ContaminantDB: Stavudine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:15:56 UTC

Update Date

2016-11-09 01:09:12 UTC

Accession Number

CHEM003729

Identification

Common Name

Stavudine

Class

Small Molecule

Description

A dideoxynucleoside analog that inhibits reverse transcriptase and has in vitro activity against HIV.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Anti-HIV Agent
Antimetabolite
Drug
Ether
Metabolite
Organic Compound
Reverse Transcriptase Inhibitor
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine	ChEBI
2',3'-Didehydro-3'-deoxythimidine	ChEBI
3'-Deoxy-2'-thymidinene	ChEBI
d4T	ChEBI
Estavudina	ChEBI
Sanilvudine	ChEBI
Stavudinum	ChEBI
STV	ChEBI
Zerit	Kegg
ABBR D4T	Kegg
1-(2,3-Dideoxy-b-D-glycero-pent-2-enofuranosyl)thymine	Generator
1-(2,3-Dideoxy-β-D-glycero-pent-2-enofuranosyl)thymine	Generator
2',3'-Didehydro-2',3'-dideoxythmidine	HMDB
2',3' Didehydro 3' deoxythymidine	HMDB
2',3'-Didehydro-3'-deoxythymidine	HMDB
Bristol-myers squibb brand OF stavudine	HMDB
Bristol-myers brand OF stavudine	HMDB
Stavudine, monosodium salt	HMDB

Chemical Formula

C₁₀H₁₂N₂O₄

Average Molecular Mass

224.213 g/mol

Monoisotopic Mass

224.080 g/mol

CAS Registry Number

3056-17-5

IUPAC Name

1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Traditional Name

stavudine

SMILES

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

InChI Identifier

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

Not Available

Direct Parent

Nucleoside and nucleotide analogues

Alternative Parents

Substituents

Pyrimidone
Hydropyrimidine
Pyrimidine
Dihydrofuran
Vinylogous amide
Heteroaromatic compound
Lactam
Urea
Organoheterocyclic compound
Azacycle
Oxacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organic molecular entity (CHEBI:63581 )
dihydrofuran (CHEBI:63581 )
nucleoside analogue (CHEBI:63581 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	159-160°C
Boiling Point	Not Available
Solubility	5-10 g/100 mL at 21°C

Predicted Properties

Property	Value	Source
Water Solubility	40.5 g/L	ALOGPS
logP	-0.73	ALOGPS
logP	-0.23	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.87 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.32 m³·mol⁻¹	ChemAxon
Polarizability	21.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-9710000000-ec1b8accee7609d895af	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fi9-9710000000-a08eaef1e27e4362b56e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-00di-0970000000-1b5ba27caa3ca46a5b79	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0fk9-0910000000-0c32425ddc6552e762c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-053i-1900000000-8995ae3343a9f5bbbd7e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-052r-1900000000-b232bf6bd07c73125776	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9000000000-b6b8d8a7acd0cee4a6be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-004i-0900000000-bfecc35d096bfac41070	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-014r-0900000000-7eaff645bdf6c4509baf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0910000000-14958ea9ed30262a4313	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0a4i-0900000000-f6122db2223358609e31	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0a4i-0900000000-c3ebc31e7ad70d77da44	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0a4i-0900000000-d5d5a96f8199343194ce	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0a4i-0900000000-2e40076ad350727ab3ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-a15778802feedb7e8702	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-5900000000-1e77dd699ba1244d96dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a7j-9600000000-42ce2a756eceb750ac46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00c0-2940000000-3e2b43ac1b4b3b11d540	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01di-3920000000-0a634444532bc0df9549	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9200000000-5a3e9da67f3d054c39c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0910000000-3590697dc556ba789bc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-4930000000-0d37f8daf0a0e84719bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9400000000-0f2472d56e156d73d0de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-2b6aa9078cee3df72a6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00bc-7960000000-a5ae84e7332328ddeee2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-22b5a0eeff96c030db6a	Spectrum

Toxicity Profile

Route of Exposure

Following oral administration, stavudine is rapidly absorbed (bioavailability is 68-104%).

Mechanism of Toxicity

Stavudine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.

Metabolism

Phosphorylated intracellularly to stavudine triphosphate, the active substrate for HIV-reverse transcriptase. Half Life: 0.8-1.5 hours (in adults)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of human immunovirus (HIV) infections.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Side effects include peripheral neuropathy tingling, burning, numbness, or pain in the hands or feet), fatal lactic acidosis has been reported in patients treated with stavudine (ZERIT) in combination with other antiretroviral agents, severe liver enlargement, inflammation (pain and swelling) of the liver, and liver failure.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00649

HMDB ID

HMDB0014787

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Purna Chandra Ray, Jagan Mohana Chary Tummanapalli, Seeta Ramanjaneyulu Gorantla, “Process for the Large Scale Production of Stavudine.” U.S. Patent US20080312428, issued December 18, 2008.

MSDS

Link

General References

Not Available

Stavudine (CHEM003729)

Structure for CHEM003729: Stavudine