Tenofovir Alafenamide
Description- Product Name
- Tenofovir Alafenamide
- CAS No.
- 379270-37-8
- Chemical Name
- Tenofovir Alafenamide
- Synonyms
- GS-7340;Alafenamide;phenyl hydrogen ((((S)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate;Tenofovir Alafenamide Base;Tenofovir Alafenamide (GS-7340);(2R,3S)-2,3-bis(4-chlorophenyl)butane-2,3-diamine;CS-1724;GS-7340-03;GS-7340/GS7340;tenofovir alafenamide
- CBNumber
- CB92627921
- Molecular Formula
- C21H29N6O5P
- Formula Weight
- 476.47
- MOL File
- 379270-37-8.mol
Tenofovir Alafenamide Property
- Melting point:
- >119°C (dec.)
- Boiling point:
- 640.4±65.0 °C(Predicted)
- Density
- 1.39±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C(protect from light)
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 4.21±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability:
- Hygroscopic
- InChIKey
- LDEKQSIMHVQZJK-QTJFZWIYNA-N
- SMILES
- C(OC(C)C)(=O)[C@H](C)NP(CO[C@H](C)CN1C2=C(N=C1)C(N)=NC=N2)(OC1=CC=CC=C1)=O |&1:6,12,r|
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H315Causes skin irritation
H318Causes serious eye damage
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P310Immediately call a POISON CENTER or doctor/physician.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 26214
- Product name
- GS-7340
- Packaging
- 5mg
- Price
- $81
- Updated
- 2024/03/01
- Product number
- 26214
- Product name
- GS-7340
- Packaging
- 100mg
- Price
- $790
- Updated
- 2024/03/01
- Product number
- 26214
- Product name
- GS-7340
- Packaging
- 10mg
- Price
- $143
- Updated
- 2024/03/01
- Product number
- 26214
- Product name
- GS-7340
- Packaging
- 50mg
- Price
- $515
- Updated
- 2024/03/01
- Product number
- T018555
- Product name
- TenofovirAlafenamide
- Packaging
- 100mg
- Price
- $305
- Updated
- 2021/12/16
Tenofovir Alafenamide Chemical Properties,Usage,Production
Description
Tenofovir Alafenamide (GS-7340) is a prodrug of tenofovir, which is a reverse transcriptase inhibitor, used to treat HIV and Hepatitis B.-Reverse Transcriptase inhibitor. It was developed by Gilead Sciences. Compared to tenofovir disoproxil fumarate, tenofovir alafenamide has a greater antiviral activity and better distribution into lymphoid tissues.
Description
Tenofovir alafenamide fumarate is an oral phosphonoamidate prodrug of the reverse transcriptase inhibitor tenofovir. It was approved by the USFDA for the treatment of chronic hepatitis B virus infection with compensated liver disease. Tenofovir alafenamide fumarate was discovered and developed by Gilead as a potentially safer form of the previously approved tenofovir disoproxil fumarate (Viread).
Uses
Tenofovir Alafenamide, also known as Tenofovir Impurity 51, is a prodrug of Tenofovir (T018500), which is a reverse transcriptase inhibitor used to treat HIV and Hepatitis B.
Definition
ChEBI: An L-alanine derivative that is isopropyl L-alaninate in which one of the amino hydrogens is replaced by an (S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)( henoxy)phosphoryl group. A prodrug for tenofovir, it is used (as the fumarate salt) in combination therapy for the treatment of HIV-1 infection.
Synthesis
A multikilogram synthesis of tenofovir alafenamide fumarate was described in a Gilead patent. Additional process improvements on specific steps of the Gilead process have been reported on 100 g scale, and these will be noted throughout the description of the synthesis. The synthesis was initiated with the alkylation of adenine (72) with (R)-propylene carbonate (73) to give hydroxypropyl adenine 74 in 75% yield. It should be noted that sodium hydroxide can be replaced by potassium bases with increased yields on 100 g scale.27 Alkylation of 74 with diethyl p-toluenesulfonyloxymethylphosphonate (75) gave intermediate 76, which was not isolated. Hydrolysis of the phosphonate esters with trimethylsilyl bromide followed by recrystallization from water gave phosphonic acid 77 in 50% yield. Interestingly, replacing Mg(Ot-Bu)2 with PhMgCl/t-BuOH led to improved yields for the alkylation step (74 ?ú 76) on a 100 g scale. Additionally, the authors note that conditions for hydrolyzing the phosphonate ester can be modified using HCl or HBr for improved yields on smaller scale. Dicyclohexylcarbodiimide (DCC) coupling of 77 with phenol produced phosphonate 78 in 51% yield. This step was also reported to proceed in higher yield on smaller scale by changing the solvent to cyclopentylmethyl ether. Monophosphonate ester 78 was treated with thionyl chloride followed by L-alanine isopropyl ester (79) and triethylamine to give tenofovir alafenamide rac-80 as a mixture of phosphonate diastereomers in 47% yield. The diastereomers were separated using simulated moving bed chromatography to give the desired diastereomer ent-80 in 47% yield and 99% diastereomeric purity. The diastereomers could also be separated using a crystallization-induced dynamic resolution of rac-80. Tenofovir alafenamide fumarate (VI) was prepared from ent-80 and fumaric acid in 83% yield.
Tenofovir Alafenamide Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Tenofovir Alafenamide manufacturers
- Product
- Tenofovir Impurity 51 379270-37-8
- Price
- US $0.00/mg
- Min. Order
- 1mg
- Purity
- above 96%
- Supply Ability
- 50mg
- Release date
- 2023-05-29
- Product
- Tenofovir Alafenamide Base 379270-37-8
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- ≥99% by HPLC
- Supply Ability
- 100Kg/,Month
- Release date
- 2023-01-05
- Product
- Tenofovir Alafenamide 379270-37-8
- Price
- US $0.00/g
- Min. Order
- 10g
- Purity
- 99%
- Supply Ability
- 50kg
- Release date
- 2023-02-08