Porfiromycin

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

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
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 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.