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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

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

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

Molecular Formula C20H30O2
Molecular Weight 302.451
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.anabolic.org/primobolan-depot-methenolone-enanthate/

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

Curator's Comment: The anabolic drug Primobolan (Methenolone enanthate) improves the CNS activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
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
Monitoring of CD59 expression in paroxysmal nocturnal hemoglobinuria treated with danazol.
2001 Dec
Masseteric hypertrophy associated with administration of anabolic steroids and unilateral mastication: a case report.
2001 Nov
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
Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.
2002 Jan
Doping control for methenolone using hair analysis by gas chromatography-tandem mass spectrometry.
2002 Jan 5
[A constrictive pericarditis on oral steroid and immunosuppressant treated with bilateral anterolateral thoracotomy; report of a case].
2004 Dec
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature.
2005 May
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
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008 Nov 28
Simultaneous doping analysis of main urinary metabolites of anabolic steroids in horse by ion-trap gas chromatography-tandem mass spectrometry.
2008 Sep
Analysis of anabolic steroids in hair: time courses in guinea pigs.
2009 Sep
Patents

Patents

Sample Use Guides

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: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:19:48 UTC 2023
Edited
by admin
on Sat Dec 16 16:19:48 UTC 2023
Record UNII
9062ZT8Q5C
Record Status Validated (UNII)
Record Version
  • Download
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 Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
DEA NO. 4000
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
WHO-VATC QA14AA04
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
WHO-ATC A14AA04
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
Code System Code Type Description
RXCUI
6833
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY RxNorm
CAS
153-00-4
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-812-0
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
DRUG CENTRAL
1743
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
INN
1223
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
MERCK INDEX
m7309
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID10165179
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
EVMPD
SUB08823MIG
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106880
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
FDA UNII
9062ZT8Q5C
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
SMS_ID
100000088226
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
NCI_THESAURUS
C175130
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
DRUG BANK
DB13710
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
PUBCHEM
3037705
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
WIKIPEDIA
Methenolone
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
MESH
D008710
Created by admin on Sat Dec 16 16:19:49 UTC 2023 , Edited by admin on Sat Dec 16 16:19:49 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY