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Details

Stereochemistry ACHIRAL
Molecular Formula C21H33N3O
Molecular Weight 343.5062
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SITAMAQUINE

SMILES

CCN(CC)CCCCCCNC1=C2N=CC=C(C)C2=CC(OC)=C1

InChI

InChIKey=RVAKDGYPIVSYEU-UHFFFAOYSA-N
InChI=1S/C21H33N3O/c1-5-24(6-2)14-10-8-7-9-12-22-20-16-18(25-4)15-19-17(3)11-13-23-21(19)20/h11,13,15-16,22H,5-10,12,14H2,1-4H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16945323

Sitamaquine (WR-6026) is an orally active 8-aminoquinoline analog in development by the Walter Reed Army Institute, in collaboration with GlaxoSmithKline (formerly SmithKline Beecham), for the potential treatment of visceral leishmaniasis. Phase III trials for the treatment of visceral leishmaniasis had been initiated by March 2002, at which time GlaxoSmithKline hoped to file an MAA in 2003. By 1999, the compound had also undergone phase I trials in HIV-infected individuals for the treatment of Pneumocystis carinii infection. Preclinical studies have been conducted in primates and rodents for the potential treatment of Babesia microti infection.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
29.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
484.3 ng/mL
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
577 ng/mL
2 mg/kg single, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
503 ng/mL
2 mg/kg 1 times / day multiple, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
639 ng/mL
2 mg/kg 1 times / day single, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
451 ng/mL
2 mg/kg 1 times / day multiple, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
6916 ng × h/mL
150 mg 1 times / day multiple, oral
dose: 150 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7147 ng × h/mL
2 mg/kg single, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8350 ng × h/mL
2 mg/kg 1 times / day multiple, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8574 ng × h/mL
2 mg/kg 1 times / day single, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
7723 ng × h/mL
2 mg/kg 1 times / day multiple, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18.3 h
2 mg/kg 1 times / day multiple, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
19.3 h
2 mg/kg 1 times / day multiple, oral
dose: 2 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SITAMAQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
DLT: Elevated triglycerides...
Disc. AE: Skin rash, Nausea...
Dose limiting toxicities:
Elevated triglycerides (5.6%)
AEs leading to
discontinuation/dose reduction:
Skin rash (11.1%)
Nausea (5.6%)
Vomiting (5.6%)
Headache (5.6%)
CPK increased (5.6%)
LDH increased (5.6%)
AST increased (5.6%)
ALT increased (5.6%)
Sources:
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
DLT: Methemoglobinemia, Methemoglobinemia...
Disc. AE: Histoplasmosis, Fever...
Dose limiting toxicities:
Methemoglobinemia (12.5%)
Methemoglobinemia (37.5%)
Elevated triglycerides (12.5%)
AEs leading to
discontinuation/dose reduction:
Histoplasmosis (12.5%)
Fever (12.5%)
Flushing (12.5%)
Skin rash (12.5%)
Sources:
2.5 mg/kg 1 times / day multiple, oral
Studied dose
Dose: 2.5 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg/kg, 1 times / day
Sources:
unhealthy, CHILD,ADULT
Health Status: unhealthy
Age Group: CHILD,ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Cardio-respiratory failure, Bone marrow depression...
AEs leading to
discontinuation/dose reduction:
Cardio-respiratory failure (grade 5, 3.6%)
Bone marrow depression (3.6%)
Bone marrow depression (3.6%)
Nephrotic syndrome (7.2%)
Glomerulonephritis (7.2%)
Acute renal failure (3.6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Skin rash 11.1%
Disc. AE
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Elevated triglycerides 5.6%
DLT
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
ALT increased 5.6%
Disc. AE
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
AST increased 5.6%
Disc. AE
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
CPK increased 5.6%
Disc. AE
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Headache 5.6%
Disc. AE
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
LDH increased 5.6%
Disc. AE
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Nausea 5.6%
Disc. AE
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Vomiting 5.6%
Disc. AE
120 mg 1 times / day multiple, oral
MTD
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Elevated triglycerides 12.5%
DLT
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Methemoglobinemia 12.5%
DLT, Disc. AE
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Fever 12.5%
Disc. AE
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Flushing 12.5%
Disc. AE
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Histoplasmosis 12.5%
Disc. AE
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Skin rash 12.5%
Disc. AE
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Methemoglobinemia 37.5%
DLT
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Acute renal failure 3.6%
Disc. AE
2.5 mg/kg 1 times / day multiple, oral
Studied dose
Dose: 2.5 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg/kg, 1 times / day
Sources:
unhealthy, CHILD,ADULT
Health Status: unhealthy
Age Group: CHILD,ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Bone marrow depression 3.6%
Disc. AE
2.5 mg/kg 1 times / day multiple, oral
Studied dose
Dose: 2.5 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg/kg, 1 times / day
Sources:
unhealthy, CHILD,ADULT
Health Status: unhealthy
Age Group: CHILD,ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Bone marrow depression 3.6%
Disc. AE
2.5 mg/kg 1 times / day multiple, oral
Studied dose
Dose: 2.5 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg/kg, 1 times / day
Sources:
unhealthy, CHILD,ADULT
Health Status: unhealthy
Age Group: CHILD,ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Glomerulonephritis 7.2%
Disc. AE
2.5 mg/kg 1 times / day multiple, oral
Studied dose
Dose: 2.5 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg/kg, 1 times / day
Sources:
unhealthy, CHILD,ADULT
Health Status: unhealthy
Age Group: CHILD,ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Nephrotic syndrome 7.2%
Disc. AE
2.5 mg/kg 1 times / day multiple, oral
Studied dose
Dose: 2.5 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg/kg, 1 times / day
Sources:
unhealthy, CHILD,ADULT
Health Status: unhealthy
Age Group: CHILD,ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Cardio-respiratory failure grade 5, 3.6%
Disc. AE
2.5 mg/kg 1 times / day multiple, oral
Studied dose
Dose: 2.5 mg/kg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg/kg, 1 times / day
Sources:
unhealthy, CHILD,ADULT
Health Status: unhealthy
Age Group: CHILD,ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 23.1093 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Transition metal complexes of quinolino[3,2-b]benzodiazepine and quinolino[3,2-b]benzoxazepine: synthesis, characterization, and antimicrobial studies.
2007
Orally effective drugs for kala-azar (visceral leishmaniasis): focus on miltefosine and sitamaquine.
2003-07
Sitamaquine (GlaxoSmithKline/Walter Reed Army Institute).
2002-10
New drug developments for opportunistic infections in immunosuppressed patients: Pneumocystis carinii.
1995-11-24
8-Aminoquinolines from Walter Reed Army Institute for Research for treatment and prophylaxis of Pneumocystis pneumonia in rat models.
1991-02
Patents

Sample Use Guides

oral sitamaquine, 2 mg/kg/day, once a day for 21 days
Route of Administration: Oral
Sitamaquine (1 ug/ml) almost completely inhibited P carinii growth in human lung fibroblasts over 10 days. Some inhibition was seen at 0.1 ug/ml, which was a similar level of activity to that of primaquine.
Name Type Language
SITAMAQUINE
INN   MI   WHO-DD  
INN  
Official Name English
WR-6026
Preferred Name English
sitamaquine [INN]
Common Name English
Sitamaquine [WHO-DD]
Common Name English
SITAMAQUINE [MI]
Common Name English
Code System Code Type Description
PUBCHEM
42548
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
INN
7834
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
DRUG BANK
DB04909
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
MERCK INDEX
m9961
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY Merck Index
SMS_ID
100000129177
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
EPA CompTox
DTXSID70206395
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
FDA UNII
5AIJ4TGC6B
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
EVMPD
SUB37607
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
CAS
57695-04-2
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
NCI_THESAURUS
C73010
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
ChEMBL
CHEMBL57004
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY
MESH
C080436
Created by admin on Mon Mar 31 18:28:40 GMT 2025 , Edited by admin on Mon Mar 31 18:28:40 GMT 2025
PRIMARY