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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H32O5
Molecular Weight 388.4981
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BIMATOPROST ACID

SMILES

C(\[H])(=C(\[H])/C[C@]1([H])[C@@]([H])(/C(/[H])=C(\[H])/[C@]([H])(CCc2ccccc2)O)[C@@]([H])(C[C@]1([H])O)O)/CCCC(=O)O

InChI

InChIKey=YFHHIZGZVLHBQZ-KDACTHKWSA-N
InChI=1S/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1

HIDE SMILES / InChI
Bimatoprost acid is a metabolically stable analog of prostaglandin F2alpha, exhibits a relatively high affinity for the FP, EP1, and EP3 receptors and exhibits functional activity at the EP1 and FP receptors. Clinical pharmacological studies with bimatoprost reveal that it is not significantly metabolized due to the absence of free acid hydrolysis product in the systemic circulation after topical ocular administration to human volunteers. The hydrolysis of bimatoprost to a free acid occurs at very low rate.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P43088
Gene ID: 5737
Gene Symbol: PTGFR
Target Organism: Homo sapiens (Human)
83 nM [Ki]
Target ID: P34995
Gene ID: 5731
Gene Symbol: PTGER1
Target Organism: Homo sapiens (Human)
95 nM [Ki]
Target ID: P43115|||Q16546
Gene ID: 5733
Gene Symbol: PTGER3
Target Organism: Homo sapiens (Human)
387 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Bimatoprost and its free acid are prostaglandin FP receptor agonists.
2001 Dec 7
The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist.
2002 Aug
Hydrolysis of bimatoprost (Lumigan) to its free acid by ocular tissue in vitro.
2003 Feb
Aqueous humor concentrations of bimatoprost free acid, bimatoprost and travoprost free acid in cataract surgical patients administered multiple topical ocular doses of LUMIGAN or TRAVATAN.
2010 Apr
Patents

Patents

Name Type Language
BIMATOPROST ACID
Common Name English
5-HEPTENOIC ACID, 7-(3,5-DIHYDROXY-2-(3-HYDROXY-5-PHENYL-1- PENTENYL)CYCLOPENTYL)-, (1R- (1.ALPHA.(Z),2.BETA.(1E,3S*),3.ALPHA.,5.ALPHA.))-
Common Name English
BIMATOPROST IMPURITY C
Common Name English
17-PHENYL-18,19,20-TRINORPROSTAGLANDIN F2.ALPHA.
Common Name English
U-35687
Code English
5-HEPTENOIC ACID, 7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E,3S)-3-HYDROXY-5-PHENYL-1-PENTEN-1-YL)CYCLOPENTYL)-, (5Z)-
Common Name English
17-PHENYL-18,19,20-TRINOR-PGF2.ALPHA.
Common Name English
PHXA 70
Code English
(5Z)-7-((1R,2R,3R,5S)-3,5-DIHYDROXY-2-((1E,3S)-3-HYDROXY-5-PHENYL-1-PENTEN-1-YL)CYCLOPENTYL)-5-HEPTENOIC ACID
Systematic Name English
U 35687
Code English
17-PHENYL-TRINOR PGF 2.ALPHA.
Common Name English
PHXA-70
Code English
Code System Code Type Description
FDA UNII
2683MK55HG
Created by admin on Fri Jun 25 23:36:05 UTC 2021 , Edited by admin on Fri Jun 25 23:36:05 UTC 2021
PRIMARY
PUBCHEM
5283081
Created by admin on Fri Jun 25 23:36:05 UTC 2021 , Edited by admin on Fri Jun 25 23:36:05 UTC 2021
PRIMARY
CAS
38344-08-0
Created by admin on Fri Jun 25 23:36:05 UTC 2021 , Edited by admin on Fri Jun 25 23:36:05 UTC 2021
PRIMARY