Chemicals and Drugs

Toyocamycin

4-Amino-5-cyano-7-(D-ribofuranosyl)-7H- pyrrolo(2,3-d)pyrimidine. Antibiotic antimetabolite isolated from Streptomyces toyocaensis cultures. It is an analog of adenosine, blocks RNA synthesis and ribosome function, and is used mainly as a tool in biochemistry.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

4-Amino-5-cyano-7-(D-ribofuranosyl)-7H- pyrrolo(2,3-d)pyrimidine. Antibiotic antimetabolite isolated from Streptomyces toyocaensis cultures. It is an analog of adenosine, blocks RNA synthesis and ribosome function, and is used mainly as a tool in biochemistry.

Chemical Identity

Chemical Information

Molecular Formula
C12H13N5O4
Molecular Weight
291.26 g/mol
CAS Registry No.
606-58-6
IUPAC Name
4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
InChIKey
XOKJUSAYZUAMGJ-WOUKDFQISA-N
SMILES
C1=C(C2=C(N=CN=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)C#N
MeSH Unique ID
D014127
Source
PubChem CID 11824

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

2 entry terms
  • Deazacyanoadenosine
  • Toyokamycin

MeSH Record

Aspects Covered

26 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

Indexing Annotation

an antineoplastic antibiotic & antimetabolite

MeSH Record

History Note

91(75); was see under ANTIBIOTICS, AMINOGLYCOSIDE 1981-90; was see under ANTIBIOTICS, ANTINEOPLASTIC 1975-80

MeSH Record

Previous Indexing

  • Nitriles (1966-1974)
  • Nucleosides (1966-1972)
  • Pyrimidine Nucleosides (1974)
  • Pyrroles (1966-1974)
  • Ribonucleosides (1973-1974)

MeSH Hierarchy

Tree Number

  1. D13.570w.800w.840w

AMA Style

References

  1. National Library of Medicine. Toyocamycin. Medical Subject Headings (MeSH). 2026. Unique ID D014127. http://id.nlm.nih.gov/mesh/2026/D014127
  2. Toyocamycin. In: Wikipedia. https://en.wikipedia.org/wiki/Toyocamycin
  3. Toyocamycin. In: Wikidata. https://www.wikidata.org/wiki/Q27282806
  4. Toyocamycin. In: PubChem Compound. CID 11824. https://pubchem.ncbi.nlm.nih.gov/compound/11824