Compound Detail

CHEMBL63

ROLIPRAM

🧪 Phase II

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🧪 Phase II

COc1ccc(C2CNC(=O)C2)cc1OC1CCCC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL63
Name	ROLIPRAM
Phase	Phase II
Structure Type	MOL
InChI Key	HJORMJIFDVBMOB-UHFFFAOYSA-N

Known Names

(r,s)-rolipram NSC-760125 Rolipram SB-95952 ZK 62 711 ZK-62711 ZK-62771

Targets

331

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

275.4

MW (Da)

2.62

ALogP

HBA

HBD

47.6

PSA (Å²)

0.92

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Racemic

Flags

Natural Product

USAN Year

1980

Extended Properties

Molecular Formula	C16H21NO3
MW	275.35
Aromatic Rings	1
Heavy Atoms	20
NP-Likeness	0.66

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Phosphodiesterase 4 inhibitor	INHIBITOR	Phosphodiesterase 4	✓	✓

Indications

Multiple Sclerosis Depressive Disorder Depressive Disorder, Major Huntington Disease Nervous System Diseases

Activity Summary

IC50 285 meas. best 9.51

Ki 30 meas. best 8.8

EC50 15 meas. best 7.58

Kd 1 meas. best 8.0

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Phosphodiesterase 4 CHEMBL2094267	IC50	9.51	7.685	0.3	18
Phosphodiesterase 4 CHEMBL2093863	Ki	8.8	7.8142	1.6	12
Unchecked CHEMBL612545	Ki	8.68	7.95	2.1	2
Unchecked CHEMBL612545	IC50	8.6	6.3312	2.5	26
Phosphodiesterase 4 CHEMBL2111373	IC50	8.4	8.4	4.0	3
3',5'-cyclic-AMP phosphodiesterase 4A CHEMBL254	IC50	8.4	6.9217	4.0	12
3',5'-cyclic-AMP phosphodiesterase 4B CHEMBL275	Ki	8.3	6.82	5.0	5
Phosphodiesterase 4 CHEMBL2093863	Kd	8.0	8.0	10.0	1
Phosphodiesterase 4 CHEMBL2094267	Ki	7.96	7.96	11.0	1
Phosphodiesterase 4 CHEMBL2093863	IC50	7.7	6.213	20.0	47
3',5'-cyclic-AMP phosphodiesterase 4B CHEMBL275	IC50	7.7	6.2846	20.0	52
Trachea CHEMBL4296541	EC50	7.58	7.3575	26.3	4
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	IC50	7.5	6.3786	31.6	69
Homo sapiens CHEMBL372	IC50	7.42	6.4414	37.9	7
Rattus norvegicus CHEMBL376	IC50	7.4	7.0	40.0	2
Zika virus CHEMBL4296612	IC50	7.35	7.35	44.6	1
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	Ki	7.23	6.2871	58.9	7
PBMC CHEMBL613107	IC50	7.22	6.2429	60.0	14
3',5'-cyclic-AMP phosphodiesterase 4C CHEMBL291	IC50	6.93	5.63	118.0	9
PBMC CHEMBL613107	EC50	6.89	6.89	130.0	1
Unchecked CHEMBL612545	EC50	6.88	6.675	131.5	2
3',5'-cyclic-AMP phosphodiesterase 4B CHEMBL275	EC50	6.8	6.73	160.0	2
Cavia porcellus CHEMBL369	IC50	6.8	6.635	160.0	2
RAW264.7 CHEMBL612557	IC50	6.72	6.72	190.0	1
Tumor necrosis factor CHEMBL1825	IC50	6.7	6.055	200.0	4
ADMET CHEMBL612558	IC50	6.51	6.4367	310.0	3
ADMET CHEMBL612558	EC50	6.5	6.5	320.0	1
3',5'-cyclic-AMP phosphodiesterase 4A CHEMBL254	EC50	6.3	5.94	500.0	2
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	EC50	6.17	6.065	670.0	2
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	IC50	6.14	6.14	720.0	1
U-937 CHEMBL612794	IC50	5.95	5.93	1120.0	3
U-937 CHEMBL612794	EC50	5.91	5.91	1230.0	1
Blood CHEMBL613416	IC50	5.83	5.83	1476.0	1
3',5'-cyclic-AMP phosphodiesterase 4B CHEMBL3382	IC50	5.57	5.57	2700.0	1
Phosphodiesterase 4A CHEMBL3333	IC50	5.44	5.44	3630.0	1
3',5'-cyclic-AMP phosphodiesterase 4A CHEMBL254	Ki	5.1	5.1	7940.0	1
Phosphodiesterase, PDE1/PDE5 CHEMBL2097161	IC50	4.02	4.02	94900.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Phosphodiesterase 4	IC50	=	0.31	nM	9.51	Inhibitory activity against purified rat liver phosphodiesterase 4	12824033
Phosphodiesterase 4	Ki	=	1.6	nM	8.8	Inhibition of rolipram binding to PDE4 from human neutrophils	11012037
Phosphodiesterase 4	Ki	=	1.6	nM	8.8	Inhibition of rolipram binding to PDE4	11140727
Phosphodiesterase 4	Ki	=	1.6	nM	8.8	Inhibition of rolipram binding to Phosphodiesterase 4	11738561
Phosphodiesterase 4	IC50	=	2.0	nM	8.7	Binding affinity to rolipram binding site in isolated rat brain by rolipram bind...	11266153
Unchecked	Ki	=	2.1	nM	8.68	Displacement of [3H]Rolipram from rolipram binding site in Wistar rat brain afte...	23403082
Unchecked	IC50	=	2.512	nM	8.6	Displacement of [3H]-Rolipram from full-length recombinant human PDE4 expressed ...	35144038
Phosphodiesterase 4	IC50	=	2.6	nM	8.59	Displacement of [3H]rolipram binding to Phosphodiesterase 4 in rat brain	1995886
Phosphodiesterase 4	IC50	=	2.6	nM	8.59	Inhibition of [3H]- rolipram binding to phosphodiesterase 4 of rat cerebral cort...	1992129
Phosphodiesterase 4	Ki	=	3.8	nM	8.42	Inhibition of rolipram binding to phosphodiesterase 4	12824031
Phosphodiesterase 4	Ki	=	3.8	nM	8.42	Displacement of [3H]- rolipram binding to guinea pig brain	10090791
Phosphodiesterase 4	IC50	=	4.0	nM	8.4	Displacement of [3H]-Rolipram from mouse brain homogenates	-
3',5'-cyclic-AMP phosphodiesterase 4A	IC50	=	4.0	nM	8.4	Inhibition of recombinant human PDE4A expressed in Sf9 cells	11052785
Phosphodiesterase 4	IC50	=	4.0	nM	8.4	Displacement of [3H]rolipram from mouse brain homogenates	8568798
Phosphodiesterase 4	IC50	=	4.0	nM	8.4	Inhibition of [3H]rolipram binding to Phosphodiesterase 4 (PDE IV)	-
Phosphodiesterase 4	Ki	=	4.5	nM	8.35	Affinity for rolipram binding site of phosphodiesterase type IV (PDE4)	9873675
Phosphodiesterase 4	Ki	=	4.5	nM	8.35	Inhibition of rolipram binding to Phosphodiesterase 4	9871649
Phosphodiesterase 4	Ki	=	4.5	nM	8.35	Binding affinity against PDE4 was determined using [3H]- rolipram in guinea pig ...	9873449
3',5'-cyclic-AMP phosphodiesterase 4B	Ki	=	5.0	nM	8.3	Binding affinity to human recombinant full length PDE4B	33412421
Phosphodiesterase 4	IC50	=	5.0	nM	8.3	Binding affinity against high affinity rolipram binding site (HARBS) was determi...	10636238

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	175
38156615	10.1021/acs.jmedchem.3c02087	Mus musculus	22
19827751	10.1021/jm900977c	3',5'-cyclic-AMP phosphodiesterase 4D	11
16263279	10.1016/j.bmcl.2005.10.026	3',5'-cyclic-AMP phosphodiesterase 4D	9
22891752	10.1021/jm300514y	Mus musculus	9
33022582	10.1016/j.ejmech.2020.112854	Mus musculus	8
11266153	10.1016/s0960-894x(00)00681-8	Phosphodiesterase 4	8
18686943	10.1021/jm800582j	3',5'-cyclic-AMP phosphodiesterase 4D	8
34311158	10.1016/j.ejmech.2021.113700	U-251	8
34311158	10.1016/j.ejmech.2021.113700	A549	8
8201604	10.1021/jm00037a021	Cavia porcellus	7
30553143	10.1016/j.ejmech.2018.12.013	Mus musculus	7
18686943	10.1021/jm800582j	3',5'-cyclic-AMP phosphodiesterase 4B	6
8709099	10.1021/jm9509096	Cavia porcellus	6
18686943	10.1021/jm800582j	Phosphodiesterase 4	6
24794103	10.1016/j.bmcl.2014.04.052	Mustela putorius furo	5
-	10.1039/C2MD00273F	Danio rerio	5
25126889	10.1021/jm500855w	3',5'-cyclic-AMP phosphodiesterase 4D	5
19303290	10.1016/j.bmcl.2009.03.007	PBMC	5
29432948	10.1016/j.ejmech.2018.01.049	PBMC	5

Data from ChEMBL 36 via Core Engine