Compound Detail

CHEMBL28079

ZAPRINAST

🧪 Phase II

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Research home View demo workspace

🧪 Phase II

CCCOc1ccccc1-c1nc2[nH]nnc2c(=O)[nH]1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL28079
Name	ZAPRINAST
Phase	Phase II
Structure Type	MOL
InChI Key	REZGGXNDEMKIQB-UHFFFAOYSA-N

Known Names

M&B 22948 M&B-22948 NSC-757885 Zaprinast

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

271.3

MW (Da)

1.50

ALogP

HBA

HBD

96.5

PSA (Å²)

0.75

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem

-ast

Extended Properties

Molecular Formula	C13H13N5O2
MW	271.28
Aromatic Rings	3
Heavy Atoms	20
NP-Likeness	-0.95

Activity Summary

IC50 59 meas. best 9.12

EC50 28 meas. best 9.15

Ki 7 meas. best 6.89

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
G-protein coupled receptor 35 CHEMBL1293267	EC50	9.15	6.2432	0.7	22
Unchecked CHEMBL612545	IC50	9.12	5.668	0.8	5
G-protein coupled receptor 35 CHEMBL1293267	IC50	7.32	6.03	48.1	4
G protein-coupled receptor GPR35 CHEMBL2390812	EC50	7.21	7.21	61.1	1
Unchecked CHEMBL612545	EC50	7.0	7.0	100.0	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	Ki	6.89	6.89	130.0	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	IC50	6.7	5.8936	200.0	14
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL3478	IC50	6.7	6.435	200.0	4
G-protein coupled receptor 35 CHEMBL1293267	Ki	6.4	6.305	401.0	2
Phosphodiesterase 6 CHEMBL2097163	Ki	6.4	6.4	400.0	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL2304402	IC50	6.12	6.12	760.0	1
G-protein coupled receptor 35 CHEMBL2390813	EC50	6.01	6.005	980.0	2
Phosphodiesterase 1 CHEMBL2095150	IC50	5.96	5.2225	1100.0	4
Phosphodiesterase 1 CHEMBL2097166	IC50	5.58	4.95	2600.0	3
Sus scrofa CHEMBL613488	EC50	5.32	5.32	4750.0	1
Plasmodium berghei CHEMBL612653	IC50	5.11	5.11	7790.0	1
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	Ki	5.06	5.06	8760.0	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL4567	EC50	5.05	5.05	9000.0	1
Phosphodiesterase 1 CHEMBL2111322	IC50	5.03	4.53	9400.0	2
Plasmodium falciparum CHEMBL364	IC50	5.0	4.7675	10000.0	4
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A CHEMBL2717	Ki	4.92	4.92	12000.0	1
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1C CHEMBL4619	IC50	4.89	4.89	13000.0	1
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A CHEMBL4409	IC50	4.66	4.66	22000.0	1
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A CHEMBL3535	Ki	4.46	4.46	35000.0	1
cGMP-dependent 3',5'-cyclic phosphodiesterase CHEMBL2652	IC50	4.33	4.185	46800.0	2
Phosphodiesterase 4 CHEMBL2093863	IC50	4.28	4.28	53000.0	1
Toxoplasma gondii CHEMBL612888	IC50	4.22	4.22	60000.0	1
cGMP-dependent 3',5'-cyclic phosphodiesterase CHEMBL4650	IC50	4.2	4.1	63100.0	2
Phosphodiesterase 4A CHEMBL3333	IC50	4.1	4.1	79600.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	28.0	mmHg hr-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
G-protein coupled receptor 35	EC50	=	0.71	nM	9.15	Agonist activity at GPR-35 in human HT-29 cells by DMR assay	37077394
Unchecked	IC50	=	0.76	nM	9.12	Inhibition of PDE5 (unknown origin)	35144038
G-protein coupled receptor 35	IC50	=	48.15	nM	7.32	Agonist activity at human GPR35 receptor expressed in CHO-K1 cells assessed as d...	33630609
G protein-coupled receptor GPR35	EC50	=	61.1	nM	7.21	Agonist activity at rat GPR35 expressed in CHO cells assessed as induction of be...	23713606
G-protein coupled receptor 35	EC50	=	62.83	nM	7.2	Agonist activity at human GPR35 receptor expressed in CHO-K1 cells assessed as d...	33630609
Unchecked	EC50	=	100.0	nM	7.0	Agonist activity at rat GPR35 by beta-arrestin recruitment assay	37976806
G-protein coupled receptor 35	EC50	=	110.0	nM	6.96	Agonist activity at GPR35 in human HT-29 cells assessed as induction of whole ce...	-
G-protein coupled receptor 35	EC50	=	130.0	nM	6.89	Agonist activity at human GPR35 by Ca+2 release assay	23888932
cGMP-specific 3',5'-cyclic phosphodiesterase	Ki	=	130.0	nM	6.89	Inhibition of human phosphodiesterase 5	15887951
G-protein coupled receptor 35	EC50	=	140.0	nM	6.85	Agonist activity at GPR35 in human HT-29 cells measured after 10 mins by dynamic...	24900508
G-protein coupled receptor 35	EC50	=	160.0	nM	6.8	Agonist activity at GPR35 receptor in human HT-29 cells after 10 mins by dynamic...	24900447
G-protein coupled receptor 35	EC50	=	160.0	nM	6.8	Agonist activity at GPR35 in human HT-29 cells after 1 hr by dynamic mass redist...	21950657
G-protein coupled receptor 35	EC50	=	160.0	nM	6.8	Agonist activity at GPR35 in human HT-29 cells by dynamic mass redistribution as...	22572579
G-protein coupled receptor 35	EC50	=	160.0	nM	6.8	Agonist activity at human GPR35 expressed in CHO-K1 cells by DMR assay	27976894
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	200.0	nM	6.7	Inhibition of Phosphodiesterase 5 from human	8648603
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	200.0	nM	6.7	Inhibitory activity against bovine PDE5 (phosphodiesterase-5).	14521414
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	300.0	nM	6.52	Inhibition of bovine aortic smooth muscle PDE5 using cGMP as substrate incubated...	31158744
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	300.0	nM	6.52	In vitro inhibition of phosphodiesterase (PDE V).	-
G-protein coupled receptor 35	EC50	=	340.0	nM	6.47	Agonist activity at GPR35 in human HT-29 cells by DMR assay	27976894
G-protein coupled receptor 35	EC50	=	340.0	nM	6.47	Agonist activity at human GPR35 receptor expressed in HT-29 cells assessed as dy...	33630609

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1039/C2MD20210G	G-protein coupled receptor 35	6
27976894	10.1021/acs.jmedchem.6b01431	G-protein coupled receptor 35	5
24900447	10.1021/ml2003058	G-protein coupled receptor 35	5
6292419	10.1021/jm00352a019	Unchecked	4
21950657	10.1021/jm200999f	G-protein coupled receptor 35	4
29795753	10.1021/acsmedchemlett.7b00510	G-protein coupled receptor 35	3
22572579	10.1016/j.bmcl.2012.04.057	G-protein coupled receptor 35	3
23713606	10.1021/jm400587g	G-protein coupled receptor 35	3
33630609	10.1021/acs.jmedchem.0c01624	G-protein coupled receptor 35	3
15715490	10.1021/jm030603w	3',5'-cyclic-AMP phosphodiesterase 4D	3
8648603	10.1021/jm950812j	cGMP-specific 3',5'-cyclic phosphodiesterase	2
-	10.1016/S0960-894X(96)00578-1	Unchecked	2
21504142	10.1021/jm1014617	Plasmodium falciparum	2
22380603	10.1021/jm2014666	ATP-binding cassette sub-family C member 5	2
23888932	10.1021/jm4009373	G-protein coupled receptor 35	2
29620890	10.1021/acs.jmedchem.8b00180	cGMP-specific 3',5'-cyclic phosphodiesterase	2
24900508	10.1021/ml300076u	G-protein coupled receptor 35	2
19734910	10.1038/nchembio.215	Plasmodium falciparum	2
8120866	10.1021/jm00030a007	Phosphodiesterase 4	2
21504142	10.1021/jm1014617	Unchecked	2

Data from ChEMBL 36 via Core Engine