Bimatoprost amide
CAS No:
155205-89-3
Molecular Formula：
C23H33NO4
Molecular Weight：
387.51
Storage:
Store in a tightly closed container in a cool, dry，Protect from moisture and direct sunlight.
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Technical Data
| Appearance | White powder |
|---|---|
| Identification | HNMR HPLC |
| Solubility | Freely soluble in methanol, ethanol, ethyl acetate; practically insoluble in water |
| Water content | ≤1.0% |
| 15-epimer | ≤0.2% |
| 5,6-trans isomer | ≤0.2% |
| Other max single impurity | ≤0.1% |
| Total impurities | ≤1.0% |
| Purity | ≥99.0% |
Description
An F-series prostaglandin (PG) analog in which the C-1 carboxyl group has been modified to an unsubstituted amide. PG N-ethyl amides were recently introduced as alternative PG hypotensive prodrugs.2 Although it has been claimed that PG amides are not converted to the free acids in vivo,2 studies have shown that bovine and human corneal tissue converts the amides of various PGs to the free acids with a conversion efficiency of about 10-20% relative to the hydrolysis of isopropyl esters.3 Bimatoprost amide would be expected to show the typical intraocular effects of latanoprost, but with the much slower hydrolysis pharmacokinetics of the PG N-amides.
Safety Information
GHS
Pictogram:
Signal Word:
Danger
Hazard Statements:
May be harmful if inhaled
May cause cancer
Highly flammable liquid and vapor
Precautionary Statements:
Obtain special instructions before use
Do not handle until all safety precautions have beenreadandunderstood
Use personal protective equipment as required
Keepawayfromheat/sparks/openflames/hotsurfaces.—Nosmoking
Keep container tightly closed
Ground/bond container and receiving equipment
Use only non-sparking tools
Take precautionary measures against static discharge
–
IF exposed or concerned: Get medical advice/attentionIF ON SKIN (or hair): Remove/Take off immediately all
contaminated clothing. Rinse skin with water/shower
In case of fire: Use CO2, dry chemical, or foamfor extinction
–
Store locked up Store in a well-ventilated place. Keepcool
Dispose of contents/container to an approved wastedisposalplant
References
- The pharmacology of bimatoprost (Lumigan). | Woodward, DF., et al. 2001. Surv Ophthalmol. 45 Suppl 4: S337-45. PMID: 11434936
- The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. | Maxey, KM., et al. 2002. Surv Ophthalmol. 47 Suppl 1: S34-40. PMID: 12204699
- Human trabecular meshwork cell responses induced by bimatoprost, travoprost, unoprostone, and other FP prostaglandin receptor agonist analogues. | Sharif, NA., et al. 2003. Invest Ophthalmol Vis Sci. 44: 715-21. PMID: 12556403
- Interaction of ocular hypotensive agents (PGF2 alpha analogs-bimatoprost, latanoprost, and travoprost) with MDR efflux pumps on the rabbit cornea. | Hariharan, S., et al. 2009. J Ocul Pharmacol Ther. 25: 487-98. PMID: 20028257
- Prostaglandin FP receptor antagonists: discovery, pharmacological characterization and therapeutic utility. | Sharif, NA. and Klimko, PG. 2019. Br J Pharmacol. 176: 1059-1078. PMID: 29679483
- Tear biomarkers in latanoprost and bimatoprost treated eyes. | Reddy, S., et al. 2018. PLoS One. 13: e0201740. PMID: 30080906
- Discovery to Launch of Anti-allergy (Emadine; Patanol/Pataday/Pazeo) and Anti-glaucoma (Travatan; Simbrinza) Ocular Drugs, and Generation of Novel Pharmacological Tools Such as AL-8810. | Sharif, NA. 2020. ACS Pharmacol Transl Sci. 3: 1391-1421. PMID: 33344909
- Latanoprost PF vs. Bimatoprost PF: Which Treats the Ocular Surface Better? | Dimtsas, GS., et al. 2023. J Clin Med. 12: PMID: 37959198
- From Eye Care to Hair Growth: Bimatoprost. | Zeppieri, M., et al. 2024. Pharmaceuticals (Basel). 17: PMID: 38794131
- Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds. | Bito, LZ. 1984. Exp Eye Res. 38: 181-94. PMID: 6370708
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