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
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 |
|---|---|---|---|---|
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
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SUBSTANCE RECORD
