F-amidine

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

MedKoo CAT#: 562524

CAS#: 877617-45-3

Description: F-amidine is a bioavailable irreversible inactivator of PAD4.


Chemical Structure

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F-amidine
CAS# 877617-45-3

Theoretical Analysis

MedKoo Cat#: 562524
Name: F-amidine
CAS#: 877617-45-3
Chemical Formula: C14H19FN4O2
Exact Mass: 294.1492
Molecular Weight: 294.33
Elemental Analysis: C, 57.13; H, 6.51; F, 6.45; N, 19.04; O, 10.87

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: F-amidine; F amidine;

IUPAC/Chemical Name: (S,Z)-N-(1-amino-5-((1-amino-2-fluoroethylidene)amino)-1-oxopentan-2-yl)benzamide

InChi Key: OLFDULIIJWCYCK-NSHDSACASA-N

InChi Code: InChI=1S/C14H19FN4O2/c15-9-12(16)18-8-4-7-11(13(17)20)19-14(21)10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H2,16,18)(H2,17,20)(H,19,21)/t11-/m0/s1

SMILES Code: O=C(N[C@H](C(N)=O)CCC/N=C(CF)\N)C1=CC=CC=C1

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 294.33 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.

Recalculate based on batch purity %
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

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1: Wei Y, Liu R, Liu C, Jin J, Li D, Lin J. Identification of novel PAD4 inhibitors based on a pharmacophore model derived from transition state coordinates. J Mol Graph Model. 2017 Mar;72:88-95. doi: 10.1016/j.jmgm.2016.11.016. Epub 2016 Dec 19. PubMed PMID: 28064083.

2: Li D, Liu C, Lin J. Theoretical study of the mechanism of protein arginine deiminase 4 (PAD4) inhibition by F-amidine. J Mol Graph Model. 2015 Feb;55:25-32. doi: 10.1016/j.jmgm.2014.10.014. Epub 2014 Nov 7. PubMed PMID: 25424656.

3: Bicker KL, Anguish L, Chumanevich AA, Cameron MD, Cui X, Witalison E, Subramanian V, Zhang X, Chumanevich AP, Hofseth LJ, Coonrod SA, Thompson PR. D-amino acid based protein arginine deiminase inhibitors: Synthesis, pharmacokinetics, and in cellulo efficacy. ACS Med Chem Lett. 2012 Oct 26;3(12):1081-1085. PubMed PMID: 23420624; PubMed Central PMCID: PMC3572853.

4: Jones JE, Slack JL, Fang P, Zhang X, Subramanian V, Causey CP, Coonrod SA, Guo M, Thompson PR. Synthesis and screening of a haloacetamidine containing library to identify PAD4 selective inhibitors. ACS Chem Biol. 2012 Jan 20;7(1):160-5. doi: 10.1021/cb200258q. Epub 2011 Oct 21. PubMed PMID: 22004374; PubMed Central PMCID: PMC3262960.

5: Causey CP, Jones JE, Slack JL, Kamei D, Jones LE, Subramanian V, Knuckley B, Ebrahimi P, Chumanevich AA, Luo Y, Hashimoto H, Sato M, Hofseth LJ, Thompson PR. The development of N-α-(2-carboxyl)benzoyl-N(5)-(2-fluoro-1-iminoethyl)-l-ornithine amide (o-F-amidine) and N-α-(2-carboxyl)benzoyl-N(5)-(2-chloro-1-iminoethyl)-l-ornithine amide (o-Cl-amidine) as second generation protein arginine deiminase (PAD) inhibitors. J Med Chem. 2011 Oct 13;54(19):6919-35. doi: 10.1021/jm2008985. Epub 2011 Sep 16. Erratum in: J Med Chem. 2011 Nov 24;54(22):7942. PubMed PMID: 21882827; PubMed Central PMCID: PMC3196593.

6: Slack JL, Causey CP, Luo Y, Thompson PR. Development and use of clickable activity based protein profiling agents for protein arginine deiminase 4. ACS Chem Biol. 2011 May 20;6(5):466-76. doi: 10.1021/cb1003515. Epub 2011 Feb 7. PubMed PMID: 21265574; PubMed Central PMCID: PMC3098906.

7: Knuckley B, Luo Y, Thompson PR. Profiling Protein Arginine Deiminase 4 (PAD4): a novel screen to identify PAD4 inhibitors. Bioorg Med Chem. 2008 Jan 15;16(2):739-45. Epub 2007 Oct 13. PubMed PMID: 17964793; PubMed Central PMCID: PMC2267747.

8: Luo Y, Arita K, Bhatia M, Knuckley B, Lee YH, Stallcup MR, Sato M, Thompson PR. Inhibitors and inactivators of protein arginine deiminase 4: functional and structural characterization. Biochemistry. 2006 Oct 3;45(39):11727-36. PubMed PMID: 17002273; PubMed Central PMCID: PMC1808342.

9: Luo Y, Knuckley B, Lee YH, Stallcup MR, Thompson PR. A fluoroacetamidine-based inactivator of protein arginine deiminase 4: design, synthesis, and in vitro and in vivo evaluation. J Am Chem Soc. 2006 Feb 1;128(4):1092-3. PubMed PMID: 16433522; PubMed Central PMCID: PMC1850713.