Aminoimidazole Carboxamide

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MedKoo CAT#: 584117

CAS#: 360-97-4

Description: Aminoimidazole Carboxamide is an imidazole derivative which is a metabolite of the antineoplastic agents BIC and DIC. By itself, or as the ribonucleotide, it is used as a condensation agent in the preparation of nucleosides and nucleotides. Compounded with orotic acid, it is used to treat liver diseases.

Chemical Structure

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Aminoimidazole Carboxamide
CAS# 360-97-4
Instruction

Theoretical Analysis

MedKoo Cat#: 584117
Name: Aminoimidazole Carboxamide
CAS#: 360-97-4
Chemical Formula: C4H6N4O
Exact Mass: 126.05
Molecular Weight: 126.110
Elemental Analysis: C, 38.09; H, 4.80; N, 44.42; O, 12.69

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.

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Synonym: Aminoimidazole Carboxamide; Colahepat; Diazol-C; DiazolC; Diazol C; Ba 2756; Ba-2756; Ba2756; NSC 7784; NSC-7784; NSC7784

IUPAC/Chemical Name: Imidazole-4-carboxamide, 5-amino-

InChi Key: DVNYTAVYBRSTGK-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)

SMILES Code: O=C(C1=C(N)NC=N1)N

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

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 126.11 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bazurto JV, Heitman NJ, Downs DM. Aminoimidazole Carboxamide Ribotide Exerts Opposing Effects on Thiamine Synthesis in Salmonella enterica. J Bacteriol. 2015 Sep;197(17):2821-30. doi: 10.1128/JB.00282-15. Epub 2015 Jun 22. PubMed PMID: 26100042; PubMed Central PMCID: PMC4524041.

2: Al-Moujahed A, Nicolaou F, Brodowska K, Papakostas TD, Marmalidou A, Ksander BR, Miller JW, Gragoudas E, Vavvas DG. Uveal melanoma cell growth is inhibited by aminoimidazole carboxamide ribonucleotide (AICAR) partially through activation of AMP-dependent kinase. Invest Ophthalmol Vis Sci. 2014 Apr 29;55(7):4175-85. doi: 10.1167/iovs.13-12856. PubMed PMID: 24781943; PubMed Central PMCID: PMC4089421.

3: Funk RS, van Haandel L, Becker ML, Leeder JS. Low-dose methotrexate results in the selective accumulation of aminoimidazole carboxamide ribotide in an erythroblastoid cell line. J Pharmacol Exp Ther. 2013 Oct;347(1):154-63. doi: 10.1124/jpet.113.206672. Epub 2013 Jul 25. PubMed PMID: 23887097; PubMed Central PMCID: PMC3781408.

4: Theodoropoulou S, Brodowska K, Kayama M, Morizane Y, Miller JW, Gragoudas ES, Vavvas DG. Aminoimidazole carboxamide ribonucleotide (AICAR) inhibits the growth of retinoblastoma in vivo by decreasing angiogenesis and inducing apoptosis. PLoS One. 2013;8(1):e52852. doi: 10.1371/journal.pone.0052852. Epub 2013 Jan 3. PubMed PMID: 23300996; PubMed Central PMCID: PMC3536763.

5: Suzuki J, Yoshimura T, Simeonova M, Takeuchi K, Murakami Y, Morizane Y, Miller JW, Sobrin L, Vavvas DG. Aminoimidazole carboxamide ribonucleotide ameliorates experimental autoimmune uveitis. Invest Ophthalmol Vis Sci. 2012 Jun 28;53(7):4158-69. doi: 10.1167/iovs.11-9323. PubMed PMID: 22562518; PubMed Central PMCID: PMC3392008.

6: Suzuki J, Manola A, Murakami Y, Morizane Y, Takeuchi K, Kayama M, Miller JW, Sobrin L, Vavvas DG. Inhibitory effect of aminoimidazole carboxamide ribonucleotide (AICAR) on endotoxin-induced uveitis in rats. Invest Ophthalmol Vis Sci. 2011 Aug 22;52(9):6565-71. doi: 10.1167/iovs.11-7331. PubMed PMID: 21775660.

7: Jose C, Bellance N, Chatelain EH, Benard G, Nouette-Gaulain K, Rossignol R. Antiproliferative activity of levobupivacaine and aminoimidazole carboxamide ribonucleotide on human cancer cells of variable bioenergetic profile. Mitochondrion. 2012 Jan;12(1):100-9. doi: 10.1016/j.mito.2011.03.010. Epub 2011 Apr 5. PubMed PMID: 21447405.

8: Theodoropoulou S, Kolovou PE, Morizane Y, Kayama M, Nicolaou F, Miller JW, Gragoudas E, Ksander BR, Vavvas DG. Retinoblastoma cells are inhibited by aminoimidazole carboxamide ribonucleotide (AICAR) partially through activation of AMP-dependent kinase. FASEB J. 2010 Aug;24(8):2620-30. doi: 10.1096/fj.09-152546. Epub 2010 Apr 6. Erratum in: FASEB J. 2012 Oct;26(10):4383-4. PubMed PMID: 20371623; PubMed Central PMCID: PMC2909289.

9: Dougherty MJ, Boyd JM, Downs DM. Inhibition of fructose-1,6-bisphosphatase by aminoimidazole carboxamide ribotide prevents growth of Salmonella enterica purH mutants on glycerol. J Biol Chem. 2006 Nov 10;281(45):33892-9. Epub 2006 Sep 20. PubMed PMID: 16987812.

10: Reiter AK, Bolster DR, Crozier SJ, Kimball SR, Jefferson LS. Repression of protein synthesis and mTOR signaling in rat liver mediated by the AMPK activator aminoimidazole carboxamide ribonucleoside. Am J Physiol Endocrinol Metab. 2005 May;288(5):E980-8. Epub 2004 Dec 21. PubMed PMID: 15613684.

11: Dervieux T, Furst D, Lein DO, Capps R, Smith K, Walsh M, Kremer J. Polyglutamation of methotrexate with common polymorphisms in reduced folate carrier, aminoimidazole carboxamide ribonucleotide transformylase, and thymidylate synthase are associated with methotrexate effects in rheumatoid arthritis. Arthritis Rheum. 2004 Sep;50(9):2766-74. PubMed PMID: 15457444.

12: Vergis JM, Beardsley GP. Catalytic mechanism of the cyclohydrolase activity of human aminoimidazole carboxamide ribonucleotide formyltransferase/inosine monophosphate cyclohydrolase. Biochemistry. 2004 Feb 10;43(5):1184-92. PubMed PMID: 14756554.

13: Baggott JE, Morgan SL, Koopman WJ. The effect of methotrexate and 7-hydroxymethotrexate on rat adjuvant arthritis and on urinary aminoimidazole carboxamide excretion. Arthritis Rheum. 1998 Aug;41(8):1407-10. PubMed PMID: 9704638.

14: Thomas CB, Meade JC, Holmes EW. Aminoimidazole carboxamide ribonucleoside toxicity: a model for study of pyrimidine starvation. J Cell Physiol. 1981 Jun;107(3):335-44. PubMed PMID: 6166628.

15: N'Diaye F, Hitier Y, Poiter de Courcy G, Goubern M, Bourdel G. Methionine synthesis, aminoimidazole carboxamide excretion and folate levels in pregnant rats. J Nutr. 1980 Mar;110(3):522-31. PubMed PMID: 6965714.