LODENOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12FN5O2
Molecular Weight	253.233
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]3O[C@H](CO)C[C@@H]3F

InChI

InChIKey=KBEMFSMODRNJHE-JFWOZONXSA-N

InChI=1S/C10H12FN5O2/c11-6-1-5(2-17)18-10(6)16-4-15-7-8(12)13-3-14-9(7)16/h3-6,10,17H,1-2H2,(H2,12,13,14)/t5-,6-,10+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11365997 | https://www.ncbi.nlm.nih.gov/pubmed/11367250 | https://adisinsight.springer.com/drugs/800005453

Lodenosine is the experimental HIV reverse transcriptase inhibitor. It was designed as a chemically and enzymatically stable anti-AIDS drug. A phase II trial of the nucleoside analog lodenosine was suspended after one participant died and others showed signs of liver or kidney damage.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Reverse transcriptase 8 Target ID: CHEMBL2366516 Sources: https://journals.sagepub.com/doi/abs/10.1177/095632029000100507	Inhibitor 8297		3.0 µM [Ki]

PubMed

Title	Date	PubMed
Potential anti-AIDS drugs. Lipophilic, adenosine deaminase-activated prodrugs.	1991 May	2033591
Enhancement by hydroxyurea of the anti-human immunodeficiency virus type 1 potency of 2'-beta-fluoro-2',3'-dideoxyadenosine in peripheral blood mononuclear cells.	1995 Jul 17	7632173
Comparative analysis of anti-human immunodeficiency virus type 1 activities of dideoxynucleoside analogs in resting and activated peripheral blood mononuclear cells.	1995 Nov	8585744
Lipophilic, acid-stable, adenosine deaminase-activated anti-HIV prodrugs for central nervous system delivery. 3. 6-Amino prodrugs of 2'-beta-fluoro-2',3'-dideoxyinosine.	1996 Apr 12	8648601
In vitro induction of human immunodeficiency virus type 1 variants resistant to 2'-beta-Fluoro-2',3'-dideoxyadenosine.	1997 Jun	9174190
Fluorometric determination of 2'-beta-fluoro-2',3'-dideoxyadenosine 5'-triphosphate, the active metabolite of a new anti-human immunodeficiency virus drug, in human lymphocytes.	2001 Jan 1	11141306
An industrial process for synthesizing Lodenosine (FddA).	2003 May-Aug	14565226
Determination of carrier-mediated transport of 2',3'-dideoxypurine nucleosides in the rat ileum using a bidirectional perfusion technique.	2004 Feb	15032312
Synthesis of fluorinated nucleosides.	2006 Jul	18428944

Patents

Name

Type

Language

LODENOSINE

Official Name

English

Lodenosine [WHO-DD]

Common Name

English

NSC-613792

Code

English

9H-PURIN-6-AMINE, 9-(2,3-DIDEOXY-2-FLUORO-.BETA.-D-THREO-PENTOFURANOSYL)-

Systematic Name

English

LODENOSINE [USAN]

Common Name

English

F-DDA

Code

English

lodenosine [INN]

Common Name

English

2'-.BETA.-FLUORO-2',3'-DIDEOXYADENOSINE

Common Name

English

9-(2,3-DIDEOXY-2-FLUORO-.BETA.-D-THREO-PENTOFURANOSYL) ADENINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1556