Details of the Drug

General Information of Drug (ID: DMI5OXG)

Drug Name
Latanoprost
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
Disease Entry ICD 11 Status REF
Ocular hypertension 9C61.01 Approved [1]
Open-angle glaucoma 9C61 Approved [2]
OPTN-related open angle glaucoma N.A. Approved [1]
Glaucoma/ocular hypertension 9C61 Phase 2 [3]
Ocular disease 1F00.1Z Investigative [4]
Therapeutic Class
Antihypertensive Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 432.6
Logarithm of the Partition Coefficient (xlogp) 4.3
Rotatable Bond Count (rotbonds) 14
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 53 ng/L [5]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 5 min [5]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [6]
Clearance
The sytemic clearance of drug is 7 mL/min/kg [7]
Elimination
About 88% of the latanoprost dose is recovered in the urine after topical administration [8]
Half-life
The concentration or amount of drug in body reduced by one-half in 17 minutes (from the plasma), and 2C3 hours (from the eye) [9]
Metabolism
The drug is metabolized via the esterases to become a pharmacologically active drug [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.1% [10]
Vd
The volume of distribution (Vd) of drug is 0.16 +/- 0.02 L/kg [7]
Water Solubility
The ability of drug to dissolve in water is measured as 0.05 mg/mL [6]
Chemical Identifiers
Formula
C26H40O5
IUPAC Name
propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
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
Cross-matching ID
PubChem CID
5311221
ChEBI ID
CHEBI:6384
CAS Number
130209-82-4
DrugBank ID
DB00654
TTD ID
D0C6NM
VARIDT ID
DR00168
ACDINA ID
D01199
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin F2-alpha receptor (PTGFR) TTT2ZAR PF2R_HUMAN Agonist [11]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporting polypeptide 2A1 (SLCO2A1) DT021JD SO2A1_HUMAN Substrate [12]
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [12]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Ocular hypertension
ICD Disease Classification 9C61.01
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin F2-alpha receptor (PTGFR) DTT PTGFR 8.25E-02 -0.05 -0.14
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTP OATP2B1 6.30E-05 2.52E-01 5.88E-01
Organic anion transporting polypeptide 2A1 (SLCO2A1) DTP OATP2A1 3.03E-03 -9.85E-02 -3.19E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Hydrochloric acid E00015 313 Acidulant
Ricinoleic acid E00442 643684 Emollient; Emulsifying agent
Disodium hydrogenorthophosphate E00283 24203 Buffering agent; Complexing agent
Edetate disodium E00186 8759 Complexing agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Sodium chloride E00077 5234 Diluent; Tonicity agent
Sodium hydroxide E00234 14798 Alkalizing agent
Sodium phosphate monobasic monohydrate E00428 516949 Buffering agent; Complexing agent
Water E00035 962 Solvent
Boric acid E00152 7628 Antimicrobial preservative; Buffering agent
Sodium borate E00511 11954323 Alkalizing agent; Antimicrobial preservative; Buffering agent; Emulsifying agent
Polyoxyl 15 hydroxystearate E00659 Not Available Emulsifying agent; Solubilizing agent; Surfactant
⏷ Show the Full List of 12 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Latanoprost 0.005% solution 0.01% Solution Ophthalmic
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Latanoprost FDA Label
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. (Ligand id: 1961).
3 Clinical pipeline report, company report or official report of Mati therapeutics.
4 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).
5 Sunehag A, Tigas S, Haymond MW: Contribution of plasma galactose and glucose to milk lactose synthesis during galactose ingestion. J Clin Endocrinol Metab. 2003 Jan;88(1):225-9. doi: 10.1210/jc.2002-020768.
6 BDDCS applied to over 900 drugs
7 Xalatan FDA label
8 Sandoz Latanoprost monograph
9 Latanoprost in the treatment of glaucoma. Clin Ophthalmol. 2014 Sep 26;8:1967-85. doi: 10.2147/OPTH.S59162. eCollection 2014.
10 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
11 PGF(2alpha) FP receptor contributes to brain damage following transient focal brain ischemia. Neurotox Res. 2009 Jan;15(1):62-70.
12 The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost. Invest Ophthalmol Vis Sci. 2010 May;51(5):2504-11.
13 A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. Toxicol Sci. 2013 Nov;136(1):216-41.