NAV

Drostanolone propionate

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

Identification

Generic Name
Drostanolone propionate
DrugBank Accession Number
DB14655
Background

Not Available

Type
Small Molecule
Groups
Approved, Illicit
Structure
3D
Similar Structures
Weight
Average: 360.538
Monoisotopic: 360.266445019
Chemical Formula
C23H36O3
Synonyms
  • 17β-Hydroxy-2α-methyl-5α-androstan-3-one propionate
  • 2M-DHTP
  • 2MDTP
  • 2α-Methyl-4,5-dihydrotestosterone propionate
  • Blackburn Compound
  • Dromostanolone propionate
  • Drostanolone propionate
  • Emdisterone
  • Testosterone, 4,5α-dihydro-2α-methyl-, propionate
External IDs
  • Re 346
  • RS 1567
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Pharmacology

Indication

For use in females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Dromostanolone is a synthetic androgen, or male hormone, similar to testosterone. Dromostanolone works by attaching itself to androgen receptors; this causes it to interact with the parts of the cell involved in the making of proteins. It may cause an increase in the synthesis of some proteins or a decrease in the synthesis of others. These proteins have a variety of effects, including blocking the growth of some types of breast cancer cells, stimulating cells that cause male sexual characteristics, and stimulating the production of red blood cells.

Mechanism of action

Dromostanolone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, dromostanolone binds to the androgen receptor. This causes downstream genetic transcriptional changes. This ultimately causes retention of nitrogen, potassium, and phosphorus; increases protein anabolism; and decreases amino acid catabolism. The antitumour activity of dromostanolone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production.

Absorption

Well absorbed following parenteral administration.

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

Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.

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
AbciximabDrostanolone propionate may increase the anticoagulant activities of Abciximab.
AcenocoumarolDrostanolone propionate may increase the anticoagulant activities of Acenocoumarol.
AlteplaseDrostanolone propionate may increase the anticoagulant activities of Alteplase.
AncrodDrostanolone propionate may increase the anticoagulant activities of Ancrod.
AnistreplaseDrostanolone propionate may increase the anticoagulant activities of Anistreplase.
Food Interactions
Not Available

Products

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International/Other Brands
Drolban (Lilly) / Masteril (Syntex) / Masteron (Recordati)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androgens and derivatives / 3-oxo-5-alpha-steroids / Cyclic ketones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
3-oxo-5-alpha-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Androgen-skeleton / Androstane-skeleton / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
steroid ester (CHEBI:31523)
Affected organisms
Not Available

Chemical Identifiers

UNII
X20UZ57G4O
CAS number
521-12-0
InChI Key
NOTIQUSPUUHHEH-UXOVVSIBSA-N
InChI
InChI=1S/C23H36O3/c1-5-21(25)26-20-9-8-17-16-7-6-15-12-19(24)14(2)13-23(15,4)18(16)10-11-22(17,20)3/h14-18,20H,5-13H2,1-4H3/t14-,15+,16+,17+,18+,20+,22+,23+/m1/s1
IUPAC Name
(1S,3aS,3bR,5aS,8R,9aS,9bS,11aS)-8,9a,11a-trimethyl-7-oxo-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl propanoate
SMILES
[H][C@@]12CC[C@H](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)[C@H](C)C[C@]12C

References

General References
Not Available
KEGG Drug
D01534
ChemSpider
194604
ChEBI
31523
ChEMBL
CHEMBL1201048
ZINC
ZINC000004213057
PharmGKB
PA164760855
Wikipedia
Drostanolone_propionate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000631 mg/mLALOGPS
logP4.76ALOGPS
logP5.1Chemaxon
logS-5.8ALOGPS
pKa (Strongest Basic)-6.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area43.37 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity101.96 m3·mol-1Chemaxon
Polarizability43.19 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0039000000-fa1a992398b23cc7a237
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-2009000000-5761d2e69157952d0f7b
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014r-0194000000-d83f436572945e5f5d5a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-7019000000-29d48fc5fd8417b96369
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9001000000-696eae155a247c9e313c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002r-0941000000-197aeb3f323989ef0330
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]-199.3183996
predicted
DarkChem Lite v0.1.0
[M-H]-183.39607
predicted
DeepCCS 1.0 (2019)
[M+H]+199.9264996
predicted
DarkChem Lite v0.1.0
[M+H]+185.6747
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.5310996
predicted
DarkChem Lite v0.1.0
[M+Na]+191.58722
predicted
DeepCCS 1.0 (2019)

Drug created at September 02, 2018 00:01 / Updated at February 21, 2021 18:54