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MedKoo Cat#: 592806 | Name: Amicarbalide

Description:

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

Amicarbalide is a therapeutic agent for anaplasmosis.

Chemical Structure

Amicarbalide
Amicarbalide
CAS#3459-96-9 (free base)

Theoretical Analysis

MedKoo Cat#: 592806

Name: Amicarbalide

CAS#: 3459-96-9 (free base)

Chemical Formula: C15H16N6O

Exact Mass: 296.1386

Molecular Weight: 296.33

Elemental Analysis: C, 60.80; H, 5.44; N, 28.36; O, 5.40

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
IUPAC/Chemical Name
3,3'-Diamidinocarbanilide
InChi Key
KRUVSRGJKCHYMY-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H16N6O/c16-13(17)9-3-1-5-11(7-9)20-15(22)21-12-6-2-4-10(8-12)14(18)19/h1-8H,(H3,16,17)(H3,18,19)(H2,20,21,22)
SMILES Code
O=C(NC1=CC=CC(C(N)=N)=C1)NC2=CC=CC(C(N)=N)=C2
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 296.33 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: 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. PubMed PMID: 3992668. 2: 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. PubMed PMID: 6631891. 3: De Vos AJ, Barrowman PR, Coetzer JA, Kellerman TS. Amicarbalide: a therapeutic agent for anaplasmosis. Onderstepoort J Vet Res. 1978 Sep;45(3):203-8. PubMed PMID: 750960. 4: Eyre P. Some pharmacodynamic effects of the babesicidal agents quinuronium and amicarbalide. J Pharm Pharmacol. 1967 Aug;19(8):509-19. PubMed PMID: 4382438. 5: Taylor WM, Simpson CF, Martin FG. Certain aspects of toxicity of an amicarbalide formulation to ponies. Am J Vet Res. 1972 Mar;33(3):533-41. PubMed PMID: 5014461. 6: 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. PubMed PMID: 544802. 7: Eyre P. Release of tissue histamine by the babesicidal agents quinuronium and amicarbalide. J Pharm Pharmacol. 1966 Jan;18(1):33-7. PubMed PMID: 4380701. 8: Eyre P. The anticholinesterase activity of the babesicidal agents quinuronium and amicarbalide and the influence of pyridine 2-aldoxime methiodide. Res Vet Sci. 1966 Apr;7(2):161-7. PubMed PMID: 4959552. 9: 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. PubMed PMID: 7247968. 10: 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. PubMed PMID: 8466555. 11: Clark IA, Richmond JE, Wills EJ, Allison AC. Intra-erythrocytic death of the parasite in mice recovering from infection with Babesia microti. Parasitology. 1977 Oct;75(2):189-96. PubMed PMID: 927888. 12: 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. PubMed PMID: 8997494. 13: 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. PubMed PMID: 7216881. 14: 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. PubMed PMID: 8204103. 15: 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. PubMed PMID: 2242963. 16: 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. PubMed PMID: 3137861; PubMed Central PMCID: PMC172303. 17: 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. PubMed PMID: 6730310. 18: Asghar SS, Pondman KW, Cormane RH. Inhibition of C1r, C1s and generation of C1s by amidino compounds. Biochim Biophys Acta. 1973 Aug 30;317(2):539-48. PubMed PMID: 19999737. 19: 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. PubMed PMID: 3875924. 20: 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. PubMed PMID: 28139658; PubMed Central PMCID: PMC5290327.