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Tenofovir Alafenamide

Tenofovir Alafenamide Structure
Tenofovir Alafenamide structure
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
Molecular Weight:
476.47
MDL Number:
MFCD23843796
MOL File:
379270-37-8.mol
MSDS File:
SDS
Last updated:2023-09-04 16:42:00
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Tenofovir Alafenamide Properties

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|
FDA UNII EL9943AG5J
NCI Drug Dictionary tenofovir alafenamide
ATC code J05AF13

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Signal word  Danger
Hazard statements  H315-H318-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P321-P362+P364-P332+P313-P403+P233-P405-P501
NFPA 704
0
3 0

Tenofovir Alafenamide price More Price(40)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 26214 GS-7340 379270-37-8 5mg $81 2024-03-01 Buy
Cayman Chemical 26214 GS-7340 379270-37-8 100mg $790 2024-03-01 Buy
Cayman Chemical 26214 GS-7340 379270-37-8 10mg $143 2024-03-01 Buy
Cayman Chemical 26214 GS-7340 379270-37-8 50mg $515 2024-03-01 Buy
TRC T018555 TenofovirAlafenamide 379270-37-8 100mg $305 2021-12-16 Buy
Product number Packaging Price Buy
26214 5mg $81 Buy
26214 100mg $790 Buy
26214 10mg $143 Buy
26214 50mg $515 Buy
T018555 100mg $305 Buy

Tenofovir Alafenamide Chemical Properties,Uses,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.

Synthesis_379270-37-8

Tenofovir Alafenamide synthesis

39825-33-7
379270-35-6
379270-37-8
383365-04-6
Synthesis of Tenofovir Alafenamide from L-Alanine Isopropyl Ester Hydrochloride and phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

Tenofovir Alafenamide Preparation Products And Raw materials

Raw materials

L-Alanine Isopropyl Ester Hydrochloride Tenofovir Related Compound 6 phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

Preparation Products

Tenofovir Alafenamide Suppliers

Global( 356)Suppliers
Supplier Tel Email Country ProdList Advantage
Guangzhou Tosun Pharmaceutical Limited
+8618922120635 sales@toref-standards.com China 1000 58
Alpha Biopharmaceuticals Co., Ltd 		+86-411-39042497 +8613921981412 sales@alphabiopharm.com China 886 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Nanjing Gold Pharmaceutical Technology Co. Ltd. 		025-84209270 15906146951 CHINA 115 55
Beijing Cooperate Pharmaceutical Co.,Ltd 		010-60279497 sales01@cooperate-pharm.com CHINA 1811 55
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21691 55
Hangzhou FandaChem Co.,Ltd. 		008657128800458; +8615858145714 fandachem@gmail.com China 9348 55
Nanjing ChemLin Chemical Industry Co., Ltd. 		025-83697070 product@chemlin.com.cn CHINA 3012 60
Nanjing Finetech Chemical Co., Ltd. 		025-85710122 17714198479 sales@fine-chemtech.com CHINA 885 55
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 32480 60
Supplier Advantage
Guangzhou Tosun Pharmaceutical Limited
58
Alpha Biopharmaceuticals Co., Ltd 		58
Capot Chemical Co.,Ltd. 		60
Nanjing Gold Pharmaceutical Technology Co. Ltd. 		55
Beijing Cooperate Pharmaceutical Co.,Ltd 		55
Henan Tianfu Chemical Co.,Ltd. 		55
Hangzhou FandaChem Co.,Ltd. 		55
Nanjing ChemLin Chemical Industry Co., Ltd. 		60
Nanjing Finetech Chemical Co., Ltd. 		55
ATK CHEMICAL COMPANY LIMITED 		60

View Lastest Price from Tenofovir Alafenamide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tenofovir Impurity 51 pictures 2024-04-11 Tenofovir Impurity 51
379270-37-8
 US $0.00 / mg 1mg above 96% 50mg Guangzhou Tosun Pharmaceutical Limited
Tenofovir Alafenamide Base pictures 2023-12-01 Tenofovir Alafenamide Base
379270-37-8
 US $0.00-0.00 / kg 1kg ≥99% by HPLC 100Kg/,Month Zison Pharmaceutical (Shandong) Co., Ltd.
Tenofovir Alafenamide pictures 2023-11-27 Tenofovir Alafenamide
379270-37-8
 US $0.00 / g 10g 99% 50kg Wuhan Senwayer Century Chemical Co.,Ltd

Tenofovir Alafenamide Spectrum

Tenofovir Alafenamide(379270-37-8)1HNMR

379270-37-8(Tenofovir Alafenamide)Related Search:

Thionyl chloride D-Alanine Isopropyl Ester HCl 6N-HydroxyMethyl Tenofovir Disoproxil Tenofovir Related Compound 14 Tenofovir Alafenamide PMPA Impurity
Pimecrolimus 9-[(R)-2-(Phosphonomethoxy)propyl]adenine monohydrate Tenofovir disoproxil 9-Propenyladenine Tenofovir
DNA, SINGLE STRANDED, IMM. ON CELLULOSE, FROM CALF THYMUS* diisopropyl 2,2'-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoryl)bis(azanediyl))(2S,2'S)-dipropionate compound with methane (1:1) Tenofovir Related Compound 6 Tenofovir disoproxil fumarate phenyl hydrogen ((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate
Tenofovir alafenamide hemifumarate GS-7340 (fuMarate) Tenofovir Alafenamide Impurity 30

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Tenofovir Alafenamide fumarate, N-[[S(P)]-[2-(Adenin-9-yl)-1(R)-methylethoxymethyl](phenoxy)phosphoryl]-L-alanine isopropyl ester (S)-Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate GS-7340/GS7340 GS-7340 Tenofovir alafenamide tenofovir alafenamide GS-7340-03 L-Alanine, N-[(S)-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphinyl]-, 1-methylethyl ester (S)-Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl) (2S)-isopropyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate L- Alanine,N-[(S)-[[(1R)-2-(6- N-[[S(P)]-[2-(Adenin-9-yl)-1(R)-methylethoxymethyl](phenoxy)phosphoryl]-L-alanine isopropyl ester Tenofovir Alafenamide-d6 TENOFOVIR ALAFENAMIDE; GS7340; GS 7340 CS-1724 Tenofovir Alafenamide free base propan-2-yl (2S)-2-[[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-phenoxyphosphoryl]amino]propanoate N-[(S)-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy] methyl]phenoxyphosphinyl]-L-alanine 1-methylethyl GS7340; GS-7340; GS 7340; TAF; TENOFOVIR ALAFENAMIDE; GENVOYA. Tenofovir Impurity 51 Tenofovir alafenamide Intermediate 2 Tenofovir Alafenamide Impurity Tenofovir Alafenamide(TAF)(GS-7340) Tenofovir alafenamide fumarage Tenofovir Alafenamide (100mg/mL in Methanol) isopropyl ((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)-L-alaninate Tenofovir alafenamide semifumarate Tenofovir Alafenamide USP/EP/BP N-[(S)-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphinyl]-L-alanine 1-methylethyl ester N-[[S(P)]-[2-(Adenin-9-yl)-1(R)-methylethoxymethyl](phenoxy)... propan-2-yl (2S)-2-{[(S)-({[(2R)-1-(6-amino-9H-purin-9-yl)propa n-2-yl]oxy}methyl)(phenoxy)phosphoryl]amino}pr opanoate Tenofovir Alafenamide 25 mg tablets Tenofovir Alafenamide (GS-7340) GS-7340 Alafenamide Tenofovir Alafenamide Base phenyl hydrogen ((((S)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate (2R,3S)-2,3-bis(4-chlorophenyl)butane-2,3-diamine Tenofovir Alafenamide（TAF）(Fumarate)（GS-7340） Tenofovir and alafenamide Tenofovir Alafenamide N-2 379270-37-8 79270-37-8 392275-56-7 134678-17-7 1292275-56-7 C21H29N6O5P C25H33N6O9P Inhibitors Intermediate 379270-37-8