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
Interaction of PhXA41, a new prostaglandin analogue, with pilocarpine. A study on patients with elevated intraocular pressure.	1993 May	8489450
Additive effect of latanoprost, a prostaglandin F2 alpha analogue, and timolol in patients with elevated intraocular pressure.	1994 Dec	7819171
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 Jan	8628544
Mechanism of prostaglandin E2-, F2alpha- and latanoprost acid-induced relaxation of submental veins.	1997 Dec 11	9537815
The lack of respiratory effects of the ocular hypotensive drug latanoprost in patients with moderate-steroid treated asthma.	1997 Feb	9154286
Effects of latanoprost and dipivefrin, alone or combined, on intraocular pressure and on blood-aqueous barrier permeability.	1998 Apr	9640189
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 May	9625541
Microvascular effects of selective prostaglandin analogues in the eye with special reference to latanoprost and glaucoma treatment.	2000 Jul	10785618
Diurnal intraocular pressure reduction with latanoprost 0.005% compared to timolol maleate 0.5% as monotherapy in subjects with exfoliation glaucoma.	2004 Sep	15002024
Syncope and falls due to timolol eye drops.	2006 Apr 22	16627515
Prospective comparative switch study from timolol 0.5% and latanoprost 0.005% to bimatoprost 0.03%.	2006 Jan-Feb	16644608
24-Hour control with a latanoprost-timolol fixed combination vs timolol alone.	2006 Nov	17102001
A comparison of latanoprost monotherapy with a combination therapy of timolol/dorzolamide in patients with primary open-angle glaucoma.	2006 Summer	17416939
Comparison of the effects of bimatoprost and a fixed combination of latanoprost and timolol on circadian intraocular pressure.	2007 Dec	17459480
Latanoprost-related transient incontinence.	2007 May-Jun	17539800
Efficacy and safety of latanoprost versus pilocarpine/timolol maleate fixed combination in patients with primary open-angle glaucoma or ocular hypertension.	2008 Dec	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 Jan	18166407
Outcome of raised intraocular pressure in uveitic eyes with and without a corticosteroid-induced hypertensive response.	2009 Aug	19403113
The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost.	2010 May	20019365
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.	2013 Nov	23956101
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

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