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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H30O2
Molecular Weight 302.451
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHENOLONE

SMILES

CC1=CC(=O)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C

InChI

InChIKey=ANJQEDFWRSLVBR-VHUDCFPWSA-N
InChI=1S/C20H30O2/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/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Description

Methenolone (also known as primobolan) was described in 1960. Squibb Company began producing injectable drug in 1962. Methenolone originally was prescribed in case of muscle loss after operations, infections, long-term illnesses, aggressive therapy with corticoids or malnutrition, and in some cases it was used to treat osteoporosis and breast cancer. Methenolone was commonly used to promote weight gain in infants, weighing less than normal, without any side effects. Methenolone is an anabolic steroid, modification of dihydrotestosterone (DHT) with weak androgenic activity and a moderate anabolic effect. A notable trait of methenolone is that it can firmly bind to androgen receptors, stronger than testosterone. Adult doses for the treatment of aplastic anemia are usually in a range of 1–3 mg/kg per day. Adverse side effects include fluid and electrolyte retention, hypercalcaemia, increased bone growth and skeletal weight. In men, additional side priapism, azoospermia, hirsutism, male pattern baldness, acne andoedema. In women, side effects include virilization, amenorrhoea, menstrual irregularities, suppressed lactation, and increased libido. In children, side effects may include virilization symptoms. Metenolone may enhance effects of antidiabetics, ciclosporin, levothyroxine, warfarin. Resistance to the effects of neuromuscular blockers may occur, and metenolone also has the potential to interfere with glucose tolerance and thyroidfunction tests. Metenolone enanthate (methenolone enanthate) is an ester derivative of methenolone sold commonly under the brand names Primobolan (tablet form) orPrimobolan Depot (injectable). When it interacts with the aromatase enzyme it does not form any estrogens. It is used by people who are very susceptible to estrogenic side effects, having lowerestrogenic properties than nandrolone. This trait makes primobolan to be a good fat burner. Primobolan does not convert into estradiol. As an anabolic steroid, the use of metenolone is banned from use in sports governed by the World Anti-Doping Agency. Belarusian shot putter Nadzeya Ostapchuk was stripped of her gold medal after testing positive for metenolone at the London 2012 Olympic Games. She has been excluded from future IOC events. The NBA and NBPA also banned the use of methenolone under the Anti-Drug Program. In February 2013, Hedo Türkoğlu of the Orlando Magic was suspended for 20 games without pay by the league after testing positive for methenolone. In December 2013, Natalia Volgina was stripped of her 2013 Old Mutual Two Oceans Marathon title and received a two-year competition ban, subsequent to a final guilty verdict for using the steroid Metenolone.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
[Increased hematological toxicity of antineoplastic drugs with simultaneous androgenotherapy (author's transl)].
1977 Sep 17
[Complete remission of essential thrombocythemia after recovery from severe bone marrow aplasia induced by busulfan treatment].
1997 Feb
Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases.
2003 Sep
[Treatment of adult patients with aplastic anemia in Japan].
2005 Jun
Metabolism of methenolone acetate in a veal calf.
2007 Apr
The effect of anabolic steroids on anemia in myelofibrosis with myeloid metaplasia: retrospective analysis of 39 patients in Japan.
2007 May
Liquid chromatographic-mass spectrometric analysis of glucuronide-conjugated anabolic steroid metabolites: method validation and interlaboratory comparison.
2008 Jul
Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites.
2008 Mar
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008 Nov 28
[Effect of anabolic steroids on osteoporosis].
2008 Oct
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
2008 Sep
[Pulmonary toxicity due to methenolone: a case report].
2009 Dec
Analysis of anabolic steroids in hair: time courses in guinea pigs.
2009 Sep
Acute myocardial infarction and renal infarction in a bodybuilder using anabolic steroids.
2010 Jun
Patents

Patents

Sample Use Guides

In Vivo Use Guide
recommended dose of legal Primobolan (primo) (Methenolone enanthate) is 200-400 mg/week for men and 50-100 mg/week for women and the dosages can be taken with or without meals. The ideal dose of Primo tablets for men is 50-100 mg every day and 10-25 mg every day for women while the dose of injectable Primo is 350-650 mg every week for men and 100 mg every week for women
Route of Administration: Oral; injection
Name Type Language
METHENOLONE
MI  
Common Name English
METENOLONE
INN   MART.   WHO-DD  
INN  
Official Name English
PRIMOBOLAN S
Brand Name English
METENOLONE [WHO-DD]
Common Name English
METENOLONE [INN]
Common Name English
METENOLONE [MART.]
Common Name English
METHENOLONE [MI]
Common Name English
17.BETA.-HYDROXY-1-METHYL-5.ALPHA.-ANDROST-1-EN-3-ONE
Systematic Name English
Classification Tree Code System Code
LIVERTOX 616
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
DEA NO. 4000
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
WHO-VATC QA14AA04
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
WHO-ATC A14AA04
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
Code System Code Type Description
RXCUI
6833
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY RxNorm
CAS
153-00-4
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY
ECHA (EC/EINECS)
205-812-0
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY
INN
1223
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY
MERCK INDEX
M7309
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY Merck Index
EVMPD
SUB08823MIG
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY
ChEMBL
CHEMBL2106880
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY
PUBCHEM
3037705
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY
WIKIPEDIA
Methenolone
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY
EPA CompTox
153-00-4
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY
MESH
D008710
Created by admin on Tue Oct 22 00:43:25 UTC 2019 , Edited by admin on Tue Oct 22 00:43:25 UTC 2019
PRIMARY