latanoprostene bunod   Click here for help

GtoPdb Ligand ID: 9635

Synonyms: BOL-303259-X | NCX-116 | PF-3187207 | Vyzulta®
Approved drug
latanoprostene bunod is an approved drug (FDA (2017))
Compound class: Synthetic organic
Comment: Latanoprostene bunod is a NO-donating analogue of the prostaglandin F2α agonist latanoprost (isopropyl ester) [3]. This compound benefits from the additive hypotensive actions of both the prostaglandin agonist and NO. Latanoprostene bunod is the first NO-donating prostaglandin analogue to be granted FDA marketing approval [2,4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 19
Topological polar surface area 139.36
Molecular weight 507.28
XLogP 4.47
No. Lipinski's rules broken 1
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Canonical SMILES OC(CCc1ccccc1)CCC1C(O)CC(C1CC=CCCCC(=O)OCCCCO[N+](=O)[O-])O
Isomeric SMILES O[C@@H](CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C\CCCC(=O)OCCCCO[N+](=O)[O-])O
InChI InChI=1S/C27H41NO8/c29-22(15-14-21-10-4-3-5-11-21)16-17-24-23(25(30)20-26(24)31)12-6-1-2-7-13-27(32)35-18-8-9-19-36-28(33)34/h1,3-6,10-11,22-26,29-31H,2,7-9,12-20H2/b6-1-/t22-,23+,24+,25-,26+/m0/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2017))
IUPAC Name Click here for help
4-nitrooxybutyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
International Nonproprietary Names Click here for help
INN number INN
9629 latanoprostene bunod
Synonyms Click here for help
BOL-303259-X | NCX-116 | PF-3187207 | Vyzulta®
Database Links Click here for help
Specialist databases
GPCRdb Ligand latanoprostene bunod
Other databases
CAS Registry No. 860005-21-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL2364612
DrugCentral Ligand 5261
GtoPdb PubChem SID 340590265
PubChem CID 11156438
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UniChem Compound Search for chemical match using the InChIKey LOVMMUBRQUFEAH-UIEAZXIASA-N
UniChem Connectivity Search for chemical match using the InChIKey LOVMMUBRQUFEAH-UIEAZXIASA-N