Epzicom

Base Information

• Chemical Name: Epzicom
• CAS No.: 136470-79-6
• Molecular Formula: C₁₄H₁₈N₆O
• Molecular Weight: 286.337
• UNII: X9A7099R51
• DSSTox Substance ID: DTXSID20332855
• Nikkaji Number: J1.303.600D
• Wikidata: Q27293722
• Mol file: 136470-79-6.mol

Synonyms:((1R,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-cyclopent-2-enyl)methanol;((1R,4S)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-enyl)methanol;(+)-abacavir;(+)-abacavir sulfate;(+-)-abacavir sulfate;(-)-cis-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol;(1R,4R)-abacavir;(1R,4S)-abacavir sulfate;(1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol;(1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-2-cyclopentene-1-methanol succinate (1:1) (salt);1592U89;2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1R,4S)-, sulfate (2:1);2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, (1S,4R)-, rel-, sulfate (2:1);2-cyclopentene-1-methanol, 4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)-, hydrochloride, hydrate (1:1:1), (1S,4R)-;abacavir;abacavir enantiomer;abacavir hydrochloride monohydrate;abacavir succinate;abacavir sulfate;abacavir sulfate racemic;abacavir sulfate, (+)-;abacavir sulfate, (+-)-;abacavir sulfate, (1R,4S)-;abacavir sulphate;abacavir, (+)-;abacavir, (1R,4S)-;abacavir, trans-;abacavir, trans-, (+-)-;Abamune;avacavir;DRG 0257;DRG-0257;DRG0257;trans-abacavir;trans-abacavir R,R-;Ziagen;abacavir - lamivudine;abacavir and lamivudine drug combination;abacavir sulfate and lamivudine;abacavir sulfate-lamivudine combination;abacavir, lamivudine drug combination;abacavir-lamivudine combination;Epzicom;Kivexa

Chemical Property of Epzicom

Chemical Property:

• Boiling Point: 636.0±65.0 °C(Predicted)
• PKA: 14.86±0.10(Predicted)
• PSA: 102.61000
• Density: 1.70±0.1 g/cm3(Predicted)
• LogP: 1.09540
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 286.15420922
• Heavy Atom Count: 21
• Complexity: 414

Purity/Quality:

97% ^*data from raw suppliers

ent-Abacavir ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)C4CC(C=C4)CO
• Isomeric SMILES: C1CC1NC2=C3C(=NC(=N2)N)N(C=N3)[C@H]4C[C@H](C=C4)CO
• Recent ClinicalTrials: Relative Bioavailability Study of a Fixed-dose Combination Dolutegravir/Abacavir/Lamivudine Dispersible Tablet
• Uses: The enatiomer of the nucleoside reverse transcriptase inhibitor (NRTI) Abacavir (A105000) with similar antiviral properties.

Technology Process of Epzicom

There total 71 articles about Epzicom which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol (136522-33-3,172721-00-5) + Cyclopropylamine (765-30-0) → abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

In ethanol; at 70 ℃;

DOI:10.1002/cmdc.201800361

Reference yield: 90.0%

Cyclopropylamine (765-30-0) + ((1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol hydrochloride (172015-79-1) → abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

In methanol; at 70 ℃; for 12h;

DOI:10.1080/15257770008033011

Reference yield: 90.0%

(-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide (136470-88-7) → abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

(-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide; With isopropyl alcohol; sodium hydroxide; for 1h; Reflux;

With hydrogenchloride; In water; isopropyl alcohol; at 20 - 25 ℃; pH=7.0 - 7.5; Product distribution / selectivity;

upstream raw materials:

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate

(1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol

Cyclopropylamine

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Refernces

• 1、 -. "Abacavir intermediate and method for purifying same". Paragraph 0079-0080. . Retrieved 2018/03/26.
• 2、 Thieme, Niels,Breit, Bernhard. "Enantioselective and Regiodivergent Addition of Purines to Terminal Allenes: Synthesis of Abacavir". supporting information. p. 1520 - 1524. Retrieved 2017/02/05.