Compound Detail

CHEMBL192

SILDENAFIL

💊 Approved Drug

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

💊 Approved Drug

CCCc1nn(C)c2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(C)CC4)ccc3OCC)nc12

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL192
Name	SILDENAFIL
Phase	Approved
Structure Type	MOL
InChI Key	BNRNXUUZRGQAQC-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

HIP-0908 HIP0908 Sildenafil Sildenafilo UK-92480

Targets

200

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

474.6

MW (Da)

1.61

ALogP

HBA

HBD

113.4

PSA (Å²)

0.55

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1998
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product

USAN Stem	-afil
USAN Year	1997

Extended Properties

Molecular Formula	C22H30N6O4S
MW	474.59
Aromatic Rings	3
Heavy Atoms	33
NP-Likeness	-1.51

Indications

Erectile Dysfunction Erectile Dysfunction Arterial Occlusive Diseases beta-Thalassemia Coronary Vasospasm Diabetes Mellitus Eisenmenger Complex Glaucoma Heart Failure Heart Failure Hypertension Hypertension, Pulmonary Hypertension, Pulmonary Idiopathic Pulmonary Fibrosis Lung Diseases Peripheral Arterial Disease Persistent Fetal Circulation Syndrome Rectal Neoplasms Scleroderma, Systemic Brain Diseases

ATC Classification

G04BE03

sildenafil

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: UROLOGICALS

Activity Summary

IC50 174 meas. best 9.52

Ki 14 meas. best 8.8

EC50 12 meas. best 8.1

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL4567	IC50	9.52	9.11	0.3	2
Phosphodiesterase 6 CHEMBL2097163	IC50	9.3	8.08	0.5	4
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	IC50	9.0	8.3267	1.0	54
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL2304402	IC50	9.0	8.705	1.0	2
Unchecked CHEMBL612545	IC50	8.92	7.2725	1.2	20
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	Ki	8.8	8.6167	1.6	6
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL4567	Ki	8.74	8.74	1.8	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL3478	IC50	8.22	7.6533	6.0	6
Oryctolagus cuniculus CHEMBL374	EC50	8.1	8.1	7.9	1
cGMP-specific 3',5'-cyclic phosphodiesterase CHEMBL1827	EC50	8.06	7.1467	8.7	3
Corpus cavernosum CHEMBL4651287	EC50	8.06	7.415	8.7	2
Unchecked CHEMBL612545	EC50	7.72	6.33	19.0	2
Phosphodiesterase 6 CHEMBL2096979	IC50	7.7	7.476	19.8	5
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' CHEMBL3977	IC50	7.62	7.3175	24.0	4
PDE5A/PDE6C CHEMBL4523626	Ki	7.6	7.6	25.0	1
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' CHEMBL3479	IC50	7.48	7.48	33.0	1
Phosphodiesterase 6 CHEMBL2097163	Ki	7.3	7.3	50.0	1
Aorta CHEMBL4651286	EC50	7.25	6.91	56.2	2
Artery CHEMBL4296528	EC50	6.85	6.85	140.0	1
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha CHEMBL3741	IC50	6.85	6.85	140.0	1
Adenosine receptor A2a CHEMBL251	Ki	6.85	6.775	142.0	2
Adenosine receptor A2a CHEMBL251	IC50	6.6	6.6	253.0	1
Phosphodiesterase 1 CHEMBL2111322	IC50	6.58	6.55	260.0	2
Phosphodiesterase 1 CHEMBL2095150	IC50	6.57	6.2167	270.0	6
Phosphodiesterase 1 CHEMBL2097166	IC50	6.4	6.14	400.0	5
Dual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1A CHEMBL3421	IC50	6.22	6.22	600.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.09	6.09	806.0	1
Adenosine receptor A1 CHEMBL226	Ki	6.06	6.06	871.0	1
Corpus cavernosum CHEMBL4800705	EC50	6.0	6.0	1000.0	1
ATP-binding cassette sub-family C member 5 CHEMBL2046258	Ki	5.92	5.92	1200.0	1
Alpha-1B adrenergic receptor CHEMBL315	IC50	5.84	5.84	1457.0	1
Adenosine receptor A1 CHEMBL226	IC50	5.83	5.83	1493.0	1
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A CHEMBL2717	IC50	5.64	5.3843	2300.0	7
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A CHEMBL4409	IC50	5.51	5.3167	3100.0	3
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.48	4.938	3300.0	10
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A CHEMBL3535	IC50	5.47	5.3867	3400.0	3
Indoleamine 2,3-dioxygenase 2 CHEMBL2189159	IC50	5.35	5.35	4500.0	1
Phosphodiesterase 4 CHEMBL2094267	IC50	5.34	5.34	4600.0	1
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A CHEMBL3012	IC50	5.33	4.995	4690.0	2
3',5'-cyclic-AMP phosphodiesterase 4A CHEMBL254	IC50	5.3	5.3	5000.0	1
Phosphodiesterase 3 CHEMBL2094125	IC50	5.16	4.8375	7000.0	4
Phosphodiesterase 4 CHEMBL2093863	IC50	5.11	5.0533	7800.0	6
Phosphodiesterase 3B CHEMBL5129	IC50	5.04	5.04	9200.0	2
Bile salt export pump CHEMBL6020	IC50	4.78	4.78	16430.0	1
ATP-binding cassette sub-family C member 4 CHEMBL1743128	IC50	4.7	4.7	20000.0	1
3',5'-cyclic-AMP phosphodiesterase 4D CHEMBL288	IC50	4.7	4.7	20000.0	1
3',5'-cyclic-AMP phosphodiesterase 4B CHEMBL275	IC50	4.7	4.7	20000.0	1
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3A CHEMBL241	IC50	4.58	4.58	26000.0	1
cGMP-dependent 3',5'-cyclic phosphodiesterase CHEMBL3477	IC50	4.37	4.37	43000.0	1
cGMP-dependent 3',5'-cyclic phosphodiesterase CHEMBL2652	IC50	4.2	4.2	63000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	305.0	-	Oryctolagus cuniculus
CL	6.0	mL.min-1.kg-1	Homo sapiens
CL	9.1	mL.min-1.kg-1	Homo sapiens
CL	9.1	mL.min-1.kg-1	Homo sapiens
CL	9.1	mL.min-1.kg-1	Homo sapiens
CL	9.1	mL.min-1.kg-1	Homo sapiens
CL	16.6	uL.min-1.(10^6cells)-1	Homo sapiens
CL	131.83	mL.min-1.g-1	Homo sapiens
CL	150.0	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	89.9	mL.min-1.kg-1	Homo sapiens
CL	14.8	uL.min-1.(10^6cells)-1	Homo sapiens
CL	6.0	mL.min-1.kg-1	Homo sapiens
CL	258.2	mL.min-1.g-1	Rattus norvegicus
CL	462.69	mL.min-1.kg-1	Rattus norvegicus
CL	49.32	mL.min-1.kg-1	Rattus norvegicus
CL	258.2	mL.min-1.g-1	Rattus norvegicus
CL	462.69	mL.min-1.kg-1	Rattus norvegicus
CL	49.32	mL.min-1.kg-1	Rattus norvegicus
CL	30.5	mL.min-1.kg-1	Rattus norvegicus
Cmax	160.14	nM	Rattus norvegicus
F	11.0	%	Rattus norvegicus
F	15.0	%	Rattus norvegicus
F	54.0	%	Canis lupus familiaris
F	15.0	%	Rattus norvegicus
F	54.0	%	Canis lupus familiaris
F	40.0	%	Homo sapiens
F	23.0	%	Rattus norvegicus
F	23.0	%	Rattus norvegicus
F	34.0	%	Rattus norvegicus
Fu	0.04	-	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	0.3	nM	9.52	Inhibition of Phosphodiesterase 5 from rat diaphragm	12161123
Phosphodiesterase 6	IC50	=	0.5	nM	9.3	Inhibition of PDE6 (unknown origin) using FAM-cGMP as substrate after 60 mins by...	23313637
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.0	nM	9.0	Inhibition of human platelets PDE5	31158744
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.0	nM	9.0	Inhibitory activity against phosphodiesterase 5 (PDE5) isolated from canine lung	12824030
Unchecked	IC50	=	1.2	nM	8.92	Inhibition of human PDE5A1 D563A mutant expressed in Escherichia coli BL21 incub...	32794708
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.4	nM	8.85	Inhibition of human PDE5 using [3H]cGMP as substrate incubated for 10 mins by li...	36450167
cGMP-specific 3',5'-cyclic phosphodiesterase	Ki	=	1.6	nM	8.8	Inhibition of PDE5 (unknown origin)	30245400
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.6	nM	8.8	Inhibition of PDE5 (unknown origin)	25442307
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.6	nM	8.8	Inhibition of phosphodiesterase type 5 (PDE5) of human platelets	10753463
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.6	nM	8.8	Inhibition of PDE5 from human platelets	11549447
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.6	nM	8.8	Inhibition of PDE5 of human platelets	11297448
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.6	nM	8.8	In vitro inhibitory concentration against human platelet Phosphodiesterase 5 was...	11150175
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.6	nM	8.8	Inhibition of Phosphodiesterase 5 from human platelets	12570368
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.6	nM	8.8	Inhibition of phosphodiesterase 5 from human platelets	15006407
cGMP-specific 3',5'-cyclic phosphodiesterase	IC50	=	1.78	nM	8.75	Inhibition of phosphodiesterase 5 of rabbit platelets	15080987
cGMP-specific 3',5'-cyclic phosphodiesterase	Ki	=	1.8	nM	8.74	Inhibition of phosphodiesterase 5 in rat fetal lung fibroblast (RFL-6) cells	15771456
cGMP-specific 3',5'-cyclic phosphodiesterase	Ki	=	1.87	nM	8.73	Inhibitory activity against PDE5 from human corpus cavernosum	12639576
cGMP-specific 3',5'-cyclic phosphodiesterase	Ki	=	1.87	nM	8.73	Phosphodiesterase 5 activity of human corpus cavernosum	12213052
cGMP-specific 3',5'-cyclic phosphodiesterase	Ki	=	1.91	nM	8.72	Inhibitory activity against human Phosphodiesterase 5	14736245
cGMP-specific 3',5'-cyclic phosphodiesterase	Ki	=	1.91	nM	8.72	Inhibitory activity against Phosphodiesterase 5 (PDE5) was evaluated	12540243

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	746
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	63
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
25801159	10.1016/j.bmc.2015.03.005	Unchecked	11
31021628	10.1021/acs.jmedchem.9b00123	Unchecked	10
23313637	10.1016/j.ejmech.2012.12.009	Unchecked	10
20070106	10.1021/jm901371v	Homo sapiens	8
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
29549837	10.1016/j.ejmech.2018.03.005	Unchecked	7
31021628	10.1021/acs.jmedchem.9b00123	ADMET	7
30148362	10.1021/acs.jmedchem.8b01209	ADMET	6
31021628	10.1021/acs.jmedchem.9b00123	Rattus norvegicus	6
30916555	10.1021/acs.jmedchem.8b01041	ADMET	6
15771456	10.1021/jm0401098	Unchecked	6
27606546	10.1021/acs.jmedchem.6b00908	NON-PROTEIN TARGET	6
29505934	10.1016/j.ejmech.2018.02.039	Unchecked	6
-	10.6019/CHEMBL3301361	ADMET	6
19375311	10.1016/j.bmcl.2009.03.125	Unchecked	5

Data from ChEMBL 36 via Core Engine