Porfiromycin

Porfiromycin
Clinical data
Trade names	Promycin
ATC code	L01 ;
Identifiers
	IUPAC name [(4S,6S,7R,8S)-11-amino-7-methoxy-5,12-dimethyl-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate;
CAS Number	801-52-5 ;
PubChem CID	13116;
DrugBank	DB06478;
ChemSpider	12565;
UNII	H1WK901OA6;
KEGG	D05572;
ChEMBL	ChEMBL521078;
CompTox Dashboard (EPA)	DTXSID901024646 ;
Chemical and physical data
Formula	C16H20N4O5
Molar mass	348.359 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C(=O)C2=C(C1=O)N3C[C@H]4[C@@H]([C@@]3([C@@H]2COC(=O)N)OC)N4C)N;
	InChI InChI=1S/C16H20N4O5/c1-6-10(17)13(22)9-7(5-25-15(18)23)16(24-3)14-8(19(14)2)4-20(16)11(9)12(6)21/h7-8,14H,4-5,17H2,1-3H3,(H2,18,23)/t7-,8+,14+,16-,19?/m1/s1; Key:HRHKSTOGXBBQCB-VFWICMBZSA-N;

Porfiromycin is an N-methyl derivative of the antineoplastic antibiotic, mitomycin C, which is isolated from various Streptomyces bacterial species. As an antineoplastic agent, it is under investigation for the treatment of cancer, particularly head and neck cancer.

Porfiromycin works by generating oxygen radicals and alkylating DNA, resulting in interstrand cross-links and single-strand breaks. This inhibits DNA synthesis and leads to the death of cancer cells. It has a higher toxicity towards hypoxic cells, making it an attractive option for cancer treatment.

Porfiromycin can increase the risk of methemoglobinemia when taken with certain medications. It belongs to the class of compounds known as mitomycins, which are characterized by their aziridine ring linked to a 7-amino-6-methyl-cyclohexa[b]pyrrolizine-5,8-dione structure.