1-[(2R,4R,5S)-4-Azido-5-(hydroxymethyl)oxolan-2-YL]-5-methyl-pyrimidine-2,4-dione

HCID 5726

Basic information

CAS
30516-87-1
Standard SMILES
Cc1cn(C2CC(N=[N+]=[N-])C(CO)O2)c(=O)[nH]c1=O
InChIKey
HBOMLICNUCNMMY-UHFFFAOYSA-N
Molecular formula
C10H13N5O4
Average molar mass
267.24 g/mol

Overview

See also: Zidovudine (annotation moved to).

Names & identifiers

Preferred name
1-[(2R,4R,5S)-4-Azido-5-(hydroxymethyl)oxolan-2-YL]-5-methyl-pyrimidine-2,4-dione
IUPAC
1-[4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
English name
Zidovudine
Molecular formula
C10H13N5O5
Molecular weight
283.24

Names & synonyms

Azidothymidine (AZT)S25791-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione1-[4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione1-[(2R,4R,5S)-4-AZIDO-5-(HYDROXYMETHYL)OXOLAN-2-YL]-5-METHYL-PYRIMIDINE-2,4-DIONE399024-19-2AzitidinTimazidZidovudine, AZTRecemic Zidovudine1-(4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dioneThymidine, 8CI,
Show more names
AZTAZIDOTHYMIDINE1-((2R,4S,5S)-4-azido-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-5-MethylpyriMidine-2,4(1H,3H)-dioneretrovirZDVAzitidineAZT (pharmaceutical)ZVDfuseng
Trizivir (Salt/Mix)3-Azido-3-deoxythymidineSCHEMBL13609910component of Combivir (Salt/Mix)HBOMLICNUCNMMY-UHFFFAOYSA-NHMS3369K15HMS3656A20HMS5081B07

Database identifiers

CAS
30516-87-1
PubChem CID
5726

Properties

Computed structural properties

XLogP
0
Topological polar surface area
93.2 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
19

Experimental & physicochemical properties

DrugsPharmaceuticals

Physicochemical properties

Melting point
113 · 113-115 °C (lit.)
Boiling point
410.43 °C · 410.43°C (rough estimate)
alpha
25 · D25 +99° (c = 0.5 in water)
Density
1.3382 · 1.3382 (rough estimate)
refractive index
47 ° · 47 ° (C=1, H2O)
Flash point
9 ℃ · 9℃

Safety & regulation

Safety data

F
10
PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
XP2072000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
29349990

Chemistry & industry

Applications · 6 items

DescriptionZidovudine, also known as azidothymidine (AZT), is an antiviral agent acting via reverse transcnptase inhibition. It was first launched in the U.K. and subsequently introduced in over a dozen countries for the management of severe manifestations of HIV infection. In patients with AIDS and ARC, zidovudine reduces the risk of opportunistic infections and prolongs survival time. In symptom-free patients it shows promise in halting further immunological deterioration.

UsesA potent and selective inhibitor of HIV-1 replication

UsesZidovudine is an antiretroviral drug that is clinically active against HIV-1 and is intended to treat HIV-infected patients. Zidovudine is an analog of thymidine that inhibits replication of the AIDS virus. It also turned into mono-, di-, and triphosphates by the same cellular enzymes that catalyze phosphorylation of thymidine and thymidine nucleosides. Zidovudine-triphosphate is then included in the terminal fragment of the growing chain of viral DNA by viral reverse transcriptase, thus causing the viral DNA chain to break apart in cells infected with the virus. Zidovudine has been authorized for treating patients with AIDS. It significantly prolongs the life of the patient, although it has a number of toxic effects. Synonyms of this drug are azidothymidine and retrovir.

General DescriptionSlightly off-white odorless powdery solid.

General DescriptionZidovudine, 3'-azido-3'-deoxythymidine or AZT, is ananalog of thymidine that possesses antiviral activityagainst HIV-1, HIV-2, HTLV-1, and several other retroviruses.This nucleoside was synthesized in 1978 by Linand Prusoff as an intermediate in the preparation ofamino acid analogs of thymidine. A screening program directedtoward the identification of agents potentially effectivefor the treatment of patients with AIDS led to the discoveryof its unique antiviral properties 7 years later.Zidovudine is recommended for the management of adultpatients with symptomatic HIV infection (AIDS or ARC)who have a history of confirmed Pneumocystis carinii pneumoniaor an absolute CD4+(T4 or TH cell) lymphocytecount below 200/mm3 before therapy. The hematologicaltoxicity of the drug precludes its use in asymptomatic patients.Anemia and granulocytopenia are the most commontoxic effects associated with AZT.

General DescriptionZidovudine, or 3u-azido-3udeoxythymidine, formerly known as azidothymidine (AZT; BW A509U), is an analog of the nucleoside thymidine. It is an inhibitor of the human immunodeficiency virus (HIV)-encoded enzyme reverse transcriptase. It was the first antiretroviral compound to be licenced for the treatment of people infected with HIV. The compound was synthesized much earlier, however, by Horwitz and colleagues and subsequently used in anticancer research. Zidovudine was developed by Burroughs Wellcome and is now marketed by GlaxoSmithKline under the trade name of Retrovir. Zidovudine is also available in fixed-dose cominations with other nucleoside analog reverse transcriptase inhibitors as Combivir (zidovudine with lamivudine) and Trizivir (zidovudine with lamivudine and abacavir). Generic forms of the drug have been produced by a number of companies and include AVIRO-Z (Ranbaxy Laboratories Ltd) and Zidovir (Cipla Ltd). There are also a number of generic fixed-dose products including zidovudine with lamivudine (e.g. Duovir; Cipla Ltd). Zidovudine is indicated for the treatment and prevention of HIV infection, generally given in combination with other antiretroviral agents.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Zidovudine is a pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase. It has a role as an antimetabolite, an antiviral drug and a HIV-1 reverse transcriptase inhibitor. It is an azide and a pyrimidine 2',3'-dideoxyribonucleoside.

Related reactions

13 records

Compound notes

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