Basic information
- CAS
52806-53-8- Standard SMILES
CC(C)(O)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1- InChIKey
YPQLFJODEKMJEF-UHFFFAOYSA-N- Molecular formula
- C11H11F3N2O4
- Average molar mass
- 292.21 g/mol
- Monoisotopic mass
- 292.06709132
Overview
2-hydroxyflutamide is a metabolite of flutamide. Flutamide is an oral nonsteroidal antiandrogen drug primarily used to treat prostate cancer. It competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. By doing so, it prevents them from stimulating the prostate cancer cells to grow. Flutamide has been largely replaced by a newer member of this class, bicalutamide, due to a better side-effect profile. (Wikipedia)
Names & identifiers
- Preferred name
- Hydroxyflutamide
- IUPAC
- 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
- English name
- Hydroxyflutamide
- Molecular formula
- C11H11F3N2O4
- Molecular weight
- 292.21
Names & synonyms
Show more names
Database identifiers
- CAS
52806-53-8- PubChem CID
- 91649
- DTXSID
DTXSID8033562- ChEMBL
CHEMBL491- UNII
- 31D90UKP5Y
- EC Number
- 641-868-6
- Nikkaji
- J275.223I
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 95.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 392
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 125 · 125-130°C
- Boiling point
- 443.8 · 443.8±45.0 °C(Predicted)
- Density
- 1.472 · 1.472
- storage temp.
- room temp
- solubility
- 10 mg/mL · DMSO: >10mg/mL
- pka
- 12.87 · 12.87±0.70(Predicted)
- form
- powder
- color
- white to tan
- InChI
- 1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)
- InChIKey
- YPQLFJODEKMJEF-UHFFFAOYSA-N
- SMILES
- CC(C)(O)C(=O)Nc1ccc(c(c1)C(F)(F)F)[N+]([O-])=O
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 31 D90UKP5Y · 31D90UKP5Y
- UNSPSC Code
- 51111800 · 51111800
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36/37/39
- WGK Germany
- 3 · 3
- RTECS
- 1466250 · TX1466250
- HS Code
- 2924297099 · 2924297099
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (55.7%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 88 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Toxicology
Toxicity Summary
Hydroxyflutamide is an antiandrogen. Antiandrogens alter the androgen pathway by blocking the appropriate receptors, competing for binding sites on the cell's surface, or affecting androgen production. Antiandrogens are classified as steroidal or nonsteroidal. Steroidal antiandrogens not only counter androgens, but also affect secondary sex characteristics. Steroidal antiandrogens directly affect gene expression due to their fat-soluble nature that allows them to diffuse through the plasma membrane's phospholipid bilayer and prevent the binding of testosterone and dihydrotestosterone (DHT) to the androgen receptor. Inhibition of androgen production occurs through a unique mechanism for each antiandrogen. (Wikipedia)
Safety data
- wgk
- 3
- rtecs
- TX1466250
- hs_code
- 2924297099
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37/39
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
Uses & manufacturing
Applications
Description2-hydroxy Flutamide is the major metabolite formed during the metabolism of the non-steroidal antiandrogen flutamide by cytochrome P450 (CYP) isoforms CYP1A2 and CYP3A4. Through competitive inhibition of the binding of testosterone to the nuclear androgen receptor (AR; IC50 = ~300-900), 2-hydroxy flutamide blocks the expression of AR target genes and prevents androgen-dependent stabilization of the AR. Compared to flutamide, 2-hydroxy flutamide is a more potent antiandrogen in vivo, demonstrating a higher binding affinity for the AR (0.1% binding affinity relative to dihydrotestosterone) and, thus, is the predominant contributor to the therapeutic effects of flutamide in the treatment of prostate cancer.
UsesHYDROXYFLUTAMIDE is used non-steroidal antagonist Flutamide. Shown to be an antianhydrogen.
UsesThe active metabolite of the widely used non-steroidal antagonist Flutamide (F598850). Shown to be an antianhydrogen.
UsesShown to be an antianhydrogen. The active metabolite of the widely used non-steroidal antagonist flutamide
Upstream & downstream products
Upstream raw materials
Suppliers85 total
Related reactions
No reaction records under the current filter.
Compound notes
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