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Chemistry

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Also known as: 5-ethyl-2'-deoxyuridine, 15176-29-1, 2'-deoxy-5-ethyluridine, Epoxudine, 5-ethyldeoxyuridine, Aedurid
Molecular Formula
C11H16N2O5
Molecular Weight
256.25  g/mol
InChI Key
XACKNLSZYYIACO-DJLDLDEBSA-N
FDA UNII
15ZQM81Y3R

Edoxudin
Edoxudine is a deoxythymidine analog with activity against herpes simplex virus. Edoxudine is activated by viral thymidine kinase to the 5'-monophosphate which is further phosphorylated by cellular enzymes to the 5'-triphosphate, a competitive inhibitor of the viral-coded DNA polymerase.
1 2D Structure

Edoxudin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-ethyl-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
2.1.2 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
2.1.3 InChI Key
XACKNLSZYYIACO-DJLDLDEBSA-N
2.1.4 Canonical SMILES
CCC1=CN(C(=O)NC1=O)C2CC(C(O2)CO)O
2.1.5 Isomeric SMILES
CCC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CO)O
2.2 Other Identifiers
2.2.1 UNII
15ZQM81Y3R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(2'-deoxy-beta-d-ribofuranosyl)-5-ethyluracil

2. 2'-deoxy-5-ethyluridine

3. 5-ethyl-2'-deoxyuridine

4. 5-ethyl-3-(2'-deoxyribofuranosyl)uracil

5. 5-ethyldeoxyuridine

6. Edoxudin

7. Edoxudin, (alpha)-isomer

8. Edoxudin, 2-(14)c-labeled

9. Edoxudin, 2-(14)c-labeled, (alpha)-isomer

10. Edoxudin, 4-(14)c-labeled

11. Edoxudin, 4-(14)c-labeled, (alpha)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 5-ethyl-2'-deoxyuridine

2. 15176-29-1

3. 2'-deoxy-5-ethyluridine

4. Epoxudine

5. 5-ethyldeoxyuridine

6. Aedurid

7. Beta-5-ethyldeoxyuridine

8. Orf 15817

9. Rwj 15817

10. Eudr

11. Uridine, 2'-deoxy-5-ethyl-

12. Mls000069564

13. 15zqm81y3r

14. Chembl318153

15. Orf-15817

16. Rwj-15817

17. Nsc-758405

18. Smr000058816

19. Edoxudinum [latin]

20. Edoxudina [spanish]

21. Edoxudinum

22. Edoxudin

23. Edoxudina

24. Edoxudine [usan:inn]

25. Beta-5-ethyl-2'-deoxyuridine

26. Ccris 2349

27. Einecs 239-226-1

28. Brn 0755089

29. Unii-15zqm81y3r

30. Etudr

31. 5-ethyl-durd

32. 5-ethyl-1-(2'-deoxy-beta-d-ribofuranosyl)uracil

33. Edoxudine [inn]

34. Edoxudine [mi]

35. Edoxudine (usan/inn)

36. Edoxudine [usan]

37. Opera_id_1297

38. Edoxudine [mart.]

39. 5-ethyl-2''-deoxyuridine

40. Cid_1814

41. Edoxudine [who-dd]

42. Dsstox_cid_25890

43. Dsstox_rid_81204

44. Dsstox_gsid_45890

45. Schembl65579

46. Cid_66377

47. Mls001076558

48. Dtxsid4045890

49. Chebi:135051

50. Hms2234l05

51. Hy-b1011

52. Zinc3956771

53. Tox21_111390

54. Bdbm50132292

55. Cs-4524

56. Db13421

57. Nsc 758405

58. 5-ethyl-3-(2'-deoxyribosyl)uracil

59. Cas-15176-29-1

60. D03956

61. 5-ethyl-2 Inverted Exclamation Mark -deoxyuridine

62. Q987691

63. Brd-k86892782-001-13-9

64. 5-ethyl-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione

65. 5-ethyl-1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1h,3h)-dione

66. 5-ethyl-1-((2r,5r)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1h-pyrimidine-2,4-dione

67. 5-ethyl-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione

2.4 Create Date
2005-06-29
3 Chemical and Physical Properties
Molecular Weight 256.25 g/mol
Molecular Formula C11H16N2O5
XLogP3-0.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass256.10592162 g/mol
Monoisotopic Mass256.10592162 g/mol
Topological Polar Surface Area99.1 Ų
Heavy Atom Count18
Formal Charge0
Complexity395
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Edoxudine was used in Europe, in the form of a topical antiviral, for the treatment of human herpes keratitis. Human herpes keratitis is an inflammation of the cornea in the eye caused by herpes simplex virus infection. This infection is a cause of significant morbidity whose incidence is significantly increased in the presence of recurrent infection and it can even produce corneal blindness. Edoxudine 3% cream was also indicated for the treatment of dermal herpes simplex virus. This virus can produce an infection ubiquitously and it is highly contagious. There are two types of herpes virus, type 1 that is mainly transmitted by oral-to-oral contact and type 2 that is sexually transmitted.


5 Pharmacology and Biochemistry
5.1 Pharmacology

In reports, it has been indicated that at antivirally active doses, edoxudine is phosphorylated to a much greater extent by hepatitis-infected cells when compared to mock-infected cells. Once phosphorylated, edoxudine is more highly incorporated into viral DNA than cellular DNA. The level of incorporation into viral DNA highly seems to be correlated with the concentration of edoxudine. The suppression of viral DNA synthesis caused a shutoff of viral replication and the viral titration is significantly reduced.The effect of edoxudine is also proven to reduce significantly the lesion area produced by the viral activity to an even 44% reduction.


5.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)


5.3 ATC Code

D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06B - Chemotherapeutics for topical use

D06BB - Antivirals

D06BB09 - Edoxudine


5.4 Absorption, Distribution and Excretion

Absorption

Edoxudine cream is able to penetrate the skin in a very rapid manner. This easy penetration allows edoxudine to have a greater activity when compared with other topical antivirals that have better antiviral activity in vitro. In preclinical trials in mice, after intravenous administration of edoxudine, the mean residence time was 25 min. Edoxudine presented a bioavailability of 49% with a Cmax and tmax of 2.4 mcg/g and 31.1 min respectively. The AUC in plasma of edoxudine is significantly higher when administered orally when compared with intravenous administration.


Volume of Distribution

This pharmacokinetic property is not available.


Clearance

The plasma clearance of edoxudine is reported to be 85 ml/min.


5.5 Metabolism/Metabolites

In preclinical trials it has been reported that edoxudine presents a biotransformation marked by a cleavage of the glycoside bond. The degradation of edoxudine, after oral administration, seems to be processed by the activity of phosphorylases presented in the gastrointestinal tract and by pre-systemic metabolism.


5.6 Biological Half-Life

In preclinical trials on mice, after intravenous administration, edoxudine presented a very short distribution half-life of 1.4 min. In the same trials, the elimination half-life was reported to be of 24.1 min.


5.7 Mechanism of Action

Edoxudine is a potent inhibitor of the replication of herpes simplex virus type 1 and 2. For the activation of this drug, the action of viral thymidine kinase is required to phosphorylate this molecule in order to form the 5'-monophosphate derivative. Then, it is needed to be further phosphorylated by cellular enzymes until the formation of the 5'-triphosphate derivative which is a competitive inhibitor of the viral-coded DNA polymerase. The advantage of edoxudine is that it is highly selective, this characteristic can be seen by its preferential phosphorylation in herpes-infected cells and its preferential incorporation into viral DNA.


ABOUT THIS PAGE

Edoxudin Manufacturers

A Edoxudin manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Edoxudin, including repackagers and relabelers. The FDA regulates Edoxudin manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Edoxudin API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Edoxudin Suppliers

A Edoxudin supplier is an individual or a company that provides Edoxudin active pharmaceutical ingredient (API) or Edoxudin finished formulations upon request. The Edoxudin suppliers may include Edoxudin API manufacturers, exporters, distributors and traders.

click here to find a list of Edoxudin suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Edoxudin USDMF

A Edoxudin DMF (Drug Master File) is a document detailing the whole manufacturing process of Edoxudin active pharmaceutical ingredient (API) in detail. Different forms of Edoxudin DMFs exist exist since differing nations have different regulations, such as Edoxudin USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Edoxudin DMF submitted to regulatory agencies in the US is known as a USDMF. Edoxudin USDMF includes data on Edoxudin's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Edoxudin USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Edoxudin suppliers with USDMF on PharmaCompass.

Edoxudin GMP

Edoxudin Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Edoxudin GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Edoxudin GMP manufacturer or Edoxudin GMP API supplier for your needs.

Edoxudin CoA

A Edoxudin CoA (Certificate of Analysis) is a formal document that attests to Edoxudin's compliance with Edoxudin specifications and serves as a tool for batch-level quality control.

Edoxudin CoA mostly includes findings from lab analyses of a specific batch. For each Edoxudin CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Edoxudin may be tested according to a variety of international standards, such as European Pharmacopoeia (Edoxudin EP), Edoxudin JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Edoxudin USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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