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Chemistry

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Also known as: Amotosalen hcl, 161262-45-9, S-59, Amotosalen (hydrochloride), 7h-furo(3,2-g)(1)benzopyran-7-one, 3-((2-aminoethoxy)methyl)-2,5,9-trimethyl-, hydrochloride, Amotosalen hydrochloride (usan)
Molecular Formula
C17H20ClNO4
Molecular Weight
337.8  g/mol
InChI Key
MHLAMQBABOJZQW-UHFFFAOYSA-N
FDA UNII
67B255SI5F

Amotosalen hydrochloride
Amotosalen Hydrochloride is the hydrochloride salt form of amotosalen, a synthetic psoralen and light-activated DNA, RNA crosslinking agent, with protective activity against pathogens such as bacteria, viruses, protozoa, and leukocytes. Prior to administration amotosalen is added to plasma and platelets, then in vivo the agent penetrates pathogens and targets DNA and RNA. Upon activation by ultraviolet A light, this agent is able to form interstrand DNA and RNA crosslinks and prevents replication. Inactivation of leukocytes can prevent graft versus host disease upon transfusion.
1 2D Structure

Amotosalen hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(2-aminoethoxymethyl)-2,5,9-trimethylfuro[3,2-g]chromen-7-one;hydrochloride
2.1.2 InChI
InChI=1S/C17H19NO4.ClH/c1-9-6-15(19)22-16-10(2)17-13(7-12(9)16)14(11(3)21-17)8-20-5-4-18;/h6-7H,4-5,8,18H2,1-3H3;1H
2.1.3 InChI Key
MHLAMQBABOJZQW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=O)OC2=C(C3=C(C=C12)C(=C(O3)C)COCCN)C.Cl
2.2 Other Identifiers
2.2.1 UNII
67B255SI5F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Amotosalen

2.3.2 Depositor-Supplied Synonyms

1. Amotosalen Hcl

2. 161262-45-9

3. S-59

4. Amotosalen (hydrochloride)

5. 7h-furo(3,2-g)(1)benzopyran-7-one, 3-((2-aminoethoxy)methyl)-2,5,9-trimethyl-, Hydrochloride

6. Amotosalen Hydrochloride (usan)

7. Amotosalen Hydrochloride [usan]

8. 67b255si5f

9. 3-(2-aminoethoxymethyl)-2,5,9-trimethylfuro[3,2-g]chromen-7-one;hydrochloride

10. 7h-furo[3,2-g][1]benzopyran-7-one, 3-[(2-aminoethoxy)methyl]-2,5,9-trimethyl-, Hydrochloride (1:1)

11. Unii-67b255si5f

12. Amotosalen Hydrochloride [usan:inn]

13. S 59

14. Schembl4197287

15. Chembl2104450

16. Dtxsid70167093

17. Hy-107004a

18. Amotosalen Hydrochloride [who-dd]

19. Cs-0027098

20. 161262-45-9 (hcl)

21. D02924

22. Q27264108

23. 3-((2-aminoethoxy)methyl)-2,5,9-trimethyl-7h-furo(3,2-g)(1)benzopyran-7-one Hydrochloride

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 337.8 g/mol
Molecular Formula C17H20ClNO4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass337.1080858 g/mol
Monoisotopic Mass337.1080858 g/mol
Topological Polar Surface Area74.7 Ų
Heavy Atom Count23
Formal Charge0
Complexity464
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Photosensitizing Agents

Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)


Dermatologic Agents

Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)


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