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Substance Name: Porfiromycin [USAN:INN:BAN]
RN: 801-52-5
UNII: H1WK901OA6
InChIKey: HRHKSTOGXBBQCB-VFWICMBZSA-N

Note

  • Toxic antibiotic of the mitomycin group, obtained from MITOMYCIN and also from Streptomyces ardus and other species. It is proposed as an antineoplastic agent, with some antibiotic properties.

Molecular Formula

  • C16-H20-N4-O5

Molecular Weight

  • 348.357
 

Classification Codes

  • Antibacterial
  • Antibiotics, Antineoplastic
  • Antineoplastic
  • Antineoplastic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
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Names and Synonyms

Name of Substance

  • Porfiromycin
  • Porfiromycin [USAN:INN:BAN]

MeSH Heading

  • Porfiromycin

Synonyms

  • 6-Amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethylazirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione carbamate (ester)
  • AI3-50825
  • Azirino(2',3':3,4)pyrrolo(1,2-a)-indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-
  • ENT-50825
  • Methyl mitomycin C
  • Methylmitomycin
  • Mitomycin C, N-methyl-
  • N-Methylmitomycin C
  • NSC 56410
  • NSC-56410
  • Porfiromicina
  • Porfiromicina [INN-Spanish]
  • Porfiromycin
  • Porfiromycine
  • Porfiromycine [INN-French]
  • Porfiromycinum
  • Porfiromycinum [INN-Latin]
  • Porphyromycin
  • Regamycin
  • U-14,743
  • U-14743
  • UNII-H1WK901OA6

Systematic Names

  • Azirino(2',3':3,4)pyrrolo(1,2-a)-indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b-hexahydro-8a-methoxy-1,5-dimethyl-
  • Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a- methoxy-1,5-dimethyl-, carbamate (ester) (8CI)
  • Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-1,1a,2,8,8a,8b-hexahydro-8-(hydroxymethyl)-8a-methoxy-1,5-dimethyl-, carbamate (ester)
  • Azirino(2',3':3,4)pyrrolo(1,2-a)indole-4,7-dione, 6-amino-8-(((aminocarbonyl)oxy)methyl)-1,1a,2,8,8a,8b- hexahydro-8a-methoxy-1,5-dimethyl-,(1aR-(1aalpha,8beta,8aalpha,8balpha))- (9CI)

Registry Numbers

CAS Registry Number

  • 801-52-5

FDA UNII

  • H1WK901OA6

System Generated Number

  • 0000801525

Structure Descriptors

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

InChIKey

HRHKSTOGXBBQCB-VFWICMBZSA-N

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 10mg/kg (10mg/kg) BLOOD: GRANULOCYTOPENIA

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Antibiotics and Chemotherapy Vol. 11, Pg. 445, 1961.
human TDLo intravenous 1500ug/kg (1.5mg/kg) BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA
Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 615, 1972.
monkey LD oral > 10mg/kg (10mg/kg) BLOOD: GRANULOCYTOPENIA Antibiotics and Chemotherapy Vol. 11, Pg. 445, 1961.
mouse LD50 intraperitoneal 44mg/kg (44mg/kg)   Cancer Chemotherapy Reports. Vol. 30, Pg. 9, 1963.
mouse LD50 intravenous 55mg/kg (55mg/kg)   Journal of Medicinal Chemistry. Vol. 14, Pg. 103, 1971.
mouse LD50 oral 88660ug/kg (88.66mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 subcutaneous 53500ug/kg (53.5mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
rat LD50 oral 68mg/kg (68mg/kg)   "Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -0.960 (none)   EST
Atmospheric OH Rate Constant 8.82E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.