GALIDESIVIR HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H15N5O3.ClH
Molecular Weight	301.729
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NC1=C2NC=C([C@@H]3N[C@H](CO)[C@@H](O)[C@H]3O)C2=NC=N1

InChI

InChIKey=PCCHVYNGFMEGIG-QPAIBFMUSA-N

InChI=1S/C11H15N5O3.ClH/c12-11-8-6(14-3-15-11)4(1-13-8)7-10(19)9(18)5(2-17)16-7;/h1,3,5,7,9-10,13,16-19H,2H2,(H2,12,14,15);1H/t5-,7+,9-,10+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C11H15N5O3
Molecular Weight	265.2685
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24590073
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/27838352

BCX-4430 hydrochloride is a salt of an antiviral adenosine analog BCX4430 (Immucillin-A) that acts as a viral RNA-dependent RNA polymerase (RdRp) inhibitor. It was developed as a potential treatment for deadly filovirus infections such as Ebola virus disease and Marburg virus disease but also demonstrated broad-spectrum antiviral effectiveness against a range of other RNA virus families, including, bunyaviruses, arenaviruses, paramyxoviruses, and coronaviruses. Biochemical, reporter-based and primer-extension assays indicate that BCX4430 inhibits viral RNA polymerase function, acting as a non-obligate RNA chain terminator. BCX4430 inhibits infection of distinct filoviruses in human cells. Post-exposure administration of BCX4430 protects rodents against Ebola and Marburg virus disease and cynomolgus macaques from Marburg virus when administered as late as 48 hours after infection. BCX4430 is highly active in a Syrian golden hamster model of yellow fever, even when treatment is initiated at the peak of viral replication. BCX4430 also showed efficacy against Zika virus in a mouse model.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
RNA-dependent RNA polymerase 3 Target ID: 4238976.0 Gene Symbol: L Sources: https://www.ncbi.nlm.nih.gov/pubmed/24590073	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ebola virus infection 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27095300 https://clinicaltrials.gov/ct2/show/NCT02319772	Primary		Phase I 428	Unknown Approved Use Unknown
Filovirus infections 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27095300 https://clinicaltrials.gov/ct2/show/NCT02319772	Primary		Phase I 428	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
5540 ng/mL OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT03800173	5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	GALIDESIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
10300 ng/mL OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT03800173	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	GALIDESIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
17730 ng/mL OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT03800173	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	GALIDESIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
20490 ng/mL OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT03800173	20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	GALIDESIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
21160 ng × h/mL OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT03800173	5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	GALIDESIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
37080 ng × h/mL OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT03800173	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	GALIDESIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
65860 ng × h/mL OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT03800173	15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	GALIDESIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
81230 ng × h/mL OTHER GOV'T https://clinicaltrials.gov/ct2/show/results/NCT03800173	20 mg/kg single, intravenous dose: 20 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	GALIDESIVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=363681391	inconclusive [IC50 14.581 uM]

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00BFMA	https://www.1pchem.com/search?query=1P00BFMA
1PlusChem LLC	1P00BFMB	https://www.1pchem.com/search?query=1P00BFMB
BLD Pharm	BD331043	http://www.bldpharm.com/search/Search.html?keyword=BD331043
BLD Pharm	BD630558	http://www.bldpharm.com/search/Search.html?keyword=BD630558
Cayman Chemical	16085	http://www.caymanchem.com/app/template/Product.vm/catalog/16085
Chem Scene	CS-3778	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3778
Chem Scene	CS-3779	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3779
Lab Network	LN01342442	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342442
Lab Network	LN01342444	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342444
MedChem Express	HY-18649	https://www.medchemexpress.com/search.html?q=HY-18649A&ft=&fa=&fp=
MedChem Express	HY-18649A	https://www.medchemexpress.com/search.html?q=HY-18649A&ft=&fa=&fp=
MolPort	MolPort-044-561-309	https://www.molport.com/shop/molecule-link/MolPort-044-561-309
MolPort	MolPort-046-417-217	https://www.molport.com/shop/molecule-link/MolPort-046-417-217
Molnova	M13557	https://www.molnova.com/en/serch-list.html?keywords=M13557
Molnova	M13732	https://www.molnova.com/en/serch-list.html?keywords=M13732
eMolecules	295312084	https://orderbb.emolecules.com/search/#?query=295312084
eMolecules	295312085	https://orderbb.emolecules.com/search/#?query=295312085
eMolecules	301217051	https://orderbb.emolecules.com/search/#?query=301217051
eMolecules	50550801	https://orderbb.emolecules.com/search/#?query=50550801
eMolecules	50550805	https://orderbb.emolecules.com/search/#?query=50550805
mcule	MCULE-2753927828	https://mcule.com/MCULE-2753927828/
mcule	MCULE-4826192197	https://mcule.com/MCULE-4826192197/
mcule	MCULE-5805671229	https://mcule.com/MCULE-5805671229/

PubMed

Title	Date	PubMed
Protection against filovirus diseases by a novel broad-spectrum nucleoside analogue BCX4430.	2014 Apr 17	24590073
Efficacy of the broad-spectrum antiviral compound BCX4430 against Zika virus in cell culture and in a mouse model.	2017 Jan	27838352

Patents

Sample Use Guides

In Vivo Use Guide

BCX-4430 dose of 2.5 mg/kg QD for 7 days in healthy subjects to evaluate the safety, tolerability, and pharmacokinetics of BCX4430. Up to 4 ascending dose (up to 10.0 mg/kg) cohorts treated in a sequential manner.

Route of Administration: Intramuscular

In Vitro Use Guide

Variation in and low efficiency of conversion of BCX4430 to BCX4430-TP were studied in cell lines commonly used for in vitro evaluation of antiviral activity of test agents. VERO, VERO-76, HeLa, HuH7b and MDCK cell lines were incubated with 10 uM BCX4430 for 1, 4 and 24 hours, and the levels of BCX4430-TP were quantitated by HPLC.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:18:52 GMT 2023` Edited by `admin` on `Sat Dec 16 08:18:52 GMT 2023`
Record UNII	1EL1K52SH1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GALIDESIVIR HYDROCHLORIDE

Common Name

English

BCX-4430 HYDROCHLORIDE

Code

English

3,4-PYRROLIDINEDIOL, 2-(4-AMINO-5H-PYRROLO(3,2-D)PYRIMIDIN-7-YL)-5-(HYDROXYMETHYL)-, HYDROCHLORIDE (1:1), (2S,3S,4R,5R)-

Systematic Name

English

Code System Code Type Description

CAS

222631-44-9