17-phenyl trinor Prostaglandin F ethyl amide

Item № 16820
CAS № 155206-00-1
Purity ≥97%
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL $0.00
1 mg $45.00 0.00
5 mg $203.00 0.00
10 mg $293.00 0.00
50 mg $731.00 0.00

Pricing updated 2018-02-18. Prices are subject to change without notice.

Description
Synonyms
  • Bimatoprost
  • 15(S)-Bimatoprost
  • 17-phenyl trinor PGF ethyl amide

17-phenyl trinor Prostaglandin F ethyl amide (17-phenyl trinor PGF ethyl amide) is an F-series PG analog which has been approved for use as an ocular hypotensive drug.1 Investigations in our lab have shown that 17-phenyl trinor PGF ethyl amide is converted by an amidase enzymatic activity in the bovine and human cornea to yield the corresponding free acid, with a conversion rate of about 40 µg/g corneal tissue/24 hours.2 The free acid, 17-phenyl trinor PGF, is a potent FP receptor agonist.3,4 In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity.

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Technical Information
Formal Name
N-ethyl-9α,11α,15S-trihydroxy-17-phenyl-18,19,20-trinor-prosta-5Z,13E-dien-1-amide
CAS Number
155206-00-1
Synonyms
  • Bimatoprost
  • 15(S)-Bimatoprost
  • 17-phenyl trinor PGF ethyl amide
Molecular Formula
C25H37NO4
Formula Weight
415.6
Purity
≥97%
Formulation
A crystalline solid
SMILES
CCN([H])C(CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)CCC2=CC=CC=C2)[C@H](O)C[C@@H]1O)=O
InChI Code
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
InChI Key
AQOKCDNYWBIDND-FTOWTWDKSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Woodward, D.F.,Krauss, A.H.P.,Chen, J., et al. The pharmacology of Bimatoprost (Lumigan™). Survey of Ophthalmology 45, S337-S345 (2001).

2. Maxey, K.M.,Johnson, J.,Camras, C.B., et al. The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Survey of Ophthalmology 47(4), 34-40 (2002).

3. Balapure, A.K.,Rexroad, C.E., Jr.,Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F receptor. Biochemical Pharmacology 38, 2375-2381 (1989).

4. Lake, S.,Gullberg, H.,Wahlqvist, J., et al. Cloning of the rat and human prostaglandin F receptors and the expression of the rat prostaglandin F receptor. FEBS Letters 355, 317-325 (1994).

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