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MedKoo Cat#: 531156 | Name: Amicarbalide diisethionate

Description:

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

Amicarbalide (Diampron) is an aromatic diamidine exerting piroplasmocidal properties. It is effective against bovine and equine babesiosis and anaplasmosis..

Chemical Structure

Amicarbalide diisethionate
Amicarbalide diisethionate
CAS#3671-72-5 (diisethionate)

Theoretical Analysis

MedKoo Cat#: 531156

Name: Amicarbalide diisethionate

CAS#: 3671-72-5 (diisethionate)

Chemical Formula: C19H28N6O9S2

Exact Mass: 548.1359

Molecular Weight: 548.59

Elemental Analysis: C, 41.60; H, 5.14; N, 15.32; O, 26.25; S, 11.69

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 #
3459-96-9 (free base) 3671-72-5 (diisethionate)
Synonym
Amicarbalide diisethionate
IUPAC/Chemical Name
3,3'-Diamidionocarbanilide bis((beta-hydroxy)ethanesulfonate)
InChi Key
PWUMRNFCZFZXAE-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H16N6O.2C2H6O4S/c16-13(17)9-3-1-5-11(7-9)20-15(22)21-12-6-2-4-10(8-12)14(18)19;2*3-1-2-7(4,5)6/h1-8H,(H3,16,17)(H3,18,19)(H2,20,21,22);2*3H,1-2H2,(H,4,5,6)
SMILES Code
O=C(NC1=CC=CC(C(N)=N)=C1)NC2=CC=CC(C(N)=N)=C2.OCCS(=O)(O)=O.OCCS(=O)(O)=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
>3 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 548.59 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: Duffey M, Sanchez CP, Lanzer M. Profiling of the anti-malarial drug candidate SC83288 against artemisinins in Plasmodium falciparum. Malar J. 2018 Mar 20;17(1):121. doi: 10.1186/s12936-018-2279-4. PMID: 29558913; PMCID: PMC5861637. 2: Pegoraro S, Duffey M, Otto TD, Wang Y, Rösemann R, Baumgartner R, Fehler SK, Lucantoni L, Avery VM, Moreno-Sabater A, Mazier D, Vial HJ, Strobl S, Sanchez CP, Lanzer M. SC83288 is a clinical development candidate for the treatment of severe malaria. Nat Commun. 2017 Jan 31;8:14193. doi: 10.1038/ncomms14193. Erratum in: Nat Commun. 2017 Apr 06;8:15273. PMID: 28139658; PMCID: PMC5290327. 3: Rabanal B, de Paz E, Merino G, Negro A. Determination by capillary zone electrophoresis of berenil, phenamidine, diampron and dibromopropamidine in serum and urine. J Chromatogr B Biomed Sci Appl. 2000 Feb 11;738(2):293-303. doi: 10.1016/s0378-4347(99)00530-7. PMID: 10718647. 4: Navas IM, García-Fernández AJ, Johnson RA, Reguera RM, Balaña-Fouce R, Ordóñez D. Structural determinants of putrescine uptake inhibition produced by cationic diamidines in the model of trypanosomatid Crithidia fasciculata. Biol Chem. 1996 Dec;377(12):833-6. doi: 10.1515/bchm3.1996.377.12.833. PMID: 8997494. 5: Reguera R, Balaña Fouce R, Cubria JC, Alvarez Bujidos ML, Ordoñez D. Putrescine uptake inhibition by aromatic diamidines in Leishmania infantum promastigotes. Biochem Pharmacol. 1994 May 18;47(10):1859-66. doi: 10.1016/0006-2952(94)90316-6. PMID: 8204103. 6: Cubría JC, Balaña Fouce R, Alvarez-Bujidos ML, Negro A, Ortiz AI, Ordóñez D. Aromatic diamidines are reversible inhibitors of porcine kidney diamine oxidase. Biochem Pharmacol. 1993 Mar 24;45(6):1355-7. doi: 10.1016/0006-2952(93)90290-d. PMID: 8466555. 7: Gray JS, Parr SL. In vivo assays for drug resistance in Babesia divergens using the Mongolian gerbil, Meriones unguiculatus. Res Vet Sci. 1992 Jan;52(1):126-8. doi: 10.1016/0034-5288(92)90073-b. PMID: 1553433. 8: Nott SE, O'Sullivan WJ, Gero AM, Bagnara AS. Routine screening for potential babesicides using cultures of Babesia bovis. Int J Parasitol. 1990 Oct;20(6):797-802. doi: 10.1016/0020-7519(90)90014-e. PMID: 2242963. 9: Cooper PE, Watson PM. Discontinuation of redwater treatments. Vet Rec. 1989 Jun 17;124(24):643. doi: 10.1136/vr.124.24.643-b. PMID: 2773215. 10: Walzer PD, Kim CK, Foy J, Linke MJ, Cushion MT. Cationic antitrypanosomal and other antimicrobial agents in the therapy of experimental Pneumocystis carinii pneumonia. Antimicrob Agents Chemother. 1988 Jun;32(6):896-905. doi: 10.1128/AAC.32.6.896. PMID: 3137861; PMCID: PMC172303. 11: Zivkovic D, Speksnijder JE, Kuil H, Seinen W. Immunity to Babesia in mice. III. The effects of corticosteroids and anti-thymocyte serum on mice immune to Babesia rodhaini. Vet Immunol Immunopathol. 1985 Jun;9(2):131-42. doi: 10.1016/0165-2427(85)90013-3. PMID: 3875924. 12: Yeruham I, Pipano E, Davidson M. A field strain of Babesia bovis apparently resistant to amicarbalide isethionate. Trop Anim Health Prod. 1985 Feb;17(1):29-30. doi: 10.1007/BF02356129. PMID: 3992668. 13: de Vos AJ, Stewart NP, Dalgliesh RJ. The effect of chemotherapy on Babesia bigemina in the tick vector Boophilus microplus. Int J Parasitol. 1984 Jun;14(3):249-52. doi: 10.1016/0020-7519(84)90075-4. PMID: 6469445. 14: Zivkovic D, Seinen W, Kuil H, Albers-van Bemmel CM, Speksnijder JE. Immunity to Babesia in mice. I. Adoptive transfer of immunity to Babesia rodhaini with immune spleen cells and the effect of irradiation on the protection of immune mice. Vet Immunol Immunopathol. 1984 Mar;5(4):343-57. doi: 10.1016/0165-2427(84)90003-5. PMID: 6730310. 15: Gray JS. Chemotherapy of Babesia divergens in the gerbil, Meriones unguiculatus. Res Vet Sci. 1983 Nov;35(3):318-24. PMID: 6665315. 16: Stewart CG. A comparison of the efficacy of isometamidium, amicarbalide and diminazene against Babesia canis in dogs and the effect on subsequent immunity. J S Afr Vet Assoc. 1983 Mar;54(1):47-51. PMID: 6631891. 17: Uilenberg G, Verdiesen PA, Zwart D. Imidocarb: a chemoprophylactic experiment with Babesia canis. Vet Q. 1981 Jul;3(3):118-23. doi: 10.1080/01652176.1981.9693811. PMID: 7268745. 18: Bacchi CJ, Nathan HC, Hutner SH, Duch DS, Nichol CA. Prevention by polyamines of the curative effect of amicarbalide and imidocarb for Trypanosoma brucei infections in mice. Biochem Pharmacol. 1981 Apr 15;30(8):883-6. doi: 10.1016/s0006-2952(81)80011-1. PMID: 7247968. 19: Kuttler KL. Pharmacotherapeutics of drugs used in treatment of anaplasmosis and babesiosis. J Am Vet Med Assoc. 1980 May 15;176(10 Spec No):1103-8. PMID: 7216881. 20: Nathan HC, Soto KV, Moreira R, Chunosoff L, Hutner SH, Bacchi CJ. Curative effects of the antipiroplasms amicarbalide and imidocarb on Trypanosoma brucei infection in mice. J Protozool. 1979 Nov;26(4):657-60. doi: 10.1111/j.1550-7408.1979.tb04215.x. PMID: 544802.