Olmutinib

Olmutinib
Clinical data
Other names	HM-61713, BI-1482694
Routes of; administration	By mouth
ATC code	L01EB06 (WHO) ;
Legal status
Legal status	Approved in South Korea;
Identifiers
	IUPAC name N-{3-[(2-{[4-(4-Methyl-1-piperazinyl)phenyl]amino}thieno[3,2-d]pyrimidin-4-yl)oxy]phenyl}acrylamide;
CAS Number	1353550-13-6;
PubChem CID	54758501;
ChemSpider	45743494;
UNII	CHL9B67L95;
KEGG	D10859;
CompTox Dashboard (EPA)	DTXSID001319119 ;
Chemical and physical data
Formula	C26H26N6O2S
Molar mass	486.59 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCN(CC1)c2ccc(cc2)Nc3nc4ccsc4c(n3)Oc5cccc(c5)NC(=O)C=C;
	InChI InChI=1S/C26H26N6O2S/c1-3-23(33)27-19-5-4-6-21(17-19)34-25-24-22(11-16-35-24)29-26(30-25)28-18-7-9-20(10-8-18)32-14-12-31(2)13-15-32/h3-11,16-17H,1,12-15H2,2H3,(H,27,33)(H,28,29,30); Key:FDMQDKQUTRLUBU-UHFFFAOYSA-N;

Olmutinib (INN)^[1] is an investigational anti-cancer drug. It acts by covalently bonding to a cysteine residue near the kinase domain of epidermal growth factor receptor (EGFR).^[2]

In the US, it was given a breakthrough therapy designation in non-small cell lung cancer (NSCLC) in December 2015, and In South Korea, the drug was approved in May 2016 for the second-line treatment of NSCLC with the T790M mutation of EGFR.^[2] Resistance to olmutinib has been reported; a person's cancer started progressing after they developed a C797S mutation in EGFR.^[2]^[3]

Olmutinib was discovered by Hanmi Pharmaceutical and licensed to Boehringer Ingelheim in 2015 in an agreement with a $50 million up front payment and up $680 million in milestones.^[4] In November 2015 Hanmi granted an exclusive license to sell olmutinib in China to the Chinese company ZAI Labs.^[5]

On September 30, 2016, Korean regulatory authorities issued a safety alert about olmutinib in which it described two cases of toxic epidermal necrolysis, one of which was fatal, and a case of Stevens–Johnson syndrome; Boeheringer announced the termination its deal with Hanmi the same day, citing that the decision came after a review of "all available clinical data" on the drug, and also referring to competing drugs.^[6]

References

^ "Olmutinib". AdisInsight. Springer Nature Switzerland AG. Retrieved 28 February 2017.
^ ^a ^b ^c Liao BC, Lin CC, Lee JH, Yang JC (December 2016). "Update on recent preclinical and clinical studies of T790M mutant-specific irreversible epidermal growth factor receptor tyrosine kinase inhibitors". Journal of Biomedical Science. 23 (1): 86. doi:10.1186/s12929-016-0305-9. PMC 5135794. PMID 27912760.
^ Passaro A, Guerini-Rocco E, Pochesci A, Vacirca D, Spitaleri G, Catania CM, et al. (March 2017). "Targeting EGFR T790M mutation in NSCLC: From biology to evaluation and treatment". Pharmacological Research. 117: 406–415. doi:10.1016/j.phrs.2017.01.003. PMID 28089942. S2CID 45855336.
^ Garde D (July 29, 2015). "Boehringer bets up to $730M on a new lung cancer drug". FierceBiotech.
^ Keenan J (April 14, 2016). "South Korea's Hanmi to spend $200M in China expansion". FiercePharma.
^ Carroll J (October 1, 2016). "Following lethal tox report, Boehringer scraps plans for high-speed development, kills $730M Hanmi deal". Endpoints.

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[1] "Olmutinib". AdisInsight. Springer Nature Switzerland AG. Retrieved 28 February 2017.

[Liao2016rev-2] Liao BC, Lin CC, Lee JH, Yang JC (December 2016). "Update on recent preclinical and clinical studies of T790M mutant-specific irreversible epidermal growth factor receptor tyrosine kinase inhibitors". Journal of Biomedical Science. 23 (1): 86. doi:10.1186/s12929-016-0305-9. PMC 5135794. PMID 27912760.

[Passaro2017rev-3] Passaro A, Guerini-Rocco E, Pochesci A, Vacirca D, Spitaleri G, Catania CM, et al. (March 2017). "Targeting EGFR T790M mutation in NSCLC: From biology to evaluation and treatment". Pharmacological Research. 117: 406–415. doi:10.1016/j.phrs.2017.01.003. PMID 28089942. S2CID 45855336.

[4] Garde D (July 29, 2015). "Boehringer bets up to $730M on a new lung cancer drug". FierceBiotech.

[FierceChina-5] Keenan J (April 14, 2016). "South Korea's Hanmi to spend $200M in China expansion". FiercePharma.

[6] Carroll J (October 1, 2016). "Following lethal tox report, Boehringer scraps plans for high-speed development, kills $730M Hanmi deal". Endpoints.

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