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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 112901-68-5, Anifostine trihydrate, 2-(3-aminopropylamino)ethylsulfanylphosphonic acid trihydrate, 112901-68-5 (trihydrate), M487qf2f4v, Nsc 296961

Molecular Formula

C₅H₂₁N₂O₆PS

Molecular Weight

268.27 g/mol

InChI Key

TXQPXJKRNHJWAX-UHFFFAOYSA-N

FDA UNII

M487QF2F4V

A phosphorothioate proposed as a radiation-protective agent. It causes splenic vasodilation and may block autonomic ganglia.

1 2D Structure

Amifostine Trihydrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(3-aminopropylamino)ethylsulfanylphosphonic acid;trihydrate

2.1.2 InChI

InChI=1S/C5H15N2O3PS.3H2O/c6-2-1-3-7-4-5-12-11(8,9)10;;;/h7H,1-6H2,(H2,8,9,10);3*1H2

2.1.3 InChI Key

TXQPXJKRNHJWAX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C(CN)CNCCSP(=O)(O)O.O.O.O

2.2 Other Identifiers

2.2.1 UNII

M487QF2F4V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amifostine

2. Amifostine Anhydrous

3. Amifostine Disodium Salt

4. Amifostine Monohydrate

5. Amifostine Monohydrochloride

6. Aminopropyl Aminoethylthiophosphate

7. Aminopropylaminoethylthiophosphate

8. Aminopropylaminoethylthiophosphoric Acid

9. Apaetp

10. Ethanethiol, 2-((3-aminopropyl)amino)-, Dihydrogen Phosphate (ester), Trihydrate

11. Ethiofos

12. Ethiofos Anhydrous

13. Ethyol

14. Gammaphos

15. Nsc 296961

16. Nsc-296961

17. Nsc296961

18. S-(n-(3-aminopropyl)-2-aminoethyl)thiophosphoric Acid

19. Wr 2721

20. Wr-2721

21. Wr2721

22. Ym 08310

23. Ym-08310

24. Ym08310

2.3.2 Depositor-Supplied Synonyms

1. 112901-68-5

2. Anifostine Trihydrate

3. 2-(3-aminopropylamino)ethylsulfanylphosphonic Acid Trihydrate

4. 112901-68-5 (trihydrate)

5. M487qf2f4v

6. Nsc 296961

7. S-(2-((3-aminopropyl)amino)ethyl) O,o-dihydrogen Phosphorothioate Trihydrate

8. S-(2-((3-aminopropyl)amino)ethyl) Dihydrogen Phosphorothioate, Trihydrate

9. Ethanethiol, 2-((3-aminopropyl)amino)-, Dihydrogen Phosphate (ester), Trihydrate

10. 2-(3-aminopropylamino)ethylsulfanylphosphonic Acid;trihydrate

11. Wr-2721 Trihydrate

12. Unii-m487qf2f4v

13. Amifostine (usp)

14. Wr-2721

15. Ethyol Trihydrate

16. Amifostine [usan:usp:inn:ban]

17. Amifostinetrihydrate

18. Amifostine [usan]

19. Ethyol (tn)

20. Amifostine [vandf]

21. Amifostine [mart.]

22. Amifostine [usp-rs]

23. Amifostinetrihydrateormonohydrate

24. Amifostine [orange Book]

25. Dtxsid40150210

26. Amifostine [usp Monograph]

27. Amifostine Trihydrate [mi]

28. Hms3866g03

29. S4298

30. Akos015901630

31. Amifostine Trihydrate [who-dd]

32. Ac-6800

33. Ccg-267130

34. Ft-0622271

35. Amifostine Trihydrate, >=97% (tlc), Powder

36. A14238

37. D00226

38. F21492

39. 901a685

40. J-002869

41. Q47495771

42. Amifostine, United States Pharmacopeia (usp) Reference Standard

43. Aminopropylamino)ethylsulfanylphosphonic Acid Trihydrate

44. Ethanethiol, 2-[(3-aminopropyl)amino]-, Dihydrogen Phosphate (ester),trihydrate

2.4 Create Date

2005-07-19

3 Chemical and Physical Properties

Molecular Formula	C₅H₂₁N₂O₆PS
Molecular Weight	268.27 g/mol
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	7
Exact Mass	268.08579457 g/mol
Monoisotopic Mass	268.08579457 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	152
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	4

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Radiation-Protective Agents

Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military. (See all compounds classified as Radiation-Protective Agents.)

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