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
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
DescriptionCurator's Comment: description was created based on several sources, including
http://www.anabolic.org/primobolan-depot-methenolone-enanthate/
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
Sources: http://buysteroid.en.ecplaza.net/primobolan-100mg-pharmade-raw-steroidsmethenolone--385049-3870566.html
Curator's Comment: The anabolic drug Primobolan (Methenolone enanthate) improves the CNS activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7460859 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
[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 |
|
Two cases of acute myeloblastic leukemia evolving from aplastic anemia. | 2003 Jun |
|
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 |
|
Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases. | 2003 Sep |
|
Endocrinological and pathological effects of anabolic-androgenic steroid in male rats. | 2004 Aug |
|
[A constrictive pericarditis on oral steroid and immunosuppressant treated with bilateral anterolateral thoracotomy; report of a case]. | 2004 Dec |
|
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 |
|
Hepatocellular adenomas associated with anabolic androgenic steroid abuse in bodybuilders: a report of two cases and a review of the literature. | 2005 May |
|
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
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
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
DEA NO. |
4000
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
74226
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
CHEMBL2106880
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
Metenolone acetate
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
C033244
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
252372
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
m7309
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | Merck Index | ||
|
207-097-0
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
100000092356
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
DTXSID40963004
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
29653
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | RxNorm | ||
|
SUB03196MIG
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
C170169
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
W75590VPKQ
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY | |||
|
434-05-9
Created by
admin on Fri Dec 15 15:11:12 GMT 2023 , Edited by admin on Fri Dec 15 15:11:12 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
SUBSTANCE RECORD