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Y0000408

Stavudine

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

2′,3′-Didehydro-3′-deoxythymidine, 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
MDL number:
MFCD00132921
UNSPSC Code:
41116107
PubChem Substance ID:
329830940
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

stavudine

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°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

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Stavudine EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Thymidine ≥99%

Sigma-Aldrich

T9250

Thymidine

Nilza Nascimento Guimarães et al.
Expert opinion on drug safety, 9(5), 771-781 (2010-04-10)
The nucleoside reverse transcriptase inhibitors (NRTIs) are used in antiretroviral therapy worldwide for the treatment of HIV infections. These drugs act by blocking reverse transcriptase enzyme activity, causing pro-viral DNA chain termination. As a consequence, NRTIs could cause genomic instability
R L Murphy
Antiviral therapy, 3 Suppl 4, 69-73 (2000-03-21)
Initial studies of multiple-agent antiretroviral combinations including the thymidine nucleoside analogue reverse transcriptase inhibitor (RTI) stavudine (2',3'-didehydro-2',3'-dideoxythymidine; D4T) have shown potent anti-HIV effects in both treatment-naive and -experienced patients. A number of ongoing randomized comparative trials are assessing stavudine-based multiple
G Skowron
The Journal of infectious diseases, 171 Suppl 2, S113-S117 (1995-03-01)
Data on the biologic effects and safety of stavudine in patients with AIDS and AIDS-related complex represent results of two phase I trials (n = 84), another phase I study of patients with hematologic intolerance to zidovudine (n = 23)
Alain Makinson et al.
Expert opinion on drug safety, 7(3), 283-293 (2008-05-09)
Western randomized trials and prospective cohorts in resource-limited settings have proven virological success with stavudine-based highly active antiretroviral therapy. However, stavudine is no longer recommended in first-line treatments in these two settings due to its intrinsic toxicities and side effects.
M Hurst et al.
Drugs, 58(5), 919-949 (1999-12-14)
Stavudine is a thymidine nucleoside analogue which is phosphorylated intracellularly to an active metabolite, stavudine 5'-triphosphate. This metabolite inhibits HIV replication, either by competing with thymidine 5'-triphosphate for incorporation into viral DNA by reverse transcriptase or by causing premature termination
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