Pamapimod

Pamapimod
Identifiers
	IUPAC name 6-(2,4-difluorophenoxy)-2-(1,5-dihydroxypentan-3-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one;
CAS Number	449811-01-2;
PubChem CID	16220188;
IUPHAR/BPS	9915;
ChemSpider	17347490;
KEGG	D08963;
ChEBI	CHEBI:90685;
ChEMBL	ChEMBL1090089;
PDB ligand	FLW (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID90963312 ;
Chemical and physical data
Formula	C19H20F2N4O4
Molar mass	406.390 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1C2=NC(=NC=C2C=C(C1=O)OC3=C(C=C(C=C3)F)F)NC(CCO)CCO;
	InChI InChI=InChI=1S/C19H20F2N4O4/c1-25-17-11(10-22-19(24-17)23-13(4-6-26)5-7-27)8-16(18(25)28)29-15-3-2-12(20)9-14(15)21/h2-3,8-10,13,26-27H,4-7H2,1H3,(H,22,23,24); Key:JYYLVUFNAHSSFE-UHFFFAOYSA-N;

Pamapimod is an investigational drug which is being evaluated for the treatment of autoimmune diseases. It is a p38 mitogen-activated protein kinase inhibitor.^[1] It has been evaluated in a phase 2 clinical trial for the treatment of rheumatoid arthritis, but was found not to be effective.^[2]^[3] It has subsequently been investigated as a possible treatment for osteoarthritis.^[4]^[5]

References

^ Hill RJ, Dabbagh K, Phippard D, Li C, Suttmann RT, Welch M, et al. (December 2008). "Pamapimod, a novel p38 mitogen-activated protein kinase inhibitor: preclinical analysis of efficacy and selectivity". The Journal of Pharmacology and Experimental Therapeutics. 327 (3): 610–9. doi:10.1124/jpet.108.139006. PMID 18776065.
^ Cohen S, Fleischmann R (May 2010). "Kinase inhibitors: a new approach to rheumatoid arthritis treatment". Current Opinion in Rheumatology. 22 (3): 330–5. doi:10.1097/BOR.0b013e3283378e6f. PMID 20164774.
^ Cohen SB, Cheng TT, Chindalore V, Damjanov N, Burgos-Vargas R, Delora P, et al. (February 2009). "Evaluation of the efficacy and safety of pamapimod, a p38 MAP kinase inhibitor, in a double-blind, methotrexate-controlled study of patients with active rheumatoid arthritis". Arthritis and Rheumatism. 60 (2): 335–344. doi:10.1002/art.24266. PMID 19180516.
^ Zhao X, Ning L, Xie Z, Jie Z, Li X, Wan X, et al. (May 2019). "The Novel p38 Inhibitor, Pamapimod, Inhibits Osteoclastogenesis and Counteracts Estrogen-Dependent Bone Loss in Mice". Journal of Bone and Mineral Research. 34 (5): 911–922. doi:10.1002/jbmr.3655. PMID 30615802.
^ Zhang J, Yan C, He W, Wang M, Liu J (December 2020). "Inhibition against p38/MEF2C pathway by Pamapimod protects osteoarthritis chondrocytes hypertrophy". Panminerva Medica. doi:10.23736/S0031-0808.20.04170-1. PMID 33263251.

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Identifiers

IUPAC name 6-(2,4-difluorophenoxy)-2-(1,5-dihydroxypentan-3-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one
CAS Number	449811-01-2
PubChem CID	16220188
IUPHAR/BPS	9915
ChemSpider	17347490
KEGG	D08963
ChEBI	CHEBI:90685
ChEMBL	ChEMBL1090089
PDB ligand	FLW (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID90963312
Chemical and physical data
Formula	C₁₉H₂₀F₂N₄O₄
Molar mass	406.390 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1C2=NC(=NC=C2C=C(C1=O)OC3=C(C=C(C=C3)F)F)NC(CCO)CCO
InChI InChI=InChI=1S/C19H20F2N4O4/c1-25-17-11(10-22-19(24-17)23-13(4-6-26)5-7-27)8-16(18(25)28)29-15-3-2-12(20)9-14(15)21/h2-3,8-10,13,26-27H,4-7H2,1H3,(H,22,23,24) Key:JYYLVUFNAHSSFE-UHFFFAOYSA-N