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Details

Stereochemistry ACHIRAL
Molecular Formula C23H28N8O4
Molecular Weight 480.5196
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COPANLISIB

SMILES

COC1=C2N=C(NC(=O)C3=CN=C(N)N=C3)N4CCN=C4C2=CC=C1OCCCN5CCOCC5

InChI

InChIKey=PZBCKZWLPGJMAO-UHFFFAOYSA-N
InChI=1S/C23H28N8O4/c1-33-19-17(35-10-2-6-30-8-11-34-12-9-30)4-3-16-18(19)28-23(31-7-5-25-20(16)31)29-21(32)15-13-26-22(24)27-14-15/h3-4,13-14H,2,5-12H2,1H3,(H2,24,26,27)(H,28,29,32)

HIDE SMILES / InChI

Molecular Formula C23H28N8O4
Molecular Weight 480.5196
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Copanlisib, developed by Bayer, is a phosphoinositide 3-kinase (PI3K) inhibitor with potential antineoplastic activity. Copanlisib inhibits the activation of the PI3K signaling pathway, which may result in inhibition of tumor cell growth and survival in susceptible tumor cell populations. Activation of the PI3K signaling pathway is frequently associated with tumorigenesis and dysregulated PI3K signaling may contribute to tumor resistance to a variety of antineoplastic agents. Copanlisib is currently under Phase II/III clinical trials for the treatment of non-Hodgkin lymphoma and chronic lymphocytic leukemia.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
BAY 80-6946 is a highly selective intravenous PI3K inhibitor with potent p110α and p110δ activities in tumor cell lines and xenograft models.
2013 Nov
Preliminary results of a phase II study of single agent Bay 80-6946, a Novel PI3K inhibitor, in patients with relapsed/refractory, indolent or aggressive lymphoma.
2014 Feb
Patents

Sample Use Guides

In Vivo Use Guide
60 mg in solution administered intravenously on Days 1, 8 and 15 of each 28-day treatment cycle
Route of Administration: Oral
In Vitro Use Guide
Several breast cancer, endometrial cancer, and hematologic tumor cell lines were particularly sensitive to Copanlisib, with IC50 values less than 10nmol/L
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:50:08 UTC 2019
Edited
by admin
on Mon Oct 21 20:50:08 UTC 2019
Record UNII
WI6V529FZ9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COPANLISIB
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
2-AMINO-N-(7-METHOXY-8-(3-(MORPHOLIN-4-YL)PROPOXY)-2,3-DIHYDROIMIDAZO(1,2-C)QUINAZOLIN-5-YL(PYRIMIDINE-5-CARBOXAMIDE
Common Name English
COPANLISIB [WHO-DD]
Common Name English
BAY-80-6946
Code English
2-AMINO-N-(7-METHOXY-8-(3-MORPHOLIN-4-YLPROPOXY)-2,3-DIHYDROIMIDAZO(1,2-C)QUINAZOLIN-5-YL)PYRIMIDINE-5-CARBOXAMIDE
Systematic Name English
BAY80-6946
Code English
COPANLISIB [INN]
Common Name English
5-PYRIMIDINECARBOXAMIDE, 2-AMINO-N-(2,3-DIHYDRO-7-METHOXY-8-(3-(4-MORPHOLINYL)PROPOXY)IMIDAZO(1,2-C)QUINAZOLIN-5-YL)-
Systematic Name English
BAY 80-6946
Code English
COPANLISIB [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
FDA ORPHAN DRUG 463314
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
WHO-ATC L01XX61
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
FDA ORPHAN DRUG 552416
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
NCI_THESAURUS C2152
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
FDA ORPHAN DRUG 552616
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
NDF-RT N0000175605
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
FDA ORPHAN DRUG 552516
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
EU-Orphan Drug EU/3/18/2064
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C96796
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
PRIMARY
PUBCHEM
24989044
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
PRIMARY
WIKIPEDIA
Copanlisib
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
PRIMARY
EVMPD
SUB184952
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
PRIMARY
ChEMBL
CHEMBL3218576
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
PRIMARY
CAS
1032568-63-0
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
PRIMARY
INN
9726
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
PRIMARY
EPA CompTox
1032568-63-0
Created by admin on Mon Oct 21 20:50:09 UTC 2019 , Edited by admin on Mon Oct 21 20:50:09 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
<10% OF METABOLISM
MINOR
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
90% OF METABOLISM
MAJOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
IC50
BINDER->LIGAND
BINDING
TRANSPORTER -> SUBSTRATE
TARGET -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
(DEALKYLATION BY CYP3A4), The six healthy male volunteers received a single i.v. infusion of 12 mg copanlisib (2.76 MBq (14C)copanlisib) in a total volume of 40 mL as a 1-h infusion in the morning, 1-h after a light breakfast. 5 Caucasians and 1 Asian with an age 54.8 +/- 5.2 yeas (mean +/- SD, range: 47-61 years) and a BMI of 24.8 kg/m^2. Non-smokers and reported at the most light alcohol use.
AMOUNT EXCRETED
FECAL; URINE
METABOLITE -> PARENT
(DEALKYLATION BY CYP3A4), The six healthy male volunteers received a single i.v. infusion of 12 mg copanlisib (2.76 MBq (14C)copanlisib) in a total volume of 40 mL as a 1-h infusion in the morning, 1-h after a light breakfast. 5 Caucasians and 1 Asian with an age 54.8 +/- 5.2 yeas (mean +/- SD, range: 47-61 years) and a BMI of 24.8 kg/m^2. Non-smokers and reported at the most light alcohol use.
AMOUNT EXCRETED
FECAL; URINE
METABOLITE -> PARENT
(DEALKYLATION BY CYP3A4), The six healthy male volunteers received a single i.v. infusion of 12 mg copanlisib (2.76 MBq (14C)copanlisib) in a total volume of 40 mL as a 1-h infusion in the morning, 1-h after a light breakfast. 5 Caucasians and 1 Asian with an age 54.8 +/- 5.2 yeas (mean +/- SD, range: 47-61 years) and a BMI of 24.8 kg/m^2. Non-smokers and reported at the most light alcohol use.
AMOUNT EXCRETED
FECAL; URINE
METABOLITE -> PARENT
(DEALKYLATION BY CYP3A4), The six healthy male volunteers received a single i.v. infusion of 12 mg copanlisib (2.76 MBq (14C)copanlisib) in a total volume of 40 mL as a 1-h infusion in the morning, 1-h after a light breakfast. 5 Caucasians and 1 Asian with an age 54.8 +/- 5.2 yeas (mean +/- SD, range: 47-61 years) and a BMI of 24.8 kg/m^2. Non-smokers and reported at the most light alcohol use.
AMOUNT EXCRETED
FECAL; URINE
Related Record Type Details
ACTIVE MOIETY
The six healthy male volunteers received a single i.v. infusion of 12 mg copanlisib (2.76 MBq (14C)copanlisib) in a total volume of 40 mL as a 1-h infusion in the morning, 1-h after a light breakfast. 5 Caucasians and 1 Asian with an age 54.8 +/- 5.2 yeas (mean +/- SD, range: 47-61 years) and a BMI of 24.8 kg/m^2. Non-smokers and reported at the most light alcohol use.
AMOUNT EXCRETED
FECAL; PLASMA; URINE
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC