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MedKoo Cat#: 329619 | Name: Heme arginate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Heme arginate (or haem arginate) is a compound of heme and arginine used in the treatment of acute porphyrias. Heme arginate is used clinically to manage acute intermittent porphyria (AIP) by downregulating hepatic delta-aminolevulinic acid synthase 1 (ALAS1), the rate-limiting enzyme in heme biosynthesis. Its bioactivity stems from its ability to restore intracellular heme levels, which in turn represses ALAS1 transcription and reduces accumulation of neurotoxic heme precursors like ALA and PBG. In vivo, heme arginate exhibits rapid plasma clearance and hepatic uptake, with therapeutic effects typically observed within hours of intravenous administration. It has a high affinity for heme-binding proteins such as hemopexin and albumin, aiding its delivery and reducing free heme-associated toxicity. Pharmacodynamically, it suppresses porphyrin precursor levels for several days post-dose, making it effective for short-term symptom control in AIP crises.

Chemical Structure

Heme arginate
Heme arginate
CAS#100438-92-4

Theoretical Analysis

MedKoo Cat#: 329619

Name: Heme arginate

CAS#: 100438-92-4

Chemical Formula: C40H46FeN8O6

Exact Mass: 0.0000

Molecular Weight: 790.70

Elemental Analysis: C, 60.76; H, 5.86; Fe, 7.06; N, 14.17; O, 12.14

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
haem arginate; Heme arginate; Heme arginate complex; Normosang; Hemearginat; Normosang; Heme L-arginate;
IUPAC/Chemical Name
N/A
InChi Key
ZEMXHYUDKROEFW-FCYLROMBSA-L
InChi Code
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;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);4H,1-3,7H2,(H,11,12)(H4,8,9,10);/q;;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;;/t;4-;/m.0./s1
SMILES Code
OC([C@@H](N)CCCNC(N)=N)=O.OC(CCC1=C(C2=CC3=C(C(C)=C4C=C5[N+]6=C(C(C)=C5C=C)C=C7N8C(C(CCC(O)=O)=C7C)=CC1=[N+]2[Fe-2]86N43)C=C)C)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 790.70 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Edmunds MC, Czopek A, Wigmore SJ, Kluth DC. Paradoxical effects of heme arginate on survival of myocutaneous flaps. Am J Physiol Regul Integr Comp Physiol. 2014 Jan 1;306(1):R10-22. doi: 10.1152/ajpregu.00240.2013. Epub 2013 Oct 2. PubMed PMID: 24089372; PubMed Central PMCID: PMC3921308. 2: Choudhary AK, Rennie J, Cairns C, Borthwick G, Hughes J, Morton NM, Kluth D, Conway BR. Administration of heme arginate ameliorates murine type 2 diabetes independently of heme oxygenase activity. PLoS One. 2013 Oct 30;8(10):e78209. doi: 10.1371/journal.pone.0078209. eCollection 2013 Oct 30. PubMed PMID: 24205160; PubMed Central PMCID: PMC3813508. 3: Melenovská P, Kopecká J, Krijt J, Hnízda A, Raková K, Janošík M, Wilcken B, Kožich V. Chaperone therapy for homocystinuria: the rescue of CBS mutations by heme arginate. J Inherit Metab Dis. 2015 Mar;38(2):287-94. doi: 10.1007/s10545-014-9781-9. Epub 2014 Oct 21. PubMed PMID: 25331909. 4: Andreas M, Schmid AI, Doberer D, Schewzow K, Weisshaar S, Heinze G, Bilban M, Moser E, Wolzt M. Heme arginate improves reperfusion patterns after ischemia: a randomized, placebo-controlled trial in healthy male subjects. J Cardiovasc Magn Reson. 2012 Aug 2;14:55. doi: 10.1186/1532-429X-14-55. PubMed PMID: 22857721; PubMed Central PMCID: PMC3438022. 5: Willandt B, Langendonk JG, Biermann K, Meersseman W, D'Heygere F, George C, Verslype C, Monbaliu D, Cassiman D. Liver Fibrosis Associated with Iron Accumulation Due to Long-Term Heme-Arginate Treatment in Acute Intermittent Porphyria: A Case Series. JIMD Rep. 2016;25:77-81. Epub 2015 Jun 21. PubMed PMID: 26093628; PubMed Central PMCID: PMC5059188. 6: Ndisang JF, Chibbar R, Lane N. Heme oxygenase suppresses markers of heart failure and ameliorates cardiomyopathy in L-NAME-induced hypertension. Eur J Pharmacol. 2014 Jul 5;734:23-34. doi: 10.1016/j.ejphar.2014.03.026. Epub 2014 Apr 13. PubMed PMID: 24726875. 7: Jadhav A, Ndisang JF. Treatment with heme arginate alleviates adipose tissue inflammation and improves insulin sensitivity and glucose metabolism in a rat model of Human primary aldosteronism. Free Radic Biol Med. 2012 Dec 15;53(12):2277-86. doi: 10.1016/j.freeradbiomed.2012.10.529. Epub 2012 Oct 23. PubMed PMID: 23089228. 8: Ndisang JF, Jadhav A. Heme-arginate suppresses phospholipase C and oxidative stress in the mesenteric arterioles of mineralcorticoid-induced hypertensive rats. Hypertens Res. 2010 Apr;33(4):338-47. doi: 10.1038/hr.2010.1. Epub 2010 Mar 5. PubMed PMID: 20203687. 9: Shankaran P, Vlkova L, Liskova J, Melkova Z. Heme arginate potentiates latent HIV-1 reactivation while inhibiting the acute infection. Antiviral Res. 2011 Dec;92(3):434-46. doi: 10.1016/j.antiviral.2011.09.011. Epub 2011 Oct 5. PubMed PMID: 22001321. 10: Frei P, Minder EI, Corti N, Muellhaupt B, Geier A, Adams H, Dutertre JP, Rudiger A, Dutkowski P, Maggiorini M, Ganter CC. Liver Transplantation because of Acute Liver Failure due to Heme Arginate Overdose in a Patient with Acute Intermittent Porphyria. Case Rep Gastroenterol. 2012 Jan;6(1):190-6. doi: 10.1159/000338354. Epub 2012 Apr 19. PubMed PMID: 22649331; PubMed Central PMCID: PMC3362186. 11: Tiwari S, Ndisang JF. Heme oxygenase system and hypertension: a comprehensive insight. Curr Pharm Des. 2014;20(9):1354-69. Review. PubMed PMID: 23978093. 12: Ndisang JF, Chibbar R. Heme Oxygenase Improves Renal Function by Potentiating Podocyte-Associated Proteins in Nω-Nitro-l-Arginine-Methyl Ester (l-NAME)-Induced Hypertension. Am J Hypertens. 2015 Jul;28(7):930-42. doi: 10.1093/ajh/hpu240. Epub 2014 Dec 12. PubMed PMID: 25498996. 13: Volin L, Rasi V, Vahtera E, Tenhunen R. Heme arginate: effects on hemostasis. Blood. 1988 Mar;71(3):625-8. PubMed PMID: 3345341. 14: Bharucha AE, Choi KM, Saw JJ, Gibbons SJ, Farrugia GF, Carlson DA, Zinsmeister AR. Effects of aspirin & simvastatin and aspirin, simvastatin, & lipoic acid on heme oxygenase-1 in healthy human subjects. Neurogastroenterol Motil. 2014 Oct;26(10):1437-42. doi: 10.1111/nmo.12404. Epub 2014 Jul 29. PubMed PMID: 25093998; PubMed Central PMCID: PMC4177447. 15: Ndisang JF, Jadhav A. Heme arginate therapy enhanced adiponectin and atrial natriuretic peptide, but abated endothelin-1 with attenuation of kidney histopathological lesions in mineralocorticoid-induced hypertension. J Pharmacol Exp Ther. 2010 Jul;334(1):87-98. doi: 10.1124/jpet.109.164871. Epub 2010 Apr 14. PubMed PMID: 20392817. 16: Levere RD, Martasek P, Escalante B, Schwartzman ML, Abraham NG. Effect of heme arginate administration on blood pressure in spontaneously hypertensive rats. J Clin Invest. 1990 Jul;86(1):213-9. PubMed PMID: 2114425; PubMed Central PMCID: PMC296709. 17: Sasaki T, Takahashi T, Maeshima K, Shimizu H, Toda Y, Morimatsu H, Takeuchi M, Yokoyama M, Akagi R, Morita K. Heme arginate pretreatment attenuates pulmonary NF-kappaB and AP-1 activation induced by hemorrhagic shock via heme oxygenase-1 induction. Med Chem. 2006 May;2(3):271-4. PubMed PMID: 16948473. 18: Jadhav A, Ndisang JF. Heme arginate suppresses cardiac lesions and hypertrophy in deoxycorticosterone acetate-salt hypertension. Exp Biol Med (Maywood). 2009 Jul;234(7):764-78. doi: 10.3181/0810-RM-302. Epub 2009 May 8. PubMed PMID: 19429856. 19: Mustajoki P, Mustajoki S, Rautio A, Arvela P, Pelkonen O. Effects of heme arginate on cytochrome P450-mediated metabolism of drugs in patients with variegate porphyria and in healthy men. Clin Pharmacol Ther. 1994 Jul;56(1):9-13. PubMed PMID: 8033500. 20: Rund D, Fibach E, Goldfarb A, Friedberg A, Rachmilewitz E. Heme arginate therapy for beta thalassemia: in vitro versus in vivo effects. Acta Haematol. 1998;100(2):82-4. PubMed PMID: 9792937.

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