WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100755
CAS#: 801-52-5
Description: Porfiromycin is a n N-methyl derivative of the antineoplastic antibiotic mitomycin C isolated from the bacterium Streptomyces ardus and other Streptomyces bacterial species. Bioreduced porfiromycin generates oxygen radicals and alkylates DNA, producing interstrand cross-links and single-strand breaks, thereby inhibiting DNA synthesis. Porfiromycin is preferentially toxic to hypoxic cells.
MedKoo Cat#: 100755
Name: Porfiromycin
CAS#: 801-52-5
Chemical Formula: C16H20N4O5
Exact Mass: 348.14337
Molecular Weight: 348.35
Elemental Analysis: C, 55.17; H, 5.79; N, 16.08; O, 22.96
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Synonym: methyl mitomycin; methyl mitomycin C; Methylmitomycin; porfiromycine porphyromycin; US brand name: Promycin. Code names: ENT50825; U14743; Nmethylmitomycin C.
IUPAC/Chemical Name: ((1aS,8S,8aR,8bS)-6-amino-8a-methoxy-1,5-dimethyl-4,7-dioxo-1,1a,2,4,7,8,8a,8b-octahydroazirino[2',3':3,4]pyrrolo[1,2-a]indol-8-yl)methyl carbamate
InChi Key: HRHKSTOGXBBQCB-VFWICMBZSA-N
InChi Code: 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
SMILES Code: NC(OC[C@H]1[C@]([C@](N2C)([H])[C@]2([H])C3)(OC)N3C4=C1C(C(N)=C(C)C4=O)=O)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 348.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Haffty BG, Wilson LD, Son YH, Cho EI, Papac RJ, Fischer DB, Rockwell S, Sartorelli AC, Ross DA, Sasaki CT, Fischer JJ. Concurrent chemo-radiotherapy with mitomycin C compared with porfiromycin in squamous cell cancer of the head and neck: final results of a randomized clinical trial. Int J Radiat Oncol Biol Phys. 2005 Jan 1;61(1):119-28. PubMed PMID: 15629602.
2: Lee SH, Kohn H. Cyclic disulfide C8 iminoporfiromycin: nucleophilic activation of a porfiromycin. J Am Chem Soc. 2004 Apr 7;126(13):4281-92. PubMed PMID: 15053618.
3: Lang W, Mao J, Doyle TW, Almassian B. Isolation and identification of urinary metabolites of porfiromycin in dogs and humans. Drug Metab Dispos. 2000 Aug;28(8):899-904. PubMed PMID: 10901698.
4: Lang W, Mao J, Wang Q, Niu C, Doyle TW, Almassian B. Isolation and identification of metabolites of porfiromycin formed in the presence of a rat liver preparation. J Pharm Sci. 2000 Feb;89(2):191-8. PubMed PMID: 10688748.
5: Haffty BG, Son YH, Wilson LD, Papac R, Fischer D, Rockwell S, Sartorelli AC, Ross D, Sasaki CT, Fischer JJ. Bioreductive alkylating agent porfiromycin in combination with radiation therapy for the management of squamous cell carcinoma of the head and neck. Radiat Oncol Investig. 1997;5(5):235-45. PubMed PMID: 9372546.
6: Belcourt MF, Hodnick WF, Rockwell S, Sartorelli AC. Differential toxicity of mitomycin C and porfiromycin to aerobic and hypoxic Chinese hamster ovary cells overexpressing human NADPH:cytochrome c (P-450) reductase. Proc Natl Acad Sci U S A. 1996 Jan 9;93(1):456-60. PubMed PMID: 8552660; PubMed Central PMCID: PMC40257.
7: Sartorelli AC, Belcourt MF, Hodnick WF, Keyes SR, Pritsos CA, Rockwell S. Preferential kill of hypoxic EMT6 mammary tumor cells by the bioreductive alkylating agent porfiromycin. Adv Enzyme Regul. 1995;35:117-30. PubMed PMID: 7572339.
8: Rockwell S, Hughes CS. Effects of mitomycin C and porfiromycin on exponentially growing and plateau phase cultures. Cell Prolif. 1994 Mar;27(3):153-63. PubMed PMID: 10465006.
9: Siegel D, Beall H, Kasai M, Arai H, Gibson NW, Ross D. pH-dependent inactivation of DT-diaphorase by mitomycin C and porfiromycin. Mol Pharmacol. 1993 Dec;44(6):1128-34. PubMed PMID: 8264549.
10: Yu F, Pan SS. Effect of pH on DNA alkylation by enzyme-activated mitomycin C and porfiromycin. Mol Pharmacol. 1993 Jun;43(6):863-9. PubMed PMID: 8391116.
