2',3'-Dideoxyadenosine

Names

[ Name ]:
2',3'-Dideoxyadenosine

[Synonym ]:
DDA
((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol
[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methanol
Dideoxyadenosine
Didanosine impurity G
6-Amino-9-(2',3'-dideoxy-b-D-glycero-pentofuranosyl)purine
EINECS 223-853-2
[(2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol
2-furanmethanol, 5-(6-amino-9H-purin-9-yl)tetrahydro-, (2S,5R)-
2',3'-Dideoxyadenosine
9-(2,3-Dideoxy-β-D-ribofuranosyl)adenine
MFCD00010534
9-(2,3-Dideoxy-beta-D-ribofuranosyl)adenine
[(2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydro-2-furanyl]methanol

Biological Activity

[Description]:

2',3'-Dideoxyadenosine is an inhibitor of HIV replication[1]. Antiretroviral activity[1]. Antiviral efficacy[1].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

[Target]

HIV[1]

[In Vitro]

2',3'-Dideoxyadenosine inhibits HIV-1 and simian immunodeficiency virus (SIV) in MT-4 cells with EC50s of 5.27 and 5.3 μM, respectively. 2',3'-Dideoxyadenosine inhibits HIV-1 and HIV-2 in human T-lymphocyte CEM cells with EC50s of 4 μM and 8 μM, respectively. 2',3'-Dideoxyadenosine inhibits HIV-1 and HIV-2 in Molt 4/C8 cells with EC50s of 4 μM and 5.5 μM, respectively. 2',3'-Dideoxyadenosine inhibits HIV-1 and HIV-2 in C8166 cells with EC50s of 17 μM and 22 μM, respectively. 2',3'-Dideoxyadenosine inhibits murine sarcoma virus (MSV) in C3H/3T3 cells with an EC50 of 24 μM[1].

[References]

[1]. Balzarini J, et al. Conversion of 2',3'-dideoxyadenosine (ddA) and 2',3'-didehydro-2',3'-dideoxyadenosine (d4A) to their corresponding aryloxyphosphoramidate derivatives markedly potentiates their activity against human immunodeficiency virus and hepatitis B virus. FEBS Lett. 1997 Jun 30;410(2-3):324-8.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
539.1±60.0 °C at 760 mmHg

[ Melting Point ]:
181-184 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₃N₅O₂

[ Molecular Weight ]:
235.242

[ Flash Point ]:
279.9±32.9 °C

[ Exact Mass ]:
235.106918

[ PSA ]:
99.08000

[ LogP ]:
-0.43

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.822

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU7358900

CHEMICAL NAME :: Adenosine, 2',3'-dideoxy-

CAS REGISTRY NUMBER :: 4097-22-7

BEILSTEIN REFERENCE NO. :: 0619924

LAST UPDATED :: 199612

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C10-H13-N5-O2

MOLECULAR WEIGHT :: 235.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1320 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 19600 mg/kg/28D-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 9 gm/kg/3D (Continuous)

REFERENCE :: EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 18,168,1991

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
C

[ Risk Phrases ]:
R34

[ Safety Phrases ]:
26-27-36/37/39-45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
AU7358900

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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