Darinaparsin

Darinaparsin
Clinical data
Trade names	Darvias; Zinapar
Other names	SP-02; ZIO-101; DMAs(III)G
Legal status
Legal status	Rx in Japan;
Identifiers
	IUPAC name (2S)-2-Amino-5-[[(2R)-1-(carboxymethylamino)-3-dimethylarsanylsulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid;
CAS Number	69819-86-9;
PubChem CID	11683005;
DrugBank	DB06179;
ChemSpider	9857733;
UNII	9XX54M675G;
KEGG	D08898;
ChEBI	CHEBI:94295;
ChEMBL	ChEMBL3247378;
CompTox Dashboard (EPA)	DTXSID80220108 ;
ECHA InfoCard	100.210.066
Chemical and physical data
Formula	C12H22AsN3O6S
Molar mass	411.30 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[As](C)SC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N;
	InChI InChI=1S/C12H22AsN3O6S/c1-13(2)23-6-8(11(20)15-5-10(18)19)16-9(17)4-3-7(14)12(21)22/h7-8H,3-6,14H2,1-2H3,(H,15,20)(H,16,17)(H,18,19)(H,21,22)/t7-,8-/m0/s1; Key:JGDXFQORBMPJGR-YUMQZZPRSA-N;

Darinaparsin (trade names Darvias and Zinapar) is a drug for the treatment of various types of cancer.[1] It is an arsenic-containing derivative of glutathione.[2]

The mechanism of action of darinaparsin is proposed to involve disruption of mitochondrial function, increased production of reactive oxygen species, and modulation of intracellular signal transduction pathways, thereby inducing cell cycle arrest and apoptosis in cancer cells.[3]

History

Darinaparsin and related compounds were first studied in the 1970s at Texas A&M University. It wasn't until 1998, when a connection between organoarsenic compounds and their potential use in cancer chemotherapy was reported, that interest in darinaparsin as a pharmaceutical drug began.[4] Darinaparsin was licensed to Ziopharm Oncology and then Solasia Pharma for drug development.[4]

Darinaparsin was granted Orphan Drug Designation in the US and Europe as a treatment for peripheral T-cell lymphoma (PTCL).[5]

In Japan, darinaparsin was approved for relapsed or refractory PTCL in June 2022.[6]

References

"Darinaparsin - Solasia Pharma". Adis Insight. Springer Nature Switzerland AG.
"Darinaparsin". NCI Drug Dictionary. National Cancer Institute.
"SP-02". Solasia.
Quintás-Cardama A, Verstovsek S, Freireich E, Kantarjian H, Chen YW, Zingaro R (December 2008). "Chemical and clinical development of darinaparsin, a novel organic arsenic derivative". Anti-Cancer Agents in Medicinal Chemistry. 8 (8): 904–909. doi:10.2174/187152008786847666. PMID 19075572.
"Darinaparsin". Inxight Drugs. National Institutes of Health.
"Solasia Pharma: DARVIAS® Injection 135mg (Generic Name: DARINAPARSIN /Development Code: SP-02) Approved in Japan" (Press release). June 19, 2022.

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[adisinsight-1] "Darinaparsin - Solasia Pharma". Adis Insight. Springer Nature Switzerland AG.

[nci-2] "Darinaparsin". NCI Drug Dictionary. National Cancer Institute.

[solasia-3] "SP-02". Solasia.

[Zingaro-4] Quintás-Cardama A, Verstovsek S, Freireich E, Kantarjian H, Chen YW, Zingaro R (December 2008). "Chemical and clinical development of darinaparsin, a novel organic arsenic derivative". Anti-Cancer Agents in Medicinal Chemistry. 8 (8): 904–909. doi:10.2174/187152008786847666. PMID 19075572.

[ncats-5] "Darinaparsin". Inxight Drugs. National Institutes of Health.

[businesswire-6] "Solasia Pharma: DARVIAS® Injection 135mg (Generic Name: DARINAPARSIN /Development Code: SP-02) Approved in Japan" (Press release). June 19, 2022.