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Trimethylpsoralen

Trimethylpsoralen structure

CAS No:
3902-71-4
Formula:
C14H12O3
Chemical Name:
Trimethylpsoralen
Synonyms:
7H-Furo[3,2-g][1]benzopyran-7-one,2,5,9-trimethyl-;5-Benzofuranacrylic acid,6-hydroxy-β,2,7-trimethyl-,δ-lactone;2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one;4,5′,8-Trimethylpsoralen;Trioxsalen;Trisoralen;4,5′,8-Trimethylpsoralene;Trimethylpsoralen;4,2′,8-Trimethylpsoralen;Trioxysalen;NSC 71047;TMP;2,5,9-Trimethyl-7H-furo[3,2-g]chromen-7-one;2,5,9-Trimethylfuro[3,2-g]chromen-7-one
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Trioxsalen is a furanocoumarin and a psoralen derivative, in conjunction with UV-A for phototherapy treatment of vitiligo and hand eczema. After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death.

Solid

Trioxsalen is 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis. It has a role as a photosensitizing agent and a dermatologic drug.|Trioxsalen (trimethylpsoralen, trioxysalen or trisoralen) is a furanocoumarin and a psoralen derivative obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo and hand eczema. The photoactivated form produces interstrand linkages in DNA resulting in cell apoptosis. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage.[3] The compound is has been explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair.|Trioxsalen is a Psoralen.|Pigmenting photosensitizing agent obtained from several plants, mainly Psoralea corylifolia. It is administered either topically or orally in conjunction with ultraviolet light in the treatment of vitiligo.

Trimethylpsoralen Basic Attributes

Molecular Weight：

228.24

Exact Mass：

228.24

EC Number：

223-459-0

UNII：

Y6UY8OV51T

NSC Number：

757371|71047

DSSTox ID：

DTXSID3023716

ATC Code：

D - Dermatologicals

HScode：

29322985

Characteristics

PSA：

39.4

XLogP3：

3.80

Appearance：

white powder

Density：

1.2±0.1 g/cm3

Melting Point：

234.5 °C

Boiling Point：

389.0±30.0 °C at 760 mmHg

Flash Point：

189.1±24.6 °C

Refractive Index：

1.613

Water Solubility：

DMSO: soluble

Storage Conditions：

2-8°C

Collision Cross Section：

147.4 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Hazard category：

Transport codes：

UN 1759 8/PG 1

wgk germany：

hazard class code：

34-40

safety instructions：

26-36/37/39-45

RTECS Number：

LV1576000

Marks：

Precautionary statement(s)：

P260-P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

Hazard Statements：

H314-H351

GHS Classification：

|Danger|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P201, P202, P260, P264, P280, P281, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.

Pharmacology：

Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.

MeSH：

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.)

Mechanism of Action：

After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death.

MeSH Entry Terms：

2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-one

Trimethylpsoralen Use and Manufacturing

Uses

melanizing agent, antipsoriatic

Manufacturing Info：

7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-: INACTIVE

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:228.24
XLogP3:3
Hydrogen Bond Acceptor Count:3
Exact Mass:228.078644241
Monoisotopic Mass:228.078644241
Topological Polar Surface Area:39.4
Heavy Atom Count:17
Complexity:374
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes