Drug Information

Drug (ID: DG00582) and It's Reported Resistant Information

• Name: Bimatoprost
• Synonyms: Bimatoprost; 155206-00-1; Lumigan; Latisse; AGN 192024; UNII-QXS94885MZ; AGN-192024; (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide; QXS94885MZ; CHEBI:51230; (Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-5-heptenamide; (E)-7-[3,5-dihydroxy-2-[(E)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide; bimatoprostum; Prostamide; (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; (5z)-7-{(1r,2r,3r,5s)-3,5-Dihydroxy-2-[(1e,3s)-3-Hydroxy-5-Phenylpent-1-Enyl]cyclopentyl}-N-Ethylhept-5-Enamide; Lumigan (TN); (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; Bimatoprost [USAN:INN:BAN:JAN]; Latisse (TN); LS-181817; SCHEMBL24425; 5-Heptenamide, 7-(3,5-dihydroxy-2-(3-hydrdoxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-, (1R-(1alpha(Z),2beta(1E,3S*),3alpha,5alpha))-; MLS006010039; US9271961, Bimatoprost; Bimatoprost (JAN/USAN/INN); GTPL1958; CHEMBL1200963; DTXSID30895042; BDBM220120; EX-A1769; HY-B0191; ZINC4474405; MFCD03411999; AKOS015995566; AM84507; DB00905; NCGC00181745-01; NCGC00181745-03; 5-Heptenamide, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E,3S)-3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-, (5Z)-; 5-Heptenamide, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl)-N-ethyl-, (1R-1(alpha(Z),2beta(1E,3S*)3alpha,5alpha))-; AS-35082; M052; SMR000058996; D02724; 206B001; SR-01000942224; Q2393348; SR-01000942224-1; 17-PHENYL TRINOR PROSTAGLANDIN F2ALPHA ETHYL AMIDE; 17-Phenyl-tri-norprostaglandin F2alpha-ethyl amide, >=95%, solid; 15M; 5-Heptenamide, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]cyclopentyl]-N-ethyl-, (5Z)-
• Indication:
  In total 2 Indication(s)
  Alopecia [ICD-11: ED70]; Approved; [1]
  Glaucoma/ocular hypertension [ICD-11: 9C61]; Approved; [1]
• Drug Resistance Disease(s):
  Disease(s) with Clinically Reported Resistance for This Drug (1 diseases)
  Glaucoma [ICD-11: 9C61]; [1]
• Target: Prostaglandin receptor (PTGR); NOUNIPROTAC; [1]
• Formula: C25H37NO4
• IsoSMILES: 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
• 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
• InChIKey: AQOKCDNYWBIDND-FTOWTWDKSA-N
• PubChem CID: 5311027
• ChEBI ID: CHEBI:51230
• TTD Drug ID: D0Q2XF
• INTEDE ID: DR0213
• DrugBank ID: DB00905

Type(s) of Resistant Mechanism of This Drug

  IDUE: Irregularity in Drug Uptake and Drug Efflux

Drug Resistance Data Categorized by Their Corresponding Diseases

ICD-09: Visual system diseases

Glaucoma [ICD-11: 9C61]

Drug Resistance Data Categorized by Their Corresponding Mechanisms

Irregularity in Drug Uptake and Drug Efflux (IDUE)

Key Molecule: ATP-binding cassette sub-family C5 (ABCC5) [1]

• Molecule Alteration: Expression; Regulation
• Resistant Disease: Glaucoma [ICD-11: 9C61.0]
• Experimental Note: Identified from the Human Clinical Data
• In Vitro Model: SIRC cells; Colon; Homo sapiens (Human); CVCL_2724
• In Vitro Model: SV40-HCEC cells; Kidney; Homo sapiens (Human); CVCL_1272
• Experiment for Molecule Alteration: RT-PCR; Immunoprecipitation assay; Western blot analysis; Immunostaining assay
• Experiment for Drug Resistance: Trypan blue exclusion test assay
• Mechanism Description: Taken together immunolocalization on human cornea, in vitro efflux in human, rabbit corneal and MRP5 over expressing cells, ex vivo and in vivo studies in intact rabbit cornea suggest that MRP5 on cornea can significantly lower the permeability of antiviral and glaucoma drugs.

Key Molecule: ATP-binding cassette sub-family C5 (ABCC5) [1]

• Molecule Alteration: Expression; Regulation
• Resistant Disease: Glaucoma [ICD-11: 9C61.0]
• Experimental Note: Identified from the Human Clinical Data
• In Vitro Model: SIRC cells; Colon; Homo sapiens (Human); CVCL_2724
• In Vitro Model: SV40-HCEC cells; Kidney; Homo sapiens (Human); CVCL_1272
• Experiment for Molecule Alteration: RT-PCR; Immunoprecipitation assay; Western blot analysis; Immunostaining assay
• Experiment for Drug Resistance: Trypan blue exclusion test assay
• Mechanism Description: Taken together immunolocalization on human cornea, in vitro efflux in human, rabbit corneal and MRP5 over expressing cells, ex vivo and in vivo studies in intact rabbit cornea suggest that MRP5 on cornea can significantly lower the permeability of antiviral and glaucoma drugs.

References

• Ref 1: Expression of multidrug resistance associated protein 5 (MRP5) on cornea and its role in drug efflux .J Ocul Pharmacol Ther. 2009 Apr;25(2):121-32. doi: 10.1089/jop.2008.0084. 10.1089/jop.2008.0084