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
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 |
DescriptionSources: 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/21788077Curator'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
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P43088 Gene ID: 5737.0 Gene Symbol: PTGFR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10634944 |
3.6 nM [EC50] | ||
Target ID: CHEMBL1987 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9733584 |
|||
Target ID: CHEMBL1987 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | VYZULTA Approved UseVYZULTA is a prostaglandin analog indicated for the reduction of intraocular pressure in patients with open-angle glaucoma or ocular hypertension Launch Date1.48668482E12 |
|||
Primary | VYZULTA Approved UseVYZULTA is a prostaglandin analog indicated for the reduction of intraocular pressure in patients with open-angle glaucoma or ocular hypertension Launch Date1.48668482E12 |
|||
Primary | VYZULTA Approved UseYZULTA™ (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 Date1.50949436E12 |
|||
Primary | VYZULTA Approved UseYZULTA™ (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 Date1.50949436E12 |
|||
Palliative | XALATAN Approved UseXALATAN Sterile Ophthalmic Solution is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Launch Date8.3393282E11 |
|||
Primary | XALATAN Approved UseXALATAN Sterile Ophthalmic Solution is indicated for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Launch Date8.3393282E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
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 |
T1/2
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
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: |
unhealthy, mean age 63.1 years n = 289 Health Status: unhealthy Condition: open-angle glaucoma | ocular hypertension Age Group: mean age 63.1 years Sex: M+F Population Size: 289 Sources: |
Disc. AE: Iritis, Meibomianitis... AEs leading to discontinuation/dose reduction: Iritis (grade 2, 0.3%) Sources: Meibomianitis (grade 1, 0.3%) |
11 ug/kg multiple, topical MTD Dose: 11 ug/kg Route: topical Route: multiple Dose: 11 ug/kg Sources: |
unhealthy Health Status: unhealthy Sources: |
|
10 ug/kg single, intravenous (max) Overdose Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
healthy Health Status: healthy Sources: |
Other AEs: Abdominal pain, Dizziness... Other AEs: Abdominal pain Sources: Dizziness Fatigue Hot flushes Nausea Sweating |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Meibomianitis | grade 1, 0.3% Disc. AE |
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: |
unhealthy, mean age 63.1 years n = 289 Health Status: unhealthy Condition: open-angle glaucoma | ocular hypertension Age Group: mean age 63.1 years Sex: M+F Population Size: 289 Sources: |
Iritis | grade 2, 0.3% Disc. AE |
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: |
unhealthy, mean age 63.1 years n = 289 Health Status: unhealthy Condition: open-angle glaucoma | ocular hypertension Age Group: mean age 63.1 years Sex: M+F Population Size: 289 Sources: |
Abdominal pain | 10 ug/kg single, intravenous (max) Overdose Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
healthy Health Status: healthy Sources: |
|
Dizziness | 10 ug/kg single, intravenous (max) Overdose Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
healthy Health Status: healthy Sources: |
|
Fatigue | 10 ug/kg single, intravenous (max) Overdose Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
healthy Health Status: healthy Sources: |
|
Hot flushes | 10 ug/kg single, intravenous (max) Overdose Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
healthy Health Status: healthy Sources: |
|
Nausea | 10 ug/kg single, intravenous (max) Overdose Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
healthy Health Status: healthy Sources: |
|
Sweating | 10 ug/kg single, intravenous (max) Overdose Dose: 10 ug/kg Route: intravenous Route: single Dose: 10 ug/kg Sources: |
healthy Health Status: healthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf#page=342 Page: 342.0 |
unlikely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/020597Orig1s000rev.pdf#page=342 Page: 342.0 |
unlikely |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
unlikely | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/20019365/ Page: 6.0 |
weak | |||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Corneal permeability to and ocular metabolism of phenyl substituted prostaglandin esters in vitro. | 1994 Apr |
|
Additive effect of latanoprost, a prostaglandin F2 alpha analogue, and timolol in patients with elevated intraocular pressure. | 1994 Dec |
|
A comparison of latanoprost and timolol in primary open-angle glaucoma and ocular hypertension. A 12-week study. | 1996 Aug |
|
The lack of respiratory effects of the ocular hypotensive drug latanoprost in patients with moderate-steroid treated asthma. | 1997 Feb |
|
Additive ocular hypotensive effect of latanoprost and acetazolamide. A short-term study in patients with elevated intraocular pressure. | 1997 Sep |
|
Effects of latanoprost and dipivefrin, alone or combined, on intraocular pressure and on blood-aqueous barrier permeability. | 1998 Apr |
|
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 |
|
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. | 2000 Jan 17 |
|
Microvascular effects of selective prostaglandin analogues in the eye with special reference to latanoprost and glaucoma treatment. | 2000 Jul |
|
A randomized, comparative open-label study on the efficacy of latanoprost and timolol in steroid induced ocular hypertension after photorefractive keratectomy. | 2000 Jul-Sep |
|
Syncope and falls due to timolol eye drops. | 2006 Apr 22 |
|
Comparison of the effects of bimatoprost and a fixed combination of latanoprost and timolol on circadian intraocular pressure. | 2007 Dec |
|
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 |
|
Outcome of raised intraocular pressure in uveitic eyes with and without a corticosteroid-induced hypertensive response. | 2009 Aug |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
|
Latanoprostene Bunod 0.024% in Subjects With Open-angle Glaucoma or Ocular Hypertension: Pooled Phase 3 Study Findings. | 2018 Jan |
Sample Use Guides
One drop in the affected eye(s) once daily in the evening.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27749098
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
Edited
Thu Jul 06 09:58:14 UTC 2023
by
admin
on
Thu Jul 06 09:58:14 UTC 2023
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Record UNII |
I6393O0922
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Record Status |
Validated (UNII)
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Record Version |
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Latanoprostene bunod
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5261
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100000176872
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I6393O0922
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DB11660
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1988390
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Latanoprostene Bunod
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I6393O0922
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11156438
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860005-21-6
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CHEMBL2364612
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ZZ-133
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C170095
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M12042
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DTXSID101027765
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE ACTIVE -> PRODRUG |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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