General Information of Drug (ID: DR5137)
Drug Name
Latanoprost
Prodrug Info Latanoprost is the prodrug of Latanoprost acid
Synonyms
Catioprost; Xalatan; Latanoprost free acid; L1167_SIGMA; PhXA41; XA41; AR-202; Nova-21027; PHXA-41; XA-41; Xalatan (TN); Latanoprost (JAN/USAN/INN); PhXA34 [as 15(R,S)-isomer]; Isopropyl (5Z,9alpha,11alpha,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinorprost-5-en-1-oate; Isopropyl (5Z,9alpha,11alpha,15R)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate; Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate; Propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; Propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate
Indication Glaucoma [ICD11: 9C61] Approved [1]
Herpes simplex virus infection [ICD11: ICD11: 1F00] Investigative [2]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 432.6 Topological Polar Surface Area 87
Heavy Atom Count 31 Rotatable Bond Count 14
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5311221
ChEBI ID
CHEBI:6384
CAS Number
130209-82-4
TTD Drug ID
D0C6NM
Formula
C26H40O5
Canonical SMILES
CC(C)OC(=O)CCC/C=C\\C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
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
InChIKey
GGXICVAJURFBLW-CEYXHVGTSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Latanoprost acid DM015502
6441636
Hydrolysis - Esterase hydrolysis 1 [4]
1, 2-Dinor Latanoprost Acid DM016434
92135775
Oxidation - Oxidation 2 [4]
1,2,3,4 Tetranor Latanoprost Acid DM016439
100964109
Oxidation - Oxidation 3 [4]
1,2,3,4-Tetranor-lactone of Latanoprost DM016440
100964110
Unclear - Unclear 4 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007934 Latanoprost Latanoprost acid Hydrolysis - Esterase hydrolysis CES [4]
MR007935 Latanoprost acid 1, 2-Dinor Latanoprost Acid Oxidation - Oxidation Unclear [4]
MR007936 1, 2-Dinor Latanoprost Acid 1,2,3,4 Tetranor Latanoprost Acid Oxidation - Oxidation Unclear [4]
MR007937 1,2,3,4 Tetranor Latanoprost Acid 1,2,3,4-Tetranor-lactone of Latanoprost Unclear - Unclear Unclear [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase (CES) DMEN121 Homo sapiens Not Available Not Available [3]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1961).
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 344).
3 Latanoprost in the treatment of glaucoma
4 Ocular and systemic pharmacokinetics of latanoprost in humans

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