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Amotosalen Hydrochloride

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ACTIVE PHARMA INGREDIENTS

1 NDC API

1 NDC API

Synopsis

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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 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 Formula	C₁₇H₂₀ClNO₄
Molecular Weight	337.8 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	337.1080858 g/mol
Monoisotopic Mass	337.1080858 g/mol
Topological Polar Surface Area	74.7 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	464
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	2

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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