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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H32O2
Molecular Weight 304.4669
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MESTEROLONE

SMILES

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

InChI

InChIKey=UXYRZJKIQKRJCF-TZPFWLJSSA-N
InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H32O2
Molecular Weight 304.4669
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including, https://www.steroidal.com/steroid-profiles/proviron-mesterolone/

Mesterolone is an androgen receptor agonist which was developed for hormone replacement therapy in males suffering from androgen deficiency and related disorders. Mesterolone is known under the name Proviron. The drug is also used by bodybuilders and athletes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P10275
Gene ID: 367.0
Gene Symbol: AR
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PROVIRON

Approved Use

Reduced efficiency in middle and advanced age, Potency disturbances, Hypogonadism, Infertility.
Palliative
PROVIRON

Approved Use

Reduced efficiency in middle and advanced age, Potency disturbances, Hypogonadism, Infertility.
Curative
PROVIRON

Approved Use

Reduced efficiency in middle and advanced age, Potency disturbances, Hypogonadism, Infertility.
Primary
PROVIRON

Approved Use

Reduced efficiency in middle and advanced age, Potency disturbances, Hypogonadism, Infertility.
PubMed

PubMed

TitleDatePubMed
Mass spectrometry of steroid glucuronide conjugates. II-Electron impact fragmentation of 3-keto-4-en- and 3-keto-5alpha-steroid-17-O-beta glucuronides and 5alpha-steroid-3alpha,17beta-diol 3- and 17-glucuronides.
2001 Sep
Oligospermia due to partial maturation arrest responds to low dose estrogen-testosterone combination therapy resulting in live-birth: a case report.
2002 Dec
Osteoporosis in male hypogonadism: responses to androgen substitution differ among men with primary and secondary hypogonadism.
2003
Human chorionic gonadotropin free beta-subunit in the human seminal plasma: a new marker for spermatogenesis?
2003 Feb 10
The role of the biochemistry department in the diagnosis of pituitary apoplexy.
2004 Mar
Prostate cancer after exogenous testosterone replacement therapy in a patient with pituitary insufficiency.
2005
Molecular cloning and characterization of a nuclear androgen receptor activated by 11-ketotestosterone.
2005 Aug 17
Microbial transformation of mesterolone.
2005 Mar
Metabolic studies of mesterolone in horses.
2007 Jul 16
Nonsurgical treatment of male infertility: specific and empiric therapy.
2007 Sep
Microbial oxidation of anabolic steroids.
2008
Hepatocyte nuclear phenotype: the cross-talk between anabolic androgenic steroids and exercise in transgenic mice.
2008 Nov
Adverse effect of the anabolic-androgenic steroid mesterolone on cardiac remodelling and lipoprotein profile is attenuated by aerobicz exercise training.
2008 Oct
Serum oestrogen receptor alpha and beta bioactivity are independently associated with breast cancer: a proof of principle study.
2009 Jul 7
Morphological changes in murine skeletal muscle in response to exercise and mesterolone.
2010
Successful treatment of methimazole-induced severe aplastic anaemia in a diabetic patient with other co-morbidities.
2010 Dec 20
Effect of high intensity aerobic exercise and mesterolone on remodeling of Achilles tendon of C57BL/6 transgenic mice.
2010 Feb
Patents

Sample Use Guides

The tablets should be swallowed whole with some liquid. The recommended doses are: 1 tablet (25 mg) 3 times/day (reduced efficiency and potency disturbances), 1 tablet 2-3 times/day (Infertility), 1-2 tablets 3 times/day (for development of secondary male sex characteristics in hypogonadism).
Route of Administration: Oral
Mesterolone showed activation effect on mutant androgen receptor (expressed in HeLa and COS-7 cells) at doses 0.1–300 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:57:32 GMT 2023
Edited
by admin
on Sat Dec 16 15:57:32 GMT 2023
Record UNII
0SRQ75X9I9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MESTEROLONE
EP   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
TESTIWOP
Brand Name English
ANDROVIRON
Brand Name English
NSC-75054
Code English
MESTEROLONE [MI]
Common Name English
ANDROSTAN-3-ONE, 17-HYDROXY-1-METHYL-, (1.ALPHA.,5.ALPHA.,17.BETA.)-
Systematic Name English
MESTEROLONE [MART.]
Common Name English
SH 723
Code English
MESTEROLONE [EP IMPURITY]
Common Name English
SH-723
Code English
PROVIRON
Brand Name English
Mesterolone [WHO-DD]
Common Name English
17β-Hydroxy-1α-methyl-5α-androstan-3-one
Systematic Name English
MESTEROLONE [EP MONOGRAPH]
Common Name English
mesterolone [INN]
Common Name English
MESTEROLONE [USAN]
Common Name English
Classification Tree Code System Code
DEA NO. 4000
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
WIKIPEDIA Designer-drugs-Mesterolone
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
WHO-VATC QG03BB01
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
NCI_THESAURUS C243
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
WHO-ATC G03BB01
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
Code System Code Type Description
NSC
75054
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
DRUG CENTRAL
3342
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
NCI_THESAURUS
C87227
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
ECHA (EC/EINECS)
215-836-3
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
SMS_ID
100000091044
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
RXCUI
6781
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY RxNorm
CAS
1424-00-6
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
EPA CompTox
DTXSID90878533
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
PUBCHEM
15020
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
FDA UNII
0SRQ75X9I9
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
MESH
D008655
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
EVMPD
SUB08790MIG
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
WIKIPEDIA
MESTEROLONE
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
INN
1965
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
ChEMBL
CHEMBL258918
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
DRUG BANK
DB13587
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY
MERCK INDEX
m7256
Created by admin on Sat Dec 16 15:57:32 GMT 2023 , Edited by admin on Sat Dec 16 15:57:32 GMT 2023
PRIMARY Merck Index
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