Motolimod

Motolimod
Identifiers
	IUPAC name 2-amino-N,N-dipropyl-8-[4-(pyrrolidine-1-carbonyl)phenyl]-3H-1-benzazepine-4-carboxamide;
CAS Number	926927-61-9;
PubChem CID	16049404;
DrugBank	DB12303;
ChemSpider	13177800;
UNII	WP6PY72ZH3;
KEGG	D10716;
ChEMBL	ChEMBL3301618;
CompTox Dashboard (EPA)	DTXSID10239107 ;
Chemical and physical data
Formula	C28H34N4O2
Molar mass	458.606 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCN(CCC)C(=O)C1=CC2=C(C=C(C=C2)C3=CC=C(C=C3)C(=O)N4CCCC4)N=C(C1)N;
	InChI InChI=1S/C28H34N4O2/c1-3-13-31(14-4-2)28(34)24-17-23-12-11-22(18-25(23)30-26(29)19-24)20-7-9-21(10-8-20)27(33)32-15-5-6-16-32/h7-12,17-18H,3-6,13-16,19H2,1-2H3,(H2,29,30); Key:QSPOQCXMGPDIHI-UHFFFAOYSA-N;

Motolimod (VTX-2337) is a drug which acts as a potent and selective agonist of toll-like receptor 8 (TLR8), a receptor involved in the regulation of the immune system. It is used to stimulate the immune system, and has potential application as an adjuvant therapy in cancer chemotherapy, although clinical trials have shown only modest benefits.^[1]^[2] It also worsens neuropathic pain in animal models and has been used to research the potential of targeting TLR8 in some kinds of chronic pain syndromes.^[3]^[4]

References

^ Monk BJ, Brady MF, Aghajanian C, Lankes HA, Rizack T, Leach J, et al. (May 2017). "A phase 2, randomized, double-blind, placebo-controlled study of chemo-immunotherapy combination using motolimod with pegylated liposomal doxorubicin in recurrent or persistent ovarian cancer: a Gynecologic Oncology Group partners study". Annals of Oncology. 28 (5): 996–1004. doi:10.1093/annonc/mdx049. PMC 5406764. PMID 28453702.
^ Ferris RL, Saba NF, Gitlitz BJ, Haddad R, Sukari A, Neupane P, et al. (November 2018). "Effect of Adding Motolimod to Standard Combination Chemotherapy and Cetuximab Treatment of Patients With Squamous Cell Carcinoma of the Head and Neck: The Active8 Randomized Clinical Trial". JAMA Oncology. 4 (11): 1583–1588. doi:10.1001/jamaoncol.2018.1888. PMC 6248084. PMID 29931076.
^ Zhang ZJ, Guo JS, Li SS, Wu XB, Cao DL, Jiang BC, et al. (December 2018). "TLR8 and its endogenous ligand miR-21 contribute to neuropathic pain in murine DRG". The Journal of Experimental Medicine. 215 (12): 3019–3037. doi:10.1084/jem.20180800. PMC 6279408. PMID 30455267.
^ Zhao LX, Jiang M, Bai XQ, Cao DL, Wu XB, Zhang J, et al. (December 2020). "TLR8 in the Trigeminal Ganglion Contributes to the Maintenance of Trigeminal Neuropathic Pain in Mice". Neuroscience Bulletin. doi:10.1007/s12264-020-00621-4. PMC 8055805. PMID 33355900.

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[1] Monk BJ, Brady MF, Aghajanian C, Lankes HA, Rizack T, Leach J, et al. (May 2017). "A phase 2, randomized, double-blind, placebo-controlled study of chemo-immunotherapy combination using motolimod with pegylated liposomal doxorubicin in recurrent or persistent ovarian cancer: a Gynecologic Oncology Group partners study". Annals of Oncology. 28 (5): 996–1004. doi:10.1093/annonc/mdx049. PMC 5406764. PMID 28453702.

[2] Ferris RL, Saba NF, Gitlitz BJ, Haddad R, Sukari A, Neupane P, et al. (November 2018). "Effect of Adding Motolimod to Standard Combination Chemotherapy and Cetuximab Treatment of Patients With Squamous Cell Carcinoma of the Head and Neck: The Active8 Randomized Clinical Trial". JAMA Oncology. 4 (11): 1583–1588. doi:10.1001/jamaoncol.2018.1888. PMC 6248084. PMID 29931076.

[3] Zhang ZJ, Guo JS, Li SS, Wu XB, Cao DL, Jiang BC, et al. (December 2018). "TLR8 and its endogenous ligand miR-21 contribute to neuropathic pain in murine DRG". The Journal of Experimental Medicine. 215 (12): 3019–3037. doi:10.1084/jem.20180800. PMC 6279408. PMID 30455267.

[4] Zhao LX, Jiang M, Bai XQ, Cao DL, Wu XB, Zhang J, et al. (December 2020). "TLR8 in the Trigeminal Ganglion Contributes to the Maintenance of Trigeminal Neuropathic Pain in Mice". Neuroscience Bulletin. doi:10.1007/s12264-020-00621-4. PMC 8055805. PMID 33355900.

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Identifiers

IUPAC name 2-amino-N,N-dipropyl-8-[4-(pyrrolidine-1-carbonyl)phenyl]-3H-1-benzazepine-4-carboxamide
CAS Number	926927-61-9
PubChem CID	16049404
DrugBank	DB12303
ChemSpider	13177800
UNII	WP6PY72ZH3
KEGG	D10716
ChEMBL	ChEMBL3301618
CompTox Dashboard (EPA)	DTXSID10239107
Chemical and physical data
Formula	C₂₈H₃₄N₄O₂
Molar mass	458.606 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCN(CCC)C(=O)C1=CC2=C(C=C(C=C2)C3=CC=C(C=C3)C(=O)N4CCCC4)N=C(C1)N
InChI InChI=1S/C28H34N4O2/c1-3-13-31(14-4-2)28(34)24-17-23-12-11-22(18-25(23)30-26(29)19-24)20-7-9-21(10-8-20)27(33)32-15-5-6-16-32/h7-12,17-18H,3-6,13-16,19H2,1-2H3,(H2,29,30) Key:QSPOQCXMGPDIHI-UHFFFAOYSA-N

Motolimod

See also

References