ContaminantDB: Didanosine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:16:31 UTC

Update Date

2016-11-09 01:09:12 UTC

Accession Number

CHEM003743

Identification

Common Name

Didanosine

Class

Small Molecule

Description

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.

Contaminant Sources

HMDB Contaminants - Urine
IARC Carcinogens Group 3
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
2,3-Dideoxyinosine	ChEBI
9-((2R,5S)-5-(Hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one	ChEBI
9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one	ChEBI
9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol	ChEBI
9-[(2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one	ChEBI
DDI	ChEBI
DdIno	ChEBI
Didanosina	ChEBI
Didanosinum	ChEBI
Dideoxyinosine	ChEBI
Videx	Kegg
ABBR ddi	Kegg
2',3' Dideoxyinosine	HMDB
Bristol-myers brand OF didanosine	HMDB
DdI (antiviral)	HMDB
Bristol myers squibb brand OF didanosine	HMDB
2',3'-Dideoxyinosine	HMDB
Bristol myers brand OF didanosine	HMDB
Bristol-myers squibb brand OF didanosine	HMDB

Chemical Formula

C₁₀H₁₂N₄O₃

Average Molecular Mass

236.227 g/mol

Monoisotopic Mass

236.091 g/mol

CAS Registry Number

69655-05-6

IUPAC Name

9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

Traditional Name

didanosine

SMILES

OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O

InChI Identifier

InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1

InChI Key

BXZVVICBKDXVGW-NKWVEPMBSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as purine 2',3'-dideoxyribonucleosides. Purine 2',3'-dideoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2',3'-dideoxyribonucleosides

Direct Parent

Purine 2',3'-dideoxyribonucleosides

Alternative Parents

Substituents

Purine 2',3'-dideoxyribonucleoside
6-oxopurine
Hypoxanthine
Purinone
Imidazopyrimidine
Purine
Pyrimidone
N-substituted imidazole
Pyrimidine
Heteroaromatic compound
Azole
Imidazole
Tetrahydrofuran
Vinylogous amide
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organopnictogen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

purine 2',3'-dideoxyribonucleoside (CHEBI:490877 )

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	160-163°C
Boiling Point	Not Available
Solubility	15.8 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	6.58 g/L	ALOGPS
logP	-0.99	ALOGPS
logP	-0.35	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	6.94	ChemAxon
pKa (Strongest Basic)	2.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.59 m³·mol⁻¹	ChemAxon
Polarizability	22.9 Å³	ChemAxon
Number of Rings	3	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	splash10-056u-9670000000-b8e1fdd18fda2c412cef	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-005c-7090000000-ed6dc7eca7c11c73693a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0090000000-fed0a8ffc5839fe73fe1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0490000000-0ac04c4f4e817e6da391	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0920000000-14a23956c10d3f6e7e9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0900000000-de4599cfceaa46089291	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-1900000000-10d07c81e3fc72fcfef2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-1900000000-84e8bb1bea77e6b5bfca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-6a0516d1b3cec255e050	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-fd0dfb766f1c628d170d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-3d9e0ecfaf77d867a9d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-0900000000-e0e7d0c808e14d842dbb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-1900000000-9d4b77c3e99e9f9a2c2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-000i-1900000000-2bb63f71ec2e92ce075d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-000i-1900000000-1475736d859ee324d92e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-000i-0900000000-2cd1a2d12ed969154415	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-000i-0920000000-410013d0d67e872eea6b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-000i-0900000000-544cf7886920f267da7a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-000i-0900000000-74008fe84aaa4adb23ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-000i-0900000000-532725f06bed9d035dcf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-000i-1900000000-7d5a4e68524522f15eca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0920000000-a89fd678ed8a8c16accc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-a1a5b268d419fff83602	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-1900000000-32bbc23c752210d7cd6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0190000000-383b44cf919dd28ff3bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2940000000-309e7293be866f0e29aa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052u-3900000000-0828603c96a200af867a	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Rapidly absorbed (bioavailability 30-40%) with peak plasma concentrations appearing within 0.5 and 1.5 hrs.

Mechanism of Toxicity

Didanosine (ddI) is metabolized intracellularly by a series of cellular enzymes to its active moiety, dideoxyadenosine triphosphate (ddATP), which inhibits the HIV reverse transcriptase enzyme competitively by competing with natural dATP. It also acts as a chain terminator by its incorporation into viral DNA as the lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.

Metabolism

Rapidly metabolized intracellularly to its active moiety, 2,3-dideoxyadenosine-5-triphosphate (ddA-TP). It is then further metabolized hepatically to yield hypoxanthine, xanthine, and uric acid. Route of Elimination: Based on data from in vitro and animal studies, it is presumed that the metabolism of didanosine in man occurs by the same pathways responsible for the elimination of endogenous purines. Purines are eliminated by the kidneys. Half Life: 30 minutes in plasma and more than 12 hours in intracellular environment.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (1)

Uses/Sources

For use, in combination with other antiretroviral agents, in the treatment of HIV-1 infection in adults.

Minimum Risk Level

Not Available

Health Effects

Side effects include pancreatitis, peripheral neuropathy, diarrhea, hyperuricemia and hepatic dysfunction.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00900

HMDB ID

HMDB0015037

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

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Rapolu Raji Reddy, Dasari Muralidhara Reddy, Kesireddy Subash Chander Reddy, “Novel Process for the Preparation of Didanosine Using Novel Intermediates.” U.S. Patent US20080293938, issued November 27, 2008.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10386939

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1619614

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17046264

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18549801

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=29438107

Didanosine (CHEM003743)

Structure for CHEM003743: Didanosine