U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H40O5
Molecular Weight 432.5928
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of LATANOPROST

SMILES

CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC2=CC=CC=C2

InChI

InChIKey=GGXICVAJURFBLW-CEYXHVGTSA-N
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

HIDE SMILES / InChI

Molecular Formula C26H40O5
Molecular Weight 432.5928
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P43088
Gene ID: 5737.0
Gene Symbol: PTGFR
Target Organism: Homo sapiens (Human)
3.6 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1.48668482E12
Primary
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

1.48668482E12
Primary
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

1.50949436E12
Primary
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

1.50949436E12
Palliative
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

8.3393282E11
Primary
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

8.3393282E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
53 pg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
7.15 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
16.6 min
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
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

Doses

DosePopulationAdverse 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%)
Meibomianitis (grade 1, 0.3%)
Sources:
11 ug/kg multiple, topical
MTD
unhealthy
10 ug/kg single, intravenous (max)
Overdose
Dose: 10 ug/kg
Route: intravenous
Route: single
Dose: 10 ug/kg
Sources:
healthy
Other AEs: Abdominal pain, Dizziness...
Other AEs:
Abdominal pain
Dizziness
Fatigue
Hot flushes
Nausea
Sweating
Sources:
AEs

AEs

AESignificanceDosePopulation
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
Dizziness
10 ug/kg single, intravenous (max)
Overdose
Dose: 10 ug/kg
Route: intravenous
Route: single
Dose: 10 ug/kg
Sources:
healthy
Fatigue
10 ug/kg single, intravenous (max)
Overdose
Dose: 10 ug/kg
Route: intravenous
Route: single
Dose: 10 ug/kg
Sources:
healthy
Hot flushes
10 ug/kg single, intravenous (max)
Overdose
Dose: 10 ug/kg
Route: intravenous
Route: single
Dose: 10 ug/kg
Sources:
healthy
Nausea
10 ug/kg single, intravenous (max)
Overdose
Dose: 10 ug/kg
Route: intravenous
Route: single
Dose: 10 ug/kg
Sources:
healthy
Sweating
10 ug/kg single, intravenous (max)
Overdose
Dose: 10 ug/kg
Route: intravenous
Route: single
Dose: 10 ug/kg
Sources:
healthy
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Interaction of PhXA41, a new prostaglandin analogue, with pilocarpine. A study on patients with elevated intraocular pressure.
1993 May
A comparison of latanoprost and timolol in primary open-angle glaucoma and ocular hypertension. A 12-week study.
1996 Aug
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
Mechanism of prostaglandin E2-, F2alpha- and latanoprost acid-induced relaxation of submental veins.
1997 Dec 11
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
A randomized, comparative open-label study on the efficacy of latanoprost and timolol in steroid induced ocular hypertension after photorefractive keratectomy.
2000 Jul-Sep
[Increased iris pigmentation after use of latanoprost in Japanese brown eyes].
2001 May
Latanoprost and brimonidine: therapeutic and physiologic assessment before and after oral nonsteroidal anti-inflammatory therapy.
2002 Jan
Diurnal intraocular pressure reduction with latanoprost 0.005% compared to timolol maleate 0.5% as monotherapy in subjects with exfoliation glaucoma.
2004 Sep
A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development.
2013 Nov
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

One drop in the affected eye(s) once daily in the evening.
Route of Administration: Other
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 Wed Jul 05 23:08:45 UTC 2023
Edited
by admin
on Wed Jul 05 23:08:45 UTC 2023
Record UNII
6Z5B6HVF6O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LATANOPROST
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
Isopropyl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate
Systematic Name English
PHXA41
Code English
LATANOPROST [MART.]
Common Name English
5-HEPTENOIC ACID, 7-(3,5-DIHYDROXY-2-(3-HYDROXY-5-PHENYLPENTYL)CYCLOPENTYL)-1-METHYLETHYL ESTER, (1R-(1.ALPHA.(Z),2.BETA.(R*),3.ALPHA.,5.ALPHA.))-
Common Name English
XA-41
Code English
T2345
Code English
T-2345
Code English
LATANOPROST [ORANGE BOOK]
Common Name English
latanoprost [INN]
Common Name English
XELPROS
Brand Name English
Latanoprost [WHO-DD]
Common Name English
LATANOPROST COMPONENT OF ROCKLATAN
Common Name English
XALATAN
Brand Name English
LATANOPROST [MI]
Common Name English
ROCKLATAN COMPONENT LATANOPROST
Common Name English
LATANOPROST (ISOPROPYL ESTER)
Common Name English
LATANOPROST [USAN]
Common Name English
LATANOPROST [JAN]
Common Name English
XA41
Code English
LATANOPROST [USP-RS]
Common Name English
IYUZEH
Brand Name English
LATANOPROST [EP MONOGRAPH]
Common Name English
LATANOPROST [USP MONOGRAPH]
Common Name English
LATANOPROST [VANDF]
Common Name English
PHXA-41
Code English
XALACOM COMPONENT LATANOPROST
Brand Name English
Classification Tree Code System Code
WHO-VATC QS01EE01
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
NDF-RT N0000007706
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
NCI_THESAURUS C29705
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
WHO-ATC S01EE01
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
NDF-RT N0000007706
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
NDF-RT N0000175454
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
NCI_THESAURUS C78568
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
NDF-RT N0000007706
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
Code System Code Type Description
DAILYMED
6Z5B6HVF6O
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID1041057
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
SMS_ID
100000092301
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
USAN
II-6
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
LACTMED
Latanoprost
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL1051
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
CHEBI
6384
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
INN
6980
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
MESH
C072042
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
NCI_THESAURUS
C29151
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
WIKIPEDIA
LATANOPROST
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
CAS
130209-82-4
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
DRUG CENTRAL
1551
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
EVMPD
SUB08409MIG
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
FDA UNII
6Z5B6HVF6O
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
RS_ITEM_NUM
1357475
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
DRUG BANK
DB00654
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
RXCUI
43611
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY RxNorm
IUPHAR
1961
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
PUBCHEM
5311221
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY
MERCK INDEX
M6701
Created by admin on Wed Jul 05 23:08:45 UTC 2023 , Edited by admin on Wed Jul 05 23:08:45 UTC 2023
PRIMARY Merck Index
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
PARENT -> METABOLITE
METABOLITE -> PARENT
There is an equilibrium between the acid and the lactone
MAJOR
FECAL; URINE
METABOLITE -> PARENT
MAJOR
FECAL; URINE
METABOLITE -> PARENT
MAJOR
FECAL; URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY