avitriptan   Click here for help

GtoPdb Ligand ID: 10446

Synonyms: BMS-180,048 | BMS-180048 | BMS180048
Compound class: Synthetic organic
Comment: Avitriptan (BMS-180048) is a serotonin receptor agonist with selectivity for the 5-HT1D and 5-HT1B subtypes [5]. It was investigated as an anti-mirgaine agent in the late 1990s [1-4] but never reached the market.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 9
Topological polar surface area 111.83
Molecular weight 458.21
XLogP 1.52
No. Lipinski's rules broken 0
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Canonical SMILES COc1cncnc1N1CCN(CC1)CCCc1c[nH]c2c1cc(cc2)CS(=O)(=O)NC
Isomeric SMILES COc1cncnc1N1CCN(CC1)CCCc1c[nH]c2c1cc(cc2)CS(=O)(=O)NC
InChI InChI=1S/C22H30N6O3S/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
1. Couch Jr JR, Saper J, Meloche JP. (1996)
Treatment of migraine with BMS180048: response at 2 hours. North American BMS180048 Study Group.
Headache, 36 (9): 523-30. [PMID:8916559]
2. Cutler NR, Salazar DE, Jhee SS, Fulmor IE, Ford N, Smith RA, Sramek JJ. (1998)
Pharmacokinetics and pharmacodynamics of avitriptan in patients with migraine after oral dosing.
Headache, 38 (6): 446-52. [PMID:9664749]
3. Dahlöf CG, Falk L, Risenfors M, Lewis CP. (1998)
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, 18 (8): 546-51. [PMID:9827246]
4. Ryan Jr RE, Elkind A, Goldstein J. (1997)
Twenty-four-hour effectiveness of BMS 180048 in the acute treatment of migraine headaches.
Headache, 37 (4): 245-8. [PMID:9150621]
5. Saxena PR, De Vries P, Wang W, Heiligers JP, Maassen vandenBrink A, Bax WA, Yocca FD. (1997)
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, 355 (2): 295-302. [PMID:9050026]