4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine

Product Name: 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine
CAS No.: 1011529-10-4
Chemical Name: 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine
Synonyms: Azvudine;FNC;RO 0622;Azvudine (RO 0622);Azvudine, 10 mM in DMSO;Eravacycline Impurity 9;4'-Azido-2'-deoxy-2'-fluoroaracytidine;4′-azido-2′-deoxy-2′-fluoro-β-D-arabinocytidine;4’-Azido-2’-deoxy-2’-fluoroaracytidine, Azvudine;4'-C-Azido-2'-deoxy-2'-fluoro-β-D-arabinocytidine
CBNumber: CB02641492
Molecular Formula: C9H11FN6O4
Formula Weight: 286.2198432
MOL File: 1011529-10-4.mol

More

Less

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine Property

Melting point:: 99.0-100.0℃
storage temp.: Store at -20°C
solubility: DMSO: 57 mg/mL (199.15 mM);Ethanol: 57 mg/mL (199.15 mM)
form: Solid
color: White to off-white
Water Solubility: Water: 57 mg/mL (199.15 mM)
InChI: InChI=1/C9H11FN6O4/c10-5-6(18)9(3-17,14-15-12)20-7(5)16-2-1-4(11)13-8(16)19/h1-2,5-7,17-18H,3H2,(H2,11,13,19)/t5-,6-,7+,9+/s3
InChIKey: KTOLOIKYVCHRJW-BODDTQOYNA-N
SMILES: C1(=O)N([C@H]2[C@@H](F)[C@H](O)[C@@](N=[N+]=[N-])(CO)O2)C=CC(N)=N1 |&1:3,4,6,8,r|

More

Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H228Flammable solid

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

More

Less

N-Bromosuccinimide Price

Biosynth Carbosynth

Product number: NA32212
Product name: 4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
Packaging: 250ug
Price: $75
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NA32212
Product name: 4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
Packaging: 500ug
Price: $125
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NA32212
Product name: 4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
Packaging: 1mg
Price: $225
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NA32212
Product name: 4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
Packaging: 2mg
Price: $350
Updated: 2021/12/16

AK Scientific

Product number: 0448EP
Product name: 4-Amino-1-[(5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Packaging: 2mg
Price: $522
Updated: 2021/12/16

More

Less

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine Chemical Properties,Usage,Production

Description

Azvudine is an antiviral drug produced by Genuine Biotech and was approved in China in 2021 as a first-in-class drug for the treatment of human immunodeficiency virus (HIV).

Uses

Azvudine (RO-0622) is a potent nucleoside reverse transcriptase inhibitor (NRTI), with antiviral activity on HIV, HBV and HCV. Azvudine exerts highly potent inhibition on HIV-1 (EC50s ranging from 0.03 to 6.92 nM) and HIV-2 (EC50s ranging from 0.018 to 0.025 nM). Azvudine inhibits NRTI-resistant viral strains[1]. Azvudine is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.

Application

Azvudine has also been repurposed as a treatment for COVID-19 and was approved in China in 2022 as an RNA-dependent RNA polymerase (RdRp) inhibitor, sharing the same mechanism as the previously approved molnupiravir and remdesivir. In addition to its antiviral activity, the drug's concentration in the thymus suggests that it may also have immune-targeting activity, which is unique among RdRp inhibitors.

Mechanism of action

Azvudine has a dual mechanism of action: it acts as a reverse transcriptase inhibitor and targets the viral factor/apolipoprotein B mRNA editing enzyme, catalytic subunit 3G (Vif/A3G) protein-protein interaction. Due to substitutions at its 3′-hydroxyl and 4′-ribose core, azithromycin is active against both wild-type and resistant strains of HIV.

Synthesis

The synthesis is carried out starting from benzoyl protected fluorofuranose 1.1. Bromination with HBr in acetic acid followed by displacement of bromide 1.2 with protected cytosine 1.3 gives intermediate 1.4. Deprotection of the benzoyl group with ammonia in methanol gives diol 1.5, which is then converted to the alkyl iodide 1.6 via a Mitsunobu reaction. Elimination of iodine with sodium methoxide followed by addition of sodium azide and iodine chloride to the resulting olefin gives azide 1.7. Both the alcohol and amine are reprotected with benzoyl chloride, and the iodine is displaced by m-chlorobenzoic acid in an oxidative nucleophilic substitution reaction to give the penultimate intermediate 1.9. All protecting groups are then removed in methanol-ammonia to give azithromycin (1).

IC 50

HIV-1: 0.03-6.92 nM (EC₅₀); HIV-2: 0.018-0.02 nM (EC₅₀)

References

[1] Wang RR, et al. Azvudine, a novel nucleoside reverse transcriptase inhibitor showed good drug combination features and better inhibition on drug-resistant strains than lamivudine in vitro. PLoS One. 2014 Aug 21;9(8):e105617. DOI:10.1371/journal.pone.0105617

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine Preparation Products And Raw materials

Raw materials

Preparation Products

More

Less

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine Suppliers

China 77 United States 7 Global 84

TargetMol Chemicals Inc.

Tel: 4008200310
Email: marketing@tsbiochem.com
Country: China
ProdList: 24960
Advantage: 58

Hangzhou FuRun Pharmaceutical Technology Co., Ltd

Tel: 15658004993
Email: 1900830611@qq.com
Country: China
ProdList: 980
Advantage: 58

NewCan Biotech Limited

Tel: +86-0571-86912261 +86-15658003402
Fax: 311113
Email: sales@newcanbio.com
Country: China
ProdList: 1616
Advantage: 58

Adamas Reagent, Ltd.

Tel: 400-6009262 15618770481
Fax: 021-64823266
Email: yhx@titansci.com
Country: China
ProdList: 14101
Advantage: 59

T&W GROUP

Tel: 021-61551611 13296011611
Fax: ＋86 21-50676805
Email: contact@trustwe.com
Country: China
ProdList: 9895
Advantage: 58

Hangzhou Sage Chemical Co., Ltd.

Tel: +86057186818502 13588463833
Fax: Pls mail us for more information!
Email: info@sagechem.com
Country: China
ProdList: 10266
Advantage: 58

Nanjing Baifuli Technology Co., Ltd.

Tel: 25-25-58740604 15951658055
Fax: +86-25-58356858
Email: sales@unisyn.cn
Country: China
ProdList: 606
Advantage: 58

Nanjing Sunlida Biological Technology Co., Ltd.

Tel: 025-57798810 18652991625;
Fax: 025-57019371
Email: sales@sunlidabio.com
Country: China
ProdList: 3239
Advantage: 55

NINGBO INNO PHARMCHEM CO.,LTD.

Tel: 86-574-27787657
Fax: 86-574-27912196
Email: info@dearchem.com
Country: China
ProdList: 4613
Advantage: 58

Shanghai Lollane Biological Technology Co.,Ltd.

Tel: 021-52996696，15000506266 15000506266
Fax: +86-21-52996696
Country: China
ProdList: 4827
Advantage: 55

More

Less

View Lastest Price from 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: Eravacycline Impurity 9
Price: US $0.00/mg
Min. Order: 10mg
Purity: 0.98
Supply Ability: 5g
Release date: 2025-03-21

Hangzhou ICH Biofarm Co., Ltd

Product: 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine 1011529-10-4
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 98% HPLC
Supply Ability: 100kg
Release date: 2023-07-05

Hangzhou ICH Biofarm Co., Ltd

Product: 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine 1011529-10-4
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 98% HPLC
Supply Ability: 100kg
Release date: 2023-07-05

1011529-10-4, 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidineRelated Search:

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine

2(1H)-PyriMidinone, 4-aMino-1-(4-C-azido-2-deoxy-2-fluoro-b-D-arabinofuranosyl)-

4-Amino-1-(4-C-azido-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-2(1H)-pyrimidinone

RO 0622

4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine

4'-Azido-2'-deoxy-2'-fluoroaracytidine

Azvudine (RO 0622)

4’-Azido-2’-deoxy-2’-fluoroaracytidine, Azvudine

4′-azido-2′-deoxy-2′-fluoro-β-D-arabinocytidine

resistant,Human immunodeficiency virus,NRTI,Azvudine,RO 0622,inhibit,mutation,Inhibitor,Reverse Transcriptase,HCV,Hepatitis C virus,Hepatitis B virus,HIV,analogue,HBV,RO0622

4'-C-Azido-2'-deoxy-2'-fluoro-β-D-arabinocytidine

Eravacycline Impurity 9

4-Amino-1-((2R,3S,4R,5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

Azvudine, 10 mM in DMSO

Azvudine

FNC

1011529-10-4

C9H11FN6O4

1011529-10-4