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Merck
CN

D1413

2′,3′-Didehydro-3′-deoxythymidine

≥98% (TLC)

Synonym(s):

1-(2,3-Dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine, 1-[(2R,5S)-5-(Hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-(1H,3H)-dione, 2′,3′-Anhydrothymidine, Stavudine, d4T

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About This Item

Empirical Formula (Hill Notation):
C10H12N2O4
CAS Number:
3056-17-5
Molecular Weight:
224.21
NACRES:
NA.77
PubChem Substance ID:
24278356
UNSPSC Code:
12352200
MDL number:
MFCD00132921

Key Documents

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Product Name

2′,3′-Didehydro-3′-deoxythymidine, ≥98% (TLC)

InChI

1S/C10H12N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h2-4,7-8,13H,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1

SMILES string

CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O

InChI key

XNKLLVCARDGLGL-JGVFFNPUSA-N

assay

≥98% (TLC)

form

powder

storage temp.

−20°C

Quality Level

200

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Application

2′,3′-Didehydro-3′-deoxythymidine has been used in cell treatment. It has also been used as a drug in Caenorhabditis elegans to study drug induced mitochondrial toxicity. It has also been used in the preclinical evaluation of GS-9160.

Biochem/physiol Actions

2′,3′-Didehydro-3′-deoxythymidine is a nucleoside analog, which inhibits HIV replication in vitro. Stavudine has the ability to enter the cells by non-facilitated diffusion. It possesses inhibitory activity against moloney murine leukemia virus, friend murine leukemia virus and simian immunodeficiency virus.

General description

2′,3′-Didehydro-3′-deoxythymidine (d4T), a pyrimidine analogue is the inhibitor of reverse transcriptase.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000382188
0000320030
0000382188
0000301501
0000301501

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Nittaya Phanuphak et al.
Antiviral therapy, 17(8), 1521-1531 (2012-12-12)
Due to superior long-term toxicity profiles, zidovudine (AZT) and tenofovir disoproxil fumarate (TDF) are preferred over stavudine (d4T) for first-line antiretroviral regimens. However, short-term d4T use could be beneficial in avoiding AZT-induced anaemia. We randomized (1:1:1) 150 treatment-naive Thai HIV-infected
Preclinical evaluation of GS-9160, a novel inhibitor of human immunodeficiency virus type 1 integrase
Jones G S, et al.
Antimicrobial Agents and Chemotherapy, 53(3), 1194-1203 (2009)
2?, 3?-didehydro-3?-deoxythymidine (d4T) in patients with AIDS or AIDS-related complex: a phase I trial
Browne M J, et al.
The Journal of Infectious Diseases, 167(1), 21-29 (1993)
Caenorhabditis elegans as a model system for studying drug induced mitochondrial toxicity
de Boer R, et al.
PLoS ONE, 10(5), e0126220-e0126220 (2015)
Stephen Arpadi et al.
Archives of disease in childhood, 98(4), 258-264 (2012-12-12)
Few studies have assessed metabolic and body composition alterations in perinatally HIV-infected African children on antiretroviral therapy (ART). We compared metabolic profiles and regional fat of children on ritonavir-boosted lopinavir (lopinavir/ritonavir), lamivudine and stavudine to those switched to nevirapine, lamivudine
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