A2169

3′-Azido-3′-deoxythymidine

Name: 3′-Azido-3′-deoxythymidine
Brand: SIGMA

≥98% (HPLC), powder, reverse transcriptase inhibitor

Synonym(s):

AZT, Azidothymidine, ZDV, Zidovudine

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All Photos(4)

About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₃N₅O₄

CAS Number:

30516-87-1

Molecular Weight:

267.24

NACRES:

NA.77

PubChem Substance ID:

24278143

UNSPSC Code:

12352200

MDL number:

MFCD00006536

Beilstein/REAXYS Number:

3595791

Product Name

3′-Azido-3′-deoxythymidine, ≥98% (HPLC)

InChI

1S/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1

SMILES string

CC1=CN([C@H]2C[C@H](N=[N+]=[N-])[C@@H](CO)O2)C(=O)NC1=O

InChI key

HBOMLICNUCNMMY-XLPZGREQSA-N

assay

≥98% (HPLC)

form

powder

mp

113-115 °C (lit.)

solubility

H₂O: 50 mg/mL

storage temp.

−20°C

Quality Level

200

Gene Information

human ... HIVE1(3095)
mouse ... Slc29a1(63959)

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

Application

3′-Azido-3′-deoxythymidine has been used as the reverse transcriptase inhibitor to inhibit the viral genome integration and as an antimicrobial agent to evaluate its anti-Salmonella activity.

Biochem/physiol Actions

Azidothymidine (AZT), a thymidine analogue, is a reverse transcriptase inhibitor against the HIV-1 virus. Azidothymidine has been shown to decrease CRISPR-mediated homology-directed repair (HDR) efficiency.

Reverse transcriptase inhibitor active against HIV-1 virus.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

GHS08

signalword

Warning

hcodes

H341,H351

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Carc. 2 - Muta. 2

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Protein overexpression following lentiviral infection of primary mature neutrophils is due to pseudotransduction

Geering B, et al.

Journal of Immunological Methods, 373(1-2), 209-218 (2011)

Primary role of type I interferons for the induction of functionally optimal antigen-specific CD8+ T cells in HIV infection.

Cabral-Piccin, et al.

EBioMedicine, 91, 104557-104557 (2023)

Plant thymidine kinase 1: a novel efficient suicide gene for malignant glioma therapy.

Zahidul Khan et al.

Neuro-oncology, 12(6), 549-558 (2010-02-16)

The prognosis for malignant gliomas remains poor, and new treatments are urgently needed. Targeted suicide gene therapy exploits the enzymatic conversion of a prodrug, such as a nucleoside analog, into a cytotoxic compound. Although this therapeutic strategy has been considered

In vitro activities of nucleoside analog antiviral agents against salmonellae.

Sperber S J, et al.

Antimicrobial Agents and Chemotherapy, 37(1), 106-110 (1993)

Maximizing the ovarian reserve in mice by evading LINE-1 genotoxicity.

Marla E Tharp et al.

Nature communications, 11(1), 330-330 (2020-01-18)

Female reproductive success critically depends on the size and quality of a finite ovarian reserve. Paradoxically, mammals eliminate up to 80% of the initial oocyte pool through the enigmatic process of fetal oocyte attrition (FOA). Here, we interrogate the striking

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Modulation of homology-directed repair (HDR) within the context of CRISPR-genome editing has led to the identification of small molecules that enhance CRISPR-mediated HDR efficiency in various cell types.

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