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A2169

Sigma-Aldrich

3′-Azido-3′-deoxythymidine

≥98% (HPLC)

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Synonym(s):
AZT, Azidothymidine, ZDV, Zidovudine
Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
30516-87-1
Molecular Weight:
267.24
Beilstein:
3595791
MDL number:
MFCD00006536
UNSPSC Code:
12352200
PubChem Substance ID:
24278143
NACRES:
NA.77

Quality Level

200

Assay

≥98% (HPLC)

form

powder

mp

113-115 °C (lit.)

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

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

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

InChI key

HBOMLICNUCNMMY-XLPZGREQSA-N

Gene Information

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

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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

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H341,H351

Hazard Classifications

Carc. 2 - Muta. 2

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
In vitro activities of nucleoside analog antiviral agents against salmonellae.
Sperber S J, et al.
Antimicrobial Agents and Chemotherapy, 37(1), 106-110 (1993)
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)
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
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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