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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H26N4O23P4
Molecular Weight 790.3071
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIQUAFOSOL

SMILES

O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)N4C=CC(=O)NC4=O

InChI

InChIKey=NMLMACJWHPHKGR-NCOIDOBVSA-N
InChI=1S/C18H26N4O23P4/c23-9-1-3-21(17(29)19-9)15-13(27)11(25)7(41-15)5-39-46(31,32)43-48(35,36)45-49(37,38)44-47(33,34)40-6-8-12(26)14(28)16(42-8)22-4-2-10(24)20-18(22)30/h1-4,7-8,11-16,25-28H,5-6H2,(H,31,32)(H,33,34)(H,35,36)(H,37,38)(H,19,23,29)(H,20,24,30)/t7-,8-,11-,12-,13-,14-,15-,16-/m1/s1

HIDE SMILES / InChI
Molecular Formula C18H26N4O23P4
Molecular Weight 790.3071
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.santeninc.com/newsroom/press-releases/10_04_DIQUAS.pdf | http://www.santen.com/en/therapeutic-areas/asia/dryeye/diquas/

Diquafosol, a dinucleotide Up4U, is an agonist for purinergic P2Y2 receptor. Diquafosol stimulated water and mucin secretion by acting on P2Y2 receptors on the conjunctival epithelial and goblet cell membrane and elevating intracellular calcium ion concentrations. The Japanese Ministry of Health, Labour and Welfare granted approval for DIQUAS Ophthalmic Solution 3% (diquafosol tetrasodium) for the treatment of dry eye.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 0.1 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
DIQUAS

Approved Use

DIQUAS Ophthalmic Solution 3% (generic name: diquafosol tetrasodium) should be used in patients diagnosed with dry eye, associated with keratoconjunctival epithelium disorders that accompany lacrimal fluid abnormality.

Launch Date

1.27128961E12
PubMed

PubMed

TitleDatePubMed
Improvement of corneal barrier function by the P2Y(2) agonist INS365 in a rat dry eye model.
2001 Jan
Pharmacology of INS37217 [P(1)-(uridine 5')-P(4)- (2'-deoxycytidine 5')tetraphosphate, tetrasodium salt], a next-generation P2Y(2) receptor agonist for the treatment of cystic fibrosis.
2002 Sep
Diquafosol: DE 089, diquafosol tetrasodium, INS 365, INS 365 Ophthalmic, INS 365 Respiratory, KPY 998.
2003
Therapy for chronic obstructive pulmonary disease in the 21st century.
2003
Diquafosol tetrasodium. Inspire/Allergan/Santen.
2003 Nov
Molecule of the month. Diquafosol tetrasodium.
2003 Oct
Diquafosol tetrasodium: a novel dry eye therapy.
2004 Jan
Diquafosol elicits increases in net Cl- transport through P2Y2 receptor stimulation in rabbit conjunctiva.
2004 Mar-Apr
Double-masked, placebo-controlled safety and efficacy trial of diquafosol tetrasodium (INS365) ophthalmic solution for the treatment of dry eye.
2004 Nov
Recent advances in the management of ocular complications of Sjögren's syndrome.
2005 Jul
[A molecular marker for dry eye].
2007 Mar
Topical application of nucleotides increase lysozyme levels in tears.
2008 Jun
Pyrimidine nucleotides with 4-alkyloxyimino and terminal tetraphosphate δ-ester modifications as selective agonists of the P2Y(4) receptor.
2011 Jun 23
Patents

Patents

EP2659894A1
2
JP2013227291A
2
US20060062787A1
2

Sample Use Guides

In Vivo Use Guide
DIQUAS Ophthalmic Solution 3% (generic name: diquafosol tetrasodium). Usually, instill 1 drop a time 6 times daily.
Route of Administration: Topical
In Vitro Use Guide
3% diquafosol tetrasodium had a significant, time-dependent, inhibitory effect on human corneal epithelial cells (HCEC) proliferation and cytotoxicity. HCECs treated with diquafosol detached more from the bottoms of dishes and damaged cells showed degenerative changes, such as, reduced numbers of microvilli, vacuole formation, and chromatin of the nuclear remnant condensed along the nuclear periphery.
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:59:21 UTC 2023
Edited
by admin
on Sat Dec 16 15:59:21 UTC 2023
Record UNII
7828VC80FJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIQUAFOSOL
INN   MI   WHO-DD  
INN  
Official Name English
DIURIDINE TETRAPHOSPHATE
Common Name English
P1,P4-DI(URIDINE 5'-TETRAPHOSPHATE), TETRASODIUM SALT
Common Name English
URIDINE, 5'-(PENTAHYDROGEN TETRAPHOSPHATE), P'''->5'-ESTER WITH URIDINE
Common Name English
DIQUAFOSOL [MI]
Common Name English
diquafosol [INN]
Common Name English
P1, P4-DI(URIDINE 5'-TETRAPHOSPHATE), TETRASODIUM SALT
Common Name English
Diquafosol [WHO-DD]
Common Name English
URIDINE(5')TETRAPHOSPHO(5')URIDINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78283
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID40208689
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
MESH
C403315
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
CAS
59985-21-6
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
EVMPD
SUB87041
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL221326
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
FDA UNII
7828VC80FJ
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
DRUG CENTRAL
4900
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
SMS_ID
100000139278
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
PUBCHEM
148197
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
MERCK INDEX
m4661
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY Merck Index
INN
8326
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
NCI_THESAURUS
C65436
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
CHEBI
27791
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
WIKIPEDIA
DIQUAFOSOL
Created by admin on Sat Dec 16 15:59:22 UTC 2023 , Edited by admin on Sat Dec 16 15:59:22 UTC 2023
PRIMARY
Related Record Type Details
Structure of DIQUAFOSOL TETRASODIUM
SALT/SOLVATE -> PARENT
P2Y PURINOCEPTOR 2
TARGET -> AGONIST
Related Record Type Details
Structure of DIQUAFOSOL
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