LEMUTEPORFIN

Details

Stereochemistry	UNKNOWN
Molecular Formula	C44H48N4O10
Molecular Weight	792.8727
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)C1C(=CC=C2C3=CC4=NC(=CC5=C(C)C(CCC(=O)OCCO)=C(N5)C=C6N=C(C=C(N3)C12C)C(C)=C6CCC(=O)OCCO)C(C=C)=C4C)C(=O)OC

InChI

InChIKey=PUTVMYIZBFOAFU-MTVFQPQZSA-N

InChI=1S/C44H48N4O10/c1-8-26-23(2)32-20-37-30-12-9-29(42(53)55-6)41(43(54)56-7)44(30,5)38(48-37)22-33-25(4)28(11-14-40(52)58-18-16-50)36(47-33)21-35-27(10-13-39(51)57-17-15-49)24(3)31(46-35)19-34(26)45-32/h8-9,12,19-22,41,46,48-50H,1,10-11,13-18H2,2-7H3/b34-19-,36-21-,37-20-,38-22-

HIDE SMILES / InChI

Molecular Formula	C44H46N4O10
Molecular Weight	790.8568
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://drugprofiles.informa.com/drug_profiles/618-lemuteporfin | https://www.pharmacodia.com/yaodu/html/v1/chemicals/1ad12e2680e7833bf77feaa9bb1f02e6.html | https://adisinsight.springer.com/drugs/800011953 | https://www.ncbi.nlm.nih.gov/pubmed/16097861

Lemuteporfin is a newly introduced, light-sensitive drug for use in combination photodynamic therapy (PDT). It acts on mitochrondria to initiate the apoptotic cascade resulting in cell death (apoptosis). The photosensitizer was highly potent, killing cells at low nanomolar concentrations upon exposure to activating light. The cellular uptake of lemuteporfin was rapid with maximum levels reached within 20 min. Mitogen-activated lymphoid cells accumulated more of the lemuteporfin than their quiescent equivalents, supporting selectivity. Lemuteporfin had been in phase II clinical trials for the treatment of benign prostatic hypertrophy. It is in phase I clinical trials for the treatment of acne rosacea.

Approval Year

PubMed

Title	Date	PubMed
Cellular and antitumor activity of a new diethylene glycol benzoporphyrin derivative (lemuteporfin).	2006 Jan-Feb	16097861
Ultraviolet B light stimulates interleukin-20 expression by human epithelial keratinocytes.	2006 Sep-Oct	16709143
Photobleaching kinetics of Verteporfin and Lemuteporfin in cells and optically trapped multilamellar vesicles using two-photon excitation.	2011 Jul-Aug	21488879

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:19:45 GMT 2023` Edited by `admin` on `Sat Dec 16 16:19:45 GMT 2023`
Record UNII	EZ109VJ012
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEMUTEPORFIN

Official Name

English

lemuteporfin [INN]

Common Name

English

EA-6

Code

English

LEMUTEPORFIN [USAN]

Common Name

English

23H,25H-Benzo[b]porphine-9,13-dipropanoic acid, 18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-, 9,13-bis(2-hydroxyethyl) ester

Systematic Name

English

23H,25H-Benzo[b]porphine-9,13-dipropanoic acid, 18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-, bis(2-hydroxyethyl) ester

Systematic Name

English

QLT0074

Code

English

QLT-0074

Code

English

DIMETHYL (2RS,21SR)-8-ETHENYL-13,17-BIS(3-(2-HYDROXYETHOXYCARBONYL)-3-OXOPROPYL)-2,7,12,18-TETRAMETHYL-2,21-DIHYDROBENZO(B)PORPHYRIN-21,22-DICARBOXYLATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1420