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Details

Stereochemistry ACHIRAL
Molecular Formula C34H32N4O4.Cl.Fe
Molecular Weight 651.94
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HEMIN

SMILES

[Cl-].[Fe+3].Cc1c(CCC(O)=O)c2cc3[n-]c(cc4nc(cc5[n-]c(cc1n2)c(C=C)c5C)c(C=C)c4C)c(C)c3CCC(O)=O

InChI

InChIKey=BTIJJDXEELBZFS-HXFTUNQESA-K
InChI=1S/C34H34N4O4.ClH.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);1H;/q;;+3/p-3/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;

HIDE SMILES / InChI

Molecular Formula Fe
Molecular Weight 55.845
Charge 3
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C34H30N4O4
Molecular Weight 558.6264
Charge -2
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Hemin (trade name Panhematin) is a protoporphyrin IX containing a ferric iron ion (heme B) with a chloride ligand, which is is indicated for the amelioration of recurrent attacks of acute intermittent porphyria temporally related to the menstrual cycle in susceptible women. Manifestations such as pain, hypertension, tachycardia, abnormal mental status and mild to progressive neurologic signs may be controlled in selected patients with this disorder. the therapy for the acute porphyrias is not curative. Heme acts to limit the hepatic and/or marrow synthesis of porphyrin. This action is likely due to the inhibition of δ-aminolevulinic acid synthetase, the enzyme which limits the rate of the porphyrin/heme biosynthetic pathway. The exact mechanism by which hematin produces symptomatic improvement in patients with acute episodes of the hepatic porphyrias has not been elucidated.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
200.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Prolmon
Primary
Panhematin

Cmax

ValueDoseCo-administeredAnalytePopulation
742 ng/mL
40 mg single, oral
PROTOPORPHYRIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
9.6 μg × h/mL
40 mg single, oral
PROTOPORPHYRIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4 h
40 mg single, oral
PROTOPORPHYRIN plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
5uM of protoporphyrin reduced HLA I Ab-dependent up-regulation of VCAM-1
Substance Class Chemical
Record UNII
743LRP9S7N
Record Status Validated (UNII)
Record Version