Bimatoprost

CAS No:

155206-00-1

Molecular Formula:

C25H37NO4

Molecular Weight:

415.57

Storage:

Store in a tightly closed container in a cool, dry,Protect from moisture and direct sunlight.

Synonyms:
  • Bimatoprostum
  • (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl]-N-ethylhept-5-enamide
  • 267244-98-4 (Deprecated CAS)
  • QXS94885MZ
  • 655MD9T3SC
  • CHEBI:51230
  • 5311027

IUPAC Name:

(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide

InChIKey:

AQOKCDNYWBIDND-FTOWTWDKSA-N

InChI:

InChI=1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,1H3,(H,26,30)/b8-3-,17-16+/t20-,21+,22+,23-,24+/m0/s1

SMILES:

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

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Technical Data

Description

White powder

Identification

By HPLC HNMR

Solubility

Very soluble in ethanol,methanol,sparingly to slightly
soluble in water

Water

< 0.5 %

Residue on Ignition

≤0.1%

Heavy metals

≤10PPM

Optical rotation

+33.0°~+37.0°( C=2.0,CH3ON)

Residue Solvent

Ethyl acetate ≤ 0.5%
N-hexanol ≤0.029%
Ethanol ≤0.5%
Ether ≤0.5%
Ter-butylmetyl ether≤0.5%

Purity

≥99.5%

Description

Bimatoprost is a synthetic prostamide analog primarily acting as a selective prostaglandin F2α (FP) receptor agonist. In vitro, it increases aqueous humor outflow in cultured human trabecular meshwork and ciliary muscle cells, showing dose-dependent elevation of matrix metalloproteinase (MMP) activity at 10–100 nM. In vivo, bimatoprost lowers intraocular pressure (IOP) in ocular hypertensive and normotensive animal models. In rabbits, topical doses of 0.01–0.03% reduced IOP by 25–35% within 5 hours, sustained for 24 hours. In monkeys, 0.03% topical treatment produced a maximal IOP reduction of ~30% over 24 hours. Bimatoprost also promotes eyelash growth in rodents, increasing hair length and density by 20–40% after 4 weeks of daily application. These effects are consistent with its dual role in enhancing uveoscleral outflow and modulating hair follicle activity, supporting its clinical use in glaucoma, ocular hypertension, and hypotrichosis of the eyelashes.

Safety Information

GHS

Pictogram:

GHS08

Signal Word:

Warning

Hazard Statements:

Toxic. Contains a pharmaceutically active ingredient.
Handling should only be performed by personnel trained and
familiar with handling of potent active pharmaceutical
ingredients. Moderate to severe irritant to the skin and eyes.

Precautionary Statements:

P501 : Dispose of contents/ container to an approved waste disposal plant.
P202 : Do not handle until all safety precautions have been read and understood.
P201 : Obtain special instructions before use.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P308 + P313 : IF exposed or concerned: Get medical advice/ attention.
P405 : Store locked up.

References

  1. Vagiakis I, Papadopoulou EP, Amaxilati E, Tsiropoulos GN, Konstas AG, Panos GD. Bimatoprost Intracameral Implant (Durysta®): A New Era in Glaucoma Management Through Sustained-Release InnovationDrug Des Devel Ther. 2025年1月31日;19:703-714. doi: 10.2147/DDDT.S506520. PMID: 39906697; PMCID: PMC11792881.

  2. Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Bimatoprost. 2024年12月15日. PMID: 30000734.

  3. Zeppieri M, Gagliano C, Spadea L, Salati C, Chukwuyem EC, Enaholo ES, D’Esposito F, Musa M. From Eye Care to Hair Growth: BimatoprostPharmaceuticals (Basel). 2024年4月27日;17(5):561. doi: 10.3390/ph17050561. PMID: 38794131; PMCID: PMC11124470.

  4. Sirinek PE, Lin MM. Intracameral sustained release bimatoprost implants (Durysta)Semin Ophthalmol. 2022年4月3日;37(3):385-390. doi: 10.1080/08820538.2021.1985145. Epub 2021年9月29日. PMID: 34586961.

  5. Deveau AP, da Silva FN, Ly TY, Hussain A. Periocular invasive melanoma manifestation in a patient using bimatoprost: case report and literature reviewOrbit. 2023年2月;42(1):73-80. doi: 10.1080/01676830.2021.1955392. Epub 2021年7月28日. PMID: 34320913.

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