Porfiromycin

Porfiromycin is an N-methyl derivative of the antineoplastic antibiotic, mitomycin C, which is isolated from various Streptomyces bacterial species.[2] As an antineoplastic agent, it is under investigation for the treatment of cancer, particularly head and neck cancer.[1]

Porfiromycin

Clinical data
Trade names	Promycin[1]
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[2][1]
PubChem CID	13116
DrugBank	DB06478
ChemSpider	12565
KEGG	D05572
ChEMBL	ChEMBL521078
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.[2]

Porfiromycin can increase the risk of methemoglobinemia when taken with certain medications.[1] 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.[1]