NCX 470 | CAS#1194396-71-8 | IOP reducer

NCX 470
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 464695

CAS#: 1194396-71-8

Description: 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

NCX 470

CAS# 1194396-71-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 464695
Name: NCX 470
CAS#: 1194396-71-8
Chemical Formula: C31H46N2O8
Exact Mass: 574.33
Molecular Weight: 574.715
Elemental Analysis: C, 64.79; H, 8.07; N, 4.87; O, 22.27

Price and Availability

Size	Price	Availability
5mg	USD 650	2 Weeks
10mg	USD 1150	2 Weeks
25mg	USD 1950	2 Weeks
50mg	USD 3250	2 Weeks
100mg	USD 4850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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: Solid powder

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	10.0	17.40
	Ethanol	10.0	17.40

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. 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.

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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.

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