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MedKoo Cat#: 128297 | Name: AICAR phosphate
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Description:

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

AICAR, also known as AICA riboside, is a purine precursor with antineoplastic activity. It is important in treatment of metabolic diseases such as type 2 diabetes as well as possible treatment of various cancer types.

Chemical Structure

AICAR phosphate
AICAR phosphate
CAS#681006-28-0 (phosphate)

Theoretical Analysis

MedKoo Cat#: 128297

Name: AICAR phosphate

CAS#: 681006-28-0 (phosphate)

Chemical Formula: C9H17N4O9P

Exact Mass: 356.0733

Molecular Weight: 356.23

Elemental Analysis: C, 30.35; H, 4.81; N, 15.73; O, 40.42; P, 8.69

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
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Related CAS #
3031-94-5 (free base) 681006-28-0 (phosphate)
Synonym
AICA-Ribotide; AICA-Riboside-5'-phosphate; 5-Aminoimidazole-4-Carboxamide Ribonucelotide; NSC 283955; NSC283955; NSC-283955; NSC 29222; NSC29222; NSC-29222
IUPAC/Chemical Name
5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carboxamide phosphate
InChi Key
BPVGMEHURDEDAZ-GWTDSMLYSA-N
InChi Code
InChI=1S/C9H14N4O5.H3O4P/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9;1-5(2,3)4/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17);(H3,1,2,3,4)/t3-,5-,6-,9-;/m1./s1
SMILES Code
OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C=NC(C(N)=O)=C2N)O1.O=P(O)(O)O
Appearance
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 356.23 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
1: Višnjić D, Lalić H, Dembitz V, Tomić B, Smoljo T. AICAr, a Widely Used AMPK Activator with Important AMPK-Independent Effects: A Systematic Review. Cells. 2021 May 4;10(5):1095. doi: 10.3390/cells10051095. PMID: 34064363; PMCID: PMC8147799. 2: Hinkle JS, Rivera CN, Vaughan RA. AICAR stimulates mitochondrial biogenesis and BCAA catabolic enzyme expression in C2C12 myotubes. Biochimie. 2022 Apr;195:77-85. doi: 10.1016/j.biochi.2021.11.004. Epub 2021 Nov 16. PMID: 34798200. 3: Wu Y, Duan X, Gao Z, Yang N, Xue F. AICAR attenuates postoperative abdominal adhesion formation by inhibiting oxidative stress and promoting mesothelial cell repair. PLoS One. 2022 Sep 1;17(9):e0272928. doi: 10.1371/journal.pone.0272928. PMID: 36048820; PMCID: PMC9436141. 4: Tukhovskaya EA, Shaykhutdinova ER, Pakhomova IA, Slashcheva GA, Goryacheva NA, Sadovnikova ES, Rasskazova EA, Kazakov VA, Dyachenko IA, Frolova AA, Brovkin AN, Kaluzhsky VE, Beburov MY, Murashev AN. AICAR Improves Outcomes of Metabolic Syndrome and Type 2 Diabetes Induced by High-Fat Diet in C57Bl/6 Male Mice. Int J Mol Sci. 2022 Dec 11;23(24):15719. doi: 10.3390/ijms232415719. PMID: 36555360; PMCID: PMC9778872. 5: Pyla R, Hartney TJ, Segar L. AICAR promotes endothelium-independent vasorelaxation by activating AMP-activated protein kinase via increased ZMP and decreased ATP/ADP ratio in aortic smooth muscle. J Basic Clin Physiol Pharmacol. 2022 May 4;33(6):759-768. doi: 10.1515/jbcpp-2021-0308. PMID: 35503763; PMCID: PMC9664587. 6: Sobolevsky T, Piper T, Ahrens B, Thevis M. AICAr to SAICAr ratio can serve as additional marker of AICAr use. Drug Test Anal. 2022 Nov;14(11-12):2017-2025. doi: 10.1002/dta.3399. Epub 2022 Nov 16. PMID: 36342242. 7: Torres RJ, Puig JG. Aicar effect in early neuronal development. Nucleosides Nucleotides Nucleic Acids. 2018;37(5):261-272. doi: 10.1080/15257770.2018.1453073. Epub 2018 Apr 10. PMID: 29634397. 8: Liu J, Liang L, Li X, Peng YL, Zhang J, Wang XL, Liu J, Nie L. AICAR suppresses cell proliferation and synergizes with decitabine in myelodysplastic syndrome via DNA damage induction. Biotechnol Lett. 2021 Jun;43(6):1131-1142. doi: 10.1007/s10529-021-03112-2. Epub 2021 Mar 31. PMID: 33788127. 9: Khorraminejad-Shirazi M, Sani M, Talaei-Khozani T, Dorvash M, Mirzaei M, Faghihi MA, Monabati A, Attar A. AICAR and nicotinamide treatment synergistically augment the proliferation and attenuate senescence-associated changes in mesenchymal stromal cells. Stem Cell Res Ther. 2020 Feb 3;11(1):45. doi: 10.1186/s13287-020-1565-6. PMID: 32014016; PMCID: PMC6998366. 10: Yan S, Yuan D, Li Q, Li S, Zhang F. AICAR enhances the cytotoxicity of PFKFB3 inhibitor in an AMPK signaling-independent manner in colorectal cancer cells. Med Oncol. 2021 Nov 10;39(1):10. doi: 10.1007/s12032-021-01601-y. PMID: 34761330. 11: Tsai WL, Hsu CN, Tain YL. Whether AICAR in Pregnancy or Lactation Prevents Hypertension Programmed by High Saturated Fat Diet: A Pilot Study. Nutrients. 2020 Feb 11;12(2):448. doi: 10.3390/nu12020448. PMID: 32053935; PMCID: PMC7071394. 12: Guo F, Liu SQ, Gao XH, Zhang LY. AICAR induces AMPK-independent programmed necrosis in prostate cancer cells. Biochem Biophys Res Commun. 2016 May 27;474(2):277-283. doi: 10.1016/j.bbrc.2016.04.077. Epub 2016 Apr 18. PMID: 27103440. 13: Nie J, Liu A, Tan Q, Zhao K, Hu K, Li Y, Yan B, Zhou L. AICAR activates ER stress-dependent apoptosis in gallbladder cancer cells. Biochem Biophys Res Commun. 2017 Jan 8;482(2):246-252. doi: 10.1016/j.bbrc.2016.11.050. Epub 2016 Nov 12. PMID: 27847321. 14: Kim YK, Hong HK, Yoo HS, Park SP, Park KH. AICAR upregulates ABCA1/ABCG1 expression in the retinal pigment epithelium and reduces Bruch's membrane lipid deposit in ApoE deficient mice. Exp Eye Res. 2021 Dec;213:108854. doi: 10.1016/j.exer.2021.108854. Epub 2021 Nov 19. PMID: 34808137. 15: Morishita M, Kawamoto T, Hara H, Onishi Y, Ueha T, Minoda M, Katayama E, Takemori T, Fukase N, Kurosaka M, Kuroda R, Akisue T. AICAR induces mitochondrial apoptosis in human osteosarcoma cells through an AMPK-dependent pathway. Int J Oncol. 2017 Jan;50(1):23-30. doi: 10.3892/ijo.2016.3775. Epub 2016 Nov 21. PMID: 27878239; PMCID: PMC5182012. 16: Tsogbadrakh B, Ryu H, Ju KD, Lee J, Yun S, Yu KS, Kim HJ, Ahn C, Oh KH. AICAR, an AMPK activator, protects against cisplatin-induced acute kidney injury through the JAK/STAT/SOCS pathway. Biochem Biophys Res Commun. 2019 Feb 12;509(3):680-686. doi: 10.1016/j.bbrc.2018.12.159. Epub 2019 Jan 4. PMID: 30616891. 17: Pokrywka A, Cholbinski P, Kaliszewski P, Kowalczyk K, Konczak D, Zembron- Lacny A. Metabolic modulators of the exercise response: doping control analysis of an agonist of the peroxisome proliferator-activated receptor δ (GW501516) and 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR). J Physiol Pharmacol. 2014 Aug;65(4):469-76. PMID: 25179079. 18: Jiang L, Liu T, Xie L, Ouyang C, Ji J, Huang T. AICAR prolongs corneal allograft survival via the AMPK-mTOR signaling pathway in mice. Biomed Pharmacother. 2019 May;113:108558. doi: 10.1016/j.biopha.2019.01.019. Epub 2019 Mar 8. PMID: 30856534. 19: Hashempour S, Shahabadi N, Adewoye A, Murphy B, Rouse C, Salvatore BA, Stratton C, Mahdavian E. Binding Studies of AICAR and Human Serum Albumin by Spectroscopic, Theoretical, and Computational Methodologies. Molecules. 2020 Nov 19;25(22):5410. doi: 10.3390/molecules25225410. PMID: 33228044; PMCID: PMC7699360. 20: Zhu XY, Liu W, Liang HT, Tang L, Zou P, You Y, Zhu XJ. AICAR and Decitabine Enhance the Sensitivity of K562 Cells to Imatinib by Promoting Mitochondrial Activity. Curr Med Sci. 2020 Oct;40(5):871-878. doi: 10.1007/s11596-020-2266-1. Epub 2020 Oct 29. PMID: 33123902.