Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H32O5 |
| Molecular Weight | 388.4972 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H](CCC1=CC=CC=C1)\C=C\[C@H]2[C@H](O)C[C@H](O)[C@@H]2C\C=C/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
| Molecular Formula | C23H32O5 |
| Molecular Weight | 388.4972 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 2 |
| Optical Activity | UNSPECIFIED |
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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P43088 Gene ID: 5737.0 Gene Symbol: PTGFR Target Organism: Homo sapiens (Human) |
83.0 nM [Ki] | ||
Target ID: P34995 Gene ID: 5731.0 Gene Symbol: PTGER1 Target Organism: Homo sapiens (Human) |
95.0 nM [Ki] | ||
Target ID: P43115|||Q16546 Gene ID: 5733.0 Gene Symbol: PTGER3 Target Organism: Homo sapiens (Human) |
387.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
Sample Use Guides
In Vitro Use Guide
Curator's Comment: Bimatoprost acid was less selective, exhibiting a relatively high affinity for the FP (Ki = 83 nM), EP1 (Ki = 95 nM), and EP3 (Ki = 387 nM) receptors. Bimatoprost acid exhibited functional activity at the EP1 (EC50 = 2.7 nM) and FP (EC50 = 2.8-3.8 nM in most cells) receptors
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 06:39:27 GMT 2023
by
admin
on
Sat Dec 16 06:39:27 GMT 2023
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| Record UNII |
2683MK55HG
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| Record Status |
Validated (UNII)
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