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MedKoo Cat#: 524314 | Name: Avitriptan Fumarate

Description:

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

Avitriptan, also known as BMS-180048, is a selective 5-HT1-like receptor agonist. Avitriptan is an effective compound for the treatment of migraine headaches with a prolonged duration of response. Avitriptan Is a Ligand and Agonist of Human Aryl Hydrocarbon Receptor That Induces CYP1A1 in Hepatic and Intestinal Cells.

Chemical Structure

Avitriptan Fumarate
Avitriptan Fumarate
CAS#171171-42-9 (fumarate)

Theoretical Analysis

MedKoo Cat#: 524314

Name: Avitriptan Fumarate

CAS#: 171171-42-9 (fumarate)

Chemical Formula: C26H34N6O7S

Exact Mass: 574.2210

Molecular Weight: 574.65

Elemental Analysis: C, 54.34; H, 5.96; N, 14.62; O, 19.49; S, 5.58

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 #
191588-96-2 (HCl) 170956-82-8 (2HCl) 151140-97-5 (3HCl) 151140-96-4 (free base) 171171-42-9 (fumarate) 171171-42-9 (maleate)
Synonym
Avitriptan Fumarate; BMS 180048; BMS-180048; BMS180048;
IUPAC/Chemical Name
1H-Indole-5-methanesulfonamide, 3-(3-(4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl)propyl)-N-methyl-, (E)-2-butenedioate (1:1)
InChi Key
FMXXORRZIQGUIN-WLHGVMLRSA-N
InChi Code
InChI=1S/C22H30N6O3S.C4H4O4/c1-23-32(29,30)15-17-5-6-20-19(12-17)18(13-25-20)4-3-7-27-8-10-28(11-9-27)22-21(31-2)14-24-16-26-22;5-3(6)1-2-4(7)8/h5-6,12-14,16,23,25H,3-4,7-11,15H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
SMILES Code
C(=O)(O)\C=C\C(=O)O.[nH]1cc(c2cc(ccc12)CS(=O)(=O)NC)CCCN1CCN(CC1)c1ncncc1OC
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, 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

Preparing Stock Solutions

The following data is based on the product molecular weight 574.65 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: Vyhlídalová B, Krasulová K, Pečinková P, Poulíková K, Vrzal R, Andrysík Z, Chandran A, Mani S, Dvorak Z. Antimigraine Drug Avitriptan Is a Ligand and Agonist of Human Aryl Hydrocarbon Receptor That Induces CYP1A1 in Hepatic and Intestinal Cells. Int J Mol Sci. 2020 Apr 17;21(8):2799. doi: 10.3390/ijms21082799. PMID: 32316498; PMCID: PMC7216230. 2: Fang W, Bauer F, Dong Y, Breit B. A domino reaction for generating β-aryl aldehydes from alkynes by substrate recognition catalysis. Nat Commun. 2019 Oct 25;10(1):4868. doi: 10.1038/s41467-019-12770-w. PMID: 31653836; PMCID: PMC6814718. 3: Puente J, Jaque M, Carrasco C, Cruz C, Valenzuela M, Wolf M, Mosnaim A. Triptan drugs, natural killer cell cytotoxicity, and neutrophils pro-matrix metalloproteinase-9 secretion. Headache. 2008 Nov-Dec;48(10):1482-9. doi: 10.1111/j.1526-4610.2008.01136.x. Epub 2008 May 9. PMID: 18479418. 4: Schmidt LE, Dalhoff K. Food-drug interactions. Drugs. 2002;62(10):1481-502. doi: 10.2165/00003495-200262100-00005. PMID: 12093316. 5: Bhalla P, Sharma HS, Wurch T, Pauwels PJ, Saxena PR. Molecular cloning and expression of the porcine trigeminal ganglion cDNA encoding a 5-ht(1F) receptor. Eur J Pharmacol. 2002 Feb 1;436(1-2):23-33. doi: 10.1016/s0014-2999(01)01605-3. PMID: 11834243. 6: Maslov LN, Krylatov AV, Lishmanov AIu, Solenkova NV, Bogomaz SA. Tolerantnost' serdtsa krys k aritmogennym vozdeĭstviiam v usloviiakh farmakologicheskoĭ aktivatsii K(ATP)-kanalov [Myocardial tolerance to arrhythmogenic exposure and pharmacological activation of K(ATP)-channels in rats]. Eksp Klin Farmakol. 2001 Mar-Apr;64(2):41-4. Russian. PMID: 11548447. 7: Knight YE, Edvinsson L, Goadsby PJ. Blockade of calcitonin gene-related peptide release after superior sagittal sinus stimulation in cat: a comparison of avitriptan and CP122,288. Neuropeptides. 1999 Feb;33(1):41-6. doi: 10.1054/npep.1999.0009. PMID: 10657470. 8: Roon KI, Maassen Van Den Brink A, Ferrari MD, Saxena PR. Bovine isolated middle cerebral artery contractions to antimigraine drugs. Naunyn Schmiedebergs Arch Pharmacol. 1999 Nov;360(5):591-6. doi: 10.1007/s002109900095. PMID: 10598799. 9: Nilsson T, Longmore J, Shaw D, Olesen IJ, Edvinsson L. Contractile 5-HT1B receptors in human cerebral arteries: pharmacological characterization and localization with immunocytochemistry. Br J Pharmacol. 1999 Nov;128(6):1133-40. doi: 10.1038/sj.bjp.0702773. PMID: 10578124; PMCID: PMC1571736. 10: Sharma A, Jusko WJ, Fulmor IE, Norton J, Uderman HD, Salazar DE. Pharmacokinetics and pharmacodynamics of avitriptan during intravenous administration in healthy subjects. J Clin Pharmacol. 1999 Jul;39(7):685-94. doi: 10.1177/00912709922008326. PMID: 10392323. 11: Jhee SS, Salazar DE, Ford NF, Fulmor IE, Sramek JJ, Cutler NR. A double- blind, randomized, crossover assessment of blood pressure following administration of avitriptan, sumatriptan, or placebo to patients with mild to moderate hypertension. Cephalalgia. 1999 Mar;19(2):95-9. doi: 10.1046/j.1468-2982.1999.019002095.x. PMID: 10214534. 12: Swan L, Hood S, Birnie DH, Muir DF, McCann GP, Hillis WS. The haemodynamic effect of the 5HT1 agonist BMS-180048: a class effect of triptans? Br J Clin Pharmacol. 1999 Feb;47(2):189-94. doi: 10.1046/j.1365-2125.1999.00875.x. PMID: 10190654; PMCID: PMC2014163. 13: Dahlöf CG, Falk L, Risenfors M, Lewis CP. Safety trial with the 5HT1B/1D agonist avitriptan (BMS-180048) in patients with migraine who have experienced pressure, tightness, and/or pain in the chest, neck, and/or throat following sumatriptan. Cephalalgia. 1998 Oct;18(8):546-51. doi: 10.1046/j.1468-2982.1998.1808546.x. PMID: 9827246. 14: Marathe PH, Sandefer EP, Kollia GE, Greene DS, Barbhaiya RH, Lipper RA, Page RC, Doll WJ, Ryo UY, Digenis GA. In vivo evaluation of the absorption and gastrointestinal transit of avitriptan in fed and fasted subjects using gamma scintigraphy. J Pharmacokinet Biopharm. 1998 Feb;26(1):1-20. doi: 10.1023/a:1023236823320. PMID: 9773390. 15: Marathe PH, Greene DS, Kollia GD, Barbhaiya RH. Evaluation of the effect of food on the pharmacokinetics of avitriptan. Biopharm Drug Dispos. 1998 Sep;19(6):381-94. doi: 10.1002/(sici)1099-081x(199809)19:6<381::aid- bdd118>3.0.co;2-j. PMID: 9737819. 16: MaassenVanDenBrink A, Reekers M, Bax WA, Ferrari MD, Saxena PR. Coronary side-effect potential of current and prospective antimigraine drugs. Circulation. 1998 Jul 7;98(1):25-30. doi: 10.1161/01.cir.98.1.25. PMID: 9665056. 17: Cutler NR, Salazar DE, Jhee SS, Fulmor IE, Ford N, Smith RA, Sramek JJ. Pharmacokinetics and pharmacodynamics of avitriptan in patients with migraine after oral dosing. Headache. 1998 Jun;38(6):446-52. doi: 10.1046/j.1526-4610.1998.3806446.x. PMID: 9664749. 18: Marathe PH, Greene DS, Lee JS, Barbhaiya RH. Assessment of effect of food, gender, and intra-subject variability in the pharmacokinetics of avitriptan. Biopharm Drug Dispos. 1998 Apr;19(3):153-7. doi: 10.1002/(sici)1099-081x(199804)19:3<153::aid-bdd90>3.0.co;2-t. PMID: 9569997. 19: Marathe PH, Greene DS, Kollia GD, Barbhaiya RH. A pharmacokinetic interaction study of avitriptan and propranolol. Clin Pharmacol Ther. 1998 Mar;63(3):367-78. doi: 10.1016/S0009-9236(98)90168-0. PMID: 9542480. 20: Marathe PH, Greene DS, Kollia GD, Barbhaiya RH. The effects of age and gender on the single dose pharmacokinetics of avitriptan administered to healthy volunteers. J Clin Pharmacol. 1997 Oct;37(10):937-45. doi: 10.1002/j.1552-4604.1997.tb04268.x. PMID: 9505985.