Structure via PubChem · Public domain (PubChem)
dutasteride
Sign in to saveAlso known as alpha,alpha,alpha,alpha',alpha',alpha'-hexafluoro-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxy-2',5'-xylidide, (5alpha,17beta)-N-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-4-azaandrost-1-ene-17-carboxamide
Dutasteride, sold under the brand name Avodart among others, is a medication primarily used to treat the symptoms of a benign prostatic hyperplasia (BPH), an enlarged prostate not associated with cancer. A few months may be required before benefits occur. It is also used for scalp hair loss in men and as a part of hormone therapy in transgender women. It is usually taken by mouth.
Key facts
- Drug.ChEMBL
- 1200969
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 461091686
- Drug.image
- Dutasteride.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.tradename
- Avodart, others
- Drug.MedlinePlus
- a603001
- Drug.DailyMedID
- Dutasteride
- Drug.pregnancy_category
- Not to be used during pregnancy
- Drug.routes_of_administration
- By mouth
- Drug.class
- 5α-Reductase inhibitor
- Drug.ATC_prefix
- G04
- Drug.ATC_suffix
- CB02
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.bioavailability
- 60%
via Wikipedia infobox
Chemical data
- Formula
- C27H30F6N2O2
- Molecular weight
- 528.5 g/mol
- IUPAC name
- (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CC[C@@H]5[C@@]3(C=CC(=O)N5)C
- InChIKey
- JWJOTENAMICLJG-QWBYCMEYSA-N
- XLogP
- 5.4
- Polar surface area
- 58.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 528.221
Show 6 more facts
- chemical formula
- C₂₇H₃₀F₆N₂O₂
- World Health Organisation international non-proprietary name
- dutasteride
- canonical SMILES
- CC12CCC3C(C1CCC2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CCC5C3(C=CC(=O)N5)C
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CC[C@@H]5[C@@]3(C=CC(=O)N5)C
- defined daily dose
- 0.5
- Commons category
- Dutasteride
via Wikidata · CC0
~15 min read
Article
20 sectionsContents
- Medical uses
- Benign prostatic hyperplasia and prostate cancer
- Scalp hair loss and excessive hair growth
- Transgender hormone therapy
- Available forms
- Contraindications
- Adverse effects
- Overdose
- Current investigations
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- References
- Further reading
Dutasteride, sold under the brand name Avodart among others, is a medication primarily used to treat the symptoms of a benign prostatic hyperplasia (BPH), an enlarged prostate not associated with cancer. A few months may be required before benefits occur. It is also used for scalp hair loss in men and as a part of hormone therapy in transgender women. It is usually taken by mouth.
The most commonly reported side effects of dutasteride, although rare, include sexual dysfunction. In the largest available study of 6,729 men with BPH, 9% experienced erectile dysfunction (compared to 5.7% treated with a placebo), 3.3% experienced decreased sex drive (vs 1.6% of placebo), and 1.9% had enlarged breasts (vs 1% of placebo). Exposure during pregnancy is specifically contraindicated because antiandrogens such as dutasteride have been shown to interfere with the sexual development of male fetuses.