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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H42O3
Molecular Weight 414.6216
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHENOLONE ENANTHATE

SMILES

CCCCCCC(=O)O[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)C=C(C)[C@]4(C)[C@@]3([H])CC[C@@]21C

InChI

InChIKey=TXUICONDJPYNPY-FRXWOFFRSA-N
InChI=1S/C27H42O3/c1-5-6-7-8-9-25(29)30-24-13-12-22-21-11-10-19-17-20(28)16-18(2)27(19,4)23(21)14-15-26(22,24)3/h16,19,21-24H,5-15,17H2,1-4H3/t19-,21-,22-,23-,24-,26-,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula C27H42O3
Molecular Weight 414.6216
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
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
[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
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
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:45:53 UTC 2021
Edited
by admin
on Sat Jun 26 02:45:53 UTC 2021
Record UNII
0SPD480WFH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHENOLONE ENANTHATE
USAN  
USAN  
Official Name English
SQ-16374
Code English
NSC-64967
Code English
17.BETA.-HYDROXY-1-METHYL-5.ALPHA.-ANDROST-1-EN-3-ONE HEPTANOATE
Common Name English
METENOLONE ENANTHATE
JAN  
Common Name English
SH-601
Code English
SQ 16374
Code English
PRIMONABOL DEPOT
Brand Name English
PRIMOBOLAN DEPOT
Brand Name English
METENOLONE ENANTHATE [JAN]
Common Name English
METHENOLONE 17-ENANTHATE [MI]
Common Name English
METHENOLONE ENANTHATE [USAN]
Common Name English
SH 601
Code English
METHENOLONE 17-ENANTHATE
MI  
Common Name English
METENOLONE ENANTATE [WHO-DD]
Common Name English
METENOLONE ENANTATE
MART.   WHO-DD  
Common Name English
ANDROST-1-EN-3-ONE, 1-METHYL-17-((1-OXOHEPTYL)OXY)-, (5.ALPHA.,17.BETA.)-
Systematic Name English
METENOLONE ENANTATE [MART.]
Common Name English
Classification Tree Code System Code
DEA NO. 4000
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
Code System Code Type Description
CAS
303-42-4
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
WIKIPEDIA
METENOLONE ENANTHATE
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
FDA UNII
0SPD480WFH
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
RXCUI
29654
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY RxNorm
EPA CompTox
303-42-4
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL2106949
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
EVMPD
SUB03197MIG
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-141-6
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
NCI_THESAURUS
C166434
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
MESH
C028758
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
MERCK INDEX
M7309
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY Merck Index
PUBCHEM
248271
Created by admin on Sat Jun 26 02:45:53 UTC 2021 , Edited by admin on Sat Jun 26 02:45:53 UTC 2021
PRIMARY
Related Record Type Details
ACTIVE MOIETY