Document Detail

The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist.
MedLine Citation:
PMID:  12204699     Owner:  NLM     Status:  MEDLINE    
Using human and bovine corneal tissue, we investigated the in vitro metabolism of bimatoprost (17-phenyl-18,19,20-trinor-prostaglandin F(2alpha) ethyl amide, Lumigan (Allergan, Inc, Irvine, CA). Enzymatic amidase activity, which converts bimatoprost to the corresponding prostaglandin carboxylic acid, was found to be present in corneal tissue from both species. Using HPLC and mass spectrometry for analyses, conversion of bimatoprost to 17-phenyl-18,19,20-trinor prostaglandin F(2alpha) continued for at least 24 hours after excision of the cornea, with a conversion rate of approximately 25 microg/24 hours. This hydrolysis product is identical to the free acid of latanoprost with the exception of a double, rather than a single, bond at the carbon 13-14 position. Assuming that this conversion also occurs in vivo at a similar rate, this hydrolysis product may account for the reduction of intraocular pressure occurring in patients treated with bimatoprost.
Kirk M Maxey; Jennifer L Johnson; Jennifer LaBrecque
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Survey of ophthalmology     Volume:  47 Suppl 1     ISSN:  0039-6257     ISO Abbreviation:  Surv Ophthalmol     Publication Date:  2002 Aug 
Date Detail:
Created Date:  2002-09-02     Completed Date:  2002-12-20     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  0404551     Medline TA:  Surv Ophthalmol     Country:  United States    
Other Details:
Languages:  eng     Pagination:  S34-40     Citation Subset:  IM    
Cayman Chemical Company, 1180 E Ellsworth Road, Ann Arbor, MI 48108, USA.
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MeSH Terms
Antihypertensive Agents / metabolism*
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Cloprostenol / analogs & derivatives
Cornea / metabolism*
Gas Chromatography-Mass Spectrometry
Lipid Metabolism*
Receptors, Prostaglandin / agonists*,  biosynthesis*
Structure-Activity Relationship
Reg. No./Substance:
0/Amides; 0/Antihypertensive Agents; 0/Lipids; 0/Receptors, Prostaglandin; 0/bimatoprost; 0/prostaglandin F2alpha receptor; 40665-92-7/Cloprostenol

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