Hematoporphyrin: Difference between revisions

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Revision as of 11:12, 9 August 2011 editBeetstra (talk \| contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII').← Previous edit		Latest revision as of 12:56, 29 January 2023 edit undoEntranced98 (talk \| contribs)Extended confirmed users, Pending changes reviewers, Rollbackers170,249 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper
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			{{Short description\|Chemical compound}}
	{{Orphan\|date=April 2011}}

	{{Drugbox		{{Drugbox
	\| verifiedrevid = ~~415517930~~		\| verifiedrevid = 443853119
	\| IUPAC_name = 7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-21''H'',23''H''-porphine-2,18-dipropanoic acid		\| IUPAC_name = 7,12-bis(1-hydroxyethyl)-3,8,13,17-tetramethyl-21''H'',23''H''-porphine-2,18-dipropanoic acid
	\| image = Hematoporphyrin.png		\| image = Hematoporphyrin.png
			<!--Clinical data-->
	\| InChI = 1/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-
			\| tradename =
	\| InChIKey = KFKRXESVMDBTNQ-AMPAVEGJBD
		⚫	\| pregnancy_category =
⚫	\| ~~CASNo_Ref~~ = {{~~cascite~~\|correct\|~~CAS~~}}
		⚫	\| legal_status = Rx-only
		⚫	\| routes_of_administration = Oral
			<!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| metabolism =
		⚫	\| elimination_half-life =
		⚫	\| excretion =
			<!--Identifiers-->
		⚫	\| CAS_number = 14459-29-1
		⚫	\| ATC_prefix = none
		⚫	\| ATC_suffix =
		⚫	\| PubChem = 11103
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\| ChemSpiderID = 10632
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
		⚫	\| UNII = HBT6M5H379
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 317840		\| ChEMBL = 317840
			<!--Chemical data-->
		⚫	\| C=34 \| H=38 \| N=4 \| O=6
			\| 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
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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-		\| StdInChI = 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-
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = KFKRXESVMDBTNQ-AMPAVEGJSA-N		\| StdInChIKey = KFKRXESVMDBTNQ-AMPAVEGJSA-N
			\| melting_point = 172.5
⚫	\| CAS_number = 14459-29-1
⚫	\| ATC_prefix = none
⚫	\| ATC_suffix =
⚫	\| UNII = HBT6M5H379
⚫	\| PubChem = 11103
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| ChemSpiderID = 10632
⚫	\| C = 34 \| H = 38 \| N = 4 \| O = 6
	\| molecular_weight = 598.69 g/mol
	\| smiles = O=C(O)CCC=5c2nc(cc4c(c(c(cc1c(c(c(n1)cc/3nc(c2)\C(=C\3C)CCC(=O)O)C(O)C)C)n4)C(O)C)C)C=5C
⚫	\| bioavailability =
⚫	\| metabolism =
⚫	\| elimination_half-life =
⚫	\| excretion =
⚫	\| pregnancy_category =
⚫	\| legal_status = Rx-only
⚫	\| routes_of_administration = Oral
	}}		}}

	'''Hematoporphyrin''' ('''Photodyn''', '''Sensibion''') is an ] ] ~~formed~~ by ~~the~~ ] of ]. ~~Nencki~~ ~~and~~ ~~Zaleski~~ ~~determined~~ ~~its~~ ] in 1900.<ref name="urlSpringerLink - Journal Article">{{cite ~~web~~ \| ~~url~~ = ~~http://www.springerlink.com/content/r6116jm001tx1210/~~ \| title = ~~SpringerLink~~ - Journal ~~Article~~ \| ~~format~~ = \| ~~work~~ = \| ~~accessdate~~ = }}</ref>		'''Hematoporphyrin''' ('''Photodyn''', '''Sensibion''') is a ] prepared from ]. It is a derivative of ], 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 ] was determined in 1900.<ref name="urlSpringerLink - Journal Article">{{cite journal \| vauthors = Luzgina VN, Filippovich EI, Evstigneeva RP \| title = Hematoporphyrin IX \| journal = Pharmaceutical Chemistry Journal \| date = May 1977 \| volume = 11 \| issue = 5 \| pages = 613–20 \| doi = 10.1007/BF00780815 \| s2cid = 44554826 \| url = https://link.springer.com/article/10.1007%2FBF00780815 }}</ref>

			It is used as a photosensitizer in ]. 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.<ref>{{cite journal \| vauthors = Kessel D \| title = Hematoporphyrin and HPD: photophysics, photochemistry and phototherapy \| journal = Photochemistry and Photobiology \| volume = 39 \| issue = 6 \| pages = 851–9 \| date = June 1984 \| pmid = 6235529 \| doi = 10.1111/j.1751-1097.1984.tb08871.x \| s2cid = 20172683 \| doi-access = free }}</ref>
⚫	Hematoporphyrin has been used as an ] and ] since the 1920s.<ref name="isbn0-911910-13-1">{{cite book \| ~~author~~ = O'Neil, Maryadele J. \| title = The Merck index: an encyclopedia of chemicals, drugs, and biologicals \| publisher = Merck Research Laboratories \| location = Rahway, NJ \| year = 2001 ~~\| pages =~~ \| isbn = 0-911910-13-1 \| ~~oclc~~ = ~~\| doi =~~ \| url = }}</ref><ref name="~~urlHEMATOPORPHYRIN~~ AS A ~~THERAPEUTIC~~ ~~AGENT~~ IN ~~THE~~ ~~PSYCHOSES~~ -- ~~Strecker~~ et ~~al.~~ 90 ~~(6):~~ ~~1157~~ -- Am J ~~Psychiatry">{{cite~~ ~~web~~ \| ~~url = http://ajp.psychiatryonline.org/cgi/content/abstract/90/6/1157~~ \| ~~title~~ = ~~HEMATOPORPHYRIN~~ AS A ~~THERAPEUTIC~~ ~~AGENT~~ IN ~~THE~~ ~~PSYCHOSES~~ -- ~~Strecker~~ ~~et al.~~ ~~90 (~~6): ~~1157~~ -- Am ~~J Psychiatry~~ \| ~~format~~ = \| ~~work~~ = \| ~~accessdate =~~ }}</ref>

		⚫	Hematoporphyrin has also been used as an ] and ] since the 1920s.<ref name="isbn0-911910-13-1">{{cite book \| last = O'Neil \| first = Maryadele J. \| name-list-style = vanc \| title = The Merck index: an encyclopedia of chemicals, drugs, and biologicals \| publisher = Merck Research Laboratories \| location = Rahway, NJ \| year = 2001 \| isbn = 0-911910-13-1 \| url = https://archive.org/details/merckindexency00onei \| url-access = registration }}</ref><ref name="Strecker_1934">{{cite journal \| vauthors = Strecker EA, Palmer HP, Braceland FJ \| title = Hematoporphyrin as a Therapeutic Agent in the Psychoses \| journal = American Journal of Psychiatry \| volume = 90 \| issue = 6 \| pages = 1157–1173 \| doi = 10.1176/ajp.90.6.1157 \| date = May 1934 }}</ref>
	== See also ==
	* ]

	== References ==		== References ==
	{{~~Reflist~~\|2}}		{{reflist\|30em}}

	{{Antidepressants}}		{{Antidepressants}}
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	]		]
	]		]


	{{nervous-system-drug-stub}}		{{nervous-system-drug-stub}}

	]

Latest revision as of 12:56, 29 January 2023

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	14459-29-1
PubChem CID	11103
ChemSpider	10632
UNII	HBT6M5H379
ChEMBL	ChEMBL317840
CompTox Dashboard (EPA)	DTXSID901030645
ECHA InfoCard	100.034.939
Chemical and physical data
Formula	C₃₄H₃₈N₄O₆
Molar mass	598.700 g·mol
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)

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

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

Reversible: Caroxazone

Mixed: Bifemelane

MAO_ATooltip Monoamine oxidase A-selective

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 Muscarinic agonists: Xanomeline/trospium chloride Others/unknown: Azacyclonol
WHO-EM Withdrawn from market Clinical trials: Phase III Never to phase III

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