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A2169

Sigma-Aldrich

3′-Azido-3′-deoxythymidine

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

Synonym(s):

AZT, Azidothymidine, ZDV, Zidovudine

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About This Item

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

product name

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

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

Storage Class Code

11 - Combustible Solids

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)
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)
M R Difalco et al.
The Journal of pharmacology and experimental therapeutics, 284(2), 449-454 (1998-03-07)
The effect of 406, a novel fusion protein between the N-terminal sequence of the insect insulin-like peptide, bombyxin, human insulin-like growth factor II and mouse interleukin 3 was investigated in its capacity to abrogate the toxic effects of azidothymidine (AZT)
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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