Structure via PubChem · Public domain (PubChem)
ethylestrenol
Sign in to saveAlso known as Maxibolin®, Orabolin®, ethylnandrol, 19-nor-17alpha-pregn-4-en-17beta-ol, 17alpha-ethyl-17beta-hydroxy-4-estrene, 17beta-hydroxy-17alpha-ethyl-19-nor-4-androstene, 17alpha-ethylestr-4-en-17beta-ol
Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.
Chemical data
- Formula
- C20H32O
- Molecular weight
- 288.5 g/mol
- IUPAC name
- (8R,9S,10R,13S,14S,17S)-17-ethyl-13-methyl-2,3,6,7,8,9,10,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol
- SMILES
- CC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CCCC[C@H]34)C)O
- InChIKey
- AOXRBFRFYPMWLR-XGXHKTLJSA-N
- XLogP
- 5.1
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1964
- Admin. routes
- oral
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 288.245316
- Has use
- medication
Show 6 more facts
- chemical formula
- C₂₀H₃₂O
- canonical SMILES
- CCC1(CCC2C1(CCC3C2CCC4=CCCCC34)C)O
- isomeric SMILES
- CC[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CCCC[C@H]34)C)O
- World Health Organisation international non-proprietary name
- ethylestrenol
- defined daily dose
- 2
- physically interacts with
- androgen receptor
Sources (3)
via Wikidata · CC0
~6 min read
Encyclopedic overview
15 sectionsContents
- Medical uses
- Contraindications
- Side effects
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- Legal status
- References
- External links
Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.
Side effects of ethylestrenol include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has strong anabolic effects relative to its androgenic effects. The drug also has strong progestogenic effects. Ethylestrenol is a prodrug of norethandrolone.
Excerpted from Wikipedia’s “ethylestrenol” article, available under the CC BY-SA 4.0 licence.