE. It is an intermediate in the delta-5 pathway of biosynthesis of GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS.. 17alpha-hydroxypregnenolone : A hydroxypregnenolone carrying an alpha-hydroxy group at position 17.	2.04	1	0	17alpha-hydroxy-C21-steroid; 17alpha-hydroxy steroid; 3beta-hydroxy-Delta(5)-steroid; hydroxypregnenolone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
glucuronic acid Glucuronic Acid: A sugar acid formed by the oxidation of the C-6 carbon of GLUCOSE. In addition to being a key intermediate metabolite of the uronic acid pathway, glucuronic acid also plays a role in the detoxification of certain drugs and toxins by conjugating with them to form GLUCURONIDES.. D-glucuronic acid : The D-enantiomer of glucuronic acid.. D-glucopyranuronic acid : A D-glucuronic acid in cyclic pyranose form.	1.98	1	0	D-glucuronic acid	algal metabolite
bolasterone bolasterone: 7alpha, 17alpha-dimethyl-testosterone; anabolic (Merck Index, 13th ed)	2.04	1	0	3-hydroxy steroid	androgen
androsta-1,4,6-triene-3,17-dione androsta-1,4,6-triene-3,17-dione: blocks aromatization of testosterone to estradiol; aromatase antagonist. androsta-1,4,6-triene-3,17-dione : An androstanoid that is androsta-1,4,6-triene substituted by oxo groups at positions 3 and 17.	1.96	1	0	17-oxo steroid; 3-oxo-Delta(1),Delta(4)-steroid; androstanoid	EC 1.14.14.14 (aromatase) inhibitor; human xenobiotic metabolite
androsterone glucuronide androsterone glucuronide: RN given refers to (3alpha,5alpha)-isomer. androsterone 3-glucosiduronic acid : A steroid glucosiduronic acid having androsterone as the steroid component.	2.31	1	0	beta-D-glucosiduronic acid; steroid glucosiduronic acid	human metabolite; metabolite; mouse metabolite
matairesinol matairesinol: lignan that is a central precursor in plants in the biosynthesis of numerous lignans (coordinate with specific); RN refers to (3R-trans)-isomer. (-)-matairesinol : A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer).	2.04	1	0	gamma-lactone; lignan; polyphenol	angiogenesis inhibitor; anti-asthmatic agent; phytoestrogen; plant metabolite
4-androstene-3,17-diol 4-androstene-3,17-diol: RN given refers to (3alpha,17beta)-isomer	2.04	1	0	3-hydroxy steroid	androgen
androsterone sulfate androsterone sulfate: RN given refers to (3alpha,5alpha)-isomer. androsterone sulfate : A steroid sulfate that is the 3-sulfate of androsterone.	2.31	1	0	17-oxo steroid; androstanoid; steroid sulfate	human metabolite; mouse metabolite
3,4-divanillyltetrahydrofuran 3,4-divanillyltetrahydrofuran: lignan with the highest binding affinity; structure in first source	2.04	1	0
estradiol 3-benzoate 17beta-estradiol 3-benzoate : A benzoate ester resulting from the formal condensation of benzoic acid with the phenolic hydroxy group of 17beta-estradiol.	2.04	1	0	17beta-hydroxy steroid; benzoate ester	estrogen receptor agonist; xenoestrogen
cortisone [no description available]	2.04	1	0	11-oxo steroid; 17alpha-hydroxy steroid; 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; C21-steroid; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
equilin Equilin: An estrogenic steroid produced by HORSES. It has a total of four double bonds in the A- and B-ring. High concentration of euilin is found in the URINE of pregnant mares.	2.04	1	0	17-oxo steroid; 3-hydroxy steroid
stenbolone stenbolone: structure given in first source; RN given from Merck; RN given refers to the (5alpha,17beta)-isomer; RN for cpd without isomeric designation not available 7/91	6.98	1	0	3-hydroxy steroid	androgen
naringenin (S)-naringenin : The (S)-enantiomer of naringenin.	2.04	1	0	(2S)-flavan-4-one; naringenin	expectorant; plant metabolite
cortodoxone Cortodoxone: 17,21-Dihydroxypregn-4-ene-3,20-dione. A 17-hydroxycorticosteroid with glucocorticoid and anti-inflammatory activities.. 11-deoxycortisol : A deoxycortisol that is cortisol in which the hydroxy group at position 11 has been replaced by a hydrogen.	2.04	1	0	deoxycortisol; glucocorticoid; primary alpha-hydroxy ketone; tertiary alpha-hydroxy ketone	human metabolite; mouse metabolite
strychnine Strychnine: An alkaloid found in the seeds of STRYCHNOS NUX-VOMICA. It is a competitive antagonist at glycine receptors and thus a convulsant. It has been used as an analeptic, in the treatment of nonketotic hyperglycinemia and sleep apnea, and as a rat poison.. strychnine : A monoterpenoid indole alkaloid that is strychnidine bearing a keto substituent at the 10-position.	1.95	1	0	monoterpenoid indole alkaloid; organic heteroheptacyclic compound	avicide; cholinergic antagonist; glycine receptor antagonist; neurotransmitter agent; rodenticide
equilenin Equilenin: An estrogenic steroid produced by HORSES. It has a total of five double bonds in the A- and B-ring. High concentration of equilenin is found in the URINE of pregnant mares.. equilenin : A 3-hydroxy steroid that is estrone which carries two double bonds at positions 6 and 8. It is found in the urine of pregnant mare's and extensively used for estrogen replacement therapy in postmenopausal women.	2.04	1	0	17-oxo steroid; 3-hydroxy steroid	antioxidant; mammalian metabolite
diethylstilbestrol Diethylstilbestrol: A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed). diethylstilbestrol : An olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.	1.95	1	0	olefinic compound; polyphenol	antifungal agent; antineoplastic agent; autophagy inducer; calcium channel blocker; carcinogenic agent; EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor; EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor; endocrine disruptor; xenoestrogen
enclomiphene Enclomiphene: The trans or (E)-isomer of clomiphene.	6.39	13	1
D-fructopyranose [no description available]	4.03	3	1	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
tamoxifen [no description available]	2.39	2	0	stilbenoid; tertiary amino compound	angiogenesis inhibitor; antineoplastic agent; bone density conservation agent; EC 1.2.3.1 (aldehyde oxidase) inhibitor; EC 2.7.11.13 (protein kinase C) inhibitor; estrogen antagonist; estrogen receptor antagonist; estrogen receptor modulator
lithium Lithium: An element in the alkali metals family. It has the atomic symbol Li, atomic number 3, and atomic weight [6.938; 6.997]. Salts of lithium are used in treating BIPOLAR DISORDER.	4.44	1	1	alkali metal atom
methenolone Methenolone: A synthetic steroid that has been used for its anabolic action.	2.77	3	0	3-hydroxy steroid	androgen
genistein [no description available]	2.04	1	0	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
cyproterone Cyproterone: An anti-androgen that, in the form of its acetate (CYPROTERONE ACETATE), also has progestational properties. It is used in the treatment of hypersexuality in males, as a palliative in prostatic carcinoma, and, in combination with estrogen, for the therapy of severe acne and hirsutism in females.	6.97	9	3	17alpha-hydroxy steroid; 20-oxo steroid; 3-oxo-Delta(4) steroid; chlorinated steroid; tertiary alpha-hydroxy ketone	androgen antagonist
ethisterone Ethisterone: 17 alpha-Hydroxypregn-4-en-20-yn-3-one. A synthetic steroid hormone with progestational effects.. ethisterone : A 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol.	2.04	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound; tertiary alcohol	drug metabolite; progestin
sq-23377 Ionomycin: A divalent calcium ionophore that is widely used as a tool to investigate the role of intracellular calcium in cellular processes.. ionomycin : A very long-chain fatty acid that is docosa-10,16-dienoic acid which is substituted by methyl groups at positions 4, 6, 8, 12, 14, 18 and 20, by hydroxy groups at positions 11, 19 and 21, and by a (2',5-dimethyloctahydro-2,2'-bifuran-5-yl)ethanol group at position 21. An ionophore produced by Streptomyces conglobatus, it is used in research to raise the intracellular level of Ca(2+) and as a research tool to understand Ca(2+) transport across biological membranes.	1.99	1	0	cyclic ether; enol; polyunsaturated fatty acid; very long-chain fatty acid	calcium ionophore; metabolite
etonogestrel [no description available]	2.04	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; terminal acetylenic compound	contraceptive drug; female contraceptive drug; progestin
thioacetazone Thioacetazone: A thiosemicarbazone that is used in association with other antimycobacterial agents in the initial and continuation phases of antituberculosis regimens. Thiacetazone containing regimens are less effective than the short-course regimen recommended by the International Union Against Tuberculosis and are used in some developing countries to reduce drug costs. (From Martindale, The Extra Pharmacopoeia, 30th ed, p217). thiosemicarbazone : A hydrazone resulting from the formal condensation of an aldehyde or ketone with the non-thioacylated nitrogen of thiosemicarbazide or its substituted derivatives.	1.97	1	0
topterone topterone: structure	1.97	1	0
quinbolone quinbolone: structure	1.95	1	0	3-hydroxy steroid	androgen
losartan potassium Erythropoietin: Glycoprotein hormone, secreted chiefly by the KIDNEY in the adult and the LIVER in the FETUS, that acts on erythroid stem cells of the BONE MARROW to stimulate proliferation and differentiation.	1.95	1	0
sepharose agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.	2	1	0
acid phosphatase Acid Phosphatase: An enzyme that catalyzes the conversion of an orthophosphoric monoester and water to an alcohol and orthophosphate. EC 3.1.3.2.	3.74	2	1
menotropins Menotropins: Extracts of urine from menopausal women that contain high concentrations of pituitary gonadotropins, FOLLICLE STIMULATING HORMONE and LUTEINIZING HORMONE. Menotropins are used to treat infertility. The FSH:LH ratio and degree of purity vary in different preparations.	2.65	3	0
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	3.35	1	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent
norgestrel Norgestrel: A synthetic progestational agent with actions similar to those of PROGESTERONE. This racemic or (+-)-form has about half the potency of the levo form (LEVONORGESTREL). Norgestrel is used as a contraceptive, ovulation inhibitor, and for the control of menstrual disorders and endometriosis.	2.36	2	0

Condition	Relationship Strength	Studies	Trials
Acute Liver Injury, Drug-Induced [description not available]	2.21	1	0
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.21	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.08	1	0
Lower Urinary Tract Symptom [description not available]	7.1	1	0
Symptom Cluster [description not available]	3.31	2	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	7.1	1	0
Syndrome A characteristic symptom complex.	8.31	2	0
Equine Infectious Anemia Viral disease of horses caused by the equine infectious anemia virus (EIAV; INFECTIOUS ANEMIA VIRUS, EQUINE). It is characterized by intermittent fever, weakness, and anemia. Chronic infection consists of acute episodes with remissions.	2.13	1	0
Polyploid [description not available]	2.04	1	0
Left Ventricular Hypertrophy [description not available]	2.04	1	0
Hypertrophy, Left Ventricular Enlargement of the LEFT VENTRICLE of the heart. This increase in ventricular mass is attributed to sustained abnormal pressure or volume loads and is a contributor to cardiovascular morbidity and mortality.	2.04	1	0
Hypertrophy General increase in bulk of a part or organ due to CELL ENLARGEMENT and accumulation of FLUIDS AND SECRETIONS, not due to tumor formation, nor to an increase in the number of cells (HYPERPLASIA).	2.47	2	0
Affective Psychosis, Bipolar [description not available]	2.07	1	0
Bipolar Disorder A major affective disorder marked by severe mood swings (manic or major depressive episodes) and a tendency to remission and recurrence.	2.07	1	0
Hypospermatogenesis [description not available]	8.1	23	2
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.74	7	1
Sterility, Male [description not available]	9.41	32	6
Infertility, Male The inability of the male to effect FERTILIZATION of an OVUM after a specified period of unprotected intercourse. Male sterility is permanent infertility.	9.41	32	6
Hypergonadotropic Hypogonadism [description not available]	9.63	10	7
Age-Related Osteoporosis [description not available]	3.4	1	1
Hypogonadism Condition resulting from deficient gonadal functions, such as GAMETOGENESIS and the production of GONADAL STEROID HORMONES. It is characterized by delay in GROWTH, germ cell maturation, and development of secondary sex characteristics. Hypogonadism can be due to a deficiency of GONADOTROPINS (hypogonadotropic hypogonadism) or due to primary gonadal failure (hypergonadotropic hypogonadism).	9.63	10	7
Osteoporosis Reduction of bone mass without alteration in the composition of bone, leading to fractures. Primary osteoporosis can be of two major types: postmenopausal osteoporosis (OSTEOPOROSIS, POSTMENOPAUSAL) and age-related or senile osteoporosis.	3.4	1	1
Disgerminoma [description not available]	1.96	1	0
Cancer of Testis [description not available]	1.96	1	0
Dysgerminoma A malignant ovarian neoplasm, thought to be derived from primordial germ cells of the sexually undifferentiated embryonic gonad. It is the counterpart of the classical seminoma of the testis, to which it is both grossly and histologically identical. Dysgerminomas comprise 16% of all germ cell tumors but are rare before the age of 10, although nearly 50% occur before the age of 20. They are generally considered of low-grade malignancy but may spread if the tumor extends through its capsule and involves lymph nodes or blood vessels. (Dorland, 27th ed; DeVita Jr et al., Cancer: Principles & Practice of Oncology, 3d ed, p1646)	1.96	1	0
Testicular Neoplasms Tumors or cancer of the TESTIS. Germ cell tumors (GERMINOMA) of the testis constitute 95% of all testicular neoplasms.	1.96	1	0
Depression, Endogenous [description not available]	5.87	3	3
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	5.98	3	2
Depressive Disorder An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.	5.87	3	3
Sex Disorders [description not available]	1.96	1	0
Sexual Dysfunction, Physiological Physiological disturbances in normal sexual performance in either the male or the female.	1.96	1	0
Acne [description not available]	2.65	3	0
Hirsutism A condition observed in WOMEN and CHILDREN when there is excess coarse body hair of an adult male distribution pattern, such as facial and chest areas. It is the result of elevated ANDROGENS from the OVARIES, the ADRENAL GLANDS, or exogenous sources. The concept does not include HYPERTRICHOSIS, which is an androgen-independent excessive hair growth.	1.95	1	0
Acne Vulgaris A chronic disorder of the pilosebaceous apparatus associated with an increase in sebum secretion. It is characterized by open comedones (blackheads), closed comedones (whiteheads), and pustular nodules. The cause is unknown, but heredity and age are predisposing factors.	2.65	3	0
Anemia A reduction in the number of circulating ERYTHROCYTES or in the quantity of HEMOGLOBIN.	8.74	2	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	1.95	1	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	1.95	1	0
Angioneurotic Edema [description not available]	1.95	1	0
Angioedema Swelling involving the deep DERMIS, subcutaneous, or submucosal tissues, representing localized EDEMA. Angioedema often occurs in the face, lips, tongue, and larynx.	1.95	1	0
Anochlesia [description not available]	1.96	1	0
Impotence [description not available]	7.36	2	0
Erectile Dysfunction The inability in the male to have a PENILE ERECTION due to psychological or organ dysfunction.	2.36	2	0
Sterility, Female [description not available]	1.95	1	0
Anovulation Suspension or cessation of OVULATION in animals or humans with follicle-containing ovaries (OVARIAN FOLLICLE). Depending on the etiology, OVULATION may be induced with appropriate therapy.	1.95	1	0
Infertility, Female Diminished or absent ability of a female to achieve conception.	1.95	1	0
Wasting Disease [description not available]	1.99	1	0
Acquired Immune Deficiency Syndrome [description not available]	1.99	1	0
Kaposi Sarcoma [description not available]	1.99	1	0
Acquired Immunodeficiency Syndrome An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.	1.99	1	0
Sarcoma, Kaposi A multicentric, malignant neoplastic vascular proliferation characterized by the development of bluish-red cutaneous nodules, usually on the lower extremities, most often on the toes or feet, and slowly increasing in size and number and spreading to more proximal areas. The tumors have endothelium-lined channels and vascular spaces admixed with variably sized aggregates of spindle-shaped cells, and often remain confined to the skin and subcutaneous tissue, but widespread visceral involvement may occur. Kaposi's sarcoma occurs spontaneously in Jewish and Italian males in Europe and the United States. An aggressive variant in young children is endemic in some areas of Africa. A third form occurs in about 0.04% of kidney transplant patients. There is also a high incidence in AIDS patients. (From Dorland, 27th ed & Holland et al., Cancer Medicine, 3d ed, pp2105-7) HHV-8 is the suspected cause.	1.99	1	0
Autoimmune Thrombocytopenia [description not available]	2	1	0
Purpura, Thrombocytopenic, Idiopathic Thrombocytopenia occurring in the absence of toxic exposure or a disease associated with decreased platelets. It is mediated by immune mechanisms, in most cases IMMUNOGLOBULIN G autoantibodies which attach to platelets and subsequently undergo destruction by macrophages. The disease is seen in acute (affecting children) and chronic (adult) forms.	2	1	0
Adenoma, Prostatic [description not available]	1.95	1	0
Prostatic Hyperplasia Increase in constituent cells in the PROSTATE, leading to enlargement of the organ (hypertrophy) and adverse impact on the lower urinary tract function. This can be caused by increased rate of cell proliferation, reduced rate of cell death, or both.	1.95	1	0
Abnormalities, Congenital [description not available]	1.95	1	0
Dermatitis Medicamentosa [description not available]	1.95	1	0
Urinary Incontinence, Stress Involuntary discharge of URINE as a result of physical activities that increase abdominal pressure on the URINARY BLADDER without detrusor contraction or overdistended bladder. The subtypes are classified by the degree of leakage, descent and opening of the bladder neck and URETHRA without bladder contraction, and sphincter deficiency.	1.95	1	0
Blood Clot [description not available]	1.95	1	0
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	6.95	1	0
Anemia, Hypoplastic [description not available]	3.34	1	1
Anemia, Hemolytic, Acquired [description not available]	3.34	1	1
Bone Marrow Diseases Diseases involving the BONE MARROW.	3.34	1	1
Chronic Kidney Failure [description not available]	3.34	1	1
Anemia, Aplastic A form of anemia in which the bone marrow fails to produce adequate numbers of peripheral blood elements.	3.34	1	1
Anemia, Hemolytic A condition of inadequate circulating red blood cells (ANEMIA) or insufficient HEMOGLOBIN due to premature destruction of red blood cells (ERYTHROCYTES).	3.34	1	1
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	3.34	1	1
Dementia Praecox [description not available]	2.87	1	0
Aggression Behavior which may be manifested by destructive and attacking action which is verbal or physical, by covert attitudes of hostility or by obstructionism.	2.87	1	0
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	2.87	1	0
48,XXYY Syndrome [description not available]	2.64	3	0
Klinefelter Syndrome A form of male HYPOGONADISM, characterized by the presence of an extra X CHROMOSOME, small TESTES, seminiferous tubule dysgenesis, elevated levels of GONADOTROPINS, low serum TESTOSTERONE, underdeveloped secondary sex characteristics, and male infertility (INFERTILITY, MALE). Patients tend to have long legs and a slim, tall stature. GYNECOMASTIA is present in many of the patients. The classic form has the karyotype 47,XXY. Several karyotype variants include 48,XXYY; 48,XXXY; 49,XXXXY, and mosaic patterns ( 46,XY/47,XXY; 47,XXY/48,XXXY, etc.).	2.64	3	0
Varicocele A condition characterized by the dilated tortuous veins of the SPERMATIC CORD with a marked left-sided predominance. Adverse effect on male fertility occurs when varicocele leads to an increased scrotal (and testicular) temperature and reduced testicular volume.	2.36	2	0
Abnormalities, Autosome [description not available]	1.95	1	0
Chromosomal Translocation [description not available]	1.95	1	0
Ambiguous Genitalia [description not available]	1.95	1	0
Disorders of Sex Development In gonochoristic organisms, congenital conditions in which development of chromosomal, gonadal, or anatomical sex is atypical. Effects from exposure to abnormal levels of GONADAL HORMONES in the maternal environment, or disruption of the function of those hormones by ENDOCRINE DISRUPTORS are included.	1.95	1	0
Adenocarcinoma, Basal Cell [description not available]	1.95	1	0
Cancer of Prostate [description not available]	1.95	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	1.95	1	0
Prostatic Neoplasms Tumors or cancer of the PROSTATE.	1.95	1	0
Carbohydrate Metabolism, Inborn Error [description not available]	1.95	1	0
Agnogenic Myeloid Metaplasia [description not available]	1.98	1	0
Primary Myelofibrosis A de novo myeloproliferation arising from an abnormal stem cell. It is characterized by the replacement of bone marrow by fibrous tissue, a process that is mediated by CYTOKINES arising from the abnormal clone.	1.98	1	0
Alopecia Cicatrisata [description not available]	3.29	2	0
Alopecia Absence of hair from areas where it is normally present.	8.29	2	0
Enuresis Involuntary discharge of URINE after expected age of completed development of urinary control. This can happen during the daytime (DIURNAL ENURESIS) while one is awake or during sleep (NOCTURNAL ENURESIS). Enuresis can be in children or in adults (as persistent primary enuresis and secondary adult-onset enuresis).	8.36	1	1
Bonnevie-Ullrich Syndrome This syndrome that was originally observed by Ullrich, and designated as identical to TURNER SYNDROME, related the webbing of the neck, loose skin and other anomalies of the syndrome to accumulation of fluid in the embryo starting at the head and dispersing to the extremities (as observed by Bonnevie in mice). Commonly observed at birth in Turner Syndrome and NOONAN SYNDROME; EDEMA of the extremities usually recedes by one year and is an early sign of Turner syndrome, especially in female neonates.	1.97	1	0
Turner Syndrome A syndrome of defective gonadal development in phenotypic females associated with the karyotype 45,X (or 45,XO). Patients generally are of short stature with undifferentiated GONADS (streak gonads), SEXUAL INFANTILISM, HYPOGONADISM, webbing of the neck, cubitus valgus, elevated GONADOTROPINS, decreased ESTRADIOL level in blood, and CONGENITAL HEART DEFECTS. NOONAN SYNDROME (also called Pseudo-Turner Syndrome and Male Turner Syndrome) resembles this disorder; however, it occurs in males and females with a normal karyotype and is inherited as an autosomal dominant.	1.97	1	0
Chronic Illness [description not available]	3.35	1	1
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	3.35	1	1

Assay ID	Title	Year	Journal	Article
AID318680	Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin	2008	Journal of medicinal chemistry, Apr-10, Volume: 51, Issue:7	An updated steroid benchmark set and its application in the discovery of novel nanomolar ligands of sex hormone-binding globulin.
AID1079931	Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1489052	Displacement of fluormone-AL Green from recombinant rat His-tagged/GST-fused androgen receptor LBD expressed in baculovirus expression system measured after 1.5 hrs by fluorescence polarization assay	2017	Bioorganic & medicinal chemistry letters, 09-01, Volume: 27, Issue:17	Design, synthesis and biological evaluation of novel 3-oxo-4-oxa-5α-androst-17β-amide derivatives as dual 5α-reductase inhibitors and androgen receptor antagonists.
AID1079949	Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079934	Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079932	Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079937	Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079935	Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079942	Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079947	Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079936	Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079938	Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079945	Animal toxicity known. [column 'TOXIC' in source]
AID1079941	Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079948	Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079940	Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079943	Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079944	Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079933	Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079946	Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079939	Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

mesterolone

Description

Cross-References

Synonyms (71)

Research Excerpts

Overview

Effects

Treatment

Toxicity

Dosage Studied

Drug Classes (1)

Protein Targets (2)

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Bioassays (21)

Research

Studies (124)

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Research Demand Index: 77.76

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