Edoxudine

Edoxudine
Clinical data

ATC code	D06BB09 (WHO)
Identifiers
IUPAC name 5-ethyl-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
CAS Number	15176-29-1^Y
PubChem (CID)	66377
ChemSpider	59752^N
UNII	15ZQM81Y3R^Y
ChEMBL	CHEMBL318153^N
ECHA InfoCard	100.035.645
Chemical and physical data
Formula	C₁₁H₁₆N₂O₅
Molar mass	256.25514
3D model (Jmol)	Interactive image
SMILES O=C/1NC(=O)N(\C=C\1CC)[C@@H]2O[C@@H]([C@@H](O)C2)CO
InChI InChI=1S/C11H16N2O5/c1-2-6-4-13(11(17)12-10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,2-3,5H2,1H3,(H,12,16,17)/t7-,8+,9+/m0/s1^N Key:XACKNLSZYYIACO-DJLDLDEBSA-N^N
^NY (what is this?) (verify)

Edoxudine (or edoxudin) is an antiviral drug. It is an analog of thymidine, a nucleoside.

It has shown effectiveness against herpes simplex virus.^[1]

Synthesis

Edoxudine synthesis:^[2] Synthesis via organopalladium intermediates:^[3]^[4]

Mercuration of the 2'-deoxyuridine 1 leads to the organometallic derivative 2; reaction of that with ethylene in the presence dilithiopalladium tetrachloride gives the alkylation product 3; this is reduced catalytically in situ. There is thus obtained the antiviral agent edoxudine 4.

References

↑ "Topical antiviral agents for herpes simplex virus infections". Drugs Today. 34 (12): 1013–25. December 1998. doi:10.1358/dot.1998.34.12.487486. PMID 14743269.
↑ K. K. Gauri, GB 1170565; eidem, U.S. Patent 3,553,192 (1968, 1971 both to Robugen).
↑ Bergstrom, Donald E.; Ruth, Jerry L. (1976). "Synthesis of C-5 substituted pyrimidine nucleosides via organopalladium intermediates". Journal of the American Chemical Society. 98 (6): 1587–9. doi:10.1021/ja00422a056. PMID 1249369.
↑ Bergstrom, Donald E.; Ogawa, Mark K. (1978). "C-5 substituted pyrimidine nucleosides. 2. Synthesis via olefin coupling to organopalladium intermediates derived from uridine and 2'-deoxyuridine". Journal of the American Chemical Society. 100 (26): 8106–8112. doi:10.1021/ja00494a014. ISSN 0002-7863.

Antibiotics and chemotherapeutics for dermatological use (D06)

Antibiotics

Tetracycline and derivatives	Demeclocycline Chlortetracycline Oxytetracycline Tetracycline

Others	Amphenicol: Chloramphenicol Aminoglycosides: Neomycin Gentamicin Amikacin Quinolone: Nadifloxacin Streptogramin: Virginiamycin Rifamycin: Rifaximin other: Fusidic acid Bacitracin Tyrothricin Mupirocin

Chemotherapeutics

Sulfonamides	Silver sulfadiazine Sulfathiazole Mafenide Sulfamethizole Sulfanilamide Sulfamerazine

Antivirals	Aciclovir Penciclovir Idoxuridine Edoxudine Imiquimod Resiquimod Podophyllotoxin Docosanol Tromantadine Inosine Lysozyme Ibacitabine Lysine

Other	Ingenol mebutate Metronidazole

DNA virus antivirals (primarily J05, also S01AD and D06BB)

Baltimore I

Herpesvirus

DNA-synthesis
inhibitor

TK activated

Purine analogue	guanine (Aciclovir^#/Valaciclovir Ganciclovir/Valganciclovir Penciclovir/Famciclovir) adenine (Vidarabine)

Pyrimidine analogue	uridine (Idoxuridine Trifluridine (+tipiracil) Edoxudine) thymine Brivudine Sorivudine cytosine (Cytarabine)

Not TK activated

Foscarnet

Other

HPV/MC

Vaccinia

assembly: Rifampicin

Poxviridae

Methisazone

Hepatitis B (VII)

Multiple/general

Nucleic acid inhibitors	Cidofovir

Interferon	Interferon alfa 2b Peginterferon alfa-2a

Multiple/unknown	Ribavirin^#/Taribavirin^† Moroxydine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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