Hematoporphyrin

Chemical compound

none

Legal statusLegal 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^Y

UNII

HBT6M5H379

ChEMBL

ChEMBL317840^Y

CompTox Dashboard (EPA)

DTXSID901030645

ECHA InfoCard100.034.939

Chemical and physical dataFormulaC₃₄H₃₈N₄O₆Molar mass598.700 g·mol⁻¹3D model (JSmol)

Interactive image

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-^Y
Key:KFKRXESVMDBTNQ-AMPAVEGJSA-N^Y

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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]

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

^ Luzgina VN, Filippovich EI, Evstigneeva RP (May 1977). "Hematoporphyrin IX". Pharmaceutical Chemistry Journal. 11 (5): 613–20. doi:10.1007/BF00780815. S2CID 44554826.
^ 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.
^ O'Neil MJ (2001). The Merck index: an encyclopedia of chemicals, drugs, and biologicals. Rahway, NJ: Merck Research Laboratories. ISBN 0-911910-13-1.
^ 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.

Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIsTooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine^# Fluvoxamine Indalpine^‡ Paroxetine Sertraline Zimelidine^‡
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIsTooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine^‡ Bupropion Nomifensine^‡
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIsTooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMSTooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine^‡ Gepirone Indeloxazine Flupentixol Ketamine^§ Medifoxamine^‡ Metryptamine^‡ Oxaflozane^‡ Pivagabine^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAsTooltip Tricyclic antidepressants	Amineptine^‡ Amitriptyline^# Amitriptylinoxide Amoxapine Butriptyline^‡ Clomipramine^# Demexiptiline^‡ Desipramine Dibenzepin Dimetacrine^‡ Dosulepin Doxepin Imipramine Imipraminoxide^‡ Iprindole^‡ Lofepramine Melitracen Metapramine^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine^‡ Protriptyline Quinupramine^‡ Tianeptine Trimipramine
TeCAsTooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin^‡ Iproclozide^‡ Iproniazid^‡ Isocarboxazid Isoniazid^# Linezolid^# Mebanazine^‡ Nialamide^‡ Octamoxin^‡ Phenelzine Pheniprazine^‡ Phenoxypropazine^‡ Pivhydrazine^‡ Safrazine^‡ Tedizolid Tranylcypromine Reversible: Caroxazone^‡ Mixed: Bifemelane
MAO_ATooltip Monoamine oxidase A-selective	Reversible: Eprobemide Metralindole Minaprine^‡ Moclobemide Pirlindole Tetrindole Toloxatone
MAO_BTooltip Monoamine oxidase B-selective	Irreversible: Selegiline

Adjunctive therapies
Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous
Ademetionine (SAMe) GABAkine neurosteroids (brexanolone, zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Rubidium chloride (RbCl) Tryptophan

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol^# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Others/unknown: Azacyclonol
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III