Acelarin | NUC-1031 | GTPL7389 | CAS#840506-29-8

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

MedKoo CAT#: 206537

CAS#: 840506-29-8

Description: Acelarin, also known as NUC-1031, CPF-31; and GTPL7389, is a prodrug based on an aryloxy phosphoramidate derivative of gemcitabine. Upon intravenous administration and cellular uptake, NUC-1031 is converted into the active metabolites difluorodeoxycytidine di- and triphosphate (dFdCDP, dFdCTP). dFdCDP inhibits ribonucleotide reductase, thereby decreasing the deoxynucleotide pool available for DNA replication; dFdCTP is incorporated into DNA, resulting in premature termination of DNA replication and eventually induction of apoptosis.

Chemical Structure

Acelarin

CAS# 840506-29-8

Instruction

Theoretical Analysis

MedKoo Cat#: 206537
Name: Acelarin
CAS#: 840506-29-8
Chemical Formula: C25H27F2N4O8P
Exact Mass: 580.15
Molecular Weight: 580.482
Elemental Analysis: C, 51.73; H, 4.69; F, 6.55; N, 9.65; O, 22.05; P, 5.34

Price and Availability

Size	Price	Availability
25mg	USD 950	2 Weeks
50mg	USD 1650	2 Weeks
100mg	USD 2950	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: Acelarin; NUC-1031; NUC 1031; NUC1031; CPF-31; CPF31; GTPL7389; GTPL-7389; GTPL 7389.

IUPAC/Chemical Name: Benzyl (2S)-2-[({[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methoxy}(phenoxy)phosphoryl)amino]propanoate

InChi Key: NHTKGYOMICWFQZ-BSMFTPRPSA-N

InChi Code: InChI=1S/C25H27F2N4O8P/c1-16(22(33)36-14-17-8-4-2-5-9-17)30-40(35,39-18-10-6-3-7-11-18)37-15-19-21(32)25(26,27)23(38-19)31-13-12-20(28)29-24(31)34/h2-13,16,19,21,23,32H,14-15H2,1H3,(H,30,35)(H2,28,29,34)/t16-,19+,21-,23+,40?/m0/s1

SMILES Code: C[C@H](NP(OC1=CC=CC=C1)(OC[C@H]2O[C@@H](N3C=CC(N)=NC3=O)C(F)(F)[C@H]2O)=O)C(OCC4=CC=CC=C4)=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: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 580.48 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:
In vitro protocol:
In vivo protocol:

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1: Sarr A, Bré J, Um IH, Chan TH, Mullen P, Harrison DJ, Reynolds PA. Genome- scale CRISPR/Cas9 screen determines factors modulating sensitivity to ProTide NUC-1031. Sci Rep. 2019 May 21;9(1):7643. doi: 10.1038/s41598-019-44089-3. PMID: 31113993; PMCID: PMC6529431.

2: Simmons B, Liu Z, Klapars A, Bellomo A, Silverman SM. Mechanism-Based Solution to the ProTide Synthesis Problem: Selective Access to Sofosbuvir, Acelarin, and INX-08189. Org Lett. 2017 May 5;19(9):2218-2221. doi: 10.1021/acs.orglett.7b00469. Epub 2017 Apr 18. PMID: 28418681.

3: Kapacee ZA, Knox JJ, Palmer D, Blagden SP, Lamarca A, Valle JW, McNamara MG. NUC-1031, use of ProTide technology to circumvent gemcitabine resistance: current status in clinical trials. Med Oncol. 2020 Jun 11;37(7):61. doi: 10.1007/s12032-020-01386-6. PMID: 32529264.

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