Trestolone
Identification
- Generic Name
- Trestolone
- DrugBank Accession Number
- DB05830
- Background
Trestolone (7α-methyl-19-nortestosterone) is a synthetic androgen developed by the Population Council as a potential candidate drug for use in hormonal male contraceptive methods. In males, regular administration of sufficient quantities of trestolone induces a state of temporary infertility.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 288.431
Monoisotopic: 288.208930142 - Chemical Formula
- C19H28O2
- Synonyms
- 17beta-Hydroxy-7alpha-methylestr-4-en-3-one
- 17beta-Hydroxy-7alpha-methylestr-4-enone
- 19-Nor-7alpha-methyltestosterone
- 19-Nor-methyltestosterone
- 7alpha-Methyl-17beta-hydroxy-4-estren-3-one
- 7alpha-Methyl-19-nortestosterone
- 7alpha-Methyl-3-oxo-4-estren-17beta-ol
- 7alpha-Methylnandrolone
- 7α-methyl-19-nortestosterone
- MENT
- Trestolona
- Trestolone
- Trestolonum
- External IDs
- RU 27333
Pharmacology
- Indication
Investigated for use/treatment in contraception and male hormonal deficiencies/abnormalities.
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- Pharmacodynamics
Not Available
- Mechanism of action
Trestolone is a potent inhibitor of the release of the luteinizing hormone (LH) and follicle stimulating hormone (FSH). As spermatogenesis requires both testosterone and FSH, it is impaired by the reduction in FSH caused by trestolone as well as the reduction in LH, and subsequent reduction in testosterone.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Trestolone. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Trestolone. Acetaminophen The metabolism of Trestolone can be increased when combined with Acetaminophen. Acetazolamide The metabolism of Trestolone can be increased when combined with Acetazolamide. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Trestolone. Alpelisib The metabolism of Trestolone can be increased when combined with Alpelisib. Alteplase The therapeutic efficacy of Alteplase can be decreased when used in combination with Trestolone. Aminoglutethimide The metabolism of Trestolone can be increased when combined with Aminoglutethimide. Amobarbital The metabolism of Trestolone can be increased when combined with Amobarbital. Amoxicillin The therapeutic efficacy of Trestolone can be decreased when used in combination with Amoxicillin. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- MENT
Categories
- Drug Categories
- Adrenal Cortex Hormones
- Contraceptive Agents, Hormonal
- Contraceptive Agents, Male
- Estranes
- Estrenes
- Fused-Ring Compounds
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormonal Contraceptives for Systemic Use
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Reproductive Control Agents
- Steroids
- Testosterone Congeners
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 40P3287I94
- CAS number
- 3764-87-2
- InChI Key
- YSGQGNQWBLYHPE-CFUSNLFHSA-N
- InChI
- InChI=1S/C19H28O2/c1-11-9-12-10-13(20)3-4-14(12)15-7-8-19(2)16(18(11)15)5-6-17(19)21/h10-11,14-18,21H,3-9H2,1-2H3/t11-,14+,15-,16+,17+,18-,19+/m1/s1
- IUPAC Name
- (1S,3aS,3bR,4R,9aR,9bS,11aS)-1-hydroxy-4,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
- SMILES
- [H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3C[C@@H](C)[C@@]21[H]
References
- General References
- Walton MJ, Kumar N, Baird DT, Ludlow H, Anderson RA: 7alpha-methyl-19-nortestosterone (MENT) vs testosterone in combination with etonogestrel implants for spermatogenic suppression in healthy men. J Androl. 2007 Sep-Oct;28(5):679-88. Epub 2007 Apr 25. [Article]
- Ramachandra SG, Ramesh V, Krishnamurthy HN, Kumar N, Sundaram K, Hardy MP, Rao AJ: Effect of chronic administration of 7alpha-methyl-19-nortestosterone on serum testosterone, number of spermatozoa and fertility in adult male bonnet monkeys (Macaca radiata). Reproduction. 2002 Aug;124(2):301-9. [Article]
- External Links
- PubChem Compound
- 19582
- PubChem Substance
- 175427041
- ChemSpider
- 8014619
- ZINC
- ZINC000004217690
- Wikipedia
- Trestolone
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0391 mg/mL ALOGPS logP 2.65 ALOGPS logP 3.35 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 18.34 Chemaxon pKa (Strongest Basic) -0.88 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 84.5 m3·mol-1 Chemaxon Polarizability 33.92 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.973 Caco-2 permeable + 0.8984 P-glycoprotein substrate Substrate 0.6498 P-glycoprotein inhibitor I Inhibitor 0.5489 P-glycoprotein inhibitor II Non-inhibitor 0.8923 Renal organic cation transporter Non-inhibitor 0.7324 CYP450 2C9 substrate Non-substrate 0.8167 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7739 CYP450 1A2 substrate Non-inhibitor 0.9005 CYP450 2C9 inhibitor Non-inhibitor 0.95 CYP450 2D6 inhibitor Non-inhibitor 0.9452 CYP450 2C19 inhibitor Non-inhibitor 0.6668 CYP450 3A4 inhibitor Non-inhibitor 0.8812 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8683 Ames test Non AMES toxic 0.9382 Carcinogenicity Non-carcinogens 0.9483 Biodegradation Not ready biodegradable 0.9174 Rat acute toxicity 1.6259 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8938 hERG inhibition (predictor II) Non-inhibitor 0.7163
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Drug created at November 18, 2007 18:28 / Updated at February 21, 2021 18:51