LATANOPROST

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Search structure


Trade Names	LATANOPROST XALATAN XELPROS
Synonyms	Latanoprost Latanoprost (isopropyl ester) Monopost PHXA-41 PHXA41 T-2345 T2345 XA-41 XA41 Xalatan Xelpros
Status
Molecule Category	Free-form
ATC	S01EE01
UNII	6Z5B6HVF6O
EPA CompTox	DTXSID1041057


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	GGXICVAJURFBLW-CEYXHVGTSA-N
Smiles	CC(C)OC(=O)CCC/C=C\C[C@@H]1[C@@H](CC[C@@H](O)CCc2ccccc2)[C@H](O)C[C@@H]1O
InChI	InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/b8-3-/t21-,22+,23+,24-,25+/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H40O5
Molecular Weight	432.6
AlogP	4.19
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	13.0
Polar Surface Area	86.99
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	31.0

Bioactivity

Mechanism of Action	Action	Reference
Prostanoid FP receptor agonist	AGONIST	FDA


Protein: Prostanoid FP receptor Description: Prostaglandin F2-alpha receptor Organism : Homo sapiens P43088 ENSG00000122420

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Ion channel Other ion channel Pore-forming toxins (proteins and peptides)	-	-	-	-	11
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	12900	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of CETP in rabbit serum at 10 uM after 1 hr by fluorescent cholesteryl esters transfer assay	Oryctolagus cuniculus	11.4 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	13.97 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	1.96 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	18.51 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	38.15 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	28.04 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	0.35 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-2.04 %

Related Entries

Cross References

Resources	Reference
ChEBI	6384
ChEMBL	CHEMBL1051
DrugBank	DB00654
DrugCentral	1551
FDA SRS	6Z5B6HVF6O
Human Metabolome Database	HMDB0014792
Guide to Pharmacology	1961
KEGG	D00356
PubChem	5311221
SureChEMBL	SCHEMBL24698
ZINC	ZINC000012468792

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).