Hematoporphyrin

Hematoporphyrin (Photodyn, Sensibion) is a porphyrin prepared from hemin. It is a derivative of protoporphyrin IX, where the two vinyl groups have been hydrated (converted to alcohols). It is a deeply colored solid that is usually encountered as a solution. Its chemical structure was determined in 1900.[1]

Hematoporphyrin

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid
CAS Number	14459-29-1
PubChem CID	11103
ChemSpider	10632
UNII	HBT6M5H379
ChEMBL	ChEMBL317840
ECHA InfoCard	100.034.939
Chemical and physical data
Formula	C34H38N4O6
Molar mass	598.700 g·mol^−1
3D model (JSmol)	Interactive image
Melting point	172.5 °C (342.5 °F)
SMILES CC1=C(C2=CC3=NC(=CC4=NC(=CC5=C(C(=C(N5)C=C1N2)C(C)O)C)C(=C4CCC(=O)O)C)C(=C3C)CCC(=O)O)C(C)O
InChI InChI=1S/C34H38N4O6/c1-15-21(7-9-31(41)42)27-14-28-22(8-10-32(43)44)16(2)24(36-28)12-29-34(20(6)40)18(4)26(38-29)13-30-33(19(5)39)17(3)25(37-30)11-23(15)35-27/h11-14,19-20,37-40H,7-10H2,1-6H3,(H,41,42)(H,43,44)/b23-11-,24-12-,25-11-,26-13-,27-14-,28-14-,29-12-,30-13- Key:KFKRXESVMDBTNQ-AMPAVEGJSA-N
(verify)

It is used as a photosensitizer in photodynamic therapy. Acetylation of hematoporphyrin followed by hydrolysis of the product of that reaction affords a mixture called hematoporphyrin derivative (HPD), which is also used in photodynamic therapy.[2]

Hematoporphyrin has also been used as an antidepressant and antipsychotic since the 1920s.[3][4]

References

1. Luzgina VN, Filippovich EI, Evstigneeva RP (May 1977). "Hematoporphyrin IX". Pharmaceutical Chemistry Journal. 11 (5): 613–20. doi:10.1007/BF00780815 (inactive 2021-01-17).CS1 maint: DOI inactive as of January 2021 (link)
2. Kessel D (June 1984). "Hematoporphyrin and HPD: photophysics, photochemistry and phototherapy". Photochemistry and Photobiology. 39 (6): 851–9. doi:10.1111/j.1751-1097.1984.tb08871.x. PMID 6235529. S2CID 20172683.
3. O'Neil MJ (2001). The Merck index: an encyclopedia of chemicals, drugs, and biologicals. Rahway, NJ: Merck Research Laboratories. ISBN 0-911910-13-1.
4. Strecker EA, Palmer HP, Braceland FJ (May 1934). "Hematoporphyrin as a Therapeutic Agent in the Psychoses". American Journal of Psychiatry. 90 (6): 1157–1173. doi:10.1176/ajp.90.6.1157.