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Substance Name: Didanosine [USAN:USP:INN:BAN]
RN: 69655-05-6
UNII: K3GDH6OH08
InChIKey: BXZVVICBKDXVGW-NKWVEPMBSA-N

Note

  • A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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.

Molecular Formula

  • C10-H12-N4-O3

Molecular Weight

  • 236.2298
 

Classification Codes

Classification Codes

  • Anti-HIV Agents
  • Anti-Infective Agents
  • Anti-Retroviral Agents
  • Antimetabolites
  • Antiviral
  • Antiviral Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Mutation Data
  • Noxae
  • Nucleic Acid Synthesis Inhibitors
  • Reverse Transcriptase Inhibitors

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Didanosine
  • Didanosine [USAN:USP:INN:BAN]
  • Dideoxyinosine

MeSH Heading

  • Didanosine

Synonyms

  • 2',3'-Dideoxyinosine
  • BMY 40900
  • BMY-40900
  • BRN 3619529
  • CCRIS 805
  • DdI
  • Didanosina
  • Didanosina [INN-Spanish]
  • Didanosine
  • Didanosinum
  • Didanosinum [INN-Latin]
  • Dideoxyinosine
  • DRG-0016
  • HSDB 6548
  • NSC 612049
  • UNII-K3GDH6OH08
  • Videx
  • Videx EC

Systematic Names

  • 2',3'-Dideoxyinosine
  • Inosine, 2',3'-dideoxy-

Superlist Name

  • Didanosine

Registry Numbers

CAS Registry Number

  • 69655-05-6

FDA UNII

  • K3GDH6OH08

System Generated Number

  • 0069655056

Structure Descriptors

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

InChIKey

BXZVVICBKDXVGW-NKWVEPMBSA-N

Smiles

OC[C@@H]1CC[C@@H](O1)n2cnc3C(=O)NC=Nc23

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 2gm/kg (2000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
man LDLo oral 2340mg/kg/34W (2340mg/kg) LIVER: "JAUNDICE, CHOLESTATIC"

LIVER: FATTY LIVER DEGERATION
Annals of Internal Medicine. Vol. 115, Pg. 283, 1991.
mouse LD50 oral > 2gm/kg (2000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.
rat LD50 oral > 2gm/kg (2000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 23, Pg. 682, 1992.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 160-163 deg C   EXP
log P (octanol-water) -1.24E+00 (none)   EXP
Water Solubility 1.58E+04 mg/L 25 EST
Vapor Pressure 6.59E-11 mm Hg 25 EST
Henry's Law Constant 2.45E-20 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.27E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.