Bimatoprost grenod | CAS#1194396-71-8 | IOP reducer

MedKoo Cat#: 464695 | Name: Bimatoprost grenod

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bimatoprost grenod, also known as NCX 470, is a nitric oxide-donating derivative of 17-phenyl trinor PGF2α. It increases cGMP levels in rabbit aqueous humor and iris ciliary body when topically administered at a concentration of 0.042%. Topical administration of NCX 470 (0.14%) reduces intraocular hypertension (IOP) in a rabbit model of hypertonic saline-induced transient ocular pressure. It also reduces IOP in a cynomolgus monkey model of laser-induced ocular hypertension when administered topically at a concentration of 0.042%.

Chemical Structure

Bimatoprost grenod

CAS#1194396-71-8

Theoretical Analysis

MedKoo Cat#: 464695

Name: Bimatoprost grenod

CAS#: 1194396-71-8

Chemical Formula: C31H46N2O8

Exact Mass: 574.3254

Molecular Weight: 574.72

Elemental Analysis: C, 64.79; H, 8.07; N, 4.87; O, 22.27

Price and Availability

Size	Price	Availability
5mg	USD 650.00	2 Weeks
10mg	USD 1,150.00	2 Weeks
25mg	USD 1,950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

NCX 470; NCX470; NCX-470; bimatoprost grenod,

IUPAC/Chemical Name

(S,E)-1-((1R,2R,3S,5R)-2-((Z)-7-(ethylamino)-7-oxohept-2-en-1-yl)-3,5-dihydroxycyclopentyl)-5-phenylpent-1-en-3-yl 6-(nitrooxy)hexanoate

InChi Key

NTQMJNDRYSYWNJ-BPXWCPHMSA-N

InChi Code

InChI=1S/C31H46N2O8/c1-2-32-30(36)16-10-4-3-9-15-26-27(29(35)23-28(26)34)21-20-25(19-18-24-13-7-5-8-14-24)41-31(37)17-11-6-12-22-40-33(38)39/h3,5,7-9,13-14,20-21,25-29,34-35H,2,4,6,10-12,15-19,22-23H2,1H3,(H,32,36)/b9-3-,21-20+/t25-,26+,27+,28-,29+/m0/s1

SMILES Code

O[C@@H]1C[C@@H]([C@@H]([C@H]1/C=C/[C@@H](OC(CCCCCO[N+]([O-])=O)=O)CCC2=CC=CC=C2)C/C=C\CCCC(NCC)=O)O

Appearance

solution in ethanol

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

NCX 470 is a second-generation nitric oxide (NO)-donating prostaglandin analogue.

In vitro activity:

TBD

In vivo activity:

NCX 470 (0.14%, 30 μL) lowered IOP in tOHT-rabbits with an E(max) of -7.2 ± 2.8 mm Hg at 90 minutes. NCX 470 (0.042%, 30 μL) was more effective than equimolar (0.03%, 30 μL) bimatoprost in ONT-dogs (IOP change, -5.4 ± 0.7 and -3.4 ± 0.7 mm Hg, respectively, P < 0.05) and in OHT-monkeys (IOP change, -7.7 ± 1.4 and -4.8 ± 1.7 mm Hg, respectively, P < 0.05) at 18 hours post dosing. Reference: Invest Ophthalmol Vis Sci. 2015 Oct;56(11):6558-64. https://pubmed.ncbi.nlm.nih.gov/26457541/

	Solvent	mg/mL	mM
Solubility
	DMSO	10.0	17.40
	Ethanol	10.0	17.40

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 574.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Bastia E, Sgambellone S, Lucarini L, Provensi G, Brambilla S, Galli C, Almirante N, Impagnatiello F. NCX 470 Restores Ocular Hemodynamics and Retinal Cell Physiology After ET-1-Induced Ischemia/Reperfusion Injury of Optic Nerve and Retina in Rabbits. J Ocul Pharmacol Ther. 2022 Sep;38(7):496-504. doi: 10.1089/jop.2022.0004. Epub 2022 Jul 4. PMID: 35787180. 2. Impagnatiello F, Toris CB, Batugo M, Prasanna G, Borghi V, Bastia E, Ongini E, Krauss AH. Intraocular Pressure-Lowering Activity of NCX 470, a Novel Nitric Oxide-Donating Bimatoprost in Preclinical Models. Invest Ophthalmol Vis Sci. 2015 Oct;56(11):6558-64. doi: 10.1167/iovs.15-17190. PMID: 26457541.

In vitro protocol:

TBD

In vivo protocol:

1: Impagnatiello F, Bastia E, Almirante N, Brambilla S, Duquesroix B, Kothe AC, Bergamini MVW. Prostaglandin analogues and nitric oxide contribution in the treatment of ocular hypertension and glaucoma. Br J Pharmacol. 2019 Apr;176(8):1079-1089. doi: 10.1111/bph.14328. Epub 2018 May 24. PMID: 29669171; PMCID: PMC6451067. 2: Impagnatiello F, Toris CB, Batugo M, Prasanna G, Borghi V, Bastia E, Ongini E, Krauss AH. Intraocular Pressure-Lowering Activity of NCX 470, a Novel Nitric Oxide-Donating Bimatoprost in Preclinical Models. Invest Ophthalmol Vis Sci. 2015 Oct;56(11):6558-64. doi: 10.1167/iovs.15-17190. PMID: 26457541. 3: Impagnatiello F, Giambene B, Lanzi C, Pini A, Somma T, Bastia E, Ongini E, Galassi F, Masini E. The nitric oxide donating triamcinolone acetonide NCX 434 does not increase intraocular pressure and reduces endothelin-1 induced biochemical and functional changes in the rabbit eye. Br J Ophthalmol. 2012 May;96(5):757-61. doi: 10.1136/bjophthalmol-2011-300404. Epub 2012 Jan 18. PMID: 22257787.