Azetirelin
- CAS No.
- 95729-65-0
- Chemical Name:
- Azetirelin
- Synonyms
- YM-14673;Azetirelin;Azetirelina;Azetirelinum;Azetirelin (~85%);Nα-[(S)-4-Oxo-2-azetidinyl]carbonyl-L-His-L-Pro-NH2;Nα-[[(S)-4-Oxo-2-azetidinyl]carbonyl]-L-His-L-Pro-NH2;L-Prolinamide, (2S)-4-oxo-2-azetidinecarbonyl-L-histidyl-;Nα-[((S)-4-oxo-2-azetidinyl)carbonyl]-L-histidyl-L-prolineamide;1-[Nα-[[(S)-4-Oxo-2-azetidinyl]carbonyl]-L-histidyl]-L-prolinamide
- CBNumber:
- CB41178074
- Molecular Formula:
- C15H20N6O4
- Molecular Weight:
- 348.36
- MDL Number:
- MFCD00867196
- MOL File:
- 95729-65-0.mol
| Melting point | >125°C (dec.) |
|---|---|
| Boiling point | 997.1±65.0 °C(Predicted) |
| Density | 1.469±0.06 g/cm3(Predicted) |
| storage temp. | -20°C Freezer, Under inert atmosphere |
| solubility | DMSO (Slightly), Methanol (Slightly), Water (Very Slightly, Heated) |
| form | Solid |
| pka | 13.98±0.40(Predicted) |
| color | Off-White |
| FDA UNII | 70J5AWG54Q |
Azetirelin Chemical Properties,Uses,Production
Originator
Azetirelin,ZYF Pharm Chemical
Uses
Azetirelin is a thyrotropin-releasing hormone (TRH) analogue. It demonstrated neuroprotective activity in rats.
Manufacturing Process
In 13 ml of DMF was dissolved 826.0 mg of L-histidyl-L-prolinamide 2-
hydrobromide and then 2 ml of a DMF solution of 405.0 mg of triethylamine
was added to the solution under ice-cooling. After maintaining 30 min under
ice-cooling, the precipitates thus formed were filtered off to provide L-histidyl-
L-prolinamide.
In 10 ml of DMF was dissolved 230.0 mg of (S)-2-azetidinone-4-carboxylic
acid and then 351.0 mg of N-hydroxy-1,2,3-benzotriazole and 453.0 mg of
dicyclohexylcarbodiimide were added to the solution under ice-cooling. Then,
after stirring the mixture for 15 min, the reaction was maintained for 15 min
at room temperature. The reaction mixture was ice-cooled again and 15 ml of
a DMF solution of foregoing L-histidyl-L-prolinamide was added to the reaction
mixture followed by reaction overnight at 0°C. The precipitates thus formed
were filtered off, the filtrate was concentrated to dryness, the residue was
dissolved in 10 ml of chloroform-methanol (4:1) and subjected to silica gel
column chromatography. The eluates by chloroform-methanol (7:3) were
collected and concentrated to dryness to provide 509.0 mg of crude product.
When the product was subjected to silica gel column chromatography again
and eluted by a mixture of chloroform, methanol, and aqueous ammonia
(40:10:1) to provide 394.0 mg of pure Nepsilon-[(S)-2-azetidinone-4-carbonyl]-
L-histidyl-L-prolinamide, melting point 183°-185°C (crystallization from a
small amount of methanol).
Therapeutic Function
TRH analogue
Azetirelin Preparation Products And Raw materials
Azetirelin Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| TargetMol Chemicals Inc. | +1-781-999-5354 | support@targetmol.com | United States | 19973 | 58 |
| Nanjing Xinmeihe Pharmaceutical Co., Ltd. | 025-57672321 13739186949 | 2548785915@qq.com | China | 230 | 58 |
| TargetMol Chemicals Inc. | 4008200310 | marketing@tsbiochem.com | China | 24018 | 58 |
| Supplier | Advantage |
|---|---|
| TargetMol Chemicals Inc. | 58 |
| Nanjing Xinmeihe Pharmaceutical Co., Ltd. | 58 |
| TargetMol Chemicals Inc. | 58 |