LATANOPROSTENE BUNOD

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H41NO8
Molecular Weight	507.6163
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H](CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(=O)OCCCCO[N+]([O-])=O)CCC2=CC=CC=C2

InChI

InChIKey=LOVMMUBRQUFEAH-UIEAZXIASA-N

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

HIDE SMILES / InChI

Molecular Formula	C27H41NO8
Molecular Weight	507.6163
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020597s045s048lbl.pdfhttps://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207795Orig1s000lbl.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/9698288 | https://www.ncbi.nlm.nih.gov/pubmed/21788077
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/29194198 | https://clinicaltrials.gov/ct2/show/NCT01895972 | https://www.ncbi.nlm.nih.gov/pubmed/28783422 | https://clinicaltrials.gov/ct2/show/NCT01749904

Latanoprost (free acid) is a metabolite of latanoprost which has been approved for use as an ocular hypotensive drug. Latanoprost is an isopropyl ester prodrug which is converted to the Latanoprost-acid by endogenous esterase enzymes. The free acid is pharmacologically active and is 200 times more potent than latanoprost as an agonist of the human recombinant Prostaglandin F receptor. However, the free Latanoprost-acid is more irritating and less effective than Latanoprost when applied directly to the eyes of human glaucoma patients.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Prostaglandin F2-alpha receptor 12 Target ID: P43088 Gene ID: 5737.0 Gene Symbol: PTGFR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10634944	Agonist 2752	3.6 nM [EC50]
Prostanoid FP receptor 21 Target ID: CHEMBL1987 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9733584	Agonist 2752
Prostanoid FP receptor 21 Target ID: CHEMBL1987 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207795Orig1s000lbl.pdf	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Open-angle glaucoma 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207795Orig1s000lbl.pdf	Primary	Approved 8583	VYZULTA Approved Use VYZULTA is a prostaglandin analog indicated for the reduction of intraocular pressure in patients with open-angle glaucoma or ocular hypertension Launch Date 2017
Ocular hypertension 52 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207795Orig1s000lbl.pdf	Primary	Approved 8583	VYZULTA Approved Use VYZULTA is a prostaglandin analog indicated for the reduction of intraocular pressure in patients with open-angle glaucoma or ocular hypertension Launch Date 2017
Open-angle glaucoma 53 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207795Orig1s000lbl.pdf	Primary	Approved 8583	VYZULTA Approved Use YZULTA™ (latanoprostene bunod ophthalmic solution) 0.024% is indicated for the reduction of intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension. Launch Date 2017
Ocular hypertension 52 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/207795Orig1s000lbl.pdf	Primary	Approved 8583	VYZULTA Approved Use YZULTA™ (latanoprostene bunod ophthalmic solution) 0.024% is indicated for the reduction of intraocular pressure (IOP) in patients with open-angle glaucoma or ocular hypertension. Launch Date 2017
Open-angle glaucoma 53 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020597s045s048lbl.pdf	Palliative	Approved 8583	XALATAN Approved Use XALATAN Sterile Ophthalmic Solution is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Launch Date 1996
Ocular hypertension 52 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020597s045s048lbl.pdf	Primary	Approved 8583	XALATAN Approved Use XALATAN Sterile Ophthalmic Solution is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Launch Date 1996

C_max

Value	Dose	Co-administered	Analyte	Population
56.95 pg/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/207795Orig1s000ClinPharmR.pdf#page=21	2 drop 1 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
42.3 pg/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/207795Orig1s000ClinPharmR.pdf#page=21	2 drop 1 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
53 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12204697/	1.5 μg single, ocular dose: 1.5 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.0636 ng × eq/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	2.3 μg single, ocular dose: 2.3 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
12.43 ng × eq/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	216.1 μg single, intravenous dose: 216.1 μg route of administration: Intravenous experiment type: SINGLE co-administered:		LATANOPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.053 ng × eq/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	2.3 μg single, ocular dose: 2.3 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
11.6 ng × eq/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	216.1 μg single, intravenous dose: 216.1 μg route of administration: Intravenous experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
30.4 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000002/40007900_22200AMX00232_A100_1.pdf#page=12 \| https://www.pmda.go.jp/drugs/2010/P201000002/40007900_22200AMX00232000_K102_1.pdf#page=29	1.5 μg single, ocular dose: 1.5 μg route of administration: Ocular experiment type: SINGLE co-administered: TIMOLOL MALEATE	TIMOLOL MALEATE	LATANOPROST ACID aqueous humor	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
19.77 pg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_A100_1.pdf#page=11 \| https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_K100_1.pdf#page=130	2 drop 1 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
18.47 pg/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_A100_1.pdf#page=11 \| https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_K100_1.pdf#page=130	2 drop 1 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
7.15 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12204697/	3 μg/kg bw single, intravenous dose: 3 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
34 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12204697/	1.5 μg single, ocular dose: 1.5 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.165 ng × eq × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	2.3 μg single, ocular dose: 2.3 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
20.2 ng × eq × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	216.1 μg single, intravenous dose: 216.1 μg route of administration: Intravenous experiment type: SINGLE co-administered:		LATANOPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.0337 ng × eq × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	2.3 μg single, ocular dose: 2.3 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.15 ng × eq × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	216.1 μg single, intravenous dose: 216.1 μg route of administration: Intravenous experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
206 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000002/40007900_22200AMX00232_A100_1.pdf#page=12 \| https://www.pmda.go.jp/drugs/2010/P201000002/40007900_22200AMX00232000_K102_1.pdf#page=29	1.5 μg single, ocular dose: 1.5 μg route of administration: Ocular experiment type: SINGLE co-administered: TIMOLOL MALEATE	TIMOLOL MALEATE	LATANOPROST ACID aqueous humor	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.15 pg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_A100_1.pdf#page=11 \| https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_K100_1.pdf#page=130	2 drop 1 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.97 pg × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_A100_1.pdf#page=11 \| https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_K100_1.pdf#page=130	2 drop 1 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.6 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12204697/	3 μg/kg bw single, intravenous dose: 3 μg/kg bw route of administration: Intravenous experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
17 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12204697/	1.5 μg single, ocular dose: 1.5 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.842 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	2.3 μg single, ocular dose: 2.3 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.471 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	216.1 μg single, intravenous dose: 216.1 μg route of administration: Intravenous experiment type: SINGLE co-administered:		LATANOPROST plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
17 min OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	2.3 μg single, ocular dose: 2.3 μg route of administration: Ocular experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
16.6 min OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=40	216.1 μg single, intravenous dose: 216.1 μg route of administration: Intravenous experiment type: SINGLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.3 h OTHER GOV'T https://www.pmda.go.jp/drugs/2010/P201000002/40007900_22200AMX00232_A100_1.pdf#page=12 \| https://www.pmda.go.jp/drugs/2010/P201000002/40007900_22200AMX00232000_K102_1.pdf#page=29	1.5 μg single, ocular dose: 1.5 μg route of administration: Ocular experiment type: SINGLE co-administered: TIMOLOL MALEATE	TIMOLOL MALEATE	LATANOPROST ACID aqueous humor	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.3 h OTHER GOV'T https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_A100_1.pdf#page=11 \| https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_K100_1.pdf#page=130	2 drop 1 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.2 h OTHER GOV'T https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_A100_1.pdf#page=11 \| https://www.pmda.go.jp/drugs/2016/P20160921002/180078000_22800AMX00683_K100_1.pdf#page=130	2 drop 1 times / day multiple, ocular dose: 2 drop route of administration: Ocular experiment type: MULTIPLE co-administered:		LATANOPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
47% EXPERIMENT https://www.info.pmda.go.jp/go/interview/4/671450_1319817Q1020_4_1F.pdf#page=42			LATANOPROST plasma	Homo sapiens

Doses

Dose	Population	Adverse events
10 ug 1 times / day multiple, topical Highest studied dose Dose: 10 ug, 1 times / day Route: topical Route: multiple Dose: 10 ug, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1755739/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1755739/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf	Other AEs: Ocular discomfort, Hyperemia... Other AEs: Ocular discomfort (grade 1, 50%) Hyperemia (50%) Sources: https://pubmed.ncbi.nlm.nih.gov/1755739/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf
10 ug single, topical Highest studied dose Dose: 10 ug Route: topical Route: single Dose: 10 ug Sources: https://pubmed.ncbi.nlm.nih.gov/1755739/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1755739/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf	Other AEs: Hyperemia... Other AEs: Hyperemia (grade 2) Sources: https://pubmed.ncbi.nlm.nih.gov/1755739/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf
0.005 % 1 times / day multiple, topical Recommended Dose: 0.005 %, 1 times / day Route: topical Route: multiple Dose: 0.005 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf	Disc. AE: Eye irritation, Asthenopia... AEs leading to discontinuation/dose reduction: Eye irritation Asthenopia Eye pain Headache Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf
0.005 % 1 times / day multiple, topical Recommended Dose: 0.005 %, 1 times / day Route: topical Route: multiple Dose: 0.005 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf	Disc. AE: Cystoid macular edema, Iritis... AEs leading to discontinuation/dose reduction: Cystoid macular edema (0.2%) Iritis (0.2%) Meibomianitis (0.2%) Ocular hyperemia (0.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf
0.005 % 1 times / day multiple, topical Recommended Dose: 0.005 %, 1 times / day Route: topical Route: multiple Dose: 0.005 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf	Disc. AE: Conjuncitivitis, Ocular hyperemia... AEs leading to discontinuation/dose reduction: Conjuncitivitis (0.6%) Ocular hyperemia (0.6%) Eye pain (0.6%) Visual field defect (0.6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000MedR.pdf
0.005 % 1 times / day multiple, topical Recommended Dose: 0.005 %, 1 times / day Route: topical Route: multiple Dose: 0.005 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000StatR.pdf	unhealthy, mean age 63.1 years Health Status: unhealthy Age Group: mean age 63.1 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000StatR.pdf	Disc. AE: Iritis, Meibomianitis... AEs leading to discontinuation/dose reduction: Iritis (grade 2, 0.3%) Meibomianitis (grade 1, 0.3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2018/206185Orig1s000StatR.pdf
11 ug/kg multiple, topical MTD Dose: 11 ug/kg Route: topical Route: multiple Dose: 11 ug/kg Sources: https://www.ema.europa.eu/en/documents/referral/xalatan-article-29-paediatrics-chmp-assessment-report_en.pdf	unhealthy Health Status: unhealthy Sources: https://www.ema.europa.eu/en/documents/referral/xalatan-article-29-paediatrics-chmp-assessment-report_en.pdf	Sources: https://www.ema.europa.eu/en/documents/referral/xalatan-article-29-paediatrics-chmp-assessment-report_en.pdf
10 ug/kg single, intravenous Overdose Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020597s052lbl.pdf	healthy Health Status: healthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020597s052lbl.pdf	Other AEs: Abdominal pain, Dizziness... Other AEs: Abdominal pain Dizziness Fatigue Hot flushes Nausea Sweating Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020597s052lbl.pdf
0.024 % 1 times / day multiple, topical Recommended Dose: 0.024 %, 1 times / day Route: topical Route: multiple Dose: 0.024 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26875002/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/26875002/	Disc. AE: Cataract... AEs leading to discontinuation/dose reduction: Cataract (0.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/26875002/
0.024 % 1 times / day multiple, topical Recommended Dose: 0.024 %, 1 times / day Route: topical Route: multiple Dose: 0.024 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26875002/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/26875002/	Disc. AE: Conjunctival edema, Conjunctival irritation... AEs leading to discontinuation/dose reduction: Conjunctival edema (grade 1, 0.3%) Conjunctival irritation (grade 1, 0.3%) Scleritis (grade 3, 0.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/26875002/

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYPs 29 CYP450 25	CYP 303 OATP2B1 122 MRP1 113 MRP2 252 MRP5 41 P-gp 2052 BCRP 697	CYPs 17 CYP450 32

Drug as perpetrator

Target	Modality	Activity
CYPs 35	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/207795Orig1s000ClinPharmR.pdf Page: 9.0	no
CYP450 41	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf#page=342 Page: 342.0	unlikely
CYP450 41	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf#page=342 Page: 342.0	unlikely
CYPs 35	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/207795Orig1s000ClinPharmR.pdf Page: 9.0	unlikely

Drug as victim

Target	Modality	Activity
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/207795Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
P-gp 2052	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3096535/	no
BCRP 697	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3096535/	unlikely
OATP2B1 122	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20019365/ Page: 6.0	weak
MRP1 113	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3096535/	yes
MRP2 252	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3096535/	yes
MRP5 41	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3096535/	yes

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00BXFY	https://www.aablocks.com/goods/Goods/detail?id=AA00BXFY
Aaron Chemicals	AR00BY7Q	http://www.aaronchem.com/41639-83-2
Achemtek	0104-022891	http://www.achemtek.com/41639-83-2
AK Scientific, Inc. (AKSCI)	Z6154	http://www.aksci.com/item_detail.php?cat=Z6154
Alfa Chemistry	AP41639832-A	https://reagents.alfa-chemistry.com/product/latanoprost-related-compound-e-cas-41639-83-2-11264.html
Alfa Chemistry	AP41639832-B	https://reagents.alfa-chemistry.com/product/latanoprost-acid-cas-41639-83-2-11265.html
Ambinter	Amb15690628	http://www.ambinter.com/reference/15690628
Aurora Fine Chemicals LLC	A17.898.261	http://online.aurorafinechemicals.com/info?ID=A17.898.261
AvaChem Scientific	2038	http://www.avachem.com/productSearch.asp?2038
Chem Scene	CS-0068357	http://www.chemscene.com/41639-83-2.html
ChemMol	99087782	http://www.chemmol.com/chemmol/99087782.html
Chemspace	CSSB00020648370	https://chem-space.com/CSSB00020648370
eNovation Chemicals	D592348	https://www.enovationchem.com/ProductDetails.asp?ProductID=D592348
eNovation Chemicals	D758325	https://www.enovationchem.com/ProductDetails.asp?ProductID=D758325
Glentham Life Sciences	GL6689	http://www.glentham.com/products/product/GL6689/
iChemical	EBD26372	http://www.ichemical.com/products/41639-83-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01304996	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01304996
MedChem Express	HY-113756A	https://www.medchemexpress.com/latanoprost-acid.html
OChem	18671	http://www.ocheminc.com/index.php?act=psearch&pid=639L832
Sigma-Aldrich	1357533_USP	https://www.sigmaaldrich.com/catalog/product/usp/1357533?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	L1292_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/l1292?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S532544	http://www.smolecule.com/products/s532544
THE BioTek	bt-272608	https://www.thebiotek.com/product/inhibitors/bt-272608

PubMed

Title	Date	PubMed
Latanoprostene Bunod 0.024% in Subjects With Open-angle Glaucoma or Ocular Hypertension: Pooled Phase 3 Study Findings.	2018-01	29194198
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013-11	23956101
The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost.	2010-05	20019365
Outcome of raised intraocular pressure in uveitic eyes with and without a corticosteroid-induced hypertensive response.	2009-08	19403113
Efficacy and safety of latanoprost versus pilocarpine/timolol maleate fixed combination in patients with primary open-angle glaucoma or ocular hypertension.	2008-12	18721251
Comparison of the 24-hour intraocular pressure-lowering effects of latanoprost and dorzolamide/timolol fixed combination after 2 and 6 months of treatment.	2008-01	18166407
Comparison of the effects of bimatoprost and a fixed combination of latanoprost and timolol on circadian intraocular pressure.	2007-12	17459480
Latanoprost-related transient incontinence.	2007-06-02	17539800
24-Hour control with a latanoprost-timolol fixed combination vs timolol alone.	2006-11	17102001
Prospective comparative switch study from timolol 0.5% and latanoprost 0.005% to bimatoprost 0.03%.	2006-04-29	16644608
Syncope and falls due to timolol eye drops.	2006-04-22	16627515
A comparison of latanoprost monotherapy with a combination therapy of timolol/dorzolamide in patients with primary open-angle glaucoma.	2006	17416939
Diurnal intraocular pressure reduction with latanoprost 0.005% compared to timolol maleate 0.5% as monotherapy in subjects with exfoliation glaucoma.	2004-09	15002024
Latanoprost and brimonidine: therapeutic and physiologic assessment before and after oral nonsteroidal anti-inflammatory therapy.	2002-01	11755835
[Increased iris pigmentation after use of latanoprost in Japanese brown eyes].	2001-05	11406947
A randomized, comparative open-label study on the efficacy of latanoprost and timolol in steroid induced ocular hypertension after photorefractive keratectomy.	2000-11-09	11071027
Microvascular effects of selective prostaglandin analogues in the eye with special reference to latanoprost and glaucoma treatment.	2000-07	10785618
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.	2000-01-17	10634944
Comparison of the effect of latanoprost 0.005% and timolol 0.5% on the calculated ocular perfusion pressure in patients with normal-tension glaucoma.	1998-05	9625541
Effects of latanoprost and dipivefrin, alone or combined, on intraocular pressure and on blood-aqueous barrier permeability.	1998-04	9640189
Mechanism of prostaglandin E2-, F2alpha- and latanoprost acid-induced relaxation of submental veins.	1997-12-11	9537815
Additive ocular hypotensive effect of latanoprost and acetazolamide. A short-term study in patients with elevated intraocular pressure.	1997-09	9307648
The lack of respiratory effects of the ocular hypotensive drug latanoprost in patients with moderate-steroid treated asthma.	1997-02	9154286
A comparison of latanoprost and timolol in primary open-angle glaucoma and ocular hypertension. A 12-week study.	1996-08	8694726
Comparison of latanoprost and timolol in patients with ocular hypertension and glaucoma: a six-month masked, multicenter trial in the United States. The United States Latanoprost Study Group.	1996-01	8628544
Additive effect of latanoprost, a prostaglandin F2 alpha analogue, and timolol in patients with elevated intraocular pressure.	1994-12	7819171
Corneal permeability to and ocular metabolism of phenyl substituted prostaglandin esters in vitro.	1994-04	8022849
Interaction of PhXA41, a new prostaglandin analogue, with pilocarpine. A study on patients with elevated intraocular pressure.	1993-05	8489450

Patents

Sample Use Guides

In Vivo Use Guide

One drop in the affected eye(s) once daily in the evening.

Route of Administration: Other

In Vitro Use Guide

Latanoprost above concentrations of 3.125 mg/l can induce dose- and time-dependent morphological abnormality, growth retardation, viability decline, and plasma membrane permeability elevation of human corneal stromal (HCS) cells. Moreover, latanoprost can arrest the cell cycle of these cells at S phase and induce PS externalization, DNA fragmentation, and apoptotic body formation of the cells. Furthermore, latanoprost can induce activation of caspase-3, -8 and -9; disruption of MTP; downregulation of anti-apoptotic Bcl-2; upregulation of pro-apoptotic Bax; and cytoplasmic cytochrome c release

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:20:13 GMT 2025` Edited by `admin` on `Mon Mar 31 21:20:13 GMT 2025`
Record UNII	I6393O0922
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LATANOPROSTENE BUNOD

Official Name

English

latanoprostene bunod [INN]

Preferred Name

English

PF-3187207

Code

English

BOL-303259-X

Code

English

Latanoprostene bunod [WHO-DD]

Common Name

English

VYZULTA

Brand Name

English

NCX116

Code

English

LATANOPROSTENE BUNOD [ORANGE BOOK]

Common Name

English

4-(Nitrooxy)butyl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate

Systematic Name

English

LATANOPROSTENE BUNOD [MI]

Common Name

English

LATANOPROSTENE BUNOD [USAN]

Common Name

English

NCX-116

Code

English

Code System Code Type Description

WIKIPEDIA

Latanoprostene bunod