Avitriptan HCl | CAS#170956-82-8 | 5HT1B/1D Agonist

MedKoo Cat#: 573333 | Name: Avitriptan HCl

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 HCl

CAS#170956-82-8 (2HCl)

Theoretical Analysis

MedKoo Cat#: 573333

Name: Avitriptan HCl

CAS#: 170956-82-8 (2HCl)

Chemical Formula: C22H32Cl2N6O3S

Exact Mass: 458.2100

Molecular Weight: 531.50

Elemental Analysis: C, 49.72; H, 6.07; Cl, 13.34; N, 15.81; O, 9.03; S, 6.03

Price and Availability

Size	Price	Availability
1mg	USD 150.00	Ready to Ship
5mg	USD 550.00	Ready to Ship
10mg	USD 950.00	Ready to Ship
25mg	USD 1,650.00	Ready to Ship
50mg	USD 2,950.00	Ready to Ship

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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 HCl; Avitriptan hydrochloride; Avitriptan dihydrochloride; Avitriptan; BMS 180048; BMS-180048; BMS180048;

IUPAC/Chemical Name

1H-Indole-5-methanesulfonamide, 3-(3-(4-(5-methoxy-4-pyrimidinyl)-1-piperazinyl)propyl)-N-methyl-, dihydrochloride

InChi Key

LXDKLZKTSZKRLF-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H30N6O3S.2ClH/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;;/h5-6,12-14,16,23,25H,3-4,7-11,15H2,1-2H3;2*1H

SMILES Code

O=S(CC1=CC2=C(NC=C2CCCN3CCN(C4=NC=NC=C4OC)CC3)C=C1)(NC)=O.[H]Cl.[H]Cl

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#Y23X02M10

QC Data

View QC data: current batch, Lot#Y23X02M10

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Avitriptan, also known as BMS-180048, is a selective 5-HT1-like receptor agonist.

In vitro activity:

Using competitive binding assay and by homology docking, this study identified Avitriptan as a low-affinity ligand of AhR. Avitriptan triggered nuclear translocation of AhR and increased binding of AhR in CYP1A1 promotor DNA, as revealed by immune-fluorescence microscopy and chromatin immune-precipitation assay, respectively. Increased levels of CYP1A1 mRNA by Avitriptan were observed in human colon carcinoma cells LS180 but not in primary cultures of human hepatocytes. Reference: Int J Mol Sci. 2020 Apr 17;21(8):2799. https://pubmed.ncbi.nlm.nih.gov/32316498/

In vivo activity:

In anaesthetized pigs, avitriptan (10, 30, 100 and 300 micrograms.kg-1) decreased the total carotid blood flow by exclusively decreasing arteriovenous anastomotic blood flow; capillary blood flow was increased. The mean +/- SEM i.v. dose of avitriptan eliciting a 50% decrease (ED50) in the porcine carotid arteriovenous anastomotic blood flow was calculated to be 76 +/- 23 micrograms.kg-1 (132 +/- 40 nmol.kg-1) and the highest dose (300 micrograms.kg-1) produced a 72 +/- 4% reduction. Reference: Naunyn Schmiedebergs Arch Pharmacol. 1997 Feb;355(2):295-302. https://pubmed.ncbi.nlm.nih.gov/9050026/

Preparing Stock Solutions

The following data is based on the product molecular weight 531.50 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.

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:

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. Saxena PR, De Vries P, Wang W, Heiligers JP, Maassen vandenBrink A, Bax WA, Yocca FD. Effects of avitriptan, a new 5-HT 1B/1D receptor agonist, in experimental models predictive of antimigraine activity and coronary side-effect potential. Naunyn Schmiedebergs Arch Pharmacol. 1997 Feb;355(2):295-302. doi: 10.1007/pl00004946. PMID: 9050026.

In vitro protocol:

In vivo protocol:

1. Saxena PR, De Vries P, Wang W, Heiligers JP, Maassen vandenBrink A, Bax WA, Yocca FD. Effects of avitriptan, a new 5-HT 1B/1D receptor agonist, in experimental models predictive of antimigraine activity and coronary side-effect potential. Naunyn Schmiedebergs Arch Pharmacol. 1997 Feb;355(2):295-302. doi: 10.1007/pl00004946. PMID: 9050026.

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.