U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C24H28ClN3O.2H3O4P
Molecular Weight 605.942
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAPHTHOQUINE PHOSPHATE

SMILES

OP(O)(O)=O.OP(O)(O)=O.CC(C)(C)NCC1=C(O)C2=C(CCCC2)C(NC3=C4C=CC(Cl)=CC4=NC=C3)=C1

InChI

InChIKey=QTYPWHKJEDCDNH-UHFFFAOYSA-N
InChI=1S/C24H28ClN3O.2H3O4P/c1-24(2,3)27-14-15-12-22(17-6-4-5-7-18(17)23(15)29)28-20-10-11-26-21-13-16(25)8-9-19(20)21;2*1-5(2,3)4/h8-13,27,29H,4-7,14H2,1-3H3,(H,26,28);2*(H3,1,2,3,4)

HIDE SMILES / InChI
Molecular Formula H3O4P
Molecular Weight 97.9952
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C24H28ClN3O
Molecular Weight 409.952
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22363211

Naphthoquine is an antimalarial drug first synthesized in China in 1986 but which was not developed for clinical use until the late 1990s. This drug now is used in combination for treatment of Plasmodium Falciparum and Malaria. The use of anti-malarial drug combinations with artemisinin or with one of its derivatives is now widely recommended to overcome drug resistance in falciparum as well as vivax malaria. The fixed oral dose artemisinin-naphthoquine combination (ANQ, ARCO™) is a newer artemisinin-based combination (ACT) therapy undergoing clinical assessment.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
various P. falciparum strains
2
Target ID: various P. falciparum strains
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Phase IV
63
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.4 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
27.4 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
12.8 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
11.4 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
59.8 μg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
424 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
955 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
446 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
480 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1875 μg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
298.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
276.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
156.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
256.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
233.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20197487/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered: ARTEMISININ
ARTEMISININ
 NAPHTHOQUINE PHOSPHATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
1000 mg 1 times / day multiple, oral
Highest studied dose
Dose: 1000 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/27075024/
https://pubmed.ncbi.nlm.nih.gov/14628338/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/27075024/
https://pubmed.ncbi.nlm.nih.gov/14628338/
Sources:
https://pubmed.ncbi.nlm.nih.gov/27075024/
https://pubmed.ncbi.nlm.nih.gov/14628338/
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/20197487/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/20197487/
Other AEs: ALT increased...
Other AEs:
ALT increased (grade 1, 10%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20197487/
AEs

AEs

AESignificanceDosePopulation
ALT increased grade 1, 10%
600 mg single, oral
Highest studied dose
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/20197487/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/20197487/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inhibitor
2252
inhibitor
2438

substrate
1193
substrate
1388

inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1197

CYP2B6
776

CYP2C19
1119

P-gp
2052

CYP2C8
810
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
2546
 inconclusive [IC50 3.4671 uM]
CYP2C9
2497
 no
CYP3A4
2633
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
1388
 major
CYP1A2
1197
 minor
CYP2B6
776
 minor
CYP2C19
1119
 minor
CYP2C8
810
 minor
CYP2C9
1193
 minor
CYP3A4
1946
 minor
P-gp
2052
 yes
PubMed

PubMed

TitleDatePubMed
Naphthoquine: An Emerging Candidate for Artemisinin Combination Therapy.
2016-05
Open-label trial of three dosage regimens of fixed-dose combination of artemisinin and naphthoquine for treating uncomplicated falciparum malaria in Calabar, Nigeria.
2012-12-11

Sample Use Guides

In Vivo Use Guide
Patients in this treatment arm will receive on Day 0 a single dose of standard treatment of artemisinin/naphthoquine (in a fixed oral dose of ARCO tablets). Treatment will be given under supervision. Each tablet of ARCO(artemisinin/naphthoquine) contains 125 mg artemisinin and 50 mg of naphthoquine. The total dose for adults will be 1000mg of artemisinin and 400mg of naphthoquine in a fixed oral dose (ARCO tablet). The regimen for children will be calculated according to the body weight (20mg artemisinin + 8mg naphthoquine per kg body weight in a fixed oral dose(ARCO tablet)).
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:37:34 GMT 2025
Edited
by admin
on Mon Mar 31 22:37:34 GMT 2025
Record UNII
M6M6AP4KAH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-NAPHTHALENOL, 4-((7-CHLORO-4-QUINOLINYL)AMINO)-2-(((1,1-DIMETHYLETHYL)AMINO)METHYL)-5,6,7,8-TETRAHYDRO-, PHOSPHATE (1:2) (SALT)
Preferred Name English
NAPHTHOQUINE PHOSPHATE
WHO-DD  
Common Name English
Naphthoquine phosphate [WHO-DD]
Common Name English
4-(7-CHLORO-4-AMINOQUINOLINE)-2-TERT-BUTYLAMINOMETHYL-5,6,7,8-4HYDRO-1-NAPHTHOL DIPHOSPHATE
Systematic Name English
Code System Code Type Description
CAS
173531-58-3
Created by admin on Mon Mar 31 22:37:34 GMT 2025 , Edited by admin on Mon Mar 31 22:37:34 GMT 2025
PRIMARY
PUBCHEM
9851774
Created by admin on Mon Mar 31 22:37:34 GMT 2025 , Edited by admin on Mon Mar 31 22:37:34 GMT 2025
PRIMARY
EPA CompTox
DTXSID70431766
Created by admin on Mon Mar 31 22:37:34 GMT 2025 , Edited by admin on Mon Mar 31 22:37:34 GMT 2025
PRIMARY
FDA UNII
M6M6AP4KAH
Created by admin on Mon Mar 31 22:37:34 GMT 2025 , Edited by admin on Mon Mar 31 22:37:34 GMT 2025
PRIMARY
Related Record Type Details
Structure of NAPHTHOQUINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966