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

MedKoo Cat#: 206537 | Name: Acelarin

Description:

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

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

Theoretical Analysis

MedKoo Cat#: 206537

Name: Acelarin

CAS#: 840506-29-8

Chemical Formula: C25H27F2N4O8P

Exact Mass: 580.1535

Molecular Weight: 580.48

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 450.00	2 Weeks
50mg	USD 750.00	2 Weeks
100mg	USD 1,250.00	2 Weeks
200mg	USD 2,050.00	2 Weeks
500mg	USD 4,050.00	2 Weeks

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Related CAS #

No Data

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

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

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.