Cligosiban

Pharmaceutical compound From Wikipedia, the free encyclopedia

Cligosiban (INNTooltip International Nonproprietary Name; developmental code names IX-01 and PF-3274167) is an oxytocin receptor antagonist which is or was under development for the treatment of premature ejaculation.[1][4][5][2][3] It is taken orally.[1][2] The drug is a small molecule or non-peptide and is a potent, highly selective, and brain-penetrant antagonist of the oxytocin receptor.[5][2] Cligosiban was originated by Pfizer and is under development by Ixchelsis and Chorus Group.[1][4] As of December 2019, it is in phase 2 clinical trials.[1] However, another source lists the drug's development as having been discontinued.[4] The drug failed to show effectiveness in a phase 2b trial.[6]

Other namesIX-01; IX01; PF-3274167; PF3274167; PF-03274167; PF03274167; PF-327,4167
Routes of
administrationOral[1][2]
Drug classOxytocin receptor antagonist
Elimination half-life12 hours[3]
Quick facts Clinical data, Other names ...
Cligosiban
Clinical data
Other namesIX-01; IX01; PF-3274167; PF3274167; PF-03274167; PF03274167; PF-327,4167
Routes of
administration		Oral[1][2]
Drug classOxytocin receptor antagonist
Pharmacokinetic data
Elimination half-life12 hours[3]
Identifiers
  • 5-[3-[3-(2-chloro-4-fluorophenoxy)azetidin-1-yl]-5-(methoxymethyl)-1,2,4-triazol-4-yl]-2-methoxypyridine
CAS Number
PubChem CID
DrugBank
UNII
ChEMBL
Chemical and physical data
FormulaC19H19ClFN5O3
Molar mass419.84 g·mol−1
3D model (JSmol)
  • COCC1=NN=C(N1C2=CN=C(C=C2)OC)N3CC(C3)OC4=C(C=C(C=C4)F)Cl
  • InChI=1S/C19H19ClFN5O3/c1-27-11-17-23-24-19(26(17)13-4-6-18(28-2)22-8-13)25-9-14(10-25)29-16-5-3-12(21)7-15(16)20/h3-8,14H,9-11H2,1-2H3
  • Key:HNIFCPBQMKPRCX-UHFFFAOYSA-N
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