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Explore Compound5-Aminoimidazole-4-carboxamide ribonucleoside represents an indispensable chemical tool in cellular bioenergetics, acting as a cell-permeable precursor to the potent AMP-activated protein kinase (AMPK) agonist ZMP.
In modern cellular pharmacology and metabolic research, China AICAR product & products hold a dominant structural position. Known scientifically as Acadesine, AICA-riboside, or under IUPAC nomenclature as 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide (CAS 2627-69-2), the molecule serves as a critical intermediate within de novo purine biosynthesis. Upon transport across the plasma membrane via equilibrative nucleoside transporters (ENTs), AICAR undergoes phosphorylation by intracellular adenosine kinase, transforming into 5-aminoimidazole-4-carboxamide ribonucleotide (ZMP). ZMP acts as an AMP mimetic, binding directly to the cystathionine β-synthase (CBS) domains situated on the regulatory γ-subunit of AMPK.
This molecular interaction induces allosteric activation of AMPK while simultaneously inhibiting dephosphorylation of threonine-172 (Thr172) on the α-catalytic subunit by protein phosphatases. The cascade triggers a wholesale metabolic transition from anabolic ATP-consuming processes—such as lipogenesis, glycogen storage, and protein synthesis—to catabolic ATP-generating systems, including mitochondrial fatty acid β-oxidation, glycolysis, and glucose uptake via GLUT4 translocation. Consequently, global enterprise buyers from biotech hubs, contract research organizations (CROs), and specialized academic consortia view bulk chemical consistency in AICAR as an uncompromised requirement for longitudinal translational research.
| Analytical Parameter | Standard Commercial Grade | China Factory 4.0 Research Grade | Analytical Reference Standard |
|---|---|---|---|
| Chemical Formula | C₉H₁₄N₄O₅ | C₉H₁₄N₄O₅ | C₉H₁₄N₄O₅ |
| Chromatographic Purity (RP-HPLC) | ≥ 95.0% - 98.0% | ≥ 99.0% - 99.5% | ≥ 99.8% (qNMR calibrated) |
| Physical Appearance | Off-white crystalline powder | Pure white microcrystalline solid | Ultra-pure crystalline cake |
| Residual Solvents (ICH Q3C) | < 5000 ppm (unspecified) | Class 2 < Target Limit; Class 3 < 500 ppm | Residual Solvent Free (GC-HS verified) |
| Endotoxin Specification | Not specified | < 0.05 EU/mg (LAL Kinetic Chromogenic) | Ultra-low sterile ceiling |
| Specific Optical Rotation [α]²⁰D | -55.0° to -63.0° | -59.0° to -62.5° (c=1, H₂O) | -60.5° (certified absolute) |
Procurement directors within international pharmaceutical and diagnostic testing spaces encounter multifaceted supply obstacles when purchasing nucleosides and biological intermediates at metric scale.
AICAR molecules exhibit chemical sensitivity around the N-glycosidic bond connecting the imidazole core to the ribofuranose moiety. Minor pH fluctuations during industrial precipitation can induce hydrolysis into 5-aminoimidazole-4-carboxamide (AICA) base and free D-ribose. Enterprise-tier Chinese manufacturers counteract this via automated chilled-flow crystallization tanks.
Modern Western compliance teams no longer accept generic single-wavelength HPLC sheets. Authentic procurement packages demand coupled LC-MS/MS parent ion fragmentation data, 400 MHz 1H-NMR spectra showing baseline imidazole singlet peaks (approx. 7.30 ppm) and anomeric proton doublets (5.50 ppm), accompanied by Karl Fischer water titration below 1.0%.
While lyophilized dry AICAR solid exhibits decent ambient resilience over short intervals, bulk transnational transport across contrasting climate zones requires calibrated multi-barrier moisture-barrier foil packaging with desiccant chambers. Forward-looking suppliers integrate real-time temperature loggers into multi-kilogram air shipments.
The transition from legacy batch chemistry to automated enzymatic biotransformation has cemented China's status as the world's most resilient manufacturing center for high-purity nucleosides.
Modern facilities employ both total chemical synthesis—via condensation of protected D-ribose derivatives with functionalized imidazole rings—and whole-cell multi-enzyme biocatalytic fermentation, offering flexibility against upstream feedstock constraints.
Process Analytical Technology (PAT) integrates real-time near-infrared (NIR) and focused beam reflectance measurement (FBRM) sensors directly into crystallization loops, tracking crystal size distributions and eliminating batch inconsistencies.
Cleanroom Class A freeze-drying chambers equipped with automated hydraulic shelf stoppers execute programmable 48-hour sublimation profiles, yielding uniform, fast-dissolving microcrystalline cakes free of thermal collapsing.
Factory 4.0 parks run integrated membrane bioreactor (MBR) systems coupled with catalytic oxidation units, recovering 95% of process solvents and providing continuous manufacturing uptime under strict national environmental mandates.
Operating responsibly within the global biochemical supply sector demands rigorous clarity regarding the legal boundaries, therapeutic history, and strict research status of AICAR.
AICAR occupies a unique position in global pharmacology. Clinically investigated under the generic denomination Acadesine during Phase III human trials in the 1990s and 2000s (such as the RED-CABG trial), the agent demonstrated cardioprotective properties by mitigating ischemia-reperfusion injury through adenosine-regulating mechanisms. Although regulatory approval as a finished pharmaceutical product was paused due to complex efficacy end-points, the compound remains a critical active pharmaceutical ingredient (API) intermediate and reference benchmark across medical research laboratories worldwide.
Crucial Regulatory Delineation: In major jurisdictions including the United States (FDA), the European Union (EMA), and Japan (PMDA), bulk AICAR powder is traded exclusively under Laboratory Research Use Only (RUO) or as an advanced chemical intermediate for further chemical synthesis. It is not approved as a finished drug, food additive, nutritional supplement, or therapeutic device for human or veterinary administration. Legitimate Chinese factories ensure that every shipment conforms to international trade classifications (typically under HS Code 2934.99 or 2938.90), accompanied by explicit End-User Declarations (EUD) confirming institutional research accreditation.
Furthermore, because AICAR accelerates cellular bioenergetics and stimulates muscular glucose influx independent of insulin, the World Anti-Doping Agency (WADA) permanently classifies AICAR under Section S4.5 (Metabolic Modulators) of the Prohibited List. Global logistics corridors maintain stringent analytical verification systems to monitor illicit redirection, ensuring pure supplies are channeled exclusively to authenticated academic, oncology, and biotechnological testing labs.
Across university institutes, contract screening platforms, and preclinical labs, research teams deploy high-grade AICAR within precise metabolic and genetic assay regimes.
In leukemia, glioblastoma, and prostate cancer research models, AICAR administration triggers profound p53 activation, downregulating mammalian target of rapamycin (mTORC1) and arresting malignant cell replication in the G1 phase independent of glucose concentration.
Physiologists investigate AICAR's capacity to induce Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PGC-1α) transcription, stimulating mitochondrial DNA replication and oxidative capacity in skeletal muscle tissue explants.
During cold perfusion and microvascular transplantation experiments, addition of Acadesine to organ preservation solutions reduces post-hypoxic vascular injury by preserving intracellular nucleotide pools and dampening neutrophil activation.
Exhaustive technical responses compiled for lead analytical chemists, compliance officers, and international supply managers.
AICAR (free riboside, CAS 2627-69-2) exhibits pronounced solubility in sterile deionized water (up to ~50 mg/mL with gentle thermal equilibration to 25°C). In organic media, it dissolves easily in anhydrous dimethyl sulfoxide (DMSO) at concentrations ≥ 35 mg/mL, but displays poor solubility in anhydrous ethanol, chloroform, and ethyl acetate. When preparing concentrated stock solutions for cell assays, filter sterilization through a 0.22 μm hydrophilic PTFE or PES membrane is recommended, avoiding cellulose ester filters which can bind nucleosides.
Top-tier manufacturing sites deploy clean-in-place (CIP) and sterilize-in-place (SIP) automated skids coupled with dedicated Hastelloy C-276 and 316L stainless-steel reaction vessels. Cleaning validation protocols follow total organic carbon (TOC) swab limits (< 10 ppm) and swab-specific HPLC residue assays. Production runs operate within Class 100,000 synthesis workshops with negative-to-positive air lock zoning to prevent cross-contamination from adjacent peptide or hormone synthesis lines.
Lyophilized dry powder must be conserved at -20°C in an airtight amber glass vial or sealed heat-welded aluminum barrier bag containing active molecular sieve desiccants. Under these dry conditions, shelf life exceeds 24 months with degradation < 0.2%. Reconstituted aqueous solutions, however, are prone to spontaneous glycosidic hydrolysis over time; stock aliquots should be flashed-frozen in liquid nitrogen and stored at -80°C, avoiding repeated freeze-thaw cycles.
Shipments destined for international destinations are dispatched with a complete technical package: Batch-Specific Certificate of Analysis (COA) containing raw HPLC chromatogram and 1H-NMR spectrum, SDS conforming to GHS Revision 9, Commercial Invoice detailing HS Code 2934.999090, Non-Dangerous Goods Declaration for Air Transport (IATA certified), and a manufacturer's declaration confirming research-grade material status.
Yes. We regularly coordinate blind retention sampling for independent verification through recognized international analytical bodies (e.g., SGS, Eurofins, or customer-designated domestic university laboratories). Escrow terms or Letter of Credit (L/C) arrangements can be aligned with third-party verification of HPLC purity and absence of adulterants.
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Explore CompoundA systematic framework for procurement officers qualifying industrial suppliers of bulk AICAR and nucleoside analogs.
Require full analytical method validation parameters, including limits of detection (LOD) and quantitation (LOQ) for potential process impurities such as AICA base, adenosine, and ribose-1-phosphate.
Commission an initial pilot batch (100g to 1kg scale) to test reconstitution kinetics, solution clarity, heavy metal load via ICP-MS, and endotoxin compatibility in sensitive cellular cultures.
Establish rolling buffer inventory agreements in bonded logistics hubs (Shanghai, Hong Kong, or European warehouses) with contracted change-notification windows (minimum 90 days) for synthesis route updates.
