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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H15N5O3
Molecular Weight 265.2689
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALIDESIVIR

SMILES

c1c(c2c(c(=N)[nH]cn2)[nH]1)[C@@]3([H])[C@@]([H])([C@@]([H])([C@@]([H])(CO)N3)O)O

InChI

InChIKey=AMFDITJFBUXZQN-KUBHLMPHSA-N
InChI=1S/C11H15N5O3/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)/t5-,7+,9-,10+/m1/s1

HIDE SMILES / InChI

Molecular Formula C11H15N5O3
Molecular Weight 265.2689
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5540 ng/mL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
21160 ng × h/mL
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
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
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
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 14.581 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Protection against filovirus diseases by a novel broad-spectrum nucleoside analogue BCX4430.
2014 Apr 17
Possible leap ahead in filovirus therapeutics.
2014 Jun
BCX4430 - A broad-spectrum antiviral adenosine nucleoside analog under development for the treatment of Ebola virus disease.
2016 May-Jun
Efficacy of the broad-spectrum antiviral compound BCX4430 against Zika virus in cell culture and in a mouse model.
2017 Jan
Patents

Sample Use Guides

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
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 Jun 26 16:21:37 UTC 2021
Edited
by admin
on Sat Jun 26 16:21:37 UTC 2021
Record UNII
OLF97F86A7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GALIDESIVIR
INN   WHO-DD  
INN  
Official Name English
3,4-PYRROLIDINEDIOL, 2-(4-AMINO-5H-PYRROLO(3,2-D)PYRIMIDIN-7-YL)-5-(HYDROXYMETHYL)-, (2S,3S,4R,5R)-
Systematic Name English
GALIDESIVIR [WHO-DD]
Common Name English
GALIDESIVIR [INN]
Common Name English
BCX4430
Code English
BCX-4430
Code English
IMMUCILLIN A
Common Name English
Code System Code Type Description
DRUG BANK
DB11676
Created by admin on Sat Jun 26 16:21:38 UTC 2021 , Edited by admin on Sat Jun 26 16:21:38 UTC 2021
PRIMARY
NCI_THESAURUS
C172613
Created by admin on Sat Jun 26 16:21:38 UTC 2021 , Edited by admin on Sat Jun 26 16:21:38 UTC 2021
PRIMARY
WIKIPEDIA
Galidesivir
Created by admin on Sat Jun 26 16:21:38 UTC 2021 , Edited by admin on Sat Jun 26 16:21:38 UTC 2021
PRIMARY
PUBCHEM
10445549
Created by admin on Sat Jun 26 16:21:38 UTC 2021 , Edited by admin on Sat Jun 26 16:21:38 UTC 2021
PRIMARY
CAS
249503-25-1
Created by admin on Sat Jun 26 16:21:38 UTC 2021 , Edited by admin on Sat Jun 26 16:21:38 UTC 2021
PRIMARY
FDA UNII
OLF97F86A7
Created by admin on Sat Jun 26 16:21:38 UTC 2021 , Edited by admin on Sat Jun 26 16:21:38 UTC 2021
PRIMARY
INN
10284
Created by admin on Sat Jun 26 16:21:38 UTC 2021 , Edited by admin on Sat Jun 26 16:21:38 UTC 2021
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
Has shown antiviral activities in preclinical studies against many RNA viruses, including SARS and MERS.
DERIVATIVE -> PARENT
TARGET ORGANISM->INHIBITOR
SALT/SOLVATE -> PARENT
DERIVATIVE -> PARENT
TARGET ORGANISM->INHIBITOR
SALT/SOLVATE -> PARENT
ANALOGUE->PARENT
Related Record Type Details
ACTIVE MOIETY