Structure via PubChem · Public domain (PubChem)
enzalutamide
Sign in to saveAlso known as MDV-3100, MDV3100, MDV 3100
Enzalutamide, sold under the brand name Xtandi, is a nonsteroidal antiandrogen (NSAA) medication which is used in the treatment of prostate cancer. It is indicated for use in conjunction with castration in the treatment of metastatic castration-resistant prostate cancer (mCRPC), nonmetastatic castration-resistant prostate cancer, and metastatic castration-sensitive prostate cancer (mCSPC). It is taken by mouth.
Key facts
- Drug.image
- Enzalutamide-01.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.width2
- 250
- Drug.tradename
- Xtandi
- Drug.MedlinePlus
- a612033
- Drug.DailyMedID
- Enzalutamide
- Drug.pregnancy_AU
- X
- Drug.routes_of_administration
- By mouth
- Drug.class
- Nonsteroidal antiandrogen
- Drug.ATC_prefix
- L02
- Drug.ATC_suffix
- BB04
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.bioavailability
- Rats: 89.7%Humans: unknown (but at least 84.6% based on recovery from excretion)
- Drug.protein_bound
- Enzalutamide: 97–98% (primarily to albumin): 95%
via Wikipedia infobox
Chemical data
- Formula
- C21H16F4N4O2S
- Molecular weight
- 464.4 g/mol
- IUPAC name
- 4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-fluoro-N-methylbenzamide
- SMILES
- CC1(C(=O)N(C(=S)N1C2=CC(=C(C=C2)C(=O)NC)F)C3=CC(=C(C=C3)C#N)C(F)(F)F)C
- InChIKey
- WXCXUHSOUPDCQV-UHFFFAOYSA-N
- XLogP
- 3.6
- Polar surface area
- 109 Ų
- H-bond donors
- 1
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2012
- Admin. routes
- oral
- Indications
- prostate adenocarcinoma, prostate carcinoma, metastatic prostate cancer, neoplasm
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 464.09301
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₁H₁₆F₄N₄O₂S
- World Health Organisation international non-proprietary name
- enzalutamide
- canonical SMILES
- CC1(C(=O)N(C(=S)N1C2=CC(=C(C=C2)C(=O)NC)F)C3=CC(=C(C=C3)C#N)C(F)(F)F)C
- defined daily dose
- 0.16
- Commons category
- Enzalutamide
- physically interacts with
- androgen receptor
- significant drug interaction
- gemfibrozil
Sources (6)
via Wikidata · CC0
~16 min read
Encyclopedic overview
27 sectionsContents
- Medical uses
- Prostate cancer
- Other uses
- Available forms
- Contraindications
- Side effects
- Central adverse effects
- Rare adverse reactions
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Changes in hormone levels
- Comparison with other antiandrogens
- Resistance mechanisms in prostate cancer
- Cytochrome P450 modulation
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Legal status
- Economics
- Research
- Breast cancer
- Hirsutism
- See also
- References
{{Infobox drug | image = Enzalutamide-01.svg | image_class = skin-invert-image | width = 250 | alt = | width2 = 250 | alt2 =
| pronounce = | tradename = Xtandi | Drugs.com = | MedlinePlus = a612033 | DailyMedID = Enzalutamide | pregnancy_AU = X | pregnancy_AU_comment = | routes_of_administration = By mouth | class = Nonsteroidal antiandrogen | ATC_prefix = L02 | ATC_suffix = BB04 | ATC_supplemental =
Excerpted from Wikipedia’s “enzalutamide” article, available under the CC BY-SA 4.0 licence.