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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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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)
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
Stephanie Shiau et al.
The Journal of pediatrics, 162(6), 1138-1145 (2013-01-15)
To describe the effects of age at antiretroviral therapy (ART) initiation on growth outcomes among children infected with HIV followed for 48 months after treatment initiation. This secondary analysis describes anthropometric changes in children infected with HIV in Johannesburg, South
Caenorhabditis elegans as a model system for studying drug induced mitochondrial toxicity
de Boer R, et al.
PLoS ONE, 10(5), e0126220-e0126220 (2015)
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)
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