SILDENAFIL CITRATE

Search structure
Trade Names:
Synonyms:
Status: Approved (1998)
Entry Type: Small molecule
Molecule Category: Salt
UNII: BW9B0ZE037
Parent Compound: SILDENAFIL

Structure
InChI Key DEIYFTQMQPDXOT-UHFFFAOYSA-N
Smile CCCc1nn(C)c2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(C)CC4)ccc3OCC)nc12.O=C(O)CC(O)(CC(=O)O)C(=O)O
InChI
InChI=1S/C22H30N6O4S.C6H8O7/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

Physicochemical Descriptors

Property Name Value
Molecular Formula C28H38N6O11S
Molecular Weight 666.71
AlogP 1.61
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 113.42
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 33.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Phosphodiesterase 5A inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 5 Phosphodiesterase 5A
- 2-5 - - 13-91
Enzyme Phosphodiesterase Phosphodiesterase 6 Phosphodiesterase 6C
- - - - 8-85
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 26800 - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Heart Failure 3 D006333 ClinicalTrials
Raynaud Disease 3 D011928 ClinicalTrials
Scleroderma, Diffuse 3 D045743 ClinicalTrials
Scleroderma, Limited 3 D045745 ClinicalTrials
Fetal Growth Retardation 3 D005317 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Brain Injuries 2 D001930 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Hypertension 2 D006973 ClinicalTrials
Infertility 2 D007246 ClinicalTrials
Pre-Eclampsia 2 D011225 ClinicalTrials
Waldenstrom Macroglobulinemia 2 D008258 ClinicalTrials
Pulmonary Edema 2 D011654 ClinicalTrials
Post-Concussion Syndrome 2 D038223 ClinicalTrials
Emphysema 2 D004646 ClinicalTrials
Brain Concussion 2 D001924 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Macular Degeneration 2 D008268 ClinicalTrials
Hand-Foot Syndrome 1 D060831 ClinicalTrials
Persistent Fetal Circulation Syndrome 1 D010547 ClinicalTrials
Hepatitis C 1 D006526 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Stroke 1 D020521 ClinicalTrials
Hypoxia-Ischemia, Brain 1 D020925 ClinicalTrials
Dysmenorrhea 1 D004412 ClinicalTrials
Wilms Tumor 1 D009396 ClinicalTrials

Related Entries

Scaffolds

Parent

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
20.94
Injury, poisoning and procedural complications
9.59
Nervous system disorders
8.16
Reproductive system and breast disorders
7.3
Respiratory, thoracic and mediastinal disorders
6.31
Psychiatric disorders
6.19
Vascular disorders
5.72
Cardiac disorders
4.98
Skin and subcutaneous tissue disorders
4.95
Musculoskeletal and connective tissue disorders
3.46
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
3.36
Eye disorders
3.35
Gastrointestinal disorders
2.99
Investigations
2.78
Infections and infestations
2.39

Cross References

Resources Reference
ChEBI 58987
ChEMBL CHEMBL1737
EPA CompTox DTXSID4046076
FDA SRS BW9B0ZE037
Guide to Pharmacology 4743
KEGG C07259
PDB VIA
PubChem 135413523
SureChEMBL SCHEMBL33982
ZINC ZINC19796168
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