DACOPAFANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H11N3OS
Molecular Weight	245.3
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=C2CS[C@@H](N2C=C1)C3=CC=CN=C3

InChI

InChIKey=ARFOASMERCHFBY-GFCCVEGCSA-N

InChI=1S/C12H11N3OS/c13-11(16)9-3-5-15-10(9)7-17-12(15)8-2-1-4-14-6-8/h1-6,12H,7H2,(H2,13,16)/t12-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C12H11N3OS
Molecular Weight	245.3
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7515938 | https://www.ncbi.nlm.nih.gov/pubmed/2519903 | https://www.sciencedirect.com/science/article/abs/pii/S1054358908610121 | https://www.ncbi.nlm.nih.gov/pubmed/1743246

Dacopafant (R-enantiomer RP 55778, racemate RP 48740) is an antagonist fo a platelet-activating factor and an inhibitor of TNH-alpha synthesis. It was developed by Rhone-Poulenc Rorer (France, now Aventis). In vitro, treatment of HIV-1 infected monocyte-derived macrophages with dacopafant resulted in a significant decrease in TNF-alpha levels and viral production. RP 48740 inhibited [3H]PAF platelet binding with IC50 of 2.3 uM and antagonized PAF-induced platelet activation with IC50 of 16 uM. In a clinical trial on human volunteers, RP 48740 was well tolerated and inhibited ex vivo platelet aggregation by as much as 79% 6 hr after administration.

Approval Year

PubMed

Title	Date	PubMed
A platelet-activating factor antagonist, RP 55778, inhibits cytokine-dependent induction of human immunodeficiency virus expression in chronically infected promonocytic cells.	1993 Mar 15	7681601
Infection of human macrophages with an endogenous tumour necrosis factor-alpha (TNF-alpha)-independent human immunodeficiency virus type 1 isolate is unresponsive to the TNF-alpha synthesis inhibitor RP 55778.	1994 Jun	7515938
Effects of RP 55778, a tumor necrosis factor alpha synthesis inhibitor, on antiviral activity of dideoxynucleosides.	1997 Apr	9087512

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:00:40 GMT 2023` Edited by `admin` on `Sat Dec 16 17:00:40 GMT 2023`
Record UNII	H1T03Z1G60
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DACOPAFANT

Official Name

English

RP-55778

Code

English

dacopafant [INN]

Common Name

English

(3R)-3-(3-PYRIDYL)-1H,3H-PYRROLO(1,2-C)THIAZOLE-7-CARBOXAMIDE

Systematic Name

English

RP-48740

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1327