Abacavir - Moligand™, ≥98% , CAS No.136470-78-5

CAS: 136470-78-5 Cat. No.: A126552 Peso molecular: 286.33 Número EC: 620-487-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

((1s,4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)cyclopent-2-enyl)methanol | Avacavir | Epitope ID:137341 | MFCD00903850 | AVACAVIR [VANDF] | MCGSCOLBFJQGHM-SCZZXKLOSA-N | A807079 | AB01566826_01 | WR2TIP26VS | NSC 742406 | SMR004701251 | (+/-)-cis-

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

Abacavir is a powerful nucleoside analog reverse transcriptase inhibitor (NRTI) used to treat HIV and AIDS. Abacavir exhibits antiviral activity. It is associated with myocardial infarction and fatal hypersensitivity reaction (HSR).

Specifications

Sinónimos

((1s, 4r)-4-(2-amino-6-(cyclopropylamino)-9h-purin-9-yl)cyclopent-2-enyl)methanol | Avacavir | Epitope ID:137341 | MFCD00903850 | AVACAVIR [VANDF] | MCGSCOLBFJQGHM-SCZZXKLOSA-N | A807079 | AB01566826_01 | WR2TIP26VS | NSC 742406 | SMR004701251 | (+/-)-cis-

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Abacavir incorporated in the cells is converted to triphosphate containing guanine analog carbovir (CBV) and it favors the generation of higher double stranded breaks (DSBs). Abacavir sulfate is a Nucleoside analog reverse transcriptase inhibitor (NRTI);

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488189775
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488189775
• Sonrisas canónicas: C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)C4CC(C=C4)CO
• IUPAC Name: [(1S,4R)-4-[2-amino-6-(cyclopropylamino)purin-9-yl]cyclopent-2-en-1-yl]methanol
• InChIKey: MCGSCOLBFJQGHM-SCZZXKLOSA-N
• INCHI: 1S/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m1/s1
• Isómeros SMILES: C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)[C@@H]4C[C@@H](C=C4)CO
• CAS alternativo: 136777-48-5
• Peso molecular: 286.33
• Reaxy-Rn: 21292908
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=21292908&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Clase Nucleoside and nucleotide analogues
      • Subclass Cyclopentyl nucleosides
        • Level5 1,3-substituted cyclopentyl nucleosides
          • Level6 1,3-substituted cyclopentyl purine nucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Clase: Nucleoside and nucleotide analogues
• Subclass: Cyclopentyl nucleosides
• Intermediate Tree Nodes: 1,3-substituted cyclopentyl nucleosides
• Direct Parent: 1,3-substituted cyclopentyl purine nucleosides
• Alternative Parents: 6-alkylaminopurines Secondary alkylarylamines Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Heteroaromatic compounds Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 1,3-substituted cyclopentyl purine nucleoside - 6-alkylaminopurine - 6-aminopurine - Imidazopyrimidine - Purine - Aminopyrimidine - Secondary aliphatic/aromatic amine - N-substituted imidazole - Pyrimidine - Imidolactam - Heteroaromatic compound - Azole - Imidazole - Secondary amine - Organoheterocyclic compound - Azacycle - Amine - Organooxygen compound - Organonitrogen compound - Organic nitrogen compound - Organopnictogen compound - Primary alcohol - Primary amine - Organic oxygen compound - Hydrocarbon derivative - Alcohol - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as 1,3-substituted cyclopentyl purine nucleosides. These are nucleoside analogues with a structure that consists of a cyclobutane that is substituted a the 1-position with a hydroxyl group and at the 3-position with either a purine base.
• External Descriptors: 2,6-diaminopurine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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ADRB2 Tclin Beta-2 adrenergic receptor (11824 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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ADRB1 Tclin Beta-1 adrenergic receptor (6630 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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DRD2 Tclin Dopamine D2 receptor (23596 Activities)

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GABRA1 Tclin GABA receptor alpha-1 subunit (399 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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HRH2 Tclin Histamine H2 receptor (5428 Activities)

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HTR2A Tclin Serotonin 2a (5-HT2a) receptor (14758 Activities)

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HTR2C Tclin Serotonin 2c (5-HT2c) receptor (11471 Activities)

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AVPR2 Tclin Vasopressin V2 receptor (2912 Activities)

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ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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AGTR1 Tclin Type-1 angiotensin II receptor (5176 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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PTGS2 Tclin Cyclooxygenase-2 (13999 Activities)

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HRH1 Tclin Histamine H1 receptor (7573 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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AVPR1A Tclin Vasopressin V1a receptor (5412 Activities)

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OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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HTR3A Tclin Serotonin 3a (5-HT3a) receptor (3366 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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SLC29A1 Tclin Equilibrative nucleoside transporter 1 (1711 Activities)

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ADRA2B Tclin Alpha-2b adrenergic receptor (4412 Activities)

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ADRA2C Tclin Alpha-2c adrenergic receptor (4876 Activities)

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CHRM3 Tclin Muscarinic acetylcholine receptor M3 (7750 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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EDNRA Tclin Endothelin receptor ET-A (5008 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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BDKRB2 Tclin Bradykinin B2 receptor (3970 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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CHRNA4 Tclin Neuronal acetylcholine receptor protein alpha-4 subunit (1265 Activities)

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ALB Tchem Serum albumin (2651 Activities)

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MC3R Tchem Melanocortin receptor 3 (5659 Activities)

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Objetivos asociados (no humanos)

pol Human immunodeficiency virus type 1 protease (9113 Activities)

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pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

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Npy1r Neuropeptide Y receptor type 1 (8 Activities)

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Cckar Cholecystokinin A receptor (90 Activities)

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Pde4d Phosphodiesterase 4D (4 Activities)

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Abcc1 Multidrug resistance-associated protein 1 (42 Activities)

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Abcb1b P-glycoprotein 1 (174 Activities)

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Plasmodium falciparum (966862 Activities)

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Oryctolagus cuniculus (11301 Activities)

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Human alphaherpesvirus 1 (11089 Activities)

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Hepatitis B virus (7925 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Moloney murine sarcoma virus (182 Activities)

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Human immunodeficiency virus 2 (5592 Activities)

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Human immunodeficiency virus (3636 Activities)

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L1210 (27553 Activities)

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C3H/3T3 (186 Activities)

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Luciferin 4-monooxygenase (66902 Activities)

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SARS-CoV-2 (38078 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: 25°C: DMSO <1 mg/mL; Water 36 mg/mL; Ethanol<1mg/mL
• Rotación específica [α]: -54° (C=0.15,MeOH)
• Punto de fusión (°C): 161 °C(dec.)
• Peso molecular: 286.330 g/mol
• XLogP3: 0.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 286.154 Da
• Monoisotopic Mass: 286.154 Da
• Topological Polar Surface Area: 102.000 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 414.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Wang Bin, Chen Yanfen, Wu Yuanya, Weng Bo, Liu Yingshuai, Li Chang Ming.  (2016)  Synthesis of nitrogen- and iron-containing carbon dots, and their application to colorimetric and fluorometric determination of dopamine.  MICROCHIMICA ACTA,  183  (9): (2491-2500).  [PMID:] [10.1007/s00604-016-1885-5]

2. Zijun Dong, Zhihao Han, Lulu Zhang, Xiaohui Sun, Chenyu Wang, Yifeng Yang.  (2026)  Fate and Ecological Risk Assessment of Antiviral Drugs in Multiprocess Wastewater Treatment Plants and Adjacent Watersheds: A Case Study in Shenzhen, China.  ACS ES&T Water,      [PMID:] [10.1021/acsestwater.5c01216]

3. Chengzhi Zhou, Zongyu Yan, Zhenshun Hou, Yanlong Sun, Ya-nan Zhang.  (2026)  Agricultural dissolved black carbon modulates photodegradation of antiviral drug: Insights from optical and molecular signatures.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:] [10.1016/j.jhazmat.2026.141723]