MESTEROLONE

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 Search

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

Description
Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/Proviron_dr_1358760414396.pdf
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen receptor 42 Target ID: P10275 Gene ID: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10935543	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Infertility 14 Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/Proviron_dr_1358760414396.pdf	Curative	Approved 8429	PROVIRON Approved Use Reduced efficiency in middle and advanced age, Potency disturbances, Hypogonadism, Infertility.
Hypogonadism 28 Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/Proviron_dr_1358760414396.pdf	Palliative	Approved 8429	PROVIRON Approved Use Reduced efficiency in middle and advanced age, Potency disturbances, Hypogonadism, Infertility.
Potency disturbances 1 Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/Proviron_dr_1358760414396.pdf	Curative	Approved 8429	PROVIRON Approved Use Reduced efficiency in middle and advanced age, Potency disturbances, Hypogonadism, Infertility.
Androgen deficiency 1 Sources: https://www.old.health.gov.il/units/pharmacy/trufot/alonim/Proviron_dr_1358760414396.pdf	Primary	Approved 8429	PROVIRON Approved Use Reduced efficiency in middle and advanced age, Potency disturbances, Hypogonadism, Infertility.

PubMed

Title	Date	PubMed
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	11599078
Oligospermia due to partial maturation arrest responds to low dose estrogen-testosterone combination therapy resulting in live-birth: a case report.	2002 Dec	12508135
Osteoporosis in male hypogonadism: responses to androgen substitution differ among men with primary and secondary hypogonadism.	2003	12792150
Human chorionic gonadotropin free beta-subunit in the human seminal plasma: a new marker for spermatogenesis?	2003 Feb 10	12551786
The role of the biochemistry department in the diagnosis of pituitary apoplexy.	2004 Mar	15025811
Prostate cancer after exogenous testosterone replacement therapy in a patient with pituitary insufficiency.	2005	15764279
Molecular cloning and characterization of a nuclear androgen receptor activated by 11-ketotestosterone.	2005 Aug 17	16107211
Microbial transformation of mesterolone.	2005 Mar	17191988
Metabolic studies of mesterolone in horses.	2007 Jul 16	17616252
Nonsurgical treatment of male infertility: specific and empiric therapy.	2007 Sep	19707335
Microbial oxidation of anabolic steroids.	2008	19023784
Hepatocyte nuclear phenotype: the cross-talk between anabolic androgenic steroids and exercise in transgenic mice.	2008 Nov	18785119
Adverse effect of the anabolic-androgenic steroid mesterolone on cardiac remodelling and lipoprotein profile is attenuated by aerobicz exercise training.	2008 Oct	18808528
Serum oestrogen receptor alpha and beta bioactivity are independently associated with breast cancer: a proof of principle study.	2009 Jul 7	19491898
Morphological changes in murine skeletal muscle in response to exercise and mesterolone.	2010	19854955
Successful treatment of methimazole-induced severe aplastic anaemia in a diabetic patient with other co-morbidities.	2010 Dec 20	22802368
Effect of high intensity aerobic exercise and mesterolone on remodeling of Achilles tendon of C57BL/6 transgenic mice.	2010 Feb	19902256

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Mesterolone showed activation effect on mutant androgen receptor (expressed in HeLa and COS-7 cells) at doses 0.1–300 nM.

Name

Type

Language

MESTEROLONE

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