A2169

Sigma-Aldrich

3′-Azido-3′-deoxythymidine

≥98% (HPLC)

Synonym(s):
AZT, Zidovudine, Azidothymidine, ZDV
Empirical Formula (Hill Notation):
C10H13N5O4
CAS Number:
Molecular Weight:
267.24
Beilstein/REAXYS Number:
3595791
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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.

Packaging

1 g in glass bottle
25 mg in glass insert
100, 250 mg in glass bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
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.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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...
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...
Aoife G Cotter et al.
The Journal of clinical endocrinology and metabolism, 98(4), 1659-1666 (2013-02-26)
In virologically suppressed, antiretroviral-treated patients, the effect of switching to tenofovir (TDF) on bone biomarkers compared to patients remaining on stable antiretroviral therapy is unknown. We examined bone biomarkers (osteocalcin [OC], procollagen type 1 amino-terminal propeptide, and C-terminal cross-linking telopeptide...
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