General Information
Drug ID
DR01282
Drug Name
Naratriptan
Synonyms
Amerge (TN); Amerge, Naramig,Naratriptan; Colatan; N-methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide; N-methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide; N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide; Naramig; Naramig (TN); Naratriptan (INN); Naratriptanum
Drug Type
Small molecular drug
Indication Migraine Headaches [ICD11:8A80] Approved [1]
Therapeutic Class
Vasoconstrictor Agents
Structure
3D MOL 2D MOL
Formula
C17H25N3O2S
Canonical SMILES
CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C
InChI
InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3
InChIKey
AMKVXSZCKVJAGH-UHFFFAOYSA-N
CAS Number
CAS 121679-13-8
Pharmaceutical Properties Molecular Weight 335.5 Topological Polar Surface Area 73.6
Heavy Atom Count 23 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
XLogP
2
PubChem CID
4440
PubChem SID
9994 ,591979 ,4406062 ,7980085 ,8152740 ,14802133 ,29223537 ,46507243 ,46530540 ,48416313 ,49984092 ,50126335 ,50340505 ,57322272 ,85209198 ,92721601 ,93166470 ,96024943 ,103396287 ,103966995 ,104306415 ,118043420 ,124757290 ,125001918 ,125164094 ,125339313 ,126619011 ,126661482 ,126731399 ,127427940 ,134221895 ,134338167 ,135035417 ,135650691 ,135692164 ,137002440 ,139157587 ,143500462 ,144116266 ,152035273 ,152253555 ,152344169 ,160964291 ,164830541 ,174006312 ,175268422 ,176253695 ,179116807 ,196105283 ,210279333
ChEBI ID
ChEBI:7478
TTD Drug ID
D0T3KI
DT(s) Transporting This Drug 1-Oct Transporter Info Organic cation transporter 1 Substrate [2]
References
1 Naratriptan was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 OCT1 mediates hepatic uptake of sumatriptan and loss-of-function OCT1 polymorphisms affect sumatriptan pharmacokinetics. Clin Pharmacol Ther. 2016 Jun;99(6):633-41.

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