Vedaclidine

Vedaclidine (INN,^[1]^: 180 codenamed LY-297,802, NNC 11-1053) is an experimental analgesic drug which acts as a mixed agonist–antagonist at muscarinic acetylcholine receptors, being a potent and selective agonist for the M₁ and M₄ subtypes, yet an antagonist at the M₂, M₃ and M₅ subtypes.^[2]^[3] It is orally active and an effective analgesic over 3× the potency of morphine, with side effects such as salivation and tremor only occurring at many times the effective analgesic dose.^[4]^[5]^[6] Human trials showed little potential for development of dependence or abuse,^[7] and research is continuing into possible clinical application in the treatment of neuropathic pain and cancer pain relief.^[8]

Other names(S)-3-[4-(butylthio)-1,2,5-thiadiazol-3-yl]quinuclidine

Routes of
administrationoral

ATC code

None

CAS Number

141575-50-0

Quick facts Clinical data, Other names ...

Vedaclidine
Clinical data


Other names	(S)-3-[4-(butylthio)-1,2,5-thiadiazol-3-yl]quinuclidine
Routes of administration	oral
ATC code	None
Identifiers
IUPAC name (3S)-3-[4-(Butylsulfanyl)-1,2,5-thiadiazol-3-yl]quinuclidine
CAS Number	141575-50-0
PubChem CID	9889093
ChemSpider	8064764
UNII	98IW5HAV1N
ChEMBL	ChEMBL136807
CompTox Dashboard (EPA)	DTXSID30275663
Chemical and physical data
Formula	C₁₃H₂₁N₃S₂
Molar mass	283.45 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCSC1=NSN=C1[C@@H]2CN3CCC2CC3
InChI InChI=1S/C13H21N3S2/c1-2-3-8-17-13-12(14-18-15-13)11-9-16-6-4-10(11)5-7-16/h10-11H,2-9H2,1H3/t11-/m1/s1 Key:WZZPXVURFDJHGI-LLVKDONJSA-N

References

[1]
"International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 38" (PDF). World Health Organization. 1997. Retrieved 18 November 2016.
[2]
Shannon HE, Womer DE, Bymaster FP, Calligaro DO, DeLapp NC, Mitch CH, et al. (1997). "In vivo pharmacology of butylthio[2.2.2] (LY297802 / NNC11-1053), an orally acting antinociceptive muscarinic agonist". Life Sciences. 60 (13–14): 969–76. doi:10.1016/s0024-3205(97)00036-2. PMID 9121363.
[3]
Womer DE, Shannon HE (September 2000). "Reversal of pertussis toxin-induced thermal allodynia by muscarinic cholinergic agonists in mice". Neuropharmacology. 39 (12): 2499–504. doi:10.1016/S0028-3908(00)00068-X. PMID 10974334. S2CID 31065787.
[4]
Swedberg MD, Sheardown MJ, Sauerberg P, Olesen PH, Suzdak PD, Hansen KT, et al. (May 1997). "Butylthio[2.2.2] (NNC 11-1053/LY297802): an orally active muscarinic agonist analgesic". The Journal of Pharmacology and Experimental Therapeutics. 281 (2): 876–83. doi:10.1016/S0022-3565(24)36644-3. PMID 9152397.
[5]
Shannon HE, Sheardown MJ, Bymaster FP, Calligaro DO, Delapp NW, Gidda J, et al. (May 1997). "Pharmacology of butylthio[2.2.2] (LY297802/NNC11-1053): a novel analgesic with mixed muscarinic receptor agonist and antagonist activity". The Journal of Pharmacology and Experimental Therapeutics. 281 (2): 884–94. doi:10.1016/S0022-3565(24)36645-5. PMID 9152398.
[6]
Shannon HE, Jones CK, Li DL, Peters SC, Simmons RM, Iyengar S (September 2001). "Antihyperalgesic effects of the muscarinic receptor ligand vedaclidine in models involving central sensitization in rats". Pain. 93 (3): 221–7. doi:10.1016/S0304-3959(01)00319-0. PMID 11514081. S2CID 10256837.
[7]
Petry NM, Bickel WK, Huddleston J, Tzanis E, Badger GJ (April 1998). "A comparison of subjective, psychomotor and physiological effects of a novel muscarinic analgesic, LY297802 tartrate, and oral morphine in occasional drug users". Drug and Alcohol Dependence. 50 (2): 129–36. doi:10.1016/S0376-8716(98)00026-X. PMID 9649964.
[8]
Tata AM (June 2008). "Muscarinic acetylcholine receptors: new potential therapeutic targets in antinociception and in cancer therapy". Recent Patents on CNS Drug Discovery. 3 (2): 94–103. doi:10.2174/157488908784534621. PMID 18537768.

See also

References

Related Articles