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Merck
CN

11546

3′-Azido-3′-deoxythymidine

≥99.0% (HPLC)

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
PubChem Substance ID:
329749478
UNSPSC Code:
12352200
Beilstein/REAXYS Number:
3595791
MDL number:
MFCD00006536

Key Documents

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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

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

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

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H341,H351

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

Regulatory Information

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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
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
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
Hiroaki Togami et al.
Journal of virology, 87(8), 4322-4329 (2013-02-01)
Simian retrovirus type 4 (SRV-4), a simian type D retrovirus, naturally infects cynomolgus monkeys, usually without apparent symptoms. However, some infected monkeys presented with an immunosuppressive syndrome resembling that induced by simian immunodeficiency virus infection. Antiretrovirals with inhibitory activity against
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)
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