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

Molecular Formula	C10H12FN5O2
Molecular Weight	253.233
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.	1987 Nov	3499515
2',3'-Dideoxy-2'-fluoro-ara-A. An acid-stable purine nucleoside active against human immunodeficiency virus (HIV).	1987 Sep 1	3651175
Investigations on the anti-HIV activity of 2',3'-dideoxyadenosine analogues with modifications in either the pentose or purine moiety. Potent and selective anti-HIV activity of 2,6-diaminopurine 2',3'-dideoxyriboside.	1988 Apr 1	3258516
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV.	1990 Mar	2106581
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
CycloSal-2'-ara(ribo)-fluoro-2',3'-dideoxyadenosine monophosphates--an effort to solve the structure-activity relationship of 2'-fluoro-ddA.	1999 Apr-May	10432708
cycloSal-Pronucleotides of 2'-fluoro-ara- and 2'-fluoro-ribo-2',3'- dideoxyadenosine as a strategy to bypass a metabolic blockade.	1999 May 6	10229630
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
High performance liquid chromatography analysis of 9-(2',3'-dideoxy-2'beta-fluoro-D-threo-penta furanosyl) adenine and its metabolite in human plasma using solid-phase extraction on a polyfluorinated reversed stationary phase.	2001 Jun	11438969
Evaluation of a fluorogenic derivatization method for the reversed-phase HPLC analysis of 2'-beta-fluoro-2',3'-dideoxyadenosine, a new anti-AIDS drug.	2001 May	11275436
Synthesis of 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)adenine (FddA) via a purine 3'-deoxynucleoside.	2001 Nov 2	11681963
Enhanced oral bioavailability of 2'- beta-fluoro-2',3'-dideoxyadenosine (F-ddA) through local inhibition of intestinal adenosine deaminase.	2001 Sep	11683239
A facile synthetic method for 3'-alpha-fluoro-2',3'-dideoxyadenosine.	2003 May-Aug	14565260
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:43:54 UTC 2023` Edited by `admin` on `Fri Dec 15 15:43:54 UTC 2023`
Record UNII	3WB2LGT4R1
Record Status	`Validated (UNII)`
Record Version

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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