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Hematoporphyrin

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(Redirected from Haematoporphyrin) Chemical compound Pharmaceutical compound
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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.034.939 Edit this at Wikidata
Chemical and physical data
FormulaC34H38N4O6
Molar mass598.700 g·mol
3D model (JSmol)
Melting point172.5 °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)

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.

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.

Hematoporphyrin has also been used as an antidepressant and antipsychotic since the 1920s.

References

  1. Luzgina VN, Filippovich EI, Evstigneeva RP (May 1977). "Hematoporphyrin IX". Pharmaceutical Chemistry Journal. 11 (5): 613–20. doi:10.1007/BF00780815. S2CID 44554826.
  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.
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