Structure via PubChem · Public domain (PubChem)
avitriptan
Sign in to saveAvitriptan (; development code BMS-180048) is an antimigraine drug of the triptan family which was never marketed. It acts as a serotonin 5-HT1B and 5-HT1D receptor agonist. The drug reached phase 3 clinical trials prior to the discontinuation of its development.
Chemical data
- Formula
- C22H30N6O3S
- Molecular weight
- 458.6 g/mol
- IUPAC name
- 1-[3-[3-[4-(5-methoxypyrimidin-4-yl)piperazin-1-yl]propyl]-1H-indol-5-yl]-N-methylmethanesulfonamide
- SMILES
- CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCCN3CCN(CC3)C4=NC=NC=C4OC
- InChIKey
- WRZVGHXUPBWIOO-UHFFFAOYSA-N
- XLogP
- 1.8
- Polar surface area
- 112 Ų
- H-bond donors
- 2
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 458.21
Show 3 more facts
- chemical formula
- C₂₂H₃₀N₆O₃S
- canonical SMILES
- CNS(=O)(=O)CC1=CC2=C(C=C1)NC=C2CCCN3CCN(CC3)C4=NC=NC=C4OC
- Commons category
- Avitriptan
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Pharmacology
- Chemistry
- See also
- References
Avitriptan (; development code BMS-180048) is an antimigraine drug of the triptan family which was never marketed. It acts as a serotonin 5-HT1B and 5-HT1D receptor agonist. The drug reached phase 3 clinical trials prior to the discontinuation of its development.
==Pharmacology== {| class="wikitable floatleft" style="font-size:small;" |+ |- ! Target !! Affinity (Ki, nM) |- | 5-HT1A || 19 (Ki)646–>10,000 () |- | 5-HT1B || 1.6–21 (Ki)2.1–2.7 () |- | 5-HT1D || 0.78–4.4 (Ki)0.54 () |- | 5-HT1E || 3,550 (Ki)3,020–>10,000 () |- | 5-HT1F || 78–182 (Ki)81–891 () |- | 5-HT2A || 2,340 (Ki)123 () |- | 5-HT2B || 1,150 (Ki)389 () |- | 5-HT2C || (Ki) () |- | 5-HT3 || >1,000 (rat) |- | 5-HT4 || |- | 5-HT5A || |- | 5-HT6 || |- | 5-HT7 || 759 (Ki)4,170 () |- | α1A–α1D || |- | α2A–α2C || |- | β1–β3 || |- | D1–D5 || |- | H1–H4 || |- | M1–M5 || |- | I1, I2 || |- | σ1, σ2 || |- | || |- | || |- | || |- | || |- class="sortbottom" | colspan="2" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: |}
Excerpted from Wikipedia’s “avitriptan” article, available under the CC BY-SA 4.0 licence.