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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H32O3
Molecular Weight 344.4877
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHENOLONE ACETATE

SMILES

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

InChI

InChIKey=PGAUJQOPTMSERF-QWQRBHLCSA-N
InChI=1S/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20-,21-,22-/m0/s1

HIDE SMILES / InChI

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
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
Successful treatment of anabolic steroid-induced azoospermia with human chorionic gonadotropin and human menopausal gonadotropin.
2003 Jun
Severe aplastic anemia associated with thymic carcinoma and partial recovery of hematopoiesis after thymectomy.
2003 Jun
Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry.
2005 Apr 29
[Treatment of adult patients with aplastic anemia in Japan].
2005 Jun
Anabolic steroid-induced rhabdomyolysis.
2005 Jun
The development of multiple drug use among anabolic-androgenic steroid users: six subjective case reports.
2008 Nov 28
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

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
Name Type Language
METHENOLONE ACETATE
USAN  
USAN  
Official Name English
Metenolone acetate [WHO-DD]
Common Name English
17β-Hydroxy-1-methyl-5α-androst-1-en-3-one acetate
Common Name English
METHENOLONE 17-ACETATE [MI]
Common Name English
METHENOLONE ACETATE [USAN]
Common Name English
SH 567
Code English
SQ 16496
Code English
SH-567
Code English
ORAL PRIMOBOLAN
Brand Name English
METENOLONE ACETATE [JAN]
Common Name English
METENOLONE ACETATE
MART.   WHO-DD  
Common Name English
NSC-74226
Code English
PRIMOBOLAN
Brand Name English
ANDROST-1-EN-3-ONE, 17-(ACETYLOXY)-1-METHYL-, (5.ALPHA.,17.BETA.)-
Systematic Name English
METENOLONE ACETATE [MART.]
Common Name English
METHENOLONE 17-ACETATE
MI  
Common Name English
SQ-16496
Code English
Classification Tree Code System Code
DEA NO. 4000
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
Code System Code Type Description
NSC
74226
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106880
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY
WIKIPEDIA
Metenolone acetate
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
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MESH
C033244
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY
PUBCHEM
252372
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
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MERCK INDEX
M7309
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
207-097-0
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY
SMS_ID
100000092356
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
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EPA CompTox
DTXSID40963004
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY
RXCUI
29653
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY RxNorm
EVMPD
SUB03196MIG
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY
NCI_THESAURUS
C170169
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
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FDA UNII
W75590VPKQ
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
PRIMARY
CAS
434-05-9
Created by admin on Wed Jul 05 22:42:48 UTC 2023 , Edited by admin on Wed Jul 05 22:42:48 UTC 2023
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