Basic information
- CAS
55837-20-2- Standard SMILES
O=C(CC1NCCCC1O)Cn1cnc2cc(Br)c(Cl)cc2c1=O- InChIKey
LVASCWIMLIKXLA-UHFFFAOYSA-N- Molecular formula
- C16H17BrClN3O3
- Average molar mass
- 414.7 g/mol
- Monoisotopic mass
- 413.01418
Overview
7-Bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one is a member of quinazolines.
Names & identifiers
- Preferred name
- 7-Bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one
- IUPAC
- 7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]quinazolin-4-one
- English name
- Halofuginone
- Molecular formula
- C16H17BrClN3O3
- Molecular weight
- 414.68
Names & synonyms
Halofuginone [INN:BAN]C16H17BrClN3O37-Bromo-6-chloro-3-(3-(3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3H)-one7-bromo-6-chloro-3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one64544-01-0HT-100SCHEMBL1937106CHEMBL1197091SCHEMBL29351639GTPL10153TQP0820CHEBI:184758
Show more names
HALaPKC[l]trans-l)empostatinHALOFUGINONEHALOQUGINONE2HalofuginoneConstantinoneHalofuginone, >97%Halofuginone USP/EP/BP
LVASCWIMLIKXLA-UHFFFAOYSA-NHMS5086A09AKOS015962039FB29543SB19686AC-297497-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone, 9CI7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidyl)-acetonyl]-4(3H)-quinazolinone
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 82 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 533
Physicochemical properties
- Melting point
- 150 °C · >150°C dec.
- Boiling point
- 595.8 · 595.8±60.0 °C(Predicted)
- Density
- 1.73 · 1.73±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 9 mg/mL · DMSO : 9 mg/mL (21.70 mM)
- form
- Solid
- pka
- 14.61 · 14.61±0.40(Predicted)
- color
- White to off-white
- InChI
- InChI=1/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2/t14-,15+/s3
- InChIKey
- LVASCWIMLIKXLA-HRCJQKRTNA-N
- SMILES
- N1C2=C(C=C(Cl)C(Br)=C2)C(=O)N(CC(=O)C[C@@H]2[C@@H](O)CCCN2)C=1 |&1:16,17,r|
- CAS DataBase Reference
- 55837 · 55837-20-2(CAS DataBase Reference)
- FDA 21 CFR
- 556.308 · 556.308; 558.265
- FDA UNII
- 31 MM1385E · L31MM1385E
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionHalofuginone hydrobromide (Halofuginone) is a specific collagen Type I inhibitor that antagonize or inhibit the development of new blood vessels, hence can prevent intimal hyperplasia at a vascular anastomosis. It is used in the treatment or prevention of coccidiosis in both humans and animals.
UsesHalofuginone is a coccidiostat for young chickens and young turkeys. In higher doses, halofuginone is a growth depressant, impairs feed utilization, and reduces feed intake. In rats it causes alopecia. The compound is prohibited from use during the last four days before slaughter (withdrawal period).Halofuginone is extracted from enzyme-digested chicken liver as a free base into ethyl acetate and partitioned into ammonium acetate buffer solution. The halofuginone is concentrated with Sep-Pak C18 cartridges and eluted with methyl alcohol. The eluant is evaporated to dryness and the residue dissolved in the HPLC mobile phase. Analysis is achieved by HPLC using a BONDAPAK C18 column and a variable wavelength UV detector.
UsesHalofuginone is a halogenated derivative of Febrifugine (F228500). Halofuginone is used as an antiprotozoal.
UsesHalofuginone is a halogenated derivative of febrigugine. It is Used as an antiprotozoal.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
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Related reactions
1 records
Compound notes
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