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Details

Stereochemistry RACEMIC
Molecular Formula C18H26ClN3
Molecular Weight 319.8728
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLOROQUINE

SMILES

CCN(CC)CCCC(C)Nc1ccnc2cc(ccc12)Cl

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 319.8728
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
A Comparative Study of Hymenolepicides in Hymenolepis Mana Infestation of Rats.
1962 Jul
Drug-induced haemolysis and renal failure in children with glucose-6-phosphate dehydrogenase deficiency in Central Asia.
1990
Occurrence of chloroquine-induced psychotic manifestations in children with malaria.
1992
Chloroquine related complete heart block with blindness: case report.
1992 Jan
The effect of EGb 761 on the doxorubicin cardiomyopathy.
1999
Inhibition of the neuronal insulin receptor causes Alzheimer-like disturbances in oxidative/energy brain metabolism and in behavior in adult rats.
1999
[Neuromuscular complications of long-term treatment of inflammatory diseases. 3 cases].
1999 Dec
The effect of artesunate combined with standard antimalarials against chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum in vitro.
1999 Jul-Aug
Detection of color vision defects in chloroquine retinopathy.
1999 Sep
Assessment of drugs against Cryptosporidium parvum using a simple in vitro screening method.
1999 Sep 15
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
Multifocal ERG in chloroquine retinopathy: regional variance of retinal dysfunction.
2000 Jan
[Unexpected occurrence of cardiac arrest during chloroquine preventive therapy].
2000 Jun
[Complete heart block following chronic chloroquine treatment].
2000 May
Induction of glutathione synthesis in human keratinocytes by Ginkgo biloba extract (EGb761).
2001
Effect of primaquine standard dose (15 mg/day for 14 days) in the treatment of vivax malaria patients in Thailand.
2001 Dec
The anti-HIV-1 activity of chloroquine.
2001 Feb
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.
2001 Jan
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
Chlorproguanil-dapsone for treatment of drug-resistant falciparum malaria in Tanzania.
2001 Oct 13
Cardiac damage from chronic use of chloroquine: a case report and review of the literature.
2002 Jul
The first molecular evidence that autophagy relates rimmed vacuole formation in chloroquine myopathy.
2002 May
Side effects of and compliance with malaria prophylaxis in children.
2002 Nov-Dec
[Chloroquine cardiomyopathy revealed by complete atrio-ventricular block. A case report].
2002 Sep
Severe mucocutaneous necrotizing vasculitis associated with the combination of chloroquine and proguanil.
2003
Therapy of glioblastoma multiforme improved by the antimutagenic chloroquine.
2003 Feb 15
[Chloroquine-induced myopathy and neuropathy: progressive tetraparesis with areflexia that simulates a polyradiculoneuropathy. Two case reports].
2003 Mar 16-31
Identification of human cytochrome P(450)s that metabolise anti-parasitic drugs and predictions of in vivo drug hepatic clearance from in vitro data.
2003 Sep
Reactive oxygen species mediate chloroquine-induced expression of chemokines by human astroglial cells.
2004 Jul
The multifocal pattern electroretinogram in chloroquine retinopathy.
2004 Mar-Apr
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
Attenuation of chloroquine-induced renal damage by alpha-lipoic acid: possible antioxidant mechanism.
2004 Sep
Seizure associated with chloroquine therapy in a patient with systemic lupus erythematosus.
2004 Sep
[Malaria chemoprophylaxis in traveling children].
2005 Jan
CpG-B oligodeoxynucleotide promotes cell survival via up-regulation of Hsp70 to increase Bcl-xL and to decrease apoptosis-inducing factor translocation.
2006 Dec 15
[Complete auriculoventricular block secondary to cardiac toxicity due to chloroquine].
2006 Feb
[Cytochrome P-450 and the response to antimalarial drugs].
2006 Jan
Plasmodium berghei: development of an irreversible experimental malaria model in Wistar rats.
2006 Jul
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Tetrahydrocurcumin: effect on chloroquine-mediated oxidative damage in rat kidney.
2006 Nov
Expression of autophagy-associated genes in skeletal muscle: an experimental model of chloroquine-induced myopathy.
2007
[Complete auriculoventricular block during chloroquine treatment].
2007 Feb
Effect of chloroquine on gene expression of Plasmodium yoelii nigeriensis during its sporogonic development in the mosquito vector.
2007 Jul 2
Chloroquine-induced recurrent psychosis.
2007 Jul-Aug
Heart conduction disorders related to antimalarials toxicity: an analysis of electrocardiograms in 85 patients treated with hydroxychloroquine for connective tissue diseases.
2007 May
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
Autophagy inhibitors chloroquine and LY294002 enhance temozolomide cytotoxicity on cutaneous melanoma cell lines in vitro.
2017 Mar
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 Fri Jun 25 20:58:59 UTC 2021
Edited
by admin
on Fri Jun 25 20:58:59 UTC 2021
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 [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 [USP]
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 Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.5.3.2
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
LIVERTOX 193
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
EU-Orphan Drug EU/3/14/1377
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
CFR 21 CFR 522.810
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 2.4
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
IARC Chloroquine
WHO-ESSENTIAL MEDICINES LIST 6.5.3.1
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
FDA ORPHAN DRUG 475015
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
WHO-ATC P01BA01
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
NDF-RT N0000175482
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
Code System Code Type Description
DRUG CENTRAL
607
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
CAS
54-05-7
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
NCI_THESAURUS
C61671
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
LACTMED
Chloroquine
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
DRUG BANK
DB00608
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
MERCK INDEX
M3435
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY Merck Index
IUPHAR
5535
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
PUBCHEM
2719
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
INN
386
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PRIMARY
EVMPD
SUB06196MIG
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
WIKIPEDIA
CHLOROQUINE
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
FDA UNII
886U3H6UFF
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-191-2
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
HSDB
3029
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
RXCUI
2393
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY RxNorm
EPA CompTox
54-05-7
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
MESH
D002738
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
ChEMBL
CHEMBL76
Created by admin on Fri Jun 25 20:59:00 UTC 2021 , Edited by admin on Fri Jun 25 20:59:00 UTC 2021
PRIMARY
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