Abacavir acetate (Prurisol; abacavir hydroxyacetate; KM-133) is a potent and orally bioactive inhibitor of IL-20 and PRINS used for the treatment of plaque psoriasis. It can reduce the proliferation rate of skin in psoriasis as an immune modulator, and thus can be used for treating inflammatory skin problems.
Physicochemical Properties
| Molecular Formula | C16H20N6O3 |
| Molecular Weight | 344.37 |
| Exact Mass | 344.16 |
| Elemental Analysis | C, 55.80; H, 5.85; N, 24.40; O, 13.94 |
| CAS # | 1446418-48-9 |
| Related CAS # | 136470-78-5;136777-48-5 (HCl);168146-84-7 (succinate);188062-50-2 (sulfate); 1446418-48-9 (hydroxyacetate); 384380-52-3 (caeboxylate); |
| PubChem CID | 71605071 |
| Appearance | Solid powder |
| LogP | 0.638 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 25 |
| Complexity | 528 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | O(C(CO)=O)C[C@@H]1C=C[C@@H](C1)N1C=NC2C1=NC(N)=NC=2NC1CC1 |
| InChi Key | ZBBZROWQLKCFQK-KOLCDFICSA-N |
| InChi Code | InChI=1S/C16H20N6O3/c17-16-20-14(19-10-2-3-10)13-15(21-16)22(8-18-13)11-4-1-9(5-11)7-25-12(24)6-23/h1,4,8-11,23H,2-3,5-7H2,(H3,17,19,20,21)/t9-,11+/m1/s1 |
| Chemical Name | ((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl 2-hydroxyacetate |
| Synonyms | PrurisolKM133 KM 133KM-133 Abacavir hydroxyacetateAbacavir acetate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vivo | In mice, oral abacavir glycolate (10–20 mg/kg) once daily efficiently reduces psoriasis [2]. |
| Animal Protocol |
Animal/Disease Models: 6 to 8 weeks old male and female SCID (severe combined immunodeficient) mouse, implanted with psoriatic tissue [2] Doses: 10 and 20 mg/kg Route of Administration: po (oral gavage); 10-20 mg/kg Primary Experimental Results:Reduction The concentration of PRINS and 1L-20 reduces the area of skin lesions. Shows better results than methotrexate in controlling psoriasis. |
| References |
[1]. Guda A, et al. Investigational drugs in phase II clinical trials for moderate to severe plaque psoriasis - potential new treatments on the horizon. Expert Opin Investig Drugs. 2018 Nov;27(11):931-939. [2]. Menon, et al. CARBOCYCLIC NUCLEOSIDES AND THEIR PHARMACEUTICAL USE AND COMPOSITIONS. WO/2013/103601/Al. |
| Additional Infomation | Prurisol is under investigation for the treatment of Chronic Stable Plaque Psoriasis. Prurisol has been investigated for the treatment of Plaque Psoriasis. |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 100 mg/mL (~290.39 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.26 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.26 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.9039 mL | 14.5193 mL | 29.0385 mL | |
| 5 mM | 0.5808 mL | 2.9039 mL | 5.8077 mL | |
| 10 mM | 0.2904 mL | 1.4519 mL | 2.9039 mL |