NAV

Trestolone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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
3D
Similar Structures
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
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Pharmacology

Indication

Investigated for use/treatment in contraception and male hormonal deficiencies/abnormalities.

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Contraindications & Blackbox Warnings
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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
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Trestolone.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Trestolone.
AcetaminophenThe metabolism of Trestolone can be increased when combined with Acetaminophen.
AcetazolamideThe metabolism of Trestolone can be increased when combined with Acetazolamide.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Trestolone.
Food Interactions
Not Available

Products

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International/Other Brands
MENT

Categories

Drug Categories
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
  1. 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]
  2. 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]
PubChem Compound
19582
PubChem Substance
175427041
ChemSpider
8014619
ZINC
ZINC000004217690
Wikipedia
Trestolone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0391 mg/mLALOGPS
logP2.65ALOGPS
logP3.35Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)18.34Chemaxon
pKa (Strongest Basic)-0.88Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity84.5 m3·mol-1Chemaxon
Polarizability33.92 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.973
Caco-2 permeable+0.8984
P-glycoprotein substrateSubstrate0.6498
P-glycoprotein inhibitor IInhibitor0.5489
P-glycoprotein inhibitor IINon-inhibitor0.8923
Renal organic cation transporterNon-inhibitor0.7324
CYP450 2C9 substrateNon-substrate0.8167
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7739
CYP450 1A2 substrateNon-inhibitor0.9005
CYP450 2C9 inhibitorNon-inhibitor0.95
CYP450 2D6 inhibitorNon-inhibitor0.9452
CYP450 2C19 inhibitorNon-inhibitor0.6668
CYP450 3A4 inhibitorNon-inhibitor0.8812
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8683
Ames testNon AMES toxic0.9382
CarcinogenicityNon-carcinogens0.9483
BiodegradationNot ready biodegradable0.9174
Rat acute toxicity1.6259 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8938
hERG inhibition (predictor II)Non-inhibitor0.7163
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-0090000000-729c32e29acb0bae2f2d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-31a76c05f2418b517823
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-d4285d137d17ce2739a4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-2890000000-a32cd200d75868e4b9de
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-0090000000-287e43f50e7e32f9d5e1
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00s6-1910000000-00d2c116720be66cdc97
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.1937819
predicted
DarkChem Lite v0.1.0
[M+H]+179.8020819
predicted
DarkChem Lite v0.1.0
[M+Na]+179.3956819
predicted
DarkChem Lite v0.1.0

Drug created at November 18, 2007 18:28 / Updated at February 21, 2021 18:51