Pingyangmycin

Pingyangmycin
Systematic (IUPAC) name
(2R,3S,4S,5R,6R)-2-{[(2R,3S,4S,5S,6S)-2-{[(1R,2S)-2-[({6-Amino-2-[(1S)-3-amino-1-{[(2S)-2,3-diamino-3-oxopropyl]amino}-3-oxopropyl]-5-methyl-4-pyrimidinyl}carbonyl)amino]-3-{[(2R,3S,4S)-5-{[(2S,3R)-1- ({2-[4-({3-[(4-aminobutyl)amino]propyl}carbamoyl)-2,4'-bi-1,3-thiazol-2'-yl]ethyl}amino)-3-hydroxy-1-oxo-2-butanyl]amino}-3-hydroxy-4-methyl-5-oxo-2-pentanyl]amino}-1-(1H-imidazol-5-yl)-3-oxopropyl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl carbamate
Clinical data
Pregnancy
category
  • D
Routes of
administration
intravenous, intraarterial, intramuscular, intratumoral
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Metabolism amidase
Biological half-life 1.3 hours
Excretion renal (25-50%)
Identifiers
CAS Number 11116-32-8
55658-47-4 (hydrochloride)
PubChem CID 84046
ChemSpider 8232875 YesY
Synonyms Bleomycin A5
Chemical data
Formula C57H89N19O21S2
Molar mass 1440.56126

Pingyangmycin (also known as bleomycin A5) is an antitumor glycopeptide antibiotic belonging to the bleomycin family, which is produced by Streptomyces verticillus var. pingyangensis n.sp., a variety of Streptomyces verticillus. It was discovered in 1969 at Pingyang County of Zhejiang Province in China, and was brought into clinical use in 1978.[1]

In China, pingyangmycin has largely superseded bleomycin A2 (commonly known as "bleomycin"), since it is more effective, costs less, is easier to get, can treat a larger varieties of cancers (such as breast cancer and liver cancer) and causes less lung injury.[2][3] Though it also results in pulmonary fibrosis, unlike bleomycin, its most serious side effect is anaphylactic shock, which is rare, but may happen even in a low dose, and can be fatal.[4] In addition, it causes a higher incidence of fever than bleomycin; the occurrence of this complication in patients is between 20 and 50%.

References

  1. Lin, F. T.; Li, D. D.; Yang, X. P.; Li, Q.; Xue, Y. C.; Zhen, Y. S. (1979). "Antitumor activity and preclinical pharmacologic evaluation of pingyangmycin (author's transl)". Zhonghua zhong liu za zhi \Chinese journal of oncology] 1 (3): 161–166. PMID 95444.
  2. Zheng, J. W.; Yang, X. J.; Wang, Y. A.; He, Y.; Ye, W. M.; Zhang, Z. Y. (2009). "Intralesional injection of Pingyangmycin for vascular malformations in oral and maxillofacial regions: An evaluation of 297 consecutive patients". Oral Oncology 45 (10): 872–876. doi:10.1016/j.oraloncology.2009.02.011. PMID 19628423.
  3. Xu, H. Z.; Zhang, H. Y. (1980). "The isolation and identification of pingyangmycin (author's transl)". Yao xue xue bao = Acta pharmaceutica Sinica 15 (10): 609–614. PMID 6167140.
  4. Shou, B. Q.; Mao, Z.; Zhang, S. L.; Yang, Z. (2009). "Allergy caused by minidose and low concentration Pingyangmycin: A case report". Hua xi kou qiang yi xue za zhi = Huaxi kouqiang yixue zazhi = West China journal of stomatology 27 (5): 572–573. PMID 19927737.
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