Structure Database (LMSD)

Common Name
17-phenyl-trinor-PGF2alpha amide
Systematic Name
9S,11R,15S-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienamide
Synonyms
  • 17-phenyl-trinor-Prostaglandin F2alpha amide
LM ID
LMFA03010123
Formula
Exact Mass
Calculate m/z
387.240959
Status
Curated

Classification

Biological Context

17-phenyl trinor Prostaglandin F2α (17-phenyl trinor PGF2α) amide is a derivative of the FP receptor agonist 17-phenyl trinor PGF2α ethyl amide (bimatoprost) with an unsubstituted amide.1 As with bimatoprost and other prostaglandin amides, the amide of 17-phenyl trinor PGF2α amide may be hydrolyzed to the free acid form in human eyes.2,3,4 Like other amide isomers of F-type prostaglandins, 17-phenyl trinor PGF2α amide may have similar FP receptor activation and intraocular pressure (IOP) reduction activities.3 It has a lower hydrolysis rate in primary human corneas compared to isopropyl ester-protected prodrugs.4

This information has been provided by Cayman Chemical

References

1. Bito, L.Z. Comparison of the ocular hypotensive efficacy of eicosanoids and related compounds. Exp. Eye Res. 38(2), 181-184 (1984).
2. Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of bimatoprost (Lumigan™). Surv. Ophthalmol. 45(Suppl. 4), S337-S345 (2001).
3. Maxey, K.M., Johnson, J., and LaBrecque, J. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv. Ophthalmol. 47(Suppl. 1), S34-S40 (2002).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
The pharmacology of bimatoprost (Lumigan).,
Surv Ophthalmol, 2001
Pubmed ID: 11434936

String Representations

InChiKey (Click to copy)
RAGQWYIPCPFTJC-KDACTHKWSA-N
InChi (Click to copy)
InChI=1S/C23H33NO4/c24-23(28)11-7-2-1-6-10-19-20(22(27)16-21(19)26)15-14-18(25)13-12-17-8-4-3-5-9-17/h1,3-6,8-9,14-15,18-22,25-27H,2,7,10-13,16H2,(H2,24,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@H](O)CCC2C=CC=CC=2)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)N

Other Databases

CHEBI ID
LIPIDBANK ID
XPR1794
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 2
Aromatic Rings 1
Rotatable Bonds 11
Van der Waals Molecular Volume 401.16
Topological Polar Surface Area 103.78
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 3.36
Molar Refractivity 111.86

Admin

Created at
-
Updated at
5th Apr 2022