Home Other Building Blocks 4-Acridinecarboxamide, N-[4-[2-(3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-9,10-dihydro-5-methoxy-9-oxo-, hydrochloride (1:1)

4-Acridinecarboxamide, N-[4-[2-(3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-9,10-dihydro-5-methoxy-9-oxo-, hydrochloride (1:1)

CAS No.:
143851-98-3
Catalog Number:
AG001IHB
Molecular Formula:
C34H34ClN3O5
Molecular Weight:
600.1039
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
98%
1 week
United States
$183
- +
50mg
98%
1 week
United States
$471
- +
100mg
98%
1 week
United States
$790
- +
Product Description
Catalog Number:
AG001IHB
Chemical Name:
4-Acridinecarboxamide, N-[4-[2-(3,4-dihydro-6,7-dimethoxy-2(1H)-isoquinolinyl)ethyl]phenyl]-9,10-dihydro-5-methoxy-9-oxo-, hydrochloride (1:1)
CAS Number:
143851-98-3
Molecular Formula:
C34H34ClN3O5
Molecular Weight:
600.1039
MDL Number:
MFCD11040791
IUPAC Name:
N-[4-[2-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl]-5-methoxy-9-oxo-10H-acridine-4-carboxamide;hydrochloride
InChI:
InChI=1S/C34H33N3O5.ClH/c1-40-28-9-5-7-26-32(28)36-31-25(33(26)38)6-4-8-27(31)34(39)35-24-12-10-21(11-13-24)14-16-37-17-15-22-18-29(41-2)30(42-3)19-23(22)20-37;/h4-13,18-19H,14-17,20H2,1-3H3,(H,35,39)(H,36,38);1H
InChI Key:
IQOJZZHRYSSFJM-UHFFFAOYSA-N
SMILES:
COc1cc2CN(CCc3ccc(cc3)NC(=O)c3cccc4c3[nH]c3c(OC)cccc3c4=O)CCc2cc1OC.Cl
UNII:
NX2BHH1A5B
Properties
Complexity:
925  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
599.219g/mol
Formal Charge:
0
Heavy Atom Count:
43  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
600.112g/mol
Monoisotopic Mass:
599.219g/mol
Rotatable Bond Count:
8  
Topological Polar Surface Area:
89.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
Title Journal
Transport inhibition of digoxin using several common P-gp expressing cell lines is not necessarily reporting only on inhibitor binding to P-gp. PloS one 20130101
Oral availability and brain penetration of the B-RAFV600E inhibitor vemurafenib can be enhanced by the P-GLYCOprotein (ABCB1) and breast cancer resistance protein (ABCG2) inhibitor elacridar. Molecular pharmaceutics 20121105
Active efflux of Dasatinib from the brain limits efficacy against murine glioblastoma: broad implications for the clinical use of molecularly targeted agents. Molecular cancer therapeutics 20121001
Pharmacokinetic modeling to assess factors affecting the oral bioavailability of the lactone and carboxylate forms of the lipophilic camptothecin analogue AR-67 in rats. Pharmaceutical research 20120701
Exploiting transport activity of p-glycoprotein at the blood-brain barrier for the development of peripheral cannabinoid type 1 receptor antagonists. Molecular pharmaceutics 20120507
Stereoselective interaction of pantoprazole with ABCG2. I. Drug accumulation in rat milk. Drug metabolism and disposition: the biological fate of chemicals 20120501
Understanding the interplay of drug transporters involved in the disposition of rosuvastatin in the isolated perfused rat liver using a physiologically-based pharmacokinetic model. Xenobiotica; the fate of foreign compounds in biological systems 20120401
P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2) restrict brain accumulation of the active sunitinib metabolite N-desethyl sunitinib. The Journal of pharmacology and experimental therapeutics 20120401
Brain accumulation of sunitinib is restricted by P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2) and can be enhanced by oral elacridar and sunitinib coadministration. International journal of cancer 20120101
A comparative small-animal PET evaluation of [11C]tariquidar, [11C]elacridar and (R)-[11C]verapamil for detection of P-glycoprotein-expressing murine breast cancer. European journal of nuclear medicine and molecular imaging 20120101
ABCG2- and ABCG4-mediated efflux of amyloid-β peptide 1-40 at the mouse blood-brain barrier. Journal of Alzheimer's disease : JAD 20120101
Dual approach utilizing self microemulsifying technique and novel P-gp inhibitor for effective delivery of taxanes. Journal of microencapsulation 20120101
The influence of modulation of P-glycoprotein and /or cytochrome P450 3A on the pharmacokinetics and pharmacodynamics of orally administered morphine in dogs. Journal of veterinary pharmacology and therapeutics 20111001
Evaluation of the P-glycoprotein- and breast cancer resistance protein-mediated brain penetration of 11C-labeled topotecan using small-animal positron emission tomography. Nuclear medicine and biology 20110701
The bioflavonoid kaempferol is an Abcg2 substrate and inhibits Abcg2-mediated quercetin efflux. Drug metabolism and disposition: the biological fate of chemicals 20110301
Synthesis and in vivo evaluation of ¹⁸F-fluoroethyl GF120918 and XR9576 as positron emission tomography probes for assessing the function of drug efflux transporters. Bioorganic & medicinal chemistry 20110115
Intestinal absorption of HMG-CoA reductase inhibitor pitavastatin mediated by organic anion transporting polypeptide and P-glycoprotein/multidrug resistance 1. Drug metabolism and pharmacokinetics 20110101
Characterisation and manipulation of docetaxel resistant prostate cancer cell lines. Molecular cancer 20110101
P-glycoprotein and breast cancer resistance protein affect disposition of tandutinib, a tyrosine kinase inhibitor. Drug metabolism letters 20101201
The transport of gastrodin in Caco-2 cells and uptake in Bcap37 and Bcap37/MDR1 cells. Yao xue xue bao = Acta pharmaceutica Sinica 20101201
Hepatobiliary disposition of 3alpha,6alpha,7alpha,12alpha-tetrahydroxy-cholanoyl taurine: a substrate for multiple canalicular transporters. Drug metabolism and disposition: the biological fate of chemicals 20101001
Examination of the ability of the nasal administration route to confer a brain exposure advantage for three chemical inhibitors of P-glycoprotein. Journal of pharmaceutical sciences 20100701
Distribution of gefitinib to the brain is limited by P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2)-mediated active efflux. The Journal of pharmacology and experimental therapeutics 20100701
Toxicokinetics of the food-toxin IQ in human placental perfusion is not affected by ABCG2 or xenobiotic metabolism. Placenta 20100701
Dose-response assessment of tariquidar and elacridar and regional quantification of P-glycoprotein inhibition at the rat blood-brain barrier using (R)-[(11)C]verapamil PET. European journal of nuclear medicine and molecular imaging 20100501
Absorption barriers in the rat intestinal mucosa: 2. Application of physiologically based mathematical models to quantify mechanisms of drug permeation and metabolism. Journal of pharmaceutical sciences 20100201
Functional characterization of mouse organic anion transporting peptide 1a4 in the uptake and efflux of drugs across the blood-brain barrier. Drug metabolism and disposition: the biological fate of chemicals 20100101
The P-glycoprotein inhibitor GF120918 modulates Ca2+-dependent processes and lipid metabolism in Toxoplasma gondii. PloS one 20100101
Hepatitis C virus NS3 protease inhibitors: large, flexible molecules of peptide origin show satisfactory permeability across Caco-2 cells. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20091208
Investigation of the micellar effect of pluronic P85 on P-glycoprotein inhibition: cell accumulation and equilibrium dialysis studies. Journal of pharmaceutical sciences 20091101
Comparison of bidirectional lamivudine and zidovudine transport using MDCK, MDCK-MDR1, and Caco-2 cell monolayers. Journal of pharmaceutical sciences 20091101
Decreased urinary secretion of belotecan in folic acid-induced acute renal failure rats due to down-regulation of Oat1 and Bcrp. Xenobiotica; the fate of foreign compounds in biological systems 20091001
Multiple efflux pumps are involved in the transepithelial transport of colchicine: combined effect of p-glycoprotein and multidrug resistance-associated protein 2 leads to decreased intestinal absorption throughout the entire small intestine. Drug metabolism and disposition: the biological fate of chemicals 20091001
P-glycoprotein and breast cancer resistance protein influence brain distribution of dasatinib. The Journal of pharmacology and experimental therapeutics 20090901
Identification of novel specific and general inhibitors of the three major human ATP-binding cassette transporters P-gp, BCRP and MRP2 among registered drugs. Pharmaceutical research 20090801
Identification of the efflux transporter of the fluoroquinolone antibiotic ciprofloxacin in murine macrophages: studies with ciprofloxacin-resistant cells. Antimicrobial agents and chemotherapy 20090601
Brain accumulation of dasatinib is restricted by P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2) and can be enhanced by elacridar treatment. Clinical cancer research : an official journal of the American Association for Cancer Research 20090401
In vivo evaluation of P-glycoprotein and breast cancer resistance protein modulation in the brain using [(11)C]gefitinib. Nuclear medicine and biology 20090401
Substrate-dependent breast cancer resistance protein (Bcrp1/Abcg2)-mediated interactions: consideration of multiple binding sites in in vitro assay design. Drug metabolism and disposition: the biological fate of chemicals 20090301
The effect of P-gp (Mdr1a/1b), BCRP (Bcrp1) and P-gp/BCRP inhibitors on the in vivo absorption, distribution, metabolism and excretion of imatinib. Investigational new drugs 20090201
Cross-functioning between the extraneuronal monoamine transporter and multidrug resistance protein 1 in the uptake of adrenaline and export of 5-(glutathion-S-yl)adrenaline in rat cardiomyocytes. Chemical research in toxicology 20090101
Knocking down breast cancer resistance protein (Bcrp) by adenoviral vector-mediated RNA interference (RNAi) in sandwich-cultured rat hepatocytes: a novel tool to assess the contribution of Bcrp to drug biliary excretion. Molecular pharmaceutics 20090101
Molecular expression and functional evidence of a drug efflux pump (BCRP) in human corneal epithelial cells. Current eye research 20090101
N-(4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolinyl)ethyl]-phenyl)-9,10-dihydro-5-methoxy-9-oxo-4-acridine carboxamide (GF120918) as a chemical ATP-binding cassette transporter family G member 2 (Abcg2) knockout model to study nitrofurantoin transfer into milk. Drug metabolism and disposition: the biological fate of chemicals 20081201
Apparent differences in mechanisms of harmol sulfate biliary excretion in mice and rats. Drug metabolism and disposition: the biological fate of chemicals 20081101
A novel human multidrug resistance gene MDR1 variant G571A (G191R) modulates cancer drug resistance and efflux transport. The Journal of pharmacology and experimental therapeutics 20081101
Effect of the ABCB1 modulators elacridar and tariquidar on the distribution of paclitaxel in nude mice. Journal of cancer research and clinical oncology 20080501
Chemosensitivity determinants of irinotecan hydrochloride in hepatocellular carcinoma cell lines. Basic & clinical pharmacology & toxicology 20080401
P-glycoprotein restricts the penetration of oseltamivir across the blood-brain barrier. Drug metabolism and disposition: the biological fate of chemicals 20080201
Small P-gp modulating molecules: SAR studies on tetrahydroisoquinoline derivatives. Bioorganic & medicinal chemistry 20080101
P-glycoprotein-mediated active efflux of the anti-HIV1 nucleoside abacavir limits cellular accumulation and brain distribution. Drug metabolism and disposition: the biological fate of chemicals 20071101
Placental transfer of quetiapine in relation to P-glycoprotein activity. Journal of psychopharmacology (Oxford, England) 20070901
Modulation of the brain distribution of imatinib and its metabolites in mice by valspodar, zosuquidar and elacridar. Pharmaceutical research 20070901
Influence of breast cancer resistance protein (Abcg2) and p-glycoprotein (Abcb1a) on the transport of imatinib mesylate (Gleevec) across the mouse blood-brain barrier. Journal of neurochemistry 20070901
Abcg2/Bcrp1 mediates the polarized transport of antiretroviral nucleosides abacavir and zidovudine. Drug metabolism and disposition: the biological fate of chemicals 20070701
Influence of biophase distribution and P-glycoprotein interaction on pharmacokinetic-pharmacodynamic modelling of the effects of morphine on the EEG. British journal of pharmacology 20070701
Population pharmacokinetic modelling of non-linear brain distribution of morphine: influence of active saturable influx and P-glycoprotein mediated efflux. British journal of pharmacology 20070701
A phase I, randomized, open-label, parallel-cohort, dose-finding study of elacridar (GF120918) and oral topotecan in cancer patients. Clinical cancer research : an official journal of the American Association for Cancer Research 20070601
The emerging pharmacotherapeutic significance of the breast cancer resistance protein (ABCG2). British journal of pharmacology 20070501
Inhibitors of kinesin Eg5: antiproliferative activity of monastrol analogues against human glioblastoma cells. Cancer chemotherapy and pharmacology 20070201
Danofloxacin-mesylate is a substrate for ATP-dependent efflux transporters. British journal of pharmacology 20070201
Proteomic analysis to dissect mitoxantrone resistance-associated proteins in a squamous lung carcinoma. Anticancer research 20070101
An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers. Toxicology and applied pharmacology 20061201
Role of human placental efflux transporter P-glycoprotein in the transfer of buprenorphine, levo-alpha-acetylmethadol, and paclitaxel. American journal of perinatology 20061001
The complexity of intestinal absorption and exsorption of digoxin in rats. International journal of pharmaceutics 20060928
Differential in vivo sensitivity to inhibition of P-glycoprotein located in lymphocytes, testes, and the blood-brain barrier. The Journal of pharmacology and experimental therapeutics 20060601
Comparison of drug efflux transport kinetics in various blood-brain barrier models. Drug metabolism and disposition: the biological fate of chemicals 20060601
Saturable absorptive transport of the hydrophilic organic cation ranitidine in Caco-2 cells: role of pH-dependent organic cation uptake system and P-glycoprotein. Pharmaceutical research 20060601
Intestinal absorptive transport of the hydrophilic cation ranitidine: a kinetic modeling approach to elucidate the role of uptake and efflux transporters and paracellular vs. transcellular transport in Caco-2 cells. Pharmaceutical research 20060601
In vitro p-glycoprotein inhibition assays for assessment of clinical drug interaction potential of new drug candidates: a recommendation for probe substrates. Drug metabolism and disposition: the biological fate of chemicals 20060501
Interactions between the dopamine agonist, bromocriptine and the efflux protein, P-glycoprotein at the blood-brain barrier in the mouse. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20060201
Expression and functional activity of breast cancer resistance protein (BCRP, ABCG2) transporter in the human choriocarcinoma cell line BeWo. Clinical and experimental pharmacology & physiology 20060101
Role of P-glycoprotein in the hepatic metabolism of tacrolimus. Xenobiotica; the fate of foreign compounds in biological systems 20060101
The steady-state Michaelis-Menten analysis of P-glycoprotein mediated transport through a confluent cell monolayer cannot predict the correct Michaelis constant Km. Pharmaceutical research 20051001
A combined cell based approach to identify P-glycoprotein substrates and inhibitors in a single assay. International journal of pharmaceutics 20050914
Multiple mechanisms are involved in the biliary excretion of acetaminophen sulfate in the rat: role of Mrp2 and Bcrp1. Drug metabolism and disposition: the biological fate of chemicals 20050801
Functional role of P-glycoprotein in the human blood-placental barrier. Clinical pharmacology and therapeutics 20050801
The impact of pharmacologic and genetic knockout of P-glycoprotein on nelfinavir levels in the brain and other tissues in mice. Journal of pharmaceutical sciences 20050601
Flavonoid structure-activity studies identify 6-prenylchrysin and tectochrysin as potent and specific inhibitors of breast cancer resistance protein ABCG2. Cancer research 20050601
Expression, localization, and functional characteristics of breast cancer resistance protein in Caco-2 cells. Drug metabolism and disposition: the biological fate of chemicals 20050501
The effect of Bcrp1 (Abcg2) on the in vivo pharmacokinetics and brain penetration of imatinib mesylate (Gleevec): implications for the use of breast cancer resistance protein and P-glycoprotein inhibitors to enable the brain penetration of imatinib in patients. Cancer research 20050401
P-glycoprotein and mutlidrug resistance-associated proteins limit the brain uptake of saquinavir in mice. The Journal of pharmacology and experimental therapeutics 20050301
Differential sensitivities of the human ATP-binding cassette transporters ABCG2 and P-glycoprotein to cyclosporin A. Molecular pharmacology 20050301
Flavonoids chrysin and benzoflavone, potent breast cancer resistance protein inhibitors, have no significant effect on topotecan pharmacokinetics in rats or mdr1a/1b (-/-) mice. Drug metabolism and disposition: the biological fate of chemicals 20050301
Investigation of efflux transport of dehydroepiandrosterone sulfate and mitoxantrone at the mouse blood-brain barrier: a minor role of breast cancer resistance protein. The Journal of pharmacology and experimental therapeutics 20050101
Hepatobiliary disposition of the metabolically stable opioid peptide [D-Pen2, D-Pen5]-enkephalin (DPDPE): pharmacokinetic consequences of the interplay between multiple transport systems. The Journal of pharmacology and experimental therapeutics 20041201
Substrates and inhibitors of efflux proteins interfere with the MTT assay in cells and may lead to underestimation of drug toxicity. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20041001
Quantitative analysis of the P-glycoprotein inhibitor Elacridar (GF120918) in human and dog plasma using liquid chromatography with tandem mass spectrometric detection. Journal of mass spectrometry : JMS 20041001
Preclinical pharmacokinetic properties of the P-glycoprotein inhibitor GF120918A (HCl salt of GF120918, 9,10-dihydro-5-methoxy-9-oxo-N-[4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-isoquinolinyl)ethyl]phenyl]-4-acridine-carboxamide) in the mouse, rat, dog, and monkey. The Journal of pharmacology and experimental therapeutics 20040801
Efficacy of novel P-glycoprotein inhibitors to increase the oral uptake of paclitaxel in mice. Investigational new drugs 20040801
The systemic exposure of an N-methyl-D-aspartate receptor antagonist is limited in mice by the P-glycoprotein and breast cancer resistance protein efflux transporters. Drug metabolism and disposition: the biological fate of chemicals 20040701
P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharmaceutical research 20040701
Improved penetration of docetaxel into the brain by co-administration of inhibitors of P-glycoprotein. European journal of cancer (Oxford, England : 1990) 20040501
Cerebral uptake of mefloquine enantiomers with and without the P-gp inhibitor elacridar (GF1210918) in mice. British journal of pharmacology 20040401
Flavonoid permeability across an in situ model of the blood-brain barrier. Free radical biology & medicine 20040301
Reversal of breast cancer resistance protein-mediated drug resistance by tryprostatin A. International journal of cancer 20031210
Enhanced exposure of phosphatidylserine in human gastric carcinoma cells overexpressing the half-size ABC transporter BCRP (ABCG2). The Biochemical journal 20031201
Disposition of tacrolimus in isolated perfused rat liver: influence of troleandomycin, cyclosporine, and gg918. Drug metabolism and disposition: the biological fate of chemicals 20031101
Increased penetration of paclitaxel into the brain by inhibition of P-Glycoprotein. Clinical cancer research : an official journal of the American Association for Cancer Research 20030701
Effect of efflux inhibition on brain uptake of itraconazole in mice infected with Cryptococcus neoformans. Drug metabolism and disposition: the biological fate of chemicals 20030301
Assessing safety and efficacy of directed P-glycoprotein inhibition to improve the pharmacokinetic properties of saquinavir coadministered with ritonavir. The Journal of pharmacology and experimental therapeutics 20030201
A novel inhibitor of multidrug efflux pumps in Staphylococcus aureus. The Journal of antimicrobial chemotherapy 20030101
Evaluation of the permeation characteristics of a model opioid peptide, H-Tyr-D-Ala-Gly-Phe-D-Leu-OH (DADLE), and its cyclic prodrugs across the blood-brain barrier using an in situ perfused rat brain model. The Journal of pharmacology and experimental therapeutics 20021101
MDR1 modulators improve the chemotherapy response of human hepatoblastoma to doxorubicin in vitro. Journal of pediatric surgery 20021101
Induction of breast cancer resistance protein by the camptothecin derivative DX-8951f is associated with minor reduction of antitumour activity. British journal of cancer 20020909
Boosting bioavailability of topotecan: what do we gain? Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020701
Increased oral bioavailability of topotecan in combination with the breast cancer resistance protein and P-glycoprotein inhibitor GF120918. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020701
Effects of a P-glycoprotein inhibitor on brain and plasma concentrations of anti-human immunodeficiency virus drugs administered in combination in rats. Drug metabolism and disposition: the biological fate of chemicals 20020501
A mutation hot spot in the Bcrp1 (Abcg2) multidrug transporter in mouse cell lines selected for Doxorubicin resistance. Cancer research 20020415
Delineating the contribution of secretory transporters in the efflux of etoposide using Madin-Darby canine kidney (MDCK) cells overexpressing P-glycoprotein (Pgp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (cMOAT). Drug metabolism and disposition: the biological fate of chemicals 20020401
Unmasking the dynamic interplay between intestinal P-glycoprotein and CYP3A4. The Journal of pharmacology and experimental therapeutics 20020301
Anti-secretory properties of non-peptide somatostatin receptor agonists in isolated rat colon: luminal activity and possible interaction with P-glycoprotein. British journal of pharmacology 20020301
Bioanalysis and preliminary pharmacokinetics of the acridonecarboxamide derivative GF120918 in plasma of mice and humans by ion-pairing reversed-phase high-performance liquid chromatography with fluorescence detection. Journal of chromatography. B, Biomedical sciences and applications 20010805
Circumvention of breast cancer resistance protein (BCRP)-mediated resistance to camptothecins in vitro using non-substrate drugs or the BCRP inhibitor GF120918. Clinical cancer research : an official journal of the American Association for Cancer Research 20010401
Screening of multidrug-resistance sensitive drugs by in situ brain perfusion in P-glycoprotein-deficient mice. Pharmaceutical research 20010201
In vitro and in vivo reversal of P-glycoprotein-mediated multidrug resistance by a novel potent modulator, XR9576. Cancer research 20010115
Inhibition of BCRP-mediated drug efflux by fumitremorgin-type indolyl diketopiperazines. Bioorganic & medicinal chemistry letters 20010108
Co-administration of GF120918 significantly increases the systemic exposure to oral paclitaxel in cancer patients. British journal of cancer 20010101
[Possible structural-functional organization of the system of local cerebral blood flow regulation]. Fiziologicheskii zhurnal SSSR imeni I. M. Sechenova 19751001
Properties