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

Details

Stereochemistry RACEMIC
Molecular Formula C18H26ClN3
Molecular Weight 319.872
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLOROQUINE

SMILES

CCN(CC)CCCC(C)NC1=CC=NC2=C1C=CC(Cl)=C2

InChI

InChIKey=WHTVZRBIWZFKQO-UHFFFAOYSA-N
InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)

HIDE SMILES / InChI

Molecular Formula C18H26ClN3
Molecular Weight 319.872
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Chloroquine (brand name Aralen) is indicated for the suppressive treatment and for acute attacks of malaria due to P. vivax, P.malariae, P. ovale, and susceptible strains of P. falciparum. The drug is also indicated for the treatment of extraintestinal amebiasis. In addition, chloroquine is in clinical trials as an investigational antiretroviral in humans with HIV-1/AIDS and as a potential antiviral agent against chikungunya fever. The mechanism of plasmodicidal action of chloroquine is not completely certain. However, is existed theory, that like other quinoline derivatives, it is thought to inhibit heme polymerase activity. The heme moiety consists of a porphyrin ring called Fe(II)-protoporphyrin IX (FP). To avoid destruction by this molecule, the parasite biocrystallizes heme to form hemozoin, a non-toxic molecule. Chloroquine enters the red blood cell, inhabiting parasite cell, and digestive vacuole by simple diffusion. Chloroquine then becomes protonated (to CQ2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup. Chloroquine binds to heme (or FP) to form what is known as the FP-Chloroquine complex; this complex is highly toxic to the cell and disrupts membrane function.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rat. Human data not available.

Originator

Curator's Comment: # Hans Andersag and coworkers at the Bayer laboratories

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ARALEN

Approved Use

ARALEN is indicated for the suppressive treatment and for acute attacks of malaria due to P. vivax, P.malariae, P. ovale, and susceptible strains of P. falciparum. The drug is also indicated for the treatment of extraintestinal amebiasis. ARALEN does not prevent relapses in patients with vivax or malariae malaria because it is not effective against exoerythrocytic forms of the parasite, nor will it prevent vivax or malariae infection when administered as a prophylactic. It is highly effective as a suppressive agent in patients with vivax or malariae malaria, in terminating acute attacks, and significantly lengthening the interval between treatment and relapse. In patients with falciparum malaria it abolishes the acute attack and effects complete cure of the infection, unless due to a resistant strain of P. falciparum.

Launch Date

-6.3650883E11
Curative
ARALEN

Approved Use

ARALEN is indicated for the suppressive treatment and for acute attacks of malaria due to P. vivax, P.malariae, P. ovale, and susceptible strains of P. falciparum. The drug is also indicated for the treatment of extraintestinal amebiasis. ARALEN does not prevent relapses in patients with vivax or malariae malaria because it is not effective against exoerythrocytic forms of the parasite, nor will it prevent vivax or malariae infection when administered as a prophylactic. It is highly effective as a suppressive agent in patients with vivax or malariae malaria, in terminating acute attacks, and significantly lengthening the interval between treatment and relapse. In patients with falciparum malaria it abolishes the acute attack and effects complete cure of the infection, unless due to a resistant strain of P. falciparum.

Launch Date

-6.3650883E11
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
700 ng/mL
5 mg/kg 1 times / day multiple, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CHLOROQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
134087 ng × h/mL
5 mg/kg 1 times / day multiple, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CHLOROQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
209 h
5 mg/kg 1 times / day multiple, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CHLOROQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
5 mg/kg 1 times / day multiple, oral
dose: 5 mg/kg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
CHLOROQUINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3 g single, oral
Overdose
Dose: 3 g
Route: oral
Route: single
Dose: 3 g
Sources:
unknown, 14 years
n = 1
Health Status: unknown
Age Group: 14 years
Sex: F
Population Size: 1
Sources:
Other AEs: Cardiac arrest...
Other AEs:
Cardiac arrest
Sources:
600 mg 2 times / day multiple, oral (starting)
Highest studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
pregnant, 20.7 years
n = 300
Health Status: pregnant
Condition: malaria
Age Group: 20.7 years
Sex: F
Population Size: 300
Sources:
Other AEs: Dizziness, Vomiting...
Other AEs:
Dizziness (19%)
Vomiting (17%)
Palpitations (5%)
Headache (6%)
Nausea (5%)
Abdominal pain (2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Cardiac arrest
3 g single, oral
Overdose
Dose: 3 g
Route: oral
Route: single
Dose: 3 g
Sources:
unknown, 14 years
n = 1
Health Status: unknown
Age Group: 14 years
Sex: F
Population Size: 1
Sources:
Vomiting 17%
600 mg 2 times / day multiple, oral (starting)
Highest studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
pregnant, 20.7 years
n = 300
Health Status: pregnant
Condition: malaria
Age Group: 20.7 years
Sex: F
Population Size: 300
Sources:
Dizziness 19%
600 mg 2 times / day multiple, oral (starting)
Highest studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
pregnant, 20.7 years
n = 300
Health Status: pregnant
Condition: malaria
Age Group: 20.7 years
Sex: F
Population Size: 300
Sources:
Abdominal pain 2%
600 mg 2 times / day multiple, oral (starting)
Highest studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
pregnant, 20.7 years
n = 300
Health Status: pregnant
Condition: malaria
Age Group: 20.7 years
Sex: F
Population Size: 300
Sources:
Nausea 5%
600 mg 2 times / day multiple, oral (starting)
Highest studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
pregnant, 20.7 years
n = 300
Health Status: pregnant
Condition: malaria
Age Group: 20.7 years
Sex: F
Population Size: 300
Sources:
Palpitations 5%
600 mg 2 times / day multiple, oral (starting)
Highest studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
pregnant, 20.7 years
n = 300
Health Status: pregnant
Condition: malaria
Age Group: 20.7 years
Sex: F
Population Size: 300
Sources:
Headache 6%
600 mg 2 times / day multiple, oral (starting)
Highest studied dose
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
pregnant, 20.7 years
n = 300
Health Status: pregnant
Condition: malaria
Age Group: 20.7 years
Sex: F
Population Size: 300
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no (co-administration study)
Comment: chloroquine did not affect the activities of CYP1A2, CYP2C19, CYP2E1, CYP3A4
no
no (co-administration study)
Comment: chloroquine did not affect the activities of CYP1A2, CYP2C19, CYP2E1, CYP3A4
no
no (co-administration study)
Comment: chloroquine did not affect the activities of CYP1A2, CYP2C19, CYP2E1, CYP3A4
no
no (co-administration study)
Comment: chloroquine did not affect the activities of CYP1A2, CYP2C19, CYP2E1, CYP3A4
yes [IC50 1096 uM]
yes [IC50 2.5 uM]
yes [Ki 12 uM]
weak (co-administration study)
Comment: selective inhibiton; Chloroquine produced a reduction in the metabolism of debrisoquine as evaluated by the debrisoquine recovery ratio, a measure of CYP2D6 activity. This reduction was progressive from the first to the seventh dose. This decrease in metabolism was modest (about 7% after the first dose and about 18% after seven doses) but statistically significant
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes
yes (co-administration study)
Comment: Concomitant administration of a single dose of chloroquine and cimetidine daily starting 4 days prior to chloroquine, resulted in a 50% increase in chloroquine half-life, associated with a 50% decrease in its clearance.Since the AUC of desethylchloroquine decreased by 47%, cimetidine probably decreased chloroquine clearance by inhibiting its hepatic desethylation.
yes
yes (co-administration study)
Comment: Concomitant administration of a single dose of chloroquine and cimetidine daily starting 4 days prior to chloroquine, resulted in a 50% increase in chloroquine half-life, associated with a 50% decrease in its clearance.Since the AUC of desethylchloroquine decreased by 47%, cimetidine probably decreased chloroquine clearance by inhibiting its hepatic desethylation.
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Tumor- and drug-induced cutaneous neuro-phospholipidosis.
1975
Nivaquine and urethral pain.
1976 Dec
Kinetics of the uptake and elimination of chloroquine in children with malaria.
1982 Oct
Inhibition of human immunodeficiency virus infectivity by chloroquine.
1990 Apr
Seizures associated with chloroquine therapy.
1992 Aug
Ocular toxicology.
1994 Dec
Calcitriol-mediated hypercalcaemia and increased interleukins in a patient with sarcoid myopathy.
1999
[Neuromuscular complications of long-term treatment of inflammatory diseases. 3 cases].
1999 Dec
Complete heart block as a rare complication of treatment with chloroquine.
1999 Jun
Cadmium-mediated oxidative stress in kidney proximal tubule cells induces degradation of Na+/K(+)-ATPase through proteasomal and endo-/lysosomal proteolytic pathways.
1999 Oct
Chloroquine exerts an additive in vitro anti-HIV type 1 effect when associated with didanosine and hydroxyurea.
1999 Sep 20
Atovaquone-proguanil versus chloroquine-proguanil for malaria prophylaxis in non-immune travellers: a randomised, double-blind study. Malarone International Study Team.
2000 Dec 2
[Unexpected occurrence of cardiac arrest during chloroquine preventive therapy].
2000 Jun
In vivo antimalarial activity of the beta-carboline alkaloid manzamine A.
2000 Jun
[Complete heart block following chronic chloroquine treatment].
2000 May
The additive in vitro anti-HIV-1 effect of chloroquine, when combined with zidovudine and hydroxyurea.
2001 Jun 15
Cardiac toxicity secondary to long term treatment with chloroquine.
2001 Mar
Chloroquine-induced neuronal cell death is p53 and Bcl-2 family-dependent but caspase-independent.
2001 Oct
Effects of Ginkgo biloba extract (EGb 761) and quercetin on lipopolysaccharide-induced signaling pathways involved in the release of tumor necrosis factor-alpha.
2001 Oct 1
Side effects of and compliance with malaria prophylaxis in children.
2002 Nov-Dec
Control of mammary tumor cell growth in vitro by novel cell differentiation and apoptosis agents.
2002 Sep
Therapy of glioblastoma multiforme improved by the antimutagenic chloroquine.
2003 Feb 15
Acute neuropharmacologic action of chloroquine on cortical neurons in vitro.
2003 Jan 10
[Chloroquine-induced myopathy and neuropathy: progressive tetraparesis with areflexia that simulates a polyradiculoneuropathy. Two case reports].
2003 Mar 16-31
Heart transplantation in a patient with chloroquine-induced cardiomyopathy.
2004 Feb
Reactive oxygen species mediate chloroquine-induced expression of chemokines by human astroglial cells.
2004 Jul
Survival and surface adherence ability of bacterial pathogens in oral liquid pharmaceuticals and their containers.
2004 Jun
The ability of chloroquine to prevent tat-induced cytokine secretion by monocytes is implicated in its in vivo anti-human immunodeficiency virus type 1 activity.
2004 Nov
Chloroquine-induced cardiomyopathy-echocardiographic features.
2005 Apr
Skeletal muscle expression of clathrin and mannose 6-phosphate receptor in experimental chloroquine-induced myopathy.
2005 Apr
Enhanced anticryptococcal activity of chloroquine in phosphatidylserine-containing liposomes in a murine model.
2005 Feb
[Malaria chemoprophylaxis in traveling children].
2005 Jan
Chloroquine-induced lipidosis mimicking Fabry disease.
2005 May
[Complete auriculoventricular block secondary to cardiac toxicity due to chloroquine].
2006 Feb
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Antimalarial myopathy: an underdiagnosed complication? Prospective longitudinal study of 119 patients.
2006 Mar
Effect of chloroquine on gene expression of Plasmodium yoelii nigeriensis during its sporogonic development in the mosquito vector.
2007 Jul 2
[Reversible restrictive cardiomyopathy secondary to chloroquine].
2007 Jun 23
A randomised controlled trial to assess the efficacy of dihydroartemisinin-piperaquine for the treatment of uncomplicated falciparum malaria in Peru.
2007 Oct 31
Conduction disorder and QT prolongation secondary to long-term treatment with chloroquine.
2008 Jul 4
Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain.
2014 Jul 15
Patents

Sample Use Guides

The dosage of chloroquine phosphate is often expressed in terms of equivalent chloroquine base. Each 500 mg tablet of ARALEN (chloroquine phosphate) contains the equivalent of 300 mg chloroquine base. In infants and children the dosage is preferably calculated by body weight. Malaria: Suppression—Adult Dose: 500 mg (= 300 mg base) on exactly the same day of each week. Pediatric Dose: The weekly suppressive dosage is 5 mg calculated as base, per kg of body weight, but should not exceed the adult dose regardless of weight. If circumstances permit, suppressive therapy should begin two weeks prior to exposure. However, failing this in adults, an initial double (loading) dose of 1 g (= 600 mg base), or in children 10 mg base/kg may be taken in two divided doses, six hours apart. The suppressive therapy should be continued for eight weeks after leaving the endemic area. For Treatment of Acute Attack. Adults: An initial dose of 1 g (=600 mg base) followed by an additional 500 mg (= 300 mg base) after six to eight hours and a single dose of 500 mg (= 300 mg base) on each of two consecutive days. This represents a total dose of 2.5 g chloroquine phosphate or 1.5 g base in three days. The dosage for adults of low body weight and for infants and children should be determined as follows: First dose: 10 mg base per kg (but not exceeding a single dose of 600 mg base) Second dose: (6 hours after first dose) 5 mg base per kg (but not exceeding a single dose of 300 mg base) Third dose: (24 hours after first dose) 5mg base per kg Fourth dose: (36 hours after first dose) 5 mg base per kg For radical cure of vivax and malariae malaria concomitant therapy with an 8-aminoquinoline compound is necessary. Extraintestinal Amebiasis: Adults, 1 g (600 mg base) daily for two days, followed by 500 mg (300 mg base) daily for at least two to three weeks. Treatment is usually combined with an effective intestinal amebicide.
Route of Administration: Oral
Chloroquine inhibited mouse colon cancer cell line CT26 cells proliferation by concentration- and time-dependent manner. This effect was associated with apoptosis induction and decreased level of phosphorylated p42/44 mitogen-activated protein kinase and phosphorylated Akt. The cytotoxicity of chloroquine on CT26 cells was determined by the MTT assay. Cells were seeded in 96-well plates at the density of 2000/well and cultured for 24 hr, followed by chloroquine treatment (100, 50, 25, 12.5, 6.25, and 3.125 μ mol/L) for 24, 48, and 72 hr, respectively.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:39:29 UTC 2023
Edited
by admin
on Wed Jul 05 22:39:29 UTC 2023
Record UNII
886U3H6UFF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHLOROQUINE
HSDB   INN   MART.   MI   USP   VANDF   WHO-DD  
INN  
Official Name English
CHLOROQUINE [MI]
Common Name English
chloroquine [INN]
Common Name English
CHLOROQUINE [USP IMPURITY]
Common Name English
CHLOROQUINE [VANDF]
Common Name English
1,4-PENTANEDIAMINE, N(SUP 4)-(7-CHLORO-4-QUINOLINYL)-N(SUP 1),N (SUP 1)-DIETHYL-
Common Name English
7-Chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline
Systematic Name English
CHLOROQUINE [USP MONOGRAPH]
Common Name English
CHLOROQUINE [MART.]
Common Name English
Chloroquine [WHO-DD]
Common Name English
NSC-187208
Code English
CHLOROQUINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C271
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.5.3.2
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
LIVERTOX NBK548224
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
EU-Orphan Drug EU/3/14/1377
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
CFR 21 CFR 522.810
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 2.4
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
IARC Chloroquine
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
FDA ORPHAN DRUG 475015
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
WHO-ATC P01BA01
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
NDF-RT N0000175482
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
Code System Code Type Description
DRUG CENTRAL
607
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
DAILYMED
886U3H6UFF
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
CAS
54-05-7
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PRIMARY
NCI_THESAURUS
C61671
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
SMS_ID
100000088282
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
CHEBI
3638
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
LACTMED
Chloroquine
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
DRUG BANK
DB00608
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
MERCK INDEX
M3435
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PRIMARY Merck Index
IUPHAR
5535
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PRIMARY
PUBCHEM
2719
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PRIMARY
INN
386
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PRIMARY
EVMPD
SUB06196MIG
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PRIMARY
WIKIPEDIA
CHLOROQUINE
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
FDA UNII
886U3H6UFF
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-191-2
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
HSDB
3029
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
NSC
187208
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PRIMARY
RXCUI
2393
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID2040446
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
MESH
D002738
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL76
Created by admin on Wed Jul 05 22:39:29 UTC 2023 , Edited by admin on Wed Jul 05 22:39:29 UTC 2023
PRIMARY
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