U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C34H34N4O4.C6H14N4O2.Fe
Molecular Weight 792.704
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of HEME ARGINATE

SMILES

[Fe++].N[C@@H](CCCNC(N)=N)C(O)=O.CC1=C(CCC(O)=O)C2=CC3=NC(=CC4=C(C=C)C(C)=C(N4)C=C5N=C(C=C1N2)C(C)=C5C=C)C(C)=C3CCC(O)=O

InChI

InChIKey=BONOMRJXDYBFLR-FCYLROMBSA-N
InChI=1S/C34H34N4O4.C6H14N4O2.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;7-4(5(11)12)2-1-3-10-6(8)9;/h7-8,13-16,36-37H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42);4H,1-3,7H2,(H,11,12)(H4,8,9,10);/q;;+2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;/t;4-;/m.0./s1

HIDE SMILES / InChI

Molecular Formula C6H13N4O2
Molecular Weight 173.193
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Fe
Molecular Weight 55.845
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C34H31N4O4
Molecular Weight 559.6343
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Heme arginate (or haem arginate, brand name NORMOSANG) has been used to treat acute porphyrias. NORMOSANG successful uses in Europe and South Africa, but it has not been approved for use in the United States. Heme arginate consists of haem complexed with the amino acid arginine. This forms a stable compound. Haem arginate works by replenishing haem stores within the body. By negative feedback, haem arginate inhibits the initial rate-limiting enzyme of the haem synthetic pathway, ALA synthase (Delta-aminolevulinic acid dehydratase). The most frequent complication is phlebitis at the site of infusion. This can be reduced by giving the infusion of haem arginate in a protein buffer such as stabilized human serum or human serum albumin. In addition, there were studies, which revealed, that heme arginate induced beneficial effects in some myelodysplastic syndrome (MDS) patients and had very few side effects. In addition was shown, that heme arginate could be useful in the treatment of thalassemia intermedia.

CNS Activity

Curator's Comment: Known to be CNS non-penetrant in rabbite. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P13196
Gene ID: 211.0
Gene Symbol: ALAS1
Target Organism: Homo sapiens (Human)
Target ID: P22557
Gene ID: 212.0
Gene Symbol: ALAS2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Normosang

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The effects of inhibition of haem biosynthesis by griseofulvin on intestinal iron absorption.
2004 Apr
Patents

Patents

Sample Use Guides

Use a standard dose of 250 mg (5 ml) given daily for four days. Mix the haem arginate into 100 ml human serum albumin or stabilised human serum. Infuse intravenously over 20 minutes.
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:21:58 GMT 2023
Edited
by admin
on Fri Dec 15 19:21:58 GMT 2023
Record UNII
R1B526117P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HEME ARGINATE
Common Name English
Haem arginate [WHO-DD]
Common Name English
HAEM ARGINATE
WHO-DD  
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 79893
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
FDA ORPHAN DRUG 9185
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
Code System Code Type Description
FDA UNII
R1B526117P
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
PRIMARY
EVMPD
SUB14045MIG
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
PRIMARY
CAS
100438-92-4
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
PRIMARY
MESH
C048849
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
PRIMARY
SMS_ID
100000077902
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
PRIMARY
RXCUI
26506
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
HEME ARGINATE
Created by admin on Fri Dec 15 19:21:58 GMT 2023 , Edited by admin on Fri Dec 15 19:21:58 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE