All Photos(1)
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
Empirical Formula (Hill Notation):
C10H12N2O4
CAS Number:
Molecular Weight:
224.21
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
Assay
≥98% (TLC)
form
powder
storage temp.
−20°C
SMILES string
CC1=CN([C@@H]2O[C@H](CO)C=C2)C(=O)NC1=O
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
InChI key
XNKLLVCARDGLGL-JGVFFNPUSA-N
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General description
2′,3′-Didehydro-3′-deoxythymidine (d4T), a pyrimidine analogue is the inhibitor of reverse transcriptase.
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.
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
Caenorhabditis elegans as a model system for studying drug induced mitochondrial toxicity
de Boer R, et al.
PLoS ONE, 10(5), e0126220-e0126220 (2015)
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)
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
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