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

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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|

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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..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 26214
Product name: GS-7340
Packaging: 5mg
Price: $81
Updated: 2024/03/01

Cayman Chemical

Product number: 26214
Product name: GS-7340
Packaging: 100mg
Price: $790
Updated: 2024/03/01

Cayman Chemical

Product number: 26214
Product name: GS-7340
Packaging: 10mg
Price: $143
Updated: 2024/03/01

Cayman Chemical

Product number: 26214
Product name: GS-7340
Packaging: 50mg
Price: $515
Updated: 2024/03/01

TRC

Product number: T018555
Product name: TenofovirAlafenamide
Packaging: 100mg
Price: $305
Updated: 2021/12/16

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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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Tenofovir Alafenamide Suppliers

China 323 India 22 United Kingdom 1 United States 16 Global 362

BOC Sciences

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Target molecule Corp.

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TargetMol Chemicals Inc.

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InvivoChem

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Cckinase, Inc.

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BOC Sciences

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Cato Research Chemicals Inc.

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Cayman Chemical Company

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MYLAN LABORATORIES LTD

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Matrix Scientific

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View Lastest Price from Tenofovir Alafenamide manufacturers

Baoji Guokang Bio-Technology Co., Ltd.

Product: Tenofovir Alafenamide 379270-37-8
Price: US $2210.00/g/Bag
Min. Order: 500g
Purity: 98
Supply Ability: 10kg
Release date: 2021-06-04

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.

Product: Tenofovir Alafenamide 379270-37-8
Price: US $0.00/g
Min. Order: 1g
Purity: More Than 99%
Supply Ability: 100kg/Month
Release date: 2024-09-04

Cangzhou Kangrui Pharma Tech Co. Ltd.,

Product: Tenofovir alafenamide 379270-37-8
Price: US $0.00-0.00/g
Min. Order: 100g
Purity: 99%
Supply Ability: 100kgs
Release date: 2024-11-04

379270-37-8, Tenofovir AlafenamideRelated 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

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

Tenofovir Alafenamide (GS-7340)

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

(2R,3S)-2,3-bis(4-chlorophenyl)butane-2,3-diamine

(S)-Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)

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

Alafenamide

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

Tenofovir Alafenamide Base

GS7340; GS-7340; GS 7340; TAF; TENOFOVIR ALAFENAMIDE; GENVOYA.

(2S)-isopropyl 2-((((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate

phenyl hydrogen ((((S)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate

GS-7340

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（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