Identification

Name
Quinacrine
Accession Number
DB01103  (APRD00317)
Type
Small Molecule
Groups
Approved, Investigational
Description

An acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.

Structure
Thumb
Synonyms
  • 2-methoxy-6-chloro-9-diethylaminopentylaminoacridine
  • 3-chloro-7-methoxy-9-(1-methyl-4-diethylaminobutylamino)acridine
  • 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxyacridine
  • Mepacrine
  • N4-(6-chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-1,4-pentanediamine
Product Ingredients
IngredientUNIICASInChI Key
Quinacrine dihydrochloride81A613ZZ6X69-05-6UDKVBVICMUEIKS-UHFFFAOYSA-N
Quinacrine dihydrochloride dihydrateG6242H2NAA6151-30-0RZFNKJVCPDLQQA-UHFFFAOYSA-N
International/Other Brands
Atabrine
Categories
UNII
H0C805XYDE
CAS number
83-89-6
Weight
Average: 399.957
Monoisotopic: 399.207740304
Chemical Formula
C23H30ClN3O
InChI Key
GPKJTRJOBQGKQK-UHFFFAOYSA-N
InChI
InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
IUPAC Name
6-chloro-N-[5-(diethylamino)pentan-2-yl]-2-methoxyacridin-9-amine
SMILES
CCN(CC)CCCC(C)NC1=C2C=C(OC)C=CC2=NC2=C1C=CC(Cl)=C2

Pharmacology

Indication

For the treatment of giardiasis and cutaneous leishmaniasis and the management of malignant effusions.

Structured Indications
Not Available
Pharmacodynamics

Quinacrine has been used as an antimalarial drug and as an antibiotic. It is used to treat giardiasis, a protozoal infection of the intestinal tract, and certain types of lupus erythematosus, an inflammatory disease that affects the joints, tendons, and other connective tissues and organs. Quinacrine may be injected into the space surrounding the lungs to prevent reoccurrence of pneumothorax. The exact way in which quinacrine works is unknown. It appears to interfere with the parasite's metabolism.

Mechanism of action

The exact mechanism of antiparasitic action is unknown; however, quinacrine binds to deoxyribonucleic acid (DNA) in vitro by intercalation between adjacent base pairs, inhibiting transcription and translation to ribonucleic acid (RNA). Quinacrine does not appear to localize to the nucleus of Giaridia trophozoites, suggesting that DNA binding may not be the primary mechanism of its antimicrobial action. Fluorescence studies using Giardia suggest that the outer membranes may be involved. Quinacrine inhibits succinate oxidation and interferes with electron transport. In addition, by binding to nucleoproteins, quinacrine suppress the lupus erythematous cell factor and acts as a strong inhibitor of cholinesterase.

TargetActionsOrganism
ADNA
intercalation
Human
A85/88 kDa calcium-independent phospholipase A2
inhibitor
Human
ACytosolic phospholipase A2
inhibitor
Human
AInactive phospholipase C-like protein 1
inhibitor
Human
Absorption

Absorbed rapidly from the gastrointestinal tract following oral administration.

Volume of distribution
Not Available
Protein binding

80-90%

Metabolism
Not Available
Route of elimination
Not Available
Half life

5 to 14 days

Clearance
Not Available
Toxicity

Oral, rat: LD50 = 900 mg/kg; Oral, mouse: LD50 = 1000 mg/kg. Symptoms of overdose include seizures, hypotension, cardiac arrhythmias, and cardiovascular collapse.

Affected organisms
  • Parasitic protozoa and helminths
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcepromazineThe serum concentration of Acepromazine can be increased when it is combined with Quinacrine.Approved, Vet Approved
AceprometazineThe serum concentration of Aceprometazine can be increased when it is combined with Quinacrine.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Quinacrine.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Quinacrine.Experimental
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Quinacrine.Approved
AlimemazineThe serum concentration of Alimemazine can be increased when it is combined with Quinacrine.Approved, Vet Approved
AmiodaroneThe metabolism of Quinacrine can be decreased when combined with Amiodarone.Approved, Investigational
AmodiaquineThe serum concentration of Quinacrine can be decreased when it is combined with Amodiaquine.Approved, Investigational
AprepitantThe serum concentration of Quinacrine can be increased when it is combined with Aprepitant.Approved, Investigational
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Quinacrine.Approved
AtazanavirThe metabolism of Quinacrine can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Quinacrine can be decreased when combined with Atomoxetine.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Quinacrine.Approved, Investigational
BL-1020The serum concentration of BL-1020 can be increased when it is combined with Quinacrine.Investigational
BoceprevirThe metabolism of Quinacrine can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Quinacrine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Quinacrine can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Quinacrine.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Quinacrine.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Quinacrine.Approved
CarbamazepineThe metabolism of Quinacrine can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Quinacrine can be increased when it is combined with Ceritinib.Approved
ChloroquineThe serum concentration of Quinacrine can be decreased when it is combined with Chloroquine.Approved, Vet Approved
ChlorproethazineThe serum concentration of Chlorproethazine can be increased when it is combined with Quinacrine.Experimental
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Quinacrine.Approved, Vet Approved
ClarithromycinThe metabolism of Quinacrine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Quinacrine can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Quinacrine can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Quinacrine can be decreased when combined with Cobicistat.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Quinacrine.Approved
ConivaptanThe serum concentration of Quinacrine can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Quinacrine can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Quinacrine.Approved, Investigational
CyclosporineThe metabolism of Quinacrine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Quinacrine.Experimental
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Quinacrine.Approved
DabrafenibThe serum concentration of Quinacrine can be decreased when it is combined with Dabrafenib.Approved
DapsoneThe risk or severity of adverse effects can be increased when Quinacrine is combined with Dapsone.Approved, Investigational
DarunavirThe metabolism of Quinacrine can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Quinacrine can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Quinacrine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Quinacrine can be decreased when combined with Delavirdine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Quinacrine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Quinacrine.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Quinacrine.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Quinacrine.Approved
DihydroergotamineThe metabolism of Quinacrine can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Quinacrine can be decreased when combined with Diltiazem.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Quinacrine.Approved, Investigational
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Quinacrine.Approved, Investigational
DoxycyclineThe metabolism of Quinacrine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Quinacrine can be decreased when combined with Dronedarone.Approved
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Quinacrine.Approved
EnzalutamideThe serum concentration of Quinacrine can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Quinacrine can be decreased when combined with Erythromycin.Approved, Vet Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Quinacrine.Approved
FluconazoleThe metabolism of Quinacrine can be decreased when combined with Fluconazole.Approved
FluphenazineThe serum concentration of Fluphenazine can be increased when it is combined with Quinacrine.Approved
FluvoxamineThe metabolism of Quinacrine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Quinacrine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Quinacrine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Quinacrine can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Quinacrine can be increased when it is combined with Fusidic Acid.Approved
GitoformateGitoformate may decrease the cardiotoxic activities of Quinacrine.Experimental
HydroxychloroquineThe serum concentration of Quinacrine can be decreased when it is combined with Hydroxychloroquine.Approved
ImatinibThe metabolism of Quinacrine can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Quinacrine can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Quinacrine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Quinacrine can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Quinacrine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Quinacrine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Quinacrine can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Quinacrine.Experimental
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Quinacrine.Approved
LopinavirThe metabolism of Quinacrine can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Quinacrine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Quinacrine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Quinacrine can be increased when combined with Lumacaftor.Approved
LumefantrineThe risk or severity of adverse effects can be increased when Quinacrine is combined with Lumefantrine.Approved
MesoridazineThe serum concentration of Mesoridazine can be increased when it is combined with Quinacrine.Approved, Investigational
MethotrimeprazineThe serum concentration of Methotrimeprazine can be increased when it is combined with Quinacrine.Approved
Methylene blueThe serum concentration of Methylene blue can be increased when it is combined with Quinacrine.Approved, Investigational
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Quinacrine.Experimental
MifepristoneThe serum concentration of Quinacrine can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Quinacrine can be decreased when it is combined with Mitotane.Approved
MoricizineThe serum concentration of Moricizine can be increased when it is combined with Quinacrine.Approved, Investigational, Withdrawn
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Quinacrine.Approved
NefazodoneThe metabolism of Quinacrine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Quinacrine can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Quinacrine can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Quinacrine can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Quinacrine can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Quinacrine can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Quinacrine.Experimental, Investigational
OsimertinibThe serum concentration of Quinacrine can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Quinacrine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Quinacrine.Approved, Vet Approved
PalbociclibThe serum concentration of Quinacrine can be increased when it is combined with Palbociclib.Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Quinacrine.Approved
PentobarbitalThe metabolism of Quinacrine can be increased when combined with Pentobarbital.Approved, Vet Approved
PerazineThe serum concentration of Perazine can be increased when it is combined with Quinacrine.Investigational
PerphenazineThe serum concentration of Perphenazine can be increased when it is combined with Quinacrine.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Quinacrine.Experimental
PhenobarbitalThe metabolism of Quinacrine can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Quinacrine can be increased when combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe metabolism of Quinacrine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrimaquineThe serum concentration of Quinacrine can be decreased when it is combined with Primaquine.Approved
PrimidoneThe metabolism of Quinacrine can be increased when combined with Primidone.Approved, Vet Approved
ProchlorperazineThe serum concentration of Prochlorperazine can be increased when it is combined with Quinacrine.Approved, Vet Approved
PromazineThe serum concentration of Promazine can be increased when it is combined with Quinacrine.Approved, Vet Approved
PromethazineThe serum concentration of Promethazine can be increased when it is combined with Quinacrine.Approved
PropericiazineThe serum concentration of Propericiazine can be increased when it is combined with Quinacrine.Approved
PropiopromazineThe serum concentration of Propiopromazine can be increased when it is combined with Quinacrine.Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Quinacrine.Experimental
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Quinacrine.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Quinacrine.Approved, Investigational
RifabutinThe metabolism of Quinacrine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Quinacrine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Quinacrine can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Quinacrine.Approved, Investigational
SaquinavirThe metabolism of Quinacrine can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Quinacrine can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Quinacrine.Approved
SiltuximabThe serum concentration of Quinacrine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Quinacrine can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Quinacrine can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Quinacrine can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Quinacrine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Quinacrine can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Quinacrine can be decreased when combined with Telithromycin.Approved
ThiazinamThe serum concentration of Thiazinam can be increased when it is combined with Quinacrine.Experimental
ThiethylperazineThe serum concentration of Thiethylperazine can be increased when it is combined with Quinacrine.Withdrawn
ThioproperazineThe serum concentration of Thioproperazine can be increased when it is combined with Quinacrine.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Quinacrine.Approved, Withdrawn
TiclopidineThe metabolism of Quinacrine can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Quinacrine can be decreased when it is combined with Tocilizumab.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Quinacrine.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Quinacrine.Approved, Investigational
TrifluoperazineThe serum concentration of Trifluoperazine can be increased when it is combined with Quinacrine.Approved
TriflupromazineThe serum concentration of Triflupromazine can be increased when it is combined with Quinacrine.Approved, Vet Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Quinacrine.Approved
VenlafaxineThe metabolism of Quinacrine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Quinacrine can be decreased when combined with Verapamil.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Quinacrine.Approved, Investigational
VoriconazoleThe metabolism of Quinacrine can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Quinacrine can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

Synthesis Reference
US2113357
General References
  1. Canete R, Escobedo AA, Gonzalez ME, Almirall P: Randomized clinical study of five days apostrophe therapy with mebendazole compared to quinacrine in the treatment of symptomatic giardiasis in children. World J Gastroenterol. 2006 Oct 21;12(39):6366-70. [PubMed:17072963]
  2. Toubi E, Kessel A, Rosner I, Rozenbaum M, Paran D, Shoenfeld Y: The reduction of serum B-lymphocyte activating factor levels following quinacrine add-on therapy in systemic lupus erythematosus. Scand J Immunol. 2006 Apr;63(4):299-303. [PubMed:16623930]
  3. Zipper J, Cole LP, Goldsmith A, Wheeler R, Rivera M: Quinacrine hydrochloride pellets: preliminary data on a nonsurgical method of female sterilization. Int J Gynaecol Obstet. 1980;18(4):275-9. [PubMed:6109672]
  4. Bhatt RV: Camp laparoscopic sterilization deaths in Gujarat State, India, 1978-1980. Asia Oceania J Obstet Gynaecol. 1991 Dec;17(4):297-301. [PubMed:1839351]
  5. Peterson HB, Lubell I, DeStefano F, Ory HW: The safety and efficacy of tubal sterilization: an international overview. Int J Gynaecol Obstet. 1983 Apr;21(2):139-44. [PubMed:6136433]
External Links
Human Metabolome Database
HMDB15235
KEGG Drug
D08179
KEGG Compound
C07339
PubChem Compound
237
PubChem Substance
46507828
ChemSpider
232
BindingDB
50015214
ChEBI
8711
ChEMBL
CHEMBL7568
Therapeutic Targets Database
DNC001181
PharmGKB
PA164745551
Wikipedia
Quinacrine
ATC Codes
P01AX05 — Mepacrine
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2Active Not RecruitingTreatmentColorectal Adenocarcinoma1
2CompletedTreatmentCreutzfeldt-Jakob Disease1
2CompletedTreatmentProstate Cancer1
2WithdrawnTreatmentRenal Cell Adenocarcinoma1
Not AvailableCompletedTreatmentPrion Disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
Not Available
Prices
Unit descriptionCostUnit
Quinacrine hcl powder8.11USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)248-250 °CNot Available
water solubilitySlightNot Available
logP5.5Not Available
pKa10.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00239 mg/mLALOGPS
logP6.13ALOGPS
logP5.15ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)10.33ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.39 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.96 m3·mol-1ChemAxon
Polarizability46.32 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.9253
Caco-2 permeable+0.596
P-glycoprotein substrateSubstrate0.8401
P-glycoprotein inhibitor IInhibitor0.7537
P-glycoprotein inhibitor IIInhibitor0.8526
Renal organic cation transporterInhibitor0.6497
CYP450 2C9 substrateNon-substrate0.8442
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.701
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9185
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9063
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5494
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.8806
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.8888 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.585
hERG inhibition (predictor II)Inhibitor0.8622
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0002-0009200000-6e09844cb8551172f45c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0002-0009200000-242960dc93e3658182f0
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0002-0019100000-85abeddd06ff2cce1fc9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0000900000-171d21b8fffe35f493d3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udl-0423900000-9f5ab94c444b1766bd01
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0934000000-afa177ceaf2f17c89180
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0964000000-cb8056f84bdb3a200fba
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0591000000-00e303f9525d62f012d4

Taxonomy

Description
This compound belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Benzoquinolines
Direct Parent
Acridines
Alternative Parents
Chloroquinolines / Anisoles / Alkyl aryl ethers / Pyridines and derivatives / Aryl chlorides / Secondary ketimines / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents
Acridine / Haloquinoline / Chloroquinoline / Anisole / Alkyl aryl ether / Aryl chloride / Aryl halide / Pyridine / Benzenoid / Secondary ketimine
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, aromatic ether, organochlorine compound, acridines (CHEBI:8711)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Intercalation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Hossain M, Giri P, Kumar GS: DNA intercalation by quinacrine and methylene blue: a comparative binding and thermodynamic characterization study. DNA Cell Biol. 2008 Feb;27(2):81-90. [PubMed:17924822]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Phospholipase a2 activity
Specific Function
Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukot...
Gene Name
PLA2G6
Uniprot ID
O60733
Uniprot Name
85/88 kDa calcium-independent phospholipase A2
Molecular Weight
89902.295 Da
References
  1. Nuttle LC, Ligon AL, Farrell KR, Hester RL: Inhibition of phospholipase A2 attenuates functional hyperemia in the hamster cremaster muscle. Am J Physiol. 1999 Apr;276(4 Pt 2):H1289-94. [PubMed:10199854]
  2. Sastry BV, Hemontolor ME, Vidaver PS, Sastry WS, Janson VE: Influence of halothane on phospholipase A2 and enzymatic methylations in the rat retinal membranes. J Ocul Pharmacol Ther. 1999 Apr;15(2):165-78. [PubMed:10229494]
  3. Lohmann CH, Sagun R Jr, Sylvia VL, Cochran DL, Dean DD, Boyan BD, Schwartz Z: Surface roughness modulates the response of MG63 osteoblast-like cells to 1,25-(OH)(2)D(3) through regulation of phospholipase A(2) activity and activation of protein kinase A. J Biomed Mater Res. 1999 Nov;47(2):139-51. [PubMed:10449625]
  4. Schwartz Z, Sylvia VL, Del Toro F, Hardin RR, Dean DD, Boyan BD: 24R,25-(OH)(2)D(3) mediates its membrane receptor-dependent effects on protein kinase C and alkaline phosphatase via phospholipase A(2) and cyclooxygenase-1 but not cyclooxygenase-2 in growth plate chondrocytes. J Cell Physiol. 2000 Mar;182(3):390-401. [PubMed:10653606]
  5. Sylvia VL, Del Toro F, Dean DD, Hardin RR, Schwartz Z, Boyan BD: Effects of 1alpha,25-(OH)(2)D(3) on rat growth zone chondrocytes are mediated via cyclooxygenase-1 and phospholipase A(2). J Cell Biochem Suppl. 2001;Suppl 36:32-45. [PubMed:11455568]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Phospholipase a2 activity
Specific Function
Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory...
Gene Name
PLA2G4A
Uniprot ID
P47712
Uniprot Name
Cytosolic phospholipase A2
Molecular Weight
85238.2 Da
References
  1. Hellstrand M, Eriksson E, Nilsson CL: Dopamine D(2) receptor-induced COX-2-mediated production of prostaglandin E(2) in D(2)-transfected Chinese hamster ovary cells without simultaneous administration of a Ca(2+)-mobilizing agent. Biochem Pharmacol. 2002 Jun 15;63(12):2151-8. [PubMed:12110374]
  2. Ong WY, Lu XR, Ong BK, Horrocks LA, Farooqui AA, Lim SK: Quinacrine abolishes increases in cytoplasmic phospholipase A2 mRNA levels in the rat hippocampus after kainate-induced neuronal injury. Exp Brain Res. 2003 Feb;148(4):521-4. Epub 2002 Dec 11. [PubMed:12582837]
  3. Kim BC, Kim JH: Exogenous C2-ceramide activates c-fos serum response element via Rac-dependent signalling pathway. Biochem J. 1998 Mar 1;330 ( Pt 2):1009-14. [PubMed:9480923]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Signal transducer activity
Specific Function
Involved in an inositol phospholipid-based intracellular signaling cascade. Shows no PLC activity to phosphatidylinositol 4,5-bisphosphate and phosphatidylinositol. Component in the phospho-depende...
Gene Name
PLCL1
Uniprot ID
Q15111
Uniprot Name
Inactive phospholipase C-like protein 1
Molecular Weight
122726.98 Da
References
  1. Biondi C, Pavan B, Ferretti ME, Corradini FG, Neri LM, Vesce F: Formyl-methionyl-leucyl-phenylalanine induces prostaglandin E2 release from human amnion-derived WISH cells by phospholipase C-mediated [Ca+]i rise. Biol Reprod. 2001 Mar;64(3):865-70. [PubMed:11207202]
  2. Takuwa N, Kumada M, Yamashita K, Takuwa Y: Mechanisms of bombesin-induced arachidonate mobilization in Swiss 3T3 fibroblasts. J Biol Chem. 1991 Aug 5;266(22):14237-43. [PubMed:1860838]
  3. Otamiri T: Phospholipase C-mediated intestinal mucosal damage is ameliorated by quinacrine. Food Chem Toxicol. 1989 Jun;27(6):399-402. [PubMed:2551803]
  4. Noveral JP, Grunstein MM: Tachykinin regulation of airway smooth muscle cell proliferation. Am J Physiol. 1995 Sep;269(3 Pt 1):L339-43. [PubMed:7573467]
  5. Bjoro T, Englund K, Torjesen PA, Haug E: Inhibitors of the arachidonic acid metabolism attenuate the thyroliberin (TRH) stimulated prolactin production without modifying the production of inositolphosphates in GH4C1 pituitary cells. Scand J Clin Lab Invest. 1993 Apr;53(2):111-6. [PubMed:8469910]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Histamine n-methyltransferase activity
Specific Function
Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name
HNMT
Uniprot ID
P50135
Uniprot Name
Histamine N-methyltransferase
Molecular Weight
33294.765 Da
References
  1. Grassmann S, Apelt J, Sippl W, Ligneau X, Pertz HH, Zhao YH, Arrang JM, Ganellin CR, Schwartz JC, Schunack W, Stark H: Imidazole derivatives as a novel class of hybrid compounds with inhibitory histamine N-methyltransferase potencies and histamine hH3 receptor affinities. Bioorg Med Chem. 2003 May 15;11(10):2163-74. [PubMed:12713826]
  2. Hui JY, Taylor SL: Inhibition of in vivo histamine metabolism in rats by foodborne and pharmacologic inhibitors of diamine oxidase, histamine N-methyltransferase, and monoamine oxidase. Toxicol Appl Pharmacol. 1985 Nov;81(2):241-9. [PubMed:3933141]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Sweet DH, Pritchard JB: rOCT2 is a basolateral potential-driven carrier, not an organic cation/proton exchanger. Am J Physiol. 1999 Dec;277(6 Pt 2):F890-8. [PubMed:10600936]
  2. Dohgu S, Yamauchi A, Takata F, Sawada Y, Higuchi S, Naito M, Tsuruo T, Shirabe S, Niwa M, Katamine S, Kataoka Y: Uptake and efflux of quinacrine, a candidate for the treatment of prion diseases, at the blood-brain barrier. Cell Mol Neurobiol. 2004 Apr;24(2):205-17. [PubMed:15176436]
  3. Beck WT, Cirtain MC, Glover CJ, Felsted RL, Safa AR: Effects of indole alkaloids on multidrug resistance and labeling of P-glycoprotein by a photoaffinity analog of vinblastine. Biochem Biophys Res Commun. 1988 Jun 30;153(3):959-66. [PubMed:2898941]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Tiberghien F, Loor F: Ranking of P-glycoprotein substrates and inhibitors by a calcein-AM fluorometry screening assay. Anticancer Drugs. 1996 Jul;7(5):568-78. [PubMed:8862725]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 13:09