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Sigma-Aldrich

3′-Azido-3′-deoxythymidine

≥99.0% (HPLC)

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

biological source

synthetic

assay

≥99.0% (HPLC)

form

powder with small lumps

impurities

≤0.5% water

mp

113-115 °C (lit.)

solubility

H2O: 50 mg/mL, clear, colorless to slightly yellow

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

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Biochem/physiol Actions

Reverse transcriptase inhibitor active against HIV-1 virus.

Other Notes

A potent, selective inhibitor of human immunodeficiency virus replication in MT-4 and ATH8 cells

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J Balzarini et al.
The Journal of biological chemistry, 264(11), 6127-6133 (1989-04-15)
3'-Azido-2',3'-dideoxythymidine (AZT) and 2',3'-didehydro-2',3'-dideoxythymidine (D4T) are potent and selective inhibitors of human immunodeficiency virus replication in MT-4 and ATH8 cells. They are also inhibitory to the replication of murine retroviruses, i.e. Moloney murine sarcoma virus-induced transformation of C3H cells. In
Markus Moll et al.
European journal of immunology, 39(3), 902-911 (2009-02-07)
Invariant CD1d-restricted NKT cells play important roles in regulating both innate and adaptive immunity. They are targeted by HIV-1 infection and severely reduced in number or even lost in many infected subjects. Here, we have investigated the characteristics of NKT
Temitope O Olomola et al.
Bioorganic & medicinal chemistry, 21(7), 1964-1971 (2013-02-19)
Baylis-Hillman-derived 3-(benzylaminomethyl)coumarins have been treated, sequentially, with chloroacetyl chloride and propargylamine to afford alkynylated coumarins as substrates for Click Chemistry reactions with azidothymidine (AZT) in the presence of a Cu(I) catalyst. The dual-action HIV-1 protease (PR) and reverse transcriptase (RT)
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
Muki Shey et al.
The Cochrane database of systematic reviews, (3)(3), CD005481-CD005481 (2009-07-10)
The human immunodeficiency virus (HIV) has become one of the greatest challenges to global public health. In 2007 UNAIDS estimated that 33.2 million people were living with HIV. Currently recommended regimens for initiating HIV treatment consist of either a non-nucleoside

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