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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Agonist 2,752	3.6 nM [EC50]
Prostanoid FP receptor 21	Agonist 2,752
Prostanoid FP receptor 21	Agonist 2,752

Conditions

Condition	Modality	Highest Phase	Product
Open-angle glaucoma 53	Primary	Approved 8,583	VYZULTA
Ocular hypertension 52	Primary	Approved 8,583	VYZULTA
Open-angle glaucoma 53	Primary	Approved 8,583	VYZULTA
Ocular hypertension 52	Primary	Approved 8,583	VYZULTA
Open-angle glaucoma 53	Palliative	Approved 8,583	XALATAN
Ocular hypertension 52	Primary	Approved 8,583	XALATAN

C_max

Value	Dose	Co-administered	Analyte	Population
56.95 pg/mL	2 drop 1 times / day multiple, ocular		LATANOPROST ACID plasma	Homo sapiens
42.3 pg/mL	2 drop 1 times / day multiple, ocular		LATANOPROST ACID plasma	Homo sapiens
53 pg/mL	1.5 μg single, ocular		LATANOPROST ACID plasma	Homo sapiens
0.0636 ng × eq/mL	2.3 μg single, ocular		LATANOPROST plasma	Homo sapiens
12.43 ng × eq/mL	216.1 μg single, intravenous		LATANOPROST plasma	Homo sapiens
0.053 ng × eq/mL	2.3 μg single, ocular		LATANOPROST ACID plasma	Homo sapiens
11.6 ng × eq/mL	216.1 μg single, intravenous		LATANOPROST ACID plasma	Homo sapiens
30.4 ng/mL	1.5 μg single, ocular	TIMOLOL MALEATE	LATANOPROST ACID aqueous humor	Homo sapiens
19.77 pg/mL	2 drop 1 times / day multiple, ocular		LATANOPROST ACID plasma	Homo sapiens
18.47 pg/mL	2 drop 1 times / day multiple, ocular		LATANOPROST ACID plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
7.15 ng × h/mL	3 μg/kg bw single, intravenous		LATANOPROST ACID plasma	Homo sapiens
34 pg × h/mL	1.5 μg single, ocular		LATANOPROST ACID plasma	Homo sapiens
0.165 ng × eq × h/mL	2.3 μg single, ocular		LATANOPROST plasma	Homo sapiens
20.2 ng × eq × h/mL	216.1 μg single, intravenous		LATANOPROST plasma	Homo sapiens
0.0337 ng × eq × h/mL	2.3 μg single, ocular		LATANOPROST ACID plasma	Homo sapiens
7.15 ng × eq × h/mL	216.1 μg single, intravenous		LATANOPROST ACID plasma	Homo sapiens
206 ng × h/mL	1.5 μg single, ocular	TIMOLOL MALEATE	LATANOPROST ACID aqueous humor	Homo sapiens
6.15 pg × h/mL	2 drop 1 times / day multiple, ocular		LATANOPROST ACID plasma	Homo sapiens
4.97 pg × h/mL	2 drop 1 times / day multiple, ocular		LATANOPROST ACID plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.6 min	3 μg/kg bw single, intravenous		LATANOPROST ACID plasma	Homo sapiens
17 min	1.5 μg single, ocular		LATANOPROST ACID plasma	Homo sapiens
1.842 h	2.3 μg single, ocular		LATANOPROST plasma	Homo sapiens
1.471 h	216.1 μg single, intravenous		LATANOPROST plasma	Homo sapiens
17 min	2.3 μg single, ocular		LATANOPROST ACID plasma	Homo sapiens
16.6 min	216.1 μg single, intravenous		LATANOPROST ACID plasma	Homo sapiens
2.3 h	1.5 μg single, ocular	TIMOLOL MALEATE	LATANOPROST ACID aqueous humor	Homo sapiens
0.3 h	2 drop 1 times / day multiple, ocular		LATANOPROST ACID plasma	Homo sapiens
0.2 h	2 drop 1 times / day multiple, ocular		LATANOPROST ACID plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
47%			LATANOPROST plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
10 ug 1 times / day multiple, topical Highest studied dose	healthy, ADULT	Other AEs: Ocular discomfort, Hyperemia...
10 ug single, topical Highest studied dose	healthy, ADULT	Other AEs: Hyperemia...
0.005 % 1 times / day multiple, topical Recommended	unhealthy, ADULT	Disc. AE: Eye irritation, Asthenopia...
0.005 % 1 times / day multiple, topical Recommended	unhealthy, ADULT	Disc. AE: Cystoid macular edema, Iritis...
0.005 % 1 times / day multiple, topical Recommended	unhealthy, ADULT	Disc. AE: Conjuncitivitis, Ocular hyperemia...

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AEs

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AE	Significance	Dose	Population
Hyperemia	50%	10 ug 1 times / day multiple, topical Highest studied dose	healthy, ADULT
Ocular discomfort	grade 1, 50%	10 ug 1 times / day multiple, topical Highest studied dose	healthy, ADULT
Hyperemia	grade 2	10 ug single, topical Highest studied dose	healthy, ADULT
Asthenopia	Disc. AE	0.005 % 1 times / day multiple, topical Recommended	unhealthy, ADULT
Eye irritation	Disc. AE	0.005 % 1 times / day multiple, topical Recommended	unhealthy, ADULT

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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 2,052 BCRP 697	CYPs 17 CYP450 32

Drug as perpetrator

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Target	Modality	Activity
CYPs 35	inhibitor 4,027	no
CYP450 41	inducer 1,966	unlikely
CYP450 41	inhibitor 4,027	unlikely
CYPs 35	inducer 1,966	unlikely

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Drug as victim

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Target	Modality	Activity
CYP 303	substrate 4,014	no
P-gp 2,052	substrate 4,014	no
BCRP 697	substrate 4,014	unlikely
OATP2B1 122	substrate 4,014	weak
MRP1 113	substrate 4,014	yes

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Additive ocular hypotensive effect of latanoprost and acetazolamide. A short-term study in patients with elevated intraocular pressure.	1997 Sep	9307648
Effects of latanoprost and dipivefrin, alone or combined, on intraocular pressure and on blood-aqueous barrier permeability.	1998 Apr	9640189
A randomized, comparative open-label study on the efficacy of latanoprost and timolol in steroid induced ocular hypertension after photorefractive keratectomy.	2000 Jul-Sep	11071027
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

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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
Record UNII	I6393O0922
Record Status	`Validated (UNII)`
Record Version

Show entries

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

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Code System

Code

Type

Description

WIKIPEDIA

Latanoprostene bunod

PRIMARY

DRUG CENTRAL

5261

PRIMARY

SMS_ID

100000176872

PRIMARY

FDA UNII

I6393O0922

PRIMARY

DRUG BANK

DB11660

PRIMARY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator