Vinburnine
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MedKoo CAT#: 526559

CAS#: 4880-88-0 (free base)

Description: Vinburnine, also known as Eburnamonine, is a vasodilator. Vinburnine is a vinca alkaloid and a metabolite of vincamine.


Chemical Structure

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Vinburnine
CAS# 4880-88-0 (free base)

Theoretical Analysis

MedKoo Cat#: 526559
Name: Vinburnine
CAS#: 4880-88-0 (free base)
Chemical Formula: C19H22N2O
Exact Mass: 294.17
Molecular Weight: 294.398
Elemental Analysis: C, 77.52; H, 7.53; N, 9.52; O, 5.43

Price and Availability

Size Price Availability Quantity
25mg USD 250
50mg USD 450
100mg USD 750
200mg USD 1250
500mg USD 1850
1g USD 2450
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Related CAS #: 4880-88-0 (free base)   94134-60-8 (phosphate)  

Synonym: CH846; CH-846; CH 846; Vinburnine; Eburnal; Eburnamonine

IUPAC/Chemical Name: (13aR)-13a-ethyl-2,3,5,6,13,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12(41H)-one

InChi Key: WYJAPUKIYAZSEM-MUMRKEEXSA-N

InChi Code: InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18?,19-/m1/s1

SMILES Code: O=C1N2C3=C(C4=C2C=CC=C4)CCN5C3[C@@](CCC5)(CC)C1

Appearance: White to off-white 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, not in water

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 294.40 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Louajri A, Harraga S, Toubin G, Kantelip JP. Red blood cell metabolism and hemoglobin oxygen affinity. Effect of vinburnine on normobaric hypoxic rats. Biol Pharm Bull. 1999 Aug;22(8):773-4. PubMed PMID: 10480311.

2: Schena D, Menegazzi S, Barba A. Bullous fixed drug eruption induced by vinburnine. Contact Dermatitis. 1992 Sep;27(3):187. PubMed PMID: 1451466.

3: Acciavatti A, Domini L, Galigani C, Saletti M, Guideri F, Auteri A, Di Perri T. [The effects of vinburnine on the blood rheology parameters and on the oxyhemoglobin dissociation curve and 2,3-diphosphoglycerate. In vitro research]. Recenti Prog Med. 1990 Nov;81(11):710-5. Italian. PubMed PMID: 2287807.

4: Drago F, Grassi M, Valerio C, Spadaro F, D'Agata V, Lauria N. Effects of vinburnine on experimental models of learning and memory impairments. Pharmacol Biochem Behav. 1990 Sep;37(1):53-7. PubMed PMID: 2263666.

5: Sado PA, Gibassier D, Leverge R. [The effect of modification of excipients for the bioavailability of vinburnine]. J Pharm Belg. 1989 May-Jun;44(3):221-9. French. PubMed PMID: 2795425.

6: Sado PA, Gibassier D, Leverge R. [The oral liquid form of vinburnine: biopharmaceutics]. J Pharm Belg. 1989 Jan-Feb;44(1):50-9. French. PubMed PMID: 2724048.

7: Barzaghi F, Dragonetti M, Formento ML, Gueniau C, Nencioni A, Mantegazza P. A comparison of some of the pharmacological properties of the new eburnamenine derivative vindeburnol with those of vincamine, vinburnine, dihydroergotoxine mesilate and nicergoline. Arzneimittelforschung. 1986 Oct;36(10):1442-8. PubMed PMID: 3814205.

8: Maksay G, Bíró T, Kiss B. Vinburnine decelerates [3H]N-methylscopolamine binding to recombinant human muscarinic M1-M4 acetylcholine receptors. Eur J Pharmacol. 2004 Jan 12;483(2-3):229-32. PubMed PMID: 14729111.

9: Chauveau E, Prignet JM, Carloz E, Duval JL, Gilles B. [Lymphocytic colitis likely attributable to use of vinburnine (Cervoxan)]. Gastroenterol Clin Biol. 1998 Mar;22(3):362. French. PubMed PMID: 9762227.

10: Domini L, Acciavatti A, Galigani C, Saletti M, De Franco V, Pecchi S, Auteri A, Di Perri T. [The effects of the acute administration of vinburnine on blood rheology, oxygen transport and regional circulation under normal conditions and in hypoxemia. In vivo research]. Recenti Prog Med. 1990 Nov;81(11):716-23. Italian. PubMed PMID: 2287808.

11: Bentue-Ferrer D, Philouze V, Pape D, Reymann JM, Allain H, Van den Driessche J. Comparative evaluation of scavenger properties of exifone, piracetam and vinburnine. Fundam Clin Pharmacol. 1989;3(4):323-8. PubMed PMID: 2807130.

12: Sado PA, Gibassier D, Leverge R. [Simultaneous determination of vinburnine and 6-hydroxyvinburnine in human plasma by high-performance liquid chromatography]. J Chromatogr. 1988 Dec 29;434(1):157-67. French. PubMed PMID: 3243809.

13: Giordano F, Pavan M, La Manna A, Bettinetti GP, Pavesi L, Bovis G. Complexation behavior of vinburnine with beta and gamma cyclodextrins in aqueous solution and in the solid state. Farmaco Prat. 1988 Nov;43(11):345-55. PubMed PMID: 3243350.

14: Sado PA, Gibassier D, Leverge R. [Bioavailability of vinburnine in man: importance of combination with ascorbic acid]. J Pharm Belg. 1986 Jan-Feb;41(1):17-28. French. PubMed PMID: 3701564.

15: Sado PA, Gibassier D, Le Verge R, Acerbi D, Schiantarelli P. [Relative bioavailability of vinburnine in man (microgranules/gels)]. J Pharm Belg. 1985 Sep-Oct;40(5):308-22. French. PubMed PMID: 4087124.